Saying Goodbye

Eighteen years ago this month, I hopped in the car and drove up to Augusta to the Kennebec Valley Humane Society. They had a cat there that no one, apparently, wanted to adopt. Which, in turn, made me want to adopt him, hence the ride up north.

As it turned out, however, someone did want to adopt him, and drove off with their new cat about an hour before I got up there. They tried to talk me into coming to see a new batch of kittens that had come in, but I resisted, having had my heart set on the cat that had been adopted. Eventually I gave in because, well, kittens.

When I walked into the room with the them, they were rolling all over each other and play fighting. One of kittens looked up and saw me, sprinted over and proceeded to climb my leg like a tree. When I pried her off my hip, she was purring loudly.

Her name was Azrael. I had to have her put to sleep last week.

When she came home with me that June, I was living alone up the coast from here in Maine, far from friends and family. Az was my companion in those early years. She was my local friend. She rode in with me to the office every day, and rode home with me at night. She curled up in my lap if it was available, and next to it if it wasn’t. She would drape herself over me at night, or crawl under the blanket and go to sleep behind my knees. And her most favorite thing in the world was to be carried. She’d sit in the crook of my elbow, paws on top of my hand and just quietly sit as I wandered around randomly carrying a cat and trying to do things like laundry one handed.

My relationship with her, however, was a lot different from other people’s relationships with her. In my experience there is a type of cat that is basically a one person cat. I grew up with one. Azrael was another.

She liked Kate, which didn’t help much since she’s allergic. One of my happiest memories, meanwhile, was when she gave the newborn Eleanor a tentative lick the first time they met – and she was a very patient cat with a very affectionate toddler. She also got along just fine with my best friend Andrew.

But that was pretty much the list. She hated pretty much everyone else – even people who were kind enough to make sure she had food and water while I was traveling. Best case, they wouldn’t even see her. Worst case, there would be hissing. And if you didn’t pay attention to that and got too close, she would cut you. Happily. The last veterinarian we went to tried to get me to take a fancy plastic cat carrier for free because they were so scared of me taking her out of it. I assured them she’d be fine for me, and she was.

Azrael may have been a tiny cat, but she was fierce. Even those of my friends that didn’t like her – which is to say most of them – would allow her that much, I think.

If she wasn’t particularly friendly, however, she was adaptable. She lived in everything from a one room cottage to a loft to a basement to, when we had that finished, the RedMonk office briefly. She took it all in stride. She was on a plane more than my daughter’s been to date. She didn’t like it, but as long as I was able to stick my hand in the cat carrier so she could know that I was there, she’d settle.

I worked with a guy once whose cat crapped on his clothes as a means of expressing its displeasure when he traveled. Az never did anything at all to protest; she was just overjoyed to see me when I got back.

Throughout all of the changes in my life over the last two decades, Azrael – most commonly referred to in the house as “Pook” – was there for me. Moves. Marriage. A daughter. My deteriorating and then recovering health. My Dad’s death. Throughout all of the ups and downs, I could sit down each night, she’d curl up next to me and I’d feel loved.

Pets have many wonderful benefits, but I’m not sure there’s any that are more important than that.

Last week, I noticed a couple of things that were off. Her food bowl was fuller than it should have been and she felt lighter. And she was making a noise as if she was grinding her teeth, which had never happened before. I took her in assuming it was a dental issue. They called and told me it was a growth, very likely squamous cell cancer. In the span of about thirty seconds I went from wondering how long she’d be in for dental work to desperately trying to get around the fact I was going to have to say goodbye.

Because that was clearly what had to happen. Surgery on the mouth of an eighteen year old cat would be trading at best a few months for me to come to terms for an agonizing, painful struggle for her, which of course is no trade at all. It would mean selfishly putting her through hell so that I didn’t have to feel sad until later.

We might not always be able to be kind to people in these situations, but we can at least do that for our animals.

A half hour later, I was at the vet’s sobbing as they brought her in. True to her nature, they’d had to administer the sedative before they brought her in because she tried to cut a few of them up. Even in her weakened state, she was still fierce.

I thanked her for always being there for me and for making me happy. I told her that she’d been loved. And then they gave her the second drug, and she was gone.

You won’t find many other people who liked her, let alone loved her. You, reading this right now, probably wouldn’t have. But I did. So very much.

Goodbye Pook. You were a great cat.

Why I Walk and Why You Might Want to Walk Too

Since I started walking longer distances and have lost some weight in the process, I’ve gotten a bunch questions from people about it. My original plan was to wait and write this post answering some of those in early January, with a full regular calendar year of walking under my belt. Then it occurred to me that waiting to drop a post on walking tips until the middle of winter was a spectacularly dumb idea, even by my standards. Putting this up now in case some of you have the opportunity to use some of the following advice to walk during weather which is actually pleasant seems like a much more reasonable approach.

This particular revelation was triggered in part after reading a tweet from my friend Kim, the one here.

That reminded me of a conversation I had a few weeks ago, in which I made a similar argument to a friend when I compared walking to cameraphones. The camera in your phone might not always be the best option to take a picture, but it’s much more likely to be the camera you have on you. Similarly, walking may not always be the most metabolically efficient activity, but it’s one that most of us can nearly always do.

It may not be the sexiest exercise, but it’s accessible as hell. So here’s a bit on why I walk and how I walk, and why you might want to as well. Best case, something in here will be of use to you.

Why You Should Walk

Weight Loss

It’s not hard to find studies on the internet that tout the benefits of walking in terms like “lower mortality” or “greater longevity,” but as far as I’m concerned that all comes back to the single greatest benefit of walking for me: weight loss. As I discussed back in December, my physical condition wasn’t so hot pre-pandemic and had deteriorated to outright problematic by last fall.

Historically, the best and most enjoyable way for me to exercise was running. But when you haven’t run regularly in years and you’ve gotten out of shape in the meantime, getting back on that particular horse can be challenging.

Fortunately for me, while on hiatus from a couch-to-5K program due to a back tweaked while on said couch-to-5K program, I ran into our local walking legend Dean. After a single conversation with him about his experiences walking 10+ miles a day as someone a few decades older than I am, walking went from little more than a mere rehab activity to a primary exercise focus. Shortly after talking to Dean, I Googled for “online activity calorie calculator.” This is what it told me I might expect to burn calorically:

  • Cycling, moderate pace for 30 minutes: 375 calories
  • Running, moderate pace for 30 minutes: 675 calories
  • Swimming, mild pace for 30 minutes: 375 calories

Those aren’t bad, and literally any exercise is better than none. But given the weight I’d added, I was looking for something a little more significant, and the reality of the couch-to-5K programs I was trying to ramp up on was that it’d be a month or more before I’d even work up to 30 minutes of moderate running.

After hearing about Dean’s experiences losing weight via walking, however, I asked the calculator what kind of calories I might burn if I walked for two hours. The answer?

1150 calories. If I could find a third hour in there every so often? The number jumped to 1750 calories.

All of a sudden, walking became a lot more attractive as an option. Now most of the cyclists and runners I know will object, noting that they don’t work out at a moderate pace, they crush their workouts. But particularly when I started all of this, I simply wasn’t in a position to push like that. I was, however, willing and able to walk, and to keep walking.

As it turns out, the calories burned on those long miles pay off. Here’s a line chart of my weight over periods stretching back over a decade. As you can see, I wasn’t in a great place with my weight even before the pandemic hit, but that – and a number of other things going on, it must be said – didn’t help.

It took me just shy of 70 days of walking to get back to my pre-pandemic weight, but that was still too heavy. A hundred days after that, I was lighter than I’d been since 2011. And I’m 15 pounds lighter than that now.

More importantly, walking has become part of my day to day in ways that other exercise routines haven’t, which means that this feels more sustainable. This isn’t some crazy, crash diet sprint I can’t maintain, it’s the accumulation of a few small changes and an exercise I genuinely enjoy.

My current plan is to keep going and see if I can get to my high school / college weight; still a ways to go there. But worst case, if I can do nothing more than hold more or less where I am, that would be an enormous win versus where I was a year ago at this time.

It’s Enjoyable

I am not a morning person. I never have been, and I never will be. I’m just not wired that way, and if I needed more proof my six year old is cut from the same cloth. Getting up at five in the morning, therefore, is not something I do for fun, or even willingly without major justification.

And yet I regularly get up at that unholy hour to go for my walks, because – the 5 AM part aside – I genuinely enjoy it. The only hard part is rolling out of bed; once I’m up, out and walking I’m happy about it. Here are a few reasons why:

  • It’s meditative, for one. When all you have to do is put one foot in front of the other at a deliberate pace, your mind is free to wander, to process or just to zone out. Walking is a perfect way to temporarily detach from your day.
  • You can get to know your community better. I’ve gotten to know a bunch of other regulars out on the trails, not to mention their dogs, and they were good dogs. At the same time, they also have gotten to know me. Embarrassingly, I’ve had close to a dozen people that I don’t know other than from the trails stop me to say kind things about my progress losing weight, and to cheer me on. After seven months, one even stopped to show me a “secret” trail that I never would have found otherwise.
  • You may get to see things you wouldn’t otherwise. Chris Arnade, for example, walks 12 miles a day in cities all over the world and the pictures he’s taken are incredible. While my walking has been strictly local, however, I’ve seen all kinds of things I would otherwise miss, including some incredible sunrises like the one above (good) and a skunk that almost sprayed me (bad).
  • Lastly, while I could never manage the trick of listening to audiobooks while running – I needed music – I can while I walk, which means that I’ve been absolutely plowing through books.

No Impact

In the interest of full disclosure, “no impact” is a little bit of an exaggeration in my case, since I ended up going down on icy trails and roads this winter several times, breaking a couple of ribs on one occasion. But that was based on some poor choices on my part.

The simple fact is that relative to a number of other exercises, most notably running, walking has next to no impact. Per this study, for example, “Running produces ground reaction forces that are approximately 2.5 times body weight, while the ground reaction force during walking is in the range of 1.2 times body weight.” The cardio benefits of running offset that additional impact, to be sure, but particularly if you’re just getting started or are restarting with a fitness regimen walking is easier on the body. It is, of course, something that a lot of us do every day anyway.

It’s Easy to Scale Up

Not only is walking low impact, it’s inherently easy to scale up or down. You can start slow, and up your pace. You can walk a short distance, or walk a little further. You can also, as I’ve started to do a bit on our trails here, mix walking with running to get a little extra cardio work. It’s inherently flexible and adaptable to whatever you might have on a given day.

How To Start Walking

When you get started walking, the single most important thing – as with any exercise regime – is to start gradually and build yourself up over time. I started by walking across the bridge and back to our house. Then I started walking past the house and back via a nearby trail. Then I added a loop. A route down one side street to a local dock. Another down to the ferry. Then loops on the next next island over. And so on.

This meant two things.

  • First, my mileage grew in a slow, manageable fashion. I’d walk a route, and when I felt comfortable with it, I’d add some distance. I started out by walking 1.6 miles last October. Over a recent 12 week stretch prior to a week of travel, I averaged a tick over 8 miles per day six days a week.
  • Second, it means that I can very easily add or subtract distance based on the window of time I have available. I can walk a route as short as a half hour, as long as four or more hours, and anything in between just by manipulating my routes up or down.

A few other quick tips that may help you get started:

  • Plan: I’ve found it very helpful to map out my week on Sunday nights. I look over my schedule, the weather and – depending on the season – the sunrise/sunset/civil twilight times, and slot in tentative plans for when I’ll be walking each day and for how long. Predetermining the schedule both ensures that I’ve thought through what my windows are for each day, and also helps ensure that I’m not surprised by the days when I have to be up and out early in the dark.
  • Rest: Walking may be low impact, but I’ve found it beneficial to still build in a day per week where I have no walks planned. If nothing else, it makes me look forward to getting back out on the trail the next day.
  • Yoga: I get asked about stretching a lot: do I stretch before I walk, after or both? With the caveat that I am absolutely not the person to take advice from on this subject because even playing sports in high school and college I never really stretched, I do not at this point stretch before or after my walks. What I have found success with instead, however, is 15-30 minutes of yoga at night before bed. I’m more flexible today than I was a decade ago, and yoga is the reason why. I don’t know for certain that it’s helped me from getting tight even after three or four hours of walking, but I’d bet it’s a big part of it. Yoga With Adriene is my recommendation if you’re interested in that.
  • Injuries: When I was in high school, my coaches impressed upon us the difference between being hurt and being injured. While playing contact sports, the reality was that something was going to hurt pretty much all the time. This is also what happens as I’ve gotten older; something, somewhere is probably going to be sore. The trick is distinguishing being hurt from being injured, which is to say a situation in which continued activity might make something worse. This is a hard thing to learn, and it really depends on an individual’s history, tolerance for pain and so on. In my case, I find that when I get sore while walking, more often than not if I just keep walking the pain resolves itself, and usually pretty quickly. Every so often, however, something worse pops up and you have to take care of it. Listen to your body, but not too quickly, if that makes sense.

How to Dress for Walking


One of the things I had to adapt to while ramping up my walking, particularly as it grew colder this past fall, was working out the appropriate layers. Running generates enough body heat that even in winter, I used to run in shorts and a long sleeve top. Walking doesn’t generate anywhere near that much heat, and I have the added complication that the bridge I walk across is significantly colder than the rest of the island, so layers – lots of them – were key.

It’s a little more complicated than this depending on windspeed, precipitation and so on, but these are my starting points for different temperature bands:

  • 60 or above: shorts and a t-shirt
  • 50 – 60: pants, t-shirt and a merino 1/4 zip
  • 40 – 50: pants, t-shirt, a merino 1/4 zip and a merino vest
  • 30 – 40: pants, t-shirt, merino vest, merino hoodie, merino hat, merino glove liners
  • 20 – 30: pants, t-shirt, soft shell, merino vest, merino hat, ski gloves
  • 20 or below: pants, t-shirt, soft shell, merino 1/4 zip, merino hat, ski gloves and scarf

You’ll note that there’s a lot of merino in there. I’ve had merino gear for nearly a decade now, and as far as I’m concerned it’s the perfect fabric. It’s lightweight, keeps moisture off of you and is warm in the winter and cool in the summer. I’m in the process of replacing any clothing I can with merino alternatives, right down to my boxers.

My gear comes from a variety of manufacturers: the 1/4 zip and hat come from Minus33, my hoodies and boxers come from Woolx (if you want $20 off anything from there, incidentally, click here) and my vest and glove liners come from Ibex. All of it is good, and I recommend all three companies.

The only thing I’ve found that merino does not deal well with is pet hair, but that’s a small price to pay in my view.


With the exception of walks in heavy snow or ice, all of my walks this fall, winter and now spring have been in Hoka’s – specifically the Bondi 7. I’d never even heard of the company, but when I looked up reviews on the best cushioned running shoes Fleet Feet said the Hokas were it.

I like the Hokas so much I’m now on my third set, and I have even gone out and replaced my Salomon hiking boots with a Hoka alternative. They’re heavily cushioned, stable and great for both putting miles in on pavement and even the occasional sprint down single track trails.

Can’t recommend Hoka enough, even if some of the boots look goofy as hell.


One of the things I learned to carry early on was a backpack. As you peel layers off, it’s nice to not have to carry them or tie them around your waist. It’ll be handy come summer as well to stash water in. I picked up this cheap, ultralight pack from LL Bean. It weighs next to nothing and does exactly what I need it to do.


I’ve never worn crampons regularly before this winter, but then I’d never fallen on an icy trail and broken ribs before either. Now I carry these. They’re a bit of a pain to put on while on a trail, but they do the job nicely.

What’s the Catch?

Walking isn’t all sunshine and unicorns. A couple of the downsides.


By far the biggest catch to walking is the time it requires. With other exercises, you hit it for a half hour or an hour, and get back to your day. Walking, at least if you want it to be comparable calorically, simply takes more time because it’s much less metabolically efficient. In my case, it hasn’t been too hard to find windows because my commute for the last year and a half has not been a half hour down to Portland and a half hour back up, but the ten seconds it takes for me to walk downstairs. Between that reclaimed hour and an hour for lunch, that’s all the time I need to walk around seven to eight miles.

Still, while all of our schedules at RedMonk are flexible, they are very, very full these days. When I can’t find that window during the day, then, I have to resort to alternative tactics.

  • Go Before Everyone Wakes Up: As mentioned above, if I’m out the door a bit after 5 AM, I can get two hours in and be back in time to wake up my daughter for kindergarten at the usual time of 7:20 AM. This is admittedly easier in the spring when it’s light out and the weather is clear than the middle of winter when it’s dark and you can’t see the ice, but you do what you have to.
  • Break up the Walk: Don’t have two hours? Take an hour in one window and an hour in another. Or four half hour chunks. Whatever works.
  • Work While You Walk: This is a staple of mine particularly for longer 2.5-3 hour walks. I almost never have those kinds of windows during a weekday; but I do frequently have listen-only multi-analyst briefings, conference talks I need to catch up on and so on. I can’t really engage, because of wind noise if nothing else, but I can absolutely listen to a briefing while walking.
  • Offset Work: If all else fails, sometimes I can trade work hours for evening hours. I try not to do this too much because it was an unhealthy if necessary habit during the period of the pandemic where my daughter was home full time, but every so often it’s my only option. I go for a walk during the day, and write – or do whatever else was on my plate – at night, after everyone else has gone to bed.

The point is that there’s usually a way to find time. It might be more or it might be less depending on your situation, but generally where there’s a will there’s a way.

It is inarguable that walking is expensive in terms of your time, but it’s a cost well worth paying at least in my case.


Maybe it’s hot where you live. For me that happens, but it’s neither common nor excessive. My problem at least over the winter months is ice, and more specifically falling because of ice. The first time this happened was a shock; by the fifth or tenth time, I had the process down. Or thought so until I broke my ribs. After which point I bought crampons, which brings me to the point here: prepare for whatever your climate brings. If it’s hot, dress accordingly. If it’s cold, layers are your friend. If it’s ice, get crampons. And if it’s really, really cold rain, do what you can, and make sure to wear a raincoat that has not delaminated like the one I wore for too long, but be prepared that you’re probably just going to be really, really cold.

VO2 Max

Walking has had a major impact on my weight loss, but its effect on my overall cardio health was more muted. My VO2 max – even as measured imperfectly by an Apple Watch – has ticked up to the point that I am now technically “above average,” but the above part is literally by 0.1. So the “above” is a little bit of an exaggeration. Plan on finding higher intensity exercises, then, to augment your walking approach if cardio health is a priority.


Walking can be dangerous depending on where you live – certainly it was for Stephen King in this very state. Maybe it’s the neighborhood, maybe it’s the weather or maybe it’s the wildlife. Walking is safer statistically than some other fitness options, but it’s not risk free. A few suggestions:

  1. Walk Against Traffic: I’m always surprised when people don’t do this, but it’s surprisingly common. If you’re walking around cars, and the sidewalk isn’t an option, proceed against the flow of traffic so you can see the cars ahead of you and get off the road if necessary. Which reminds me:
  2. Mind Your Surroundings: It’s sometimes good that walking is meditative, but not always. My biggest issue in this regard was zoning out and missing the presence of black ice this winter – but after a couple of hard, painful falls, I got a lot more attentive.
  3. Don’t Freak Other People Out: I’m not that small of a person, I’m a guy, a lot of my winter attire is black and up until a couple of weeks ago, I had an often crazy beard. All of which is to say that my sudden appearance on back trails frequently elicited emotions like alarm from other users of the trail systems, particularly women on their own. Especially the time I hadn’t realized that my nose had started bleeding and crusted half my face and beard over with blood. It’s gotten better over time at least with the regulars as they’re used to seeing me, but I haven’t yet figured out how to convince new people that I’m just trying to get my work in. What I do, however, for their safety as well as my own – particularly if they have dogs – is smile, steer well clear of them, move slowly but steadily on my way. It always hurts my heart to know that people are, even temporarily, frightened of me, but that is unfortunately the world we live in. All I can do is try not to make it worse.


The Arnade piece linked to above mentions boredom as a real problem, but to be honest I am never bored. I’ve been walking variations of the same paths on the island here six days a week for months, and I can’t say that I’ve ever been bored. Probably part of that is that we live in a beautiful place, but honestly I think it’s the combination of distractions – be those in audiobook, conference talks or other forms – and the purely meditative nature of walking for me. Your mileage may vary here, however, so consider options for keeping yourself entertained.

The Net

All of the above is probably more than you ever wanted to know about walking, but if by some odd chance I missed a question you have post it here and I’ll answer it if I can.

This piece will obviously be less relevant for those of you with fitness routines that already work for you, but for those of you without that, all I can tell you is that in my life so far, there’s a before walking phase and an after walking phase, and that I’m a lot healthier in the after.

If you’re looking to get healthier yourself, you might give walking a try.

Remembering My Dad

A little more than a year after he died, our family came together yesterday to remember my Dad. It was wonderful to see so many friends and family, some for the first time in a decade or more. For those of you that would have liked to attend but were unable, the following was the eulogy I delivered, as best I was able, at the service itself.

Years ago, when my brother and his wife got married, I was seated in the front row at the church with the rest of the groomsmen. My parents were sitting in the pew directly behind me. A couple of minutes into the ceremony, I heard some sniffling, then a couple of barely suppressed sobs.

I turned around to tell my Mom to pull herself together only to discover that my Mom was just fine. My Dad, however, who I maybe saw cry four or five times as a kid, was nearly bawling. And this, after yelling at my Mom the night before because she fell apart at the rehearsal.

And for anyone inclined to doubt that story, I encourage you to swing by the reception after the service – we have pictures.

Anyway, I’m bringing this story up now for two reasons. First, because I generally don’t like reading from scripts and never do this when I have to give a talk for work. I hope you’ll all bear with me, however, as I don’t believe that I have much of a choice due to the second reason, which is that I’m very likely to have a “Dad at Nick’s wedding” style breakdown momentarily.

My brother will talk to you about who my Dad was, and he’ll do that better than I could have. I would speak to you instead of what my Dad would want you – all of you – to know. What he would want you to remember, and to be.

For a guy just shy of six feet, my Dad seemed like a literal giant as a kid. We grew up on stories of his adventures – the postcards home from Swiss Scouts talking about my Uncle Jeff swimming naked or one of his fellow scouts falling down a chimney (but not to tell his parents) were particularly entertaining. It all became the stuff of legends. As did the stories of his freak athleticism – how many people – ever – have broken their dominant wrist, trained themselves to play tennis with their off hand, and made the state semi-finals? The businesses he ran, the rare stories he’d tell from his time in the service – all of it – turned my Dad into an almost mythical character.

Honestly, the man even had a bull whip like Indiana Jones that he picked up at a scout jamboree. It was almost too on the nose.

As the years rolled by and I became yet another surly teenager, my Dad was reduced for a time from hero status to that of a mere man. I focused on what my Dad couldn’t do, or perhaps more accurately what I thought he couldn’t do, and ignored what he could.

Eventually I grew up. I had jobs. I ended up running a business of my own. I paid taxes. I had relationships, then a marriage, then a child of my own. I had to think about bills and revenue and houses and schools and tuition and what I wanted to pass on to my daughter. And I understood how hard all of that could be. How tiring.

And I understood something else: that my father did all of the above, and still found the time to coach both my brother and I in two sports. And serve on town committees. And his church.

When he retired, I used to joke with him that he was the world’s worst retired person, because he couldn’t simply be content and play golf every day, or learn to fish. Instead he became active in the local schools, the local church, the local town, the local food truck and even the local fire department.

The first thing that my Dad would tell you, then – never, ever explicitly, as that was not his way, but strictly by his own example – is this: be of service.

I never really thought about it when I was younger, but looking back it’s remarkable how many of my family’s significant moments were narrated to me by my Dad. For my cousins who are here today: each and every time one of you got into my college, it was my Dad who shared the good news with me. Same with your engagements. For my aunts and uncles, your new jobs. Whether the news was good or whether the news was bad, my Dad made sure I knew what was going on with my family.

He absolutely hated to talk about himself, but he certainly loved to talk about all of you and how well you were doing. He did that because he loved his family, and because he was proud of his family – most of all, of course, his grandchildren. 

He also loved the people his family considered family. He understood, for example, that my best friend, who had the misfortune of booking a vacation for his own family in the Caymans the week before we picked today as the date for his service, was family to me. And so my Dad treated him like family and asked after him the way he would about family – which backfired, unfortunately for him, the time he came home with me for Thanksgiving and my Mom had one of her rare but spectacular cooking misfires with an experimental pumpkin soup served in an actual pumpkin.

But maybe the best example is our wives. He adored you both, and would have done anything for the both of you. He loved the families he indirectly joined. There’s a reason those families are here today, and there’s a reason my Mom insisted that they sit in the family section. It’s because my Dad would have insisted on it.

The second thing my Dad would tell you, then, would be to cherish your family – both the family you’re born to and the family you choose.

After my Dad died, some of my first thoughts were two things.

First, the time that I drove a golf cart into a service ditch full of goose excrement with his mother sitting next to me. On the way home he was apoplectic and swore “we will never laugh about this.”

We laugh about it still, as my aunts, uncles and cousins can confirm for you at the reception.

The second thing that came to me was much less memorable, just a random morning from a couple of years ago. My daughter Eleanor had had a string of ear infections, and woke up with a fever and couldn’t go to daycare on a day when both Kate and myself had work obligations that would be difficult to reschedule. I called my parents – forty five minutes up the road – with no warning, and out of desperation, but reconciling myself to the likelihood that they would have had something else going on, busy as they both were.

I needn’t have worried, because my Dad said what he always said, “No problem. We’ll be on the road in ten.”

I honestly could not count the number of times he – and my Mom – both have bailed me out.

  • “Dad, I need you to pick up a thousand pounds of crushed rock.”
  • “Dad, I have three sheets of plywood waiting at Home Depot.”
  • “Dad, I need help moving.”
  • “Dad, I need a place to live while we get this business off the ground.”
  • “Dad, I need you to rent a wood chipper and help me get rid of this massive brushpile.”

And, my personal favorite:

  • “Dad, Eleanor’s vomiting everywhere but I’m in San Francisco and can’t get home until tomorrow: can you and Mom help Kate?”

When the news broke that he’d died, there were dozens of stories of my Dad making an introduction, getting people a job, talking them out of bad jobs, mentoring them as they progressed through their careers. There were all the kids he coached, telling us that they were passing on the lessons he taught them to their own kids or the teams they coached.

He never did any of this with a thought of reward. He would brush off any gestures of gratitude. Thanks, likewise, were unnecessary. He helped because he could help. That was it, and he didn’t think any more about it.

There are hundreds of other things that my Dad might have told you today, but the last thing I’ll leave you with, then, is that it’s not about you, it’s about being there when the people you love – particularly your family – need you.

He was always there for me, and I’ll miss him.

Goodbye, Dad, and thank you.

My 2021 in Pictures

It’s funny now, but there was a time when we all thought 2021 would kick off the new roaring twenties. Instead, we left it much as we did 2020 – meek, frightened and exhausted. The initial shocking efficacy of the vaccines and the incredible, unprecedented speed of their development led many to hope in the spring that the light at the end of the tunnel was finally in view.

As it turned out, that light was the train called Delta which plowed through all of our tentative, carefully laid plans to get back to a world that looked, well – maybe not normal but normal-adjacent – like a runaway freight car. And just when it looked like the Delta train was done rolling through the station and we could once again move forward, along came another bigger, faster one called Omicron that the epidemiological math says is worse than the measles and had countries dusting off their discarded lockdown policies and kids back in masks at schools.

But for all that 2021 was underwhelming at its best and tragic, awful and spitefully brutal at its worst, I remain grateful because it got me to 2022. It also, with one crushing exception, got my family and friends here. Given the state of the world the last year, and the decade that was March 2020 before that, that’s about all I can ask. For all that the world these days might look grim and dark around me, being here inarguably beats the alternative.

Last year, I debated whether or not to do this sort of year in pictures post. This year I didn’t think about it much, because if I could do it last year, I could do it this year – and I felt like I should.

So as always, these are the moments – significant at times but mostly not – that characterized my year personally. Blessedly, with but a few exceptions, there are no politics in here because I don’t have pictures of it. Before we get to the pictures, however, a quick check-in on travel.


Where I traveled in 2021

The tl;dr version of the travel section is that there was none. Or very little. I had desperately hoped that 2020 was the last year I’d go without seeing my best friend who lives in Colorado. It was not. Here’s hoping 2022’s the charm in that regard.

For the second consecutive year, we didn’t leave the state, though we were fortunate to see some friends who left their state to come visit ours. We played it safe and cautious for another year because Eleanor was ineligible for vaccination for the bulk of it and thus unprotected. We played it safe to the extent that I got offered Red Sox playoff tickets – twice – and turned both of the very kind offers down.

These would have been my seats for the second game.

ALCS Game 3

The Red Sox – in the form of the maligned-at-the-time deadline pickup Kyle Schwarber – would hit a grand slam in the second en route to a 12-3 win. I promise that I will recover from missing this game.


Anyway, there was one positive development travel-wise. While I did not leave the Great State of Maine, that dot at the top of the map up above, the one north of Farmington and Skowhegan marks the return of a tradition that had taken a hiatus due in part to COVID and in part to our move. But we’ll get to that.

With that, on to the pictures.

January 1

Kicked off the New Year with a lazy day in our PJs.

January 2

Took advantage of the holiday break to continue getting the shop set up, this time with a wall-mount for my drill/driver set.

January 6

Will never forget this day, sadly.

January 8

Literally counting the days until the vaccines’ arrival.

January 8

Cranked out an exceedingly poorly crafted outfeed table for the shop.

January 17

My reboot began.

January 20

Joe Biden sworn in. There was only one suitable beer to celebrate with.

January 25

Received the worst two telephone calls of my life. The first was my Mom, letting me know that my Dad was en route to the hospital and that it didn’t look good. The second, an hour later, confirmed that he had died on the way and that they had not been able to resuscitate him.

I fell apart. Did my best to pull myself back together. That night, I watched one of his favorite movies, a movie he had watched with my brother and I over and over when we were kids.

I miss him every day, but carry what he taught me and am doing my best to pass it on.

January 30

With my Dad gone, my parent’s house was too much for my Mom to manage on her own, so my brother and I began the process of helping prep her house for sale. I did what was needed on the ground, he took care of the harder, finance related questions.

February 1

Speaking of my brother, bless him, he sold my Dad’s truck remotely. Because of parts shortages the vehicle market was so bonkers it sold for better than twice what I’d hoped for.

February 5

Started down the rabbit hole of DSLR-as-webcam, which as an aside, you should never do.

February 12

Per usual, got some help loading the woodshed.

February 19

My birthday present made its debut a couple of days early.

February 20

Celebrated my birthday with Hearts. As is right and proper.

February 24

RedMonk shut down for the morning to watch one of the six year old’s favorite people absolutely smoke her dissertation defense.

March 1

We watched the first spring training game together, per tradition.

March 6

It took her less than five minutes to learn to skate better than I can.

March 18

After your kid’s been out of school for hundreds of days, you have to get creative.

March 19

Got an absolutely incredible, wildly over-the-top care package from an old friend I hadn’t talked to in far too long to cheer us up after my Dad’s death. One of my gifts – a print of my Dad and I – left me in tears. All of Eleanor’s, however, were a huge hit, not least of which the pictured squid.

In case that friend is reading this right now, as I know she checks in from time to time: thank you. I will literally never be able to communicate how touched we all were. Are.

March 20

First roof off day of the year.

March 27

Having never tried to repair audio gear before, I was mildly shocked to have successfully swapped out a broken woofer on my twenty-two year old HSU Research subwoofer. This seemed like an excellent improvement to the home theater setup until I cranked it up and discovered that it could be felt two floors up and at the opposite end of the house which made people not watching what I was watching rather unhappy.

April 2

Opening Day. At last.

April 8

Dose 1 for me. If social distancing wasn’t the rule, I would have been running around high-fiving random strangers. Thank you science.

April 10

Continued to help my Mom get ready to move.

April 30

Dose 2.

May 14

For a brief moment in time, I felt invincible.

May 26

With our oil burning furnace nearing the end of its lifespan, and afraid that if it went we’d be out of luck due to supply chain issues, we decided to bite the bullet and preemptively replace it with heat pumps.

So far, so good.

June 1

Went through box after box of things of mine that had been stored in my parents’ basement. All of my childhood and high school memorabilia. Some of my early work documentation. Remote control cars. Several dead mice.

Some real gems emerged.

June 15

Emboldened by the vaccines, I did my first meetup with the Maine tech community since the pandemic had broken out.

June 17

Tough to beat a lake house with friends.

June 20

First day of summer means only one thing.

June 21

This table – the top of it, anyway – has been in our family dating back to colonial times. Now it lives with us for the next generation of O’Grady’s.

June 25

It was Hadlock Field rather than Fenway, but this is the first time I’d been at a ballpark of any size in, what, years? My longest drought probably since I was in college.

July 3

Every July 3rd, I pay my respects, as my parents taught me.

July 4

4th. Fireworks. Friends. No masks. Life was good.

July 16

The actual move was a slow moving disaster because her buyers’ shitty realtor who almost blew everything up at the last minute due incomplete financing on their part, but my Mom managed to sell and get into her smaller, more manageable house thanks in large part to her realtor, who is incredible.

July 26

Took a ride up to Boothbay to see the trolls.

August 6

For the first time in a decade or more I didn’t make it up to my happy place last year, but I made sure to remedy this last summer. The water level was a little lower, the temperature a little warmer, but otherwise all was as I remembered it.

August 21

This was supposed to arrive a lot earlier to provide us with some distractions while she was out of school, but better late than never.

September 7

After 543 days of being out of daycare / pre-K, we had ourselves a kindergartner. It’s been a fantastic development for everyone involved.

September 21

Between the climate change-driven increase in violent weather and the fact that we live on an island, one of our top priorities after moving in was a standby generator. Step 1 began on the 21st. The good news is that the guy we had come dig the trench called DigSafe first. The bad news is that the DigSafe guys missed the cable that provided our internet, which it turns out doesn’t like backhoes much.

It turns out it’s a little challenging to work from home with no internet.

October 7

There was no Monktoberfest, sadly, but seeing a bunch of Monktoberfest people – in person – was the next best thing.

October 17

It took a month and a hell of a lot of wrangling between three different vendors – just finding a propane company willing to service a generator only account was an ordeal – but the generator finally went live.

October 29


October 31

There is no small island on this planet that has more Halloween gear than this one, I guarantee it.

November 9

Dose 1. Hallelujah.

November 13

It was a lot closer than it needed to be, but the good guys pulled it out in the end.

November 24

First time I’ve seen these nephews in something like two years.

November 30

Birthday girl.

December 1

Happy bday – here’s your second shot.

December 5

This indoor birthday party was brought to you by at home rapid tests.

Unrelated, the decision to switch from the giant wooden pole to the foam bat was a good one. The piñata was a tank.

December 12

Sections of the grout were coming up, so I regrouted them. The new grout held for approximately one week.

December 19

Wasn’t much, but technically qualified as the first plowable snow of the season, which meant the debut of our battery powered snowblower (it did just fine).

December 31

Nothing fancy, but closed out the year in fine style with sushi, quality beverages, Hearts and friends – again, thanks to testing.

The Reboot


I was taught from an early age that as bad as a given situation might be, things can always be worse. This was deeply engrained in me during my formative years, and that attitude is second nature in our family. On the occasions when we call each other with bad news, for example, the custom has always been to preface it with “well, the good news is that I don’t have cancer.”

On the one hand, this training has served me well over the years. It’s helped me maintain my perspective during periods that might otherwise have capsized me, and it’s been a reminder to appreciate what was still good in my life when things looked bleak. On the other, this is an approach that can obscure the fact that while things could be worse they, at times, could certainly be better.

Case in point was my health and fitness entering 2021. I’d successfully avoided COVID thanks to strict protocols and the privilege that allowed me to follow them. This was, inarguably, something to be appreciated: things could most certainly be worse. That enormous win aside, the trajectory of my health otherwise was headed south and picking up speed.

There were a lot of reasons for this. The pandemic took its toll on me, of course, as it did on everyone. The weight of living in isolation, holed up to protect ourselves from an invisible enemy that neither science nor our immune systems had ever seen before was bad. Adding to that load was suddenly losing half my workday to become a part time pre-K teacher as we pulled our daughter from school for 543 days. Spending that much more time with her was an incredible gift, of course, but came at the cost of pushing half my work hours into the evening, which in turn led to a serious case of revenge bedtime procrastination and very, very late nights as I’ll get to.

But it wasn’t just the pandemic, though that made everything else harder. Some of the other challenges were mundane in nature, merely physically taxing. We had to prepare our house to move in three weeks when it should have taken three months, for example, and I ended up having to do a lot of the literal heavy lifting on my own because Kate’s work blew up thanks to COVID and she ended up working 80 hour weeks. From trip after trip to storage units late into the night to blazing afternoons with a belt sander on our deck during the hottest month in Portland’s history, moving was at once the best thing we’ve done in a decade and yet deeply traumatic. And not just because of the torn rib cage muscle. 

The month before COVID ignited here in the US, meanwhile, my Dad began chemotherapy to treat an aggressive case of mesothelioma. I was only able to go with him for the first few sessions; after that, he had to go alone because they admitted patients only – thanks, again, to COVID. When I visited him and my Mom between treatments, it was almost always at a distance – on their deck if it wasn’t too hot or cold, in their garage if it was. I was able to hug my father but a handful of times during his treatment, and less than a year later he was gone.

And of course all of the above played out against the backdrop of the worst President this country has ever seen tearing through guardrail after guardrail en route to damaging, perhaps permanently, the country that I love but had lamentably taken for granted. I never thought we’d see another Nixon; instead, impossibly, we got someone worse.

Recounting all of this may sound like I’m making excuses for where I was, but I’m not. Countless people, for instance, saw their newfound ability to work from home as an opportunity to get into better shape while I, instead, ended up in a flat spin. Handed an unfortunate combination of circumstances, my job was to adapt and take advantage. I failed.

But that failure, fortunately enough, did not have to be permanent. As the man once said, “it’s not how you start; it’s how you finish.”

If I was going to have a better finish, however, clearly something had to change. Several somethings, actually.

The issues facing me were numerous. My physical activity level had cratered, my sleep patterns were a mess, my diet had declined, I wasn’t drinking more on a daily basis but I was drinking more often, my blood pressure and resting heart rates were up and various more specific measures of cardio fitness like my VO2 max were miserable.

That’s the bad news.

The good news is that after an extensive and almost completely unplanned reboot, I still have a long way to go but I’m slowly and steadily getting back on track. It took me sixty-one days, but I got back down to my pre-pandemic weight two weeks ago, which is a good start. My weight was up even before the pandemic started so I’ve got more yet to lose, but I continue to chip away. My blood pressure and resting heart rates are down, and the latter’s the best it’s been in a number of years. I’m getting more consistent sleep, and I’m down to drinks two to three days a week. As for my VO2 max, well, it still sucks but I’ve got an idea about that.

Just as it may have seemed like I was making excuses for the physical tailspin I’d found myself in, it seems possible that claims of pulling myself out of it – or, more accurately, starting to – might come across as a humblebrag. For whatever it’s worth, I assure you it’s nothing of the sort. All I’ve done so far is undo some of the damage of the last two years: there’s a lot more work to be done.

More to the point, a couple of weeks ago, one day after I set a personal record for my longest walk (we’ll get to that), my best friend ran 48 miles. At altitude. Losing weight I never should have gained in the first place, walking a few miles or getting my resting heart rate back to reasonable fitness levels is nothing to brag about.

The purpose of talking about all of this publicly – which isn’t particularly comfortable, is on the off chance that relating my own experience gives someone else who’s gotten off track some ideas, or maybe a nudge to course correct and get themselves headed back in the right direction. I’ve learned firsthand how inspiring other people’s experiences can be, as I’ll get to shortly.

Anyway, the logical question is what I’ve been doing differently. The answer is a number of things. One thing was clear early on: if I tried too hard to plan big things, it wasn’t going to work. Frankly if I’d thought about it much, I almost certainly would have fucked it up.

Instead I focused on baby steps, or an “incremental path to victory” as we might put it at work. The first of which was yoga, which is somewhat shocking given that even at my peak physical condition in high school or college I was about as flexible as a piece of cast iron.


Per YouTube’s history, at 9:34 PM on January 17th, 2021, I searched for “yoga with adriene 30 days.” Looking back, that might be where things started. I certainly didn’t think of it in those terms, yoga was just something small that I could do. While my exposure to yoga was minimal and what experience I’d had suggested that I was bad at it, it made sense for two reasons. First, it was physical activity that seemed more accessible and sustainable than, say, online HIIT workouts. And second, I hoped it would pay dividends with improved flexibility, which has only become more of an issue as I’ve gotten older.

Both of those assumptions, as it turned out, have been born out. With maybe half a dozen exceptions, I’ve practiced yoga every day since that night. I’ve gone through every 30 day Yoga with Adriene program there is (one twice), a specialized gravity yoga course for tight hips and of late have focused on yoga for my back (see below). To be clear, I’m still absolutely terrible at yoga. But while I remain comically inflexible, I’ve made enough progress that I can now at least sit cross-legged on the floor or touch my toes. Accomplishments that my six year old daughter would laugh at, of course, and appropriately so, but basics I was just too stiff for for years.

But while yoga was a fantastic addition, I wanted to kill two birds with one stone and ramp back up to some cardio work while physically getting outside more. Enter walking.


My initial efforts at cardio focused on running. If you’ve only known me in recent years, this will come as a surprise, but I used to run a lot and reasonably well over longer distances. But over the years, I gradually fell out of the habit. To the point where it’s probably been three or four years since I’ve run a mile in less than ten minutes.

Trying to get back into the habit, I had three problems:

  1. Being out of shape, the added weight and lack of recent physical activity meant that I kept getting nagging injuries even when easing back in via the various “Couch-to-5K” programs. Nothing major, but just enough to be discouraging and stall my progress.
  2. Getting back into running was also frustrating psychologically. Intellectually I understood that between age and inactivity, I couldn’t just roll out of bed and perform as I used to. But part of me expected to, and that was irritating.
  3. Perhaps most importantly, however, I wanted physical activity to not to be my primary engine for weight loss but to contribute to it, and given the ramp time of the Couch-to-5K programs it’d be months, potentially, before I’d be running for long enough periods to see any material caloric impacts.

After tweaking my back during one of these running programs, then, and putting it on pause for fear of doing more serious damage, I decided that while I was healing I could at least get myself outside and rehab by walking a bit. I started just walking across the bridge to the island we live on and back to the house. It’s a little over a mile, so it was both quick (and beautiful).

Enjoying those walks, I gradually tacked on another half mile. Then another mile. Then two. But even as my distances increased I didn’t take walking seriously as part of a fitness routine until I met an older gentleman named Dean. I mentioned above that it’s surprising how someone relating their experiences can be inspiring, but that’s exactly what happened.

Everyone on the island knows Dean, both because he’s out walking every day and because he gives every car that passes a big, exaggerated wave and a smile. That and the fact that he clearly walked serious distances as you’d see him all over town was all I knew of the man.

Then he stopped me while I was out on one of my rehab walks.

When I first started walking, Dean and I would pass each other occasionally. He’d smile and wave, I’d nod and wave back and we’d go on about our business. After this happened a couple of times, however, he must have decided that I was becoming a regular and he slowed and stopped in front of me. He asked me where I was walking, how far, and pulled out his phone to give me suggestions for new trails to try. He talked about his own routes, and the difference walking had made in his own fitness. When we parted, now as acquainted fellow walkers, it felt almost like I’d been inducted into an exclusive, private club. More importantly for my purposes, however, I came away from that conversation with two important facts. First, that walking had helped him lose weight, and second that as someone who was probably two decades my senior, he was averaging 10.6 miles per day – and sometimes exceeded that significantly.

All of a sudden I stopped thinking of walking as merely something to resort to when I was unable to run. After that one brief conversation, which could not have come at a better time for me, walking was elevated to the status of legitimate exercise option. It was low impact enough that I could sustain it without injury (with the exception of an intermittently sore lower back due to my shitty posture), and it could contribute to weight loss provided one was willing to walk for distance. Which I was.

From Halloween on, then, I’ve been slowly increasing my mileage and I’m now averaging something like 40 miles a week, with one day off. I’m a far cry from Dean’s daily pace, admittedly, but to be fair he’s retired and the master of his schedule and I am neither.

Best case, I’ll get back to some running as my overall fitness improves. I know for a fact the ability is still in there because of the Olympic-level sprint I managed a couple of weeks back when I was out for a walk and saw a skunk lift its tail at me in what seemed like slow motion. But in the meantime this is something that I can do on a sustainable basis that is pleasant, gets me outside, delivers results and can even be incorporated into my workday if I have listen only calls, conference talks to catch up on or even just need to think through a piece I’m writing. I don’t have much hope, probably, of being the most famous Stephen in the state that enjoys walking, but I can live with that.  

Few physical activities short of ultramarathons or the Iditarod are going to burn enough calories to drop weight if your diet is poor, however, which brings me to food.


Sadly, with one minor exception, I have no shocking diet tips or secrets to reveal. I’ve lost weight for the most part simply because I’m eating less. Many in the tech industry swear by keto or other nutrition hacking approaches, and more power to you if you’ve found something that works for you, but those have never held much appeal to me. The closest I come to these kinds of things is intermittent fasting, but that’s not deliberate on my part. To the extent that I practice something like that, it’s purely a function of the fact that we tend to eat dinner at six because we have a kindergartner and I haven’t eaten breakfast regularly since I was a kid.

The one minor exception I mentioned above is the Line Diet. I first encountered it via Rafe Colburn, but his site seems like it’s offline so here’s a piece from Jeremy Zawodny explaining the concept – though I never used the five day rolling average he mentions. Conceptually, it couldn’t be simpler: you enter a starting weight, a target weight and a target date. The spreadsheet (or iOS apps, search for line diet in the App Store) will then draw a line between those points and give you a weight you have to hit to stay on course. If you’re under your daily weight, you don’t need to do anything special. If you’ve over the weight, you eat light.

There’s no magic to it, but I’ve used this to successfully lose weight a couple of times in the past and it’s working well this time. It works, at least for me, because it’s an accountability mechanism. If you’re thinking about having a late night snack, for example, it forces you to consider what impact that might have on your weight tomorrow, and thus what you’ll be able to eat. It might not be the approach for everyone, but it’s what has worked for me in the past and what is working for me now. For whatever that’s worth.

One other thing I’ll mention is that I’m not rigid in my rules. Technically I don’t have “cheat days” in the way that some diets allow, but you’ll notice a pattern to the average amount of weight I lose – or don’t – per day of the week.


That’s not an accident. I’ve found that my approach is easier to sustain longer term if I allow myself the occasional indulgence on weekends. For me, as long as the overall trajectory is headed in the direction I need it to be I’m fine.

Last but not least, one thing to think about with weight loss is sleep.


If you Google “poor sleep weight gain,” you’ll find dozens of pages of search results discussing the correlation been poor sleep and weight gain. Which intuitively makes sense; if you’re tired, your decision making suffers, your self-discipline is impaired and you may feel a need to make up for the sleep-induced lack of energy artificially via food or drink.

Basically what this meant for me was that I was fighting weight gain with one arm tied around my back, because my sleep habits were an absolute disaster.

I’ve always been a night owl, and if I needed any further proof of that there’s the fact that while some people’s kids are out cold at 6 there are nights where I’m pleading with mine to get the hell to sleep at 9:30. But being a night owl is one thing. Burning the candle at both ends, as I was, just isn’t sustainable or advisable.

First, I was going to sleep too late. This is a chart of the hours at which I went to sleep since 2015 (with the exception of a couple of years for which I don’t have data). As an aside, I got the idea for these charts (and a bunch of the code) from the post here


It’s fine to go to bed at 1 AM or 2 AM if you can sleep late the next day. But I have a six year old, and you generally don’t get to sleep late with six year olds – even six year olds that are night owls. So I wasn’t getting to sleep late.


While both of these charts are a bit misleading because they include the sleepless nights of a new parent and odd sleep patterns from the days when I was traveling, what the one above says plainly is that the majority of the time I don’t get even 400 minutes of sleep, which is a tick over six and a half hours.

Now I don’t need or frankly function well on a lot of sleep – seven hours is about the most I can handle without feeling paradoxically fatigued when I get up the next day. And I can technically function on five or even fewer hours, if necessary. But constantly getting less than six hours night after night was just not helping.

Now, instead of working nights or tinkering on pet projects (like the above charts) while absentmindedly having the 80’s movies I grew up on in the background, I’ve taken to heading to bed hours earlier and reading on my Kindle. As Craig Calcaterra describes below, I’d fallen out of the reading habit and am trying to be deliberate about getting back into it. It’s early days, but the results so far are promising.

CleanShot 2021-12-14 at 23.40.48@2x

Reading at night has the twin benefits of being a more worthwhile way to spend my time than checking Twitter for the hundred time that day or watching a movie for the fiftieth time and being an act that hastens rather than delays the onset of sleep as my laptop or phone would. More reading and more sleep are a virtuous rather than vicious cycle, and the additional sleep has a tangible impact on my overall health.

That’s it for the major changes, at least at this point. There are two other minor things to mention.  

Other Things

  • Apart from yoga, I’ve mostly neglected my strength training since I stopped going to my trainer at the beginning of the pandemic. Recently, however, I’ve begun to start back up there as well. As with the above, I haven’t done anything fancy – mostly just the tried and true pushups with some upper-body bodyweight work via our TRX. I’ll post back here when or if that expands.  
  • While a range of my health metrics from BP to heart rate have improved, my VO2 max has not as mentioned above. A big part of the issue is that my normal walking routes rarely spike my heart rate beyond 130 bpm or so, and that only for brief periods. To remedy this, I’m planning on introducing some basic jump rope work. I did a lot of rope work in high school and college as part of my training for other sports, and if done well it can get the heart rate up even if done only for brief periods. We’ll see what, if any, impact it has on my other cardio metrics, but it’s worth a shot. 

The Net

If you’ve read this far, you either have too much time on your hands, we’re related or you’re looking for something. The best advice I can leave you with is this: if I can make these changes, you can too. Maybe not all at once, but the journey of a thousand steps and all that. 

As Arthur Ashe put it, “Start where you are. Use what you have. Do what you can.”

Good luck. 

543 Days

543 days ago we pulled this kid out of daycare as the outbreak picked up steam and shut huge swaths of the country down. She has not been back in a classroom until today.

Over that span, Kate and I have done the best we could to teach her, to play with her and to challenge her – even as the two of us have also been working full time jobs. Jobs that – at least in Kate’s case – were made far more challenging by the pandemic.

Restricted to half day shifts, a lot of my clients got used to email arriving well after midnight. And unsurprisingly, a lot of the rules we lived by as a family pre-pandemic – no TV or movies during the week, for example – were suspended as we struggled to balance childcare with our professional responsibilities. This was particularly true in the pre-vaccine world where we were often isolated from family and friends that might otherwise have been available to lend a hand. For large stretches there, we were on our own.

Net net, I know a lot more about the Octonauts than I ever expected to.

While this time has been taxing, I have tried to appreciate the unexpected opportunity to spend more time with my kid than I ever could have in the pre-pandemic world. I got to spend hours watching her learn to ride a bike, to read, and to devise ever more complicated games that I then got chastised for not knowing how to play in spite of the fact that she never explained the rules to me.

Due in large part to selfishness and ignorance, we’re not where we might have been as a country. I have no idea how long she’ll be able to remain in school, and I remain terribly conflicted about sending her in spite our community’s excellent vaccination rate. I’m grateful, though, that for however long it is she at least has some opportunity to be with all of her peers, because that’s the one thing we could never duplicate that every child needs.

I’m also grateful for the help and assistance we’ve gotten from our friends, family and coworkers. From the pod friends following the same protocols we did who took her in for periods in the early days to the grandparents that have been only too happy to tag in post-vaccination to the aunts, uncles and cousins who’ve babysat her over this summer to my colleagues who’ve put up with almost two years of limited and unpredictable availability from me, we could not have done this without all of you. Same to distant friends – shout out, Colorado – that have kept me sane over these last seventeen months.

Most of all, though, I’m proud of this kid. The pandemic has reshaped all of our lives, and given her formative stage I worried in the initial days of the pandemic that it would damage her irreparably. Instead, she has shown adaptability, a positive attitude and an undiminished desire to dunk on her dad at every opportunity.

If anything, this period has made her tougher and more resilient. It’s a truly awful way for her to have to learn these lessons, but if this is all we can salvage from it, it’s something.

I’m proud of you, Little Bear.

Goodbye to All That

ME: “So I saw the property.
MOM: “And?”
ME: “I have good news and I have bad news.”
MOM: “What’s the bad news?”
ME: “The bad news is that it’s an absolute shithole.”

So went the first conversation the O’Grady family ever had about what would become the O’Grady family property in Maine, for a time.

That exchange happened a little over twenty years ago. I was just outside of Portland on I-295, speeding back to my apartment in Southie. Back in those days, before I moved up here, I didn’t get much coverage north of Maine’s largest city.

As the geographically closest family member, I’d been dispatched by my parents to Georgetown, ME to look at a potential piece of property they were considering as a place to retire. So I dutifully hopped in the car and legged it up there to meet the realtor, Esther, a very nice woman in her sixties.

She drove us over the Bath bridge, down the island of Arrowsic and over a few more bridges on to the island of Georgetown. Long populated by the Abenaki tribe, the first English settlers arrived in the 1640’s, about twenty years after the Puritans landed in Plymouth. The population these days is actually down about three hundred from what it was during the 1790 census, 1333. Its primary claim to fame, among my friends at least, was that its stellar lobster shack, the Five Islands Lobster Company, was featured in a car commercial. A Nissan Maxima ad, I think it was.

The short version is that it’s a beautiful but sleepy little town. With way too many mosquitos.

The property in question had previously belonged to a retired MIT professor, one who had sadly let the property fall into disuse and then ruin prior to his death. The yard was tall grass that came up to my chest, the two cottages on the property were open to the elements and ruined and the best that could be said about the main house was that while it didn’t keep the squirrels out, it kept the rain outside.


You couldn’t beat the potential of the place. That was the good news I relayed to my Mom in my initial evaluation.

It had three separate theoretically livable structures, and it was right on the water. And I mean right on the water. The two cottages are maybe twenty feet back from the cove – a proximity that you could never achieve today with setbacks. Waking up in one of the cottages was like waking up on a yacht, not least because the entire front of both structures were windows. Georgetown, for its part, is a quiet little town, but not too far from a small city in Bath and just up the road from Reid State park which has one of the best beaches in the state.

But rehabbing the property would be a project, and a major one, and I wanted that to be crystal clear to my parents. Fortunately for them, they were in no immediate rush. Both were several years out from retirement, and the ability to break up the property rehabilitation into digestible stages via the cottages was attractive financially. They could start with the smallest cottage to make the property usable quickly, move on to the second slightly larger one to expand the usability and then finish up with the larger main house as they neared the finish line of retirement.

This was the plan, and they ended up following it, more or less. They got thrown a few curveballs, to be sure, but they did what my parents always did: they dealt with them. They tackled the construction iteratively, and they cleared and tamed the land the same way, by hand.

This was the wreck of the main house, none of which they were unfortunately able to save.

And these were the two cottages, the bones of which were in good enough shape that they were ultimately leveraged as the basis for the structures that are there today.

My parents poured everything they had into the property. They would drive up from New Jersey every chance they could, and spend the week or the weekend or whatever meager time they could spare getting up at the crack of dawn, bush-hogging the lawn, trimming back out of control growth, clearing dead trees and gradually turning the property from a tick and mosquito infested morass into a livable, enjoyable couple of acres.

Regrettably, my parents bought the property at the extreme limits of my digital history. I wasn’t as diligent about archiving everything as I should have been back then, so I have some pictures from that era, but not all. Sporadic email. A few ancient moving receipts. But what I did manage to turn up might help explain how I feel about the property, and why I’ll miss it now that it’s been sold.

As nearly as I can determine, the purchase of the property was made in July of 2002. I didn’t know it at the time, but my business partner James and I were four months away from quitting to start the firm that would become RedMonk. The timing would prove fortuitous, because the day we quit was the last day that I had any income for a while.

I had money saved up to tide me over, but when my landlord at the time in New Hampshire decided not renew my lease to give his similarly unemployed son somewhere to live I had a choice to make. I could move back to Boston, which would be tremendously beneficial to my social life but would dramatically shorten my runway for getting our little startup off the ground. Or I could move up to this new property that my parents had bought but would not be occupying for years and live rent free.

So on May 30th of 2003, I moved up to the bustling metropolis of Georgetown, ME. When I got there, the small cottage was a couple of weeks from being ready, and so for a month or two, I set up shop in what was left of the main house. When I’d come home at night, I’d hear the red squirrels running away, and all of the screens had huge holes in them so there was a sizable population of mosquitos inside. Technically there was running water from the well, but there was no filtration and no water heater, so as I preferred to shower in water that wasn’t cold, orange and laced with iron, I joined the YMCA. Oh and there was no stove, just a hot plate.

Good times.

I ended up living in Georgetown for about two years while we got RedMonk off the ground, before I decamped for Denver. Much as I loved Denver, though, and I really did love Denver, I missed Maine, I missed the water and I missed Georgetown.

The first year I moved out, in 2005, I came back east to stay in Georgetown for two weeks. The second year in Denver, I came back east for four weeks. The third year it was more like four months. The fourth year, I met Kate and I never went back. Maine was in my blood by that point.

Here are a few reasons why.

There aren’t many things better than sitting by the water, watching cormorants, ospreys and the occasional bald eagle hit the water – hard – and improbably, impossibly explode back out with a fish gripped tightly.

Every so often we’d get the occasional lost seal down our way, and the prehistoric looking sturgeon were alarming, leaping high out of the water for reasons that no one apparently understands.

It’s surprising how much satisfaction there is to be had transforming an overgrown jungle into a more balanced landscape that gets rid of – or at least limits – the role of invasive species such as Japanese knotweed and gives opportunity to the native flora. But my parents gave me that opportunity during brush cutting and collection days.

One of the handy things about having access to a property that is either about to be torn down or still under construction is that playing beer games like pong or foosball become easy decisions. Even if beer spills or things get wrecked, what’s the harm?

The house was enough of a destination that it hosted many friends over the years. We had a couple of memorable Memorial Days up there, none more so than the time we used the veritable forest of mint in the side yard to make mojitos that looked like salads.

In more recent years, friends got snowed in with us for the weekend. Which was all the excuse we needed for non-stop Hearts marathons by the wood stove.

When I first lived on the property there was neither a dock nor a boat. When I started coming back, however, these had been acquired and transformed the property completely. Instead of being landlocked, the boat and dock combination opened up a world of possibility.

I still remember being ratted out by the GPS, however.

The boat had a combination GPS/depth finder. And unbeknownst to me and unlike the GPS in, say, your car, it retained a track of your movement. It turns out docking is in fact quite hard, particularly when you’re doing it solo. This only occurred to me literally as I was on the final approach that first time. The short version of the story is that I must have made twenty or thirty passes at the dock before I was able to tie everything down on my own. The GPS recorded the maze of all of these aborted docking wave offs, but I assumed they wouldn’t persist between sessions.

I was wrong.

As soon as my parents took the boat out the next time, every single last missed pass at the dock came up as a knot of lines and my parents had questions. Questions I would have preferred not to answer.

When I lived up there on my own, I’d schedule my work calls from early morning through 1 PM or so, and then I’d pack a quick lunch and a beer or two and take the boat down to the top of the cove. I tried various hardware combinations to take calls from the boat – and one of you that might be reading this was kind enough to send me a headset with wind reduction algorithms – but I never did get any of them to work. The person on the other end of the line could always tell I was on a boat.

So anyway, once I’d cruised down the cove, I’d throw out an anchor, stretch out and read a book and have a beer. If it got hot, I’d jump into the cove, swim around to the swim platform, dry off and lay back down. Rinse, lather, repeat. Then I’d come back and, having no other obligations, work for a couple of hours after dinner.

The only time this anchor-and-swim strategy proved to be problematic was when I ventured further afield, anchoring up near the Chops just south of Merrymeeting Bay on the Kennebec. No matter what I tried, I could not get the anchor to come up, and was convinced I was going to have to dive in and follow the line down and free it by hand before the boat itself freed it for me.

Net net, though, there’s literally nothing as relaxing as taking a boat out to some quiet, calm water, parking it and relaxing with a book and a cold beverage.

While I’d lived there on my own for a number of years, Kate and I lived up in Georgetown together for a little while we house hunted and eventually bought down in Freeport. We were living in Georgetown, in fact, when we got engaged and when we got married. Our engagement dinner was at the now sadly closed Robinhood Meeting House, and this was taken while we were packing for our honeymoon.

Fishing up there took a while. First, because I decided to fish the salt water with flies. Compared to the river gear I was used to, everything was bigger, heavier and harder to cast. I gave myself golf ball sized welts on the back of my head several times hitting it with the large salt water flies, but I counted myself as lucky that I never hooked my scalp or ear. But even when I had the technique down – or at least down well enough to not hit myself in the back of the head – I couldn’t find the fish.

I caught one, pictured above, after kayaking down the cove a ways and fishing off an uninhabited small island. But I never had any real luck until the poor ospreys blew up.

Over the course of that summer, an osprey family had made a nest in a particularly unwise location just above a power transformer across the street. Around 4 AM one night, their luck ran out and the transformer exploded, showering the street with sparks, knocking out power and practically ejecting me from bed.

Unable to get back to sleep, I grabbed my rig and wandered back down to the dock to fish. As it turns out, dawn is a good time to fish. After months of striking out over and over, I pulled out a fish every other cast until my arms got tired. Nothing big, but fish after fish after fish. It was glorious, though mitigated by the poor osprey family’s demise.

Speaking of ospreys, The Osprey restaurant – a bar/tavern at the local marina – was the only place on the island to get a beer, so I spent more than a few nights there doing just that, while watching the Sox with the bartenders I’d gotten to know and looking out at the water. As local joints go, it’s tough to beat a marina bar.

I was never a regular at the lobster shack down on Five Islands, on the other hand, but it was a staple whenever anyone came to visit. There aren’t too many places where you can watch the lobsters you eat get hauled out of the water, but this is one of them. And it’s not just lobsters, please note: their onion rings are great as well.

Whenever the weather was good, whatever the season, Reid was right down the road. The water is cold, but after a minute or two you forget that. Worst case you go numb.

You can fish down at Reid too, though as I learned when I got kicked out a few times the park rangers have a very conservative definition of the word “sundown.”

If we’re being honest, though, what we all enjoyed the most about the property was bringing the kids. Whether it was picking vegetables, baking cookies or going down to the Blessing of the Fleet, they made everything fun. A lot more challenging, obviously, but fun.

The times there weren’t always good. Having to put in a ramp for my Dad after he broke his leg during his battle with cancer was an unhappy milestone.

But that’s not what I’ll choose to remember.

When I think about Georgetown, I’ll think of lazy afternoons on the dock.

Or waking up and looking out these windows, feeling like you’re at sea.

I’ll miss the Georgetown house a lot, but I’ll certainly never forget it. May it give its new owners as much happiness as it brought to the O’Grady family.

10 Things I Learned from My Dad

None of the doctors ever told me my Dad was dying. Not the surgeon at Maine Med who first went in to do the biopsy of the lung. Not the surgeon at Mass General who did the biopsy of a lymph node. Not the oncologist at Maine Cancer Care the first few chemo treatments, which were also the only ones I could attend thanks to COVID. None of them.

But they didn’t have to. Mesothelioma is hard to Google, because the search results are heavily polluted by law firms in search of riches from ignorant or irresponsible manufacturers, but you can get the gist. And the gist is that it’s not good.

Mesothelioma is a malignant tumor that is caused by inhaling asbestos fibers. How my father, who spent his career on Wall Street theoretically well removed from the material that used to be common in building materials, firefighting gear and the like ended up with these fibers in his lung is an open question. We’ll never know for sure, but the evidence strongly suggests that it’s a consequence of my father going back to work downtown shortly after the 9/11 attacks. Per WikiPedia:

As New York City’s World Trade Center collapsed following the September 11 attacks, Lower Manhattan was blanketed in a mixture of building debris and combustible materials. This complex mixture gave rise to the concern that thousands of residents and workers in the area would be exposed to known hazards in the air and in the dust, such as asbestos, lead, glass fibers, and pulverized concrete. More than 1,000 tons of asbestos are thought to have been released into the air following the buildings’ destruction.

As an aside, before someone mentions the 9/11 victims fund, he was aware of it. Given the limited pool of funds, however, this was a non-starter for him because he would never have been willing to take money away from the first responders or their families.

Anyway, my father’s commute for four decades had him walk off the Path trains into the Trade Center en route to the Exchange every day. I know this because I did it with him one summer. He was fortunate enough to be on vacation up here in Maine not just for the attempted bombing of the World Trade Center in 1993 but for 9/11 as well. It would be as tragic as it would be ironic if he survived the attack in 2001 by not being there but the air he breathed when he returned to work ended up killing him twenty years later.

Pragmatist that he was, however, he’d have taken that trade.

It’s a similar trade, in fact, to the one he took when he was first diagnosed with cancer while at Harvard Business School in the early seventies. Cancer treatments were a little less sophisticated all those years ago, and to attack the cancer that he had the doctors irradiated large swaths of his body. Today, they can apparently target areas smaller than a dime. He was told that he had an 8% chance of dying within six weeks, and a 92% chance of living out most of the rest of a normal lifespan – albeit with some side effects.

Side effects that he accepted without complaint. His immune system went haywire, for one, and he developed allergies, the worst of which was poison ivy. If that so much as touched him, it was in his blood stream and off to the races. My childhood memories are always a little hazy, but I remember that. The side effects changed his hair color and density, and it left him permanently immuno-compromised. It’s weird when you’re a kid and your Dad’s mustache randomly grows in bright red.

Not that any of that mattered much: I don’t remember him missing a single day of work, ever.

For fifty years, the deal that he’d accepted was a good deal. Despite a few scares along the way, the cancer never came back until he noticed being short of breath and developed a chronic cough two years ago. Never one to visit a doctor unnecessarily, and probably for good reason given his history, he nevertheless went and ended up on the track that led to the diagnosis and the year that was 2020.

Christmas 2019 was a sad affair. My Dad had been diagnosed merely days before, and his weight loss left him gaunt and weary. When shown pictures of the dinner later, he replied with typical bleak humor, “shit, I look dead.” Still, we tried to take an optimistic tack with 2020. If there’s one thing I’ve learned about cancer today, it’s that your primary goal if they can’t cure you immediately is to buy time, because they might be able to in future.

So that is what my Dad set out to do. Always goal oriented, his assessment was that based on trajectory at the time, he was unlikely to make it until the Fourth of July. Thus his goal was to make it beyond that date. To that end, he promised his oncologist one thing: that as long as they would agree to treat him, he would show up. At times, this meant employing some gamesmanship, no stranger to the lifelong athlete. As he continued to bleed weight he couldn’t afford to lose, he slyly wore heavier and heavier shoes to his weigh-in’s so they wouldn’t remove him from treatment.

So intent was he on continuing treatment, in fact, that he literally broke himself out of the hospital to get the toxic substance injected into his body. He’d fallen and shattered his femur – in retrospect, likely due to the fact that his heart had begun to stop unpredictably due either to a bad valve, arrhythmia’s or both.

All in all in 2020, he dealt with the cancer, a bad valve in his heart, a congenital heart murmur gone rogue, five surgeries, and the broken leg. To add insult to injury, his access to the thing that made him most happy – his grandchildren, and to a lesser extent his children – was drawn down to a trickle thanks to the pandemic.

Insult, injury or otherwise, he fought to the last. Every time he seemed to take a hard won step forward, some new fresh hell would drop him back ten steps, or even twenty. But he was a fighter, and every time he got knocked down, he picked himself up off the mat and waded back in.

He died as a fighter, Monday morning. And despite the terminal prognosis, the cancer never won. His body may have ultimately failed him, but his spirit never did. It was his heart, or maybe his brain, that killed him. Not the cancer.

That terrible endurance was something I never wanted to learn from my Dad, but I did. He taught me many other things, some of which I wrote down in an admittedly lengthy letter to my then unborn daughter. Here are ten that I’ve thought about this week.

Have Priorities

My Dad grew up with very little. What wealth his family on one side had had at one point had largely petered out, and while his father always worked, you don’t become a minister for the money. Still, the family prioritized education, and so he went to Williams like his father and brother before him, and from there it was on to Harvard Business School. That provided him with access to jobs that featured, let’s just call it, high income potential. For the first time in his life, he had money. And but for his kids, that could have been his life.

Instead, he eventually came to a fork in the road. Down one path lay wealth and comfort; the other was precarious, stressful self-employment as an independent floor broker – the upside of which was predictable hours that allowed him to get home in time to coach my brother and I, first in soccer, later adding lacrosse in the spring.

Every family has different choices to make, and I can’t imagine the financial stress both of my parents bore. But I think I can speak for my brother when I say that I’m glad he chose us.

You Do What You Have To

When my Dad enlisted in the army, he and my mother were dirt poor and living in a trailer in Georgia. Every dollar, therefore, was precious. As a semi-related aside, if you get the chance, ask my Mom what it was like to work at a K-Mart in the deep south with a wicked Boston accent.

Anyway, after finding out that paratroopers got an extra pittance per month, my Dad signed up for jump school. The only problem with this transaction was that my Dad was terrified of heights. Every morning he had to jump, then, he’d get up and vomit because he was scared. But dollars were precious, so he got his wings.

Later, in business school, he had to go in regularly to get blasted with high doses of radiation. This had the intended effect of killing off the cancer and the unintended effect of giving him nearly full time nausea. He didn’t intend to miss class, however, so he merely requested a seat on the aisle so he could get to the bathroom quickly. All professors but one complied; the hold out required an appeal to the dean. He had no such impediments while competing in tennis tournaments during treatment, however; he’d merely vomit in between sets.

My Dad never really sat us down to talk about working through fear, sickness or injury. We just watched him.

Be Yourself

All the years my Dad worked on the various exchanges, he dressed – in general – as comfortably as the dress code permitted. He had nice suits and ties when they were needed, but his normal uniform was LL Bean chinos, a plain white shirt, his trading jacket and one of a couple of ties kept in his desk. That was who he was. My Dad paid no more attention to NYC fashion then he did to bars after work or coke in the bathrooms. His worst vice was coke, the soda.

It never occurred to me that this was in some way different or unique until I moved to New York City after college. Some friends had Armani suits and Gucci loafers. I was much more likely to be the one who kept us from getting into a bar because I was dressed like a 1930’s rail-riding hobo.

Like my Dad, for better or for worse, I knew who I was, and I never worried too much about what everyone else was up to.

Let Your Kids Be Who They Are

My Dad was an athlete all his life, and a very good one. Great, even. My brother and I grew up on stories of his freak athleticism, how he started on his college teams as a freshman, all of that. So naturally what I wanted more than anything else as a kid was to be like my Dad. But it was apparent pretty early that I was not going to be like my Dad.

I wasn’t a total loss on the field. I managed to start for teams in high school and college eventually, but particularly when I was a young kid and my height outpaced my coordination, I was a far cry from what my Dad might have reasonably expected of his progeny. Some, maybe most, former athlete Dads would have been embarassed by a kid like me. Others disappointed. Maybe both.

Whether I played well, and I usually didn’t as a kid, was not relevant to him. The only thing my Dad ever cared about was my effort. It could be five minutes of garbage time at the end of the game, and all my Dad asked was whether I had fun and tried my best.

I used to take that for granted. Looking back, I wonder if it was ever hard for him to watch me struggle. If it was, he never showed it.

Help Those Less Fortunate

He never used the word, as far as I’m aware, but my Dad had an innate understanding of his privilege, his humble socioeconomic origins notwithstanding. He came by it honestly, to be fair. As my Mom tells the story, their engagement party in Michigan was an interesting event because in the day’s prior my Dad’s father had been publicly excoriated for supporting women’s access to birth control and his mother had been arrested in Detroit after being part of a sit-in to protest an urban renewal effort that, no surprise, was slated to replace low income housing.

When he returned to Williams after his military service, he and my Mom ran the ABC House in Williamstown, which brought inner city kids out to a different life in the Berkshires. One of the kids that lived with them, Ted Ferriss, became a lifelong friend, and quarantined himself for two weeks to be able to visit my Dad in Maine from New York this fall.

He also believed in gender diversity within the workplace, and I can’t articulate that any better than the following snippet which was taken from an email I received from one of his former employees.

Your dad is one of the gruffest people I know but has the absolute best twinkle in his eye and biggest heart underneath the gruffness. I was living on my brother’s couch/floor for the first month in NYC and your dad continually was checking in on my apartment hunt and making sure I was doing ok in my transient state. No one else was doing that. I also loved what a big effort he made to hire women into a predominantly male industry and ensure we were all treated equally. Granted “equally” meant he treated us all like crap and made us haul waters from the main office blocks away down to the floor of the Amex, but to this day I’ll maintain that I was treated better at [REDACTED] than any other job I ever had in NYC. He made so many ridiculous jokes, but he always made sure we were in on the jokes instead of being the unaware butt of the joke. I always felt like part of the team / one of the guys / however you want to say it. It was just a great environment thanks to him, and a pretty unique situation for a 22 year old girl on a trading floor.

He used to talk to me about the importance of hiring people from different backgrounds when I was younger, and I didn’t fully appreciate its importance, or how unusual it was for an old white guy to appreciate it. I do now.

Principles Matter

My Dad was, first and foremost, a man of principle. He was rigidly, and at times, uncomfortably, honest. His moral code did not encompass shades of gray; for better and for worse, he was a man of black and white. There was right and there was wrong, and he never struggled much to tell one from another.

This was the moral compass that led him to enlist in the army. His number would probably have him drafted anyway, but his feeling was that if his country called him to serve, it was his duty to answer that call. Whether or not he approved of the Vietnam war was immaterial. He did not, he was simply of the opinion that it would not be appropriate for him to pick and choose when to serve.

This was also the moral compass that gave him a respect and appreciation for those who refused to serve. This is something he wrote almost a decade ago.

I recently heard from an old friend from grade school (in Switzerland). He attended Stanford and was in the ROTC program. Upon graduation, he turned down his commission as an Army Officer and refused to be drafted. He did not hide in Canada. Ultimately he was arrested and convicted as he should have been (later pardoned). He asked me if that was a problem for me. My answer was that he did what he believed in – very openly and suffered the consequences. I respect him for that.

In an era of fluid and ambiguous morals, my Dad was something of an anachronism. I don’t think I ever appreciated that enough.

You’re Not Better Than Anyone

My Dad was never a people person, exactly. My Mom, in fact, likes to say that my Dad was always better with children than adults, though arguably that’s more because he was so good with kids than deficient with adults. In any event, whatever his people skills, there is one thing my Dad positively excelled at, and that was extracting people’s life stories.

There’s a truism that everyone wants to talk about themselves. What my Dad wanted to talk about was the person he was talking to. Where were they from? Where did they go to school? What did they do for a living? How was business? You’d go to dinner and by the time the check came anyone at the table could have written a thousand page biography on the server.

This made for some very long dinners, and a lot of “Dad, you can’t ask that.” It also meant that my Dad stood out, and often connected with people in his life that no one had ever asked about.

I’ll never forget the time that I was attending a client analyst day held at the New York Stock Exchange. This being well after 9/11, security was high and thorough. After looking over my license, one of the guards looked up at me and said, “are you related to that Steve O’Grady?” After hearing that I was his son, he shouted down the line that I was “Steve O’Grady’s kid.” I got the most cursory of wand treatments, and they sent me on with “say hi to your Dad for us.”

My Dad came from nothing, and whatever he became in the world, he never forgot that.

Focus on What You Have

Growing up, I don’t remember any of my friends’ parents going through a stereotypical mid-life crisis, but that’s also not really the kind of thing a parent would discuss with their kids. What I do know is that my Dad didn’t spend much if any time focused on what he didn’t have. Part of that might have been that he didn’t have the time to worry about that between working full time and coaching the rest of it. But my Dad was also someone who focused on what was in front of him, not what anyone else had.

When he got sick, we talked about the prior bouts with cancer, and his view was that at a minimum, science had bought him fifty years. If they couldn’t give him another ten or five or two, well, at least he’d banked the fifty.

We also talked about his classmates at the Officer’s Candidate School, the ones whose names are etched into the black granite of the Vietnam Memorial. He got to live his life, they did not.

Whatever else he was, my Dad was not an ungrateful man.

How You Measure Your Life

Best known for his work on the business theory of disruption, Clayton Christensen’s most significant insight might have come in terms of how one thinks about their life. This was his advice:

Don’t worry about the level of individual prominence you have achieved; worry about the individuals you have helped become better people. This is my final recommendation: Think about the metric by which your life will be judged, and make a resolution to live every day so that in the end, your life will be judged a success.

If we accept this metric, my Dad’s life was a massively underappreciated success.

Since he died, work has trickled out widely in spite of our best efforts to inform those closest to him personally. Here is a random sampling of quotes I’ve gotten from people who knew my Dad. Kids he coached, grown ups he hired, all of whom got the full, sarcastic Steve O’Grady experience.

I’m very sorry to hear about your Dad. Wanted to send my condolences to you and your family. He left me with great memories coaching us when we were kids.

Your dad was a big influence on me and I recall many of the valuable lessons he imparted as our coach growing up. He will be missed.

I actually heard about his passing from a…colleague…a little earlier today. He started a chain with about 15 of us who were all hired by Steve around the same time and the consensus is clear, he impacted all of us in such a positive way and really helped us all get our foot in the door with our first “real jobs”. I’m sure this has been a really hard week, but I hope you can take a little bit of comfort in knowing your dad was loved and respected by so many of us, and will not be forgotten.

I was so sorry to hear about your dad. I have great memories of him and his time with and impact on all of us.

I have fond memories of spending time with your father in our younger years and also later in life as we became “adults”. He loved and supported your brother and you, your interests and of course your Mom. Obviously, your Dad sometimes gave us all tough love. It makes me smile and laugh to think back on his firm and sometimes joking delivery. He will be missed.

I’m sure when word gets out more publicly, there will be many, many more of these, because if there’s one thing I’ve realized, it’s that my Dad touched a great many lives. So many more than I ever realized.

My Dad was at heart a metrics person. I don’t think it ever occurred to him, however, to think about his life in terms to the raw number of lives he impacted. If he had, I think he would have been pleased at the numbers if eager to be dimissive of his actual impact.

Put One Foot in Front of the Other

COVID has made things more complicated for everyone, but I managed to keep most of the impact at arm’s distance until May 20th. After he got sick, my Dad felt it was important to remain as active as he could, and to keep busy. On that particular day, his job was to get gas for the ride on mower. Late that morning I got a frantic call from my Mom telling me that my Dad had fallen and shattered his leg.

What we didn’t know at that time was that his heart had begun to stop irregularly, and he wasn’t lucky in his timing. Toppling over in the parking lot of a gas station, he’d annihilated his femur. It was bad enough that he passed out and fallen without an ability to break his fall, but he’d lost so much of his athletic muscle mass due to the disease that there was nothing to cushion the blow.

The ambulance came, and my Mom couldn’t ride with him. He got to the hospital and none of us could go see him. He went under the knife with no one by his side, and trying to piece together his condition by phone after the fact when he was on painkillers with no one there to advocate for him was a literal nightmare.

Right before he went under, one of the nurses asked him if we was scared. His reply might be the best summary of his life I can think of. He told her, “What good would that do? You’re going to put me out. I’ll hope to wake up, and we’ll go from there.”

There was no waking up this time, not for any lack of fight on his part. Now my family has to go on from here.

I miss you, Dad. Wherever you are, I hope they have the Coke made from the Mexican sugar cane.

My 2020 in Pictures

It was the best of times, it was the worst of times, but mostly it was the worst of times. The English language doesn’t really have vocabulary capable of articulating what it was like to live through 2020, and while pictures may be worth a thousand words the ones that follow won’t do it justice either. Historically awful and unprecedented is about the best I can do.

This year was bad enough, in fact, that I debated whether to abandon this traditional post entirely for a year.

But that idea didn’t sit well for several reasons. Most obviously, while this was a genuinely terrible year for me, my experience was a cake walk next to that of millions of Americans. Unlike actually essential workers, I was able to seamlessly transition to working from home full time. Unlike restaurant owners and staff, the impact on my industry was relatively light, and my employment was unaffected. And with a few notable exceptions, most of my friends, coworkers and loved ones were likewise not part of the 384,000 and counting Americans that lost their lives at least in part due to a complete and unmitigated failure on the part of the federal government to protect its citizens. What was a bad year for me, then, was a living hell for far too many.

Stupidly, not posting my annual year in pictures also felt like surrender, and a lack of gratitude for the few good – even great – things that happened to me this year. The more I thought about it, the more posting seemed mandatory rather than optional.

So here we are.

As always, these are the moments – significant or mostly not – that characterized my year personally. Blessedly, there’s basically no politics in here because I don’t have any images of that horror. Before we get to the pictures, however, a quick check-in on travel.


Normally this is the part where I mine and TripIt for travel stats like miles flown, number of airports, etc that make me sad, lamenting both the time spent in flying metal tubes and the time away from my family. This year’s travel update is easy, because there was no travel. I have not been on an aircraft since December of 2019, which is very likely my longest stretch without a flight since high school.

I never left the country, obviously, and with the exception of a quick hop down to Boston in January, I never even left the state. I’ve spent the balance of the year hunkered down, rarely straying more than a twenty minute drive from home – and then only for curbside pickups. This unprecedented time at home, along with a growing kid, led to space issues that led to a move, but I’ll get to that.

The question for me, sitting here in January 2021, still under lockdown conditions, is what happens when we’re on the other side of the global pandemic. Do things snap back to normal? Or has my industry proven that travel is less necessity than luxury, and my time away is scaled way back from its one time heights.

As a Dad who cherishes doing bedtime with my kid every night, including our ritual of looking at shark pictures, I know what I hope for in that regard. I was not taught to blindly expect the best outcome, however, but to prepare for the worst. If I’m writing this a year from today, then, I’ll be very curious what I have to say about my travel and any return to normalcy.

The one trip I do want to make when it’s safe is out to Colorado. 2020 was the first year since 1993 that I didn’t see my best friend at least once. I hope not to repeat that.

With that, on to the pictures.

January 1

The year opened innocently enough with a day of good sledding.

January 12

Went to a local concert, which is hard to imagine now.

January 21

Man I had no idea.

January 23

It took some doing, but I snagged Pearl Jam tickets for Denver, and we planned a four day weekend out there for the family to go see the band with my best friend and his wife. This would have been Eleanor’s first time on a plane, and she was very excited for it.


January 23

After the high of scoring Pearl Jam tickets it was off to the low of heading with my parents to my Dad’s first chemotherapy appointment (I have not been able to go with them since March). I haven’t talked about this publicly before, and I’ll save the details for another time, but 2020 has been a roller coaster for my poor father, who’s endured cancer, a badly shattered femur and a heart that began stopping for five to ten seconds at a time, not to mention a hospital stay in which none of us were allowed in to be with him or even see him and five surgeries – a record for him, as he pointed out.

Through it all, my parents have handled the situation exactly as anyone who knows my parents would expect: by focusing on putting one foot in front of the other, and by relying on each other. Before he went in for surgery on his leg, one of the nurses asked my Dad if he was scared to be going under with no family or friends around to lean on. He replied, “What good would that do? You’re going to put me out, I’ll hope to wake up and we’ll go from there.”

When chemo began, my Dad promised his oncologist that as long as they would treat him, he would show up no matter how terrible he felt. The average number of treatments most patients who have what he has can endure is a tick under four. My Dad had eight – and he had to break himself out of the hospital while in a wheelchair to get to one of those – before they transitioned him to his current regimen, which brings the total up to 22 and counting. All of which is not particularly surprising, of course, because this is the same man who, during his first bout with cancer fifty years ago, played in tennis tournaments and attended classes at Harvard Business School while having to vomit every twenty minutes from the massive doses of radiation that were the standard treatment at that time.

My Mom, meanwhile, took on her new role as caregiver with the same indomitable outlook and unflinching sense of responsibility that she inherited from her father. She pivoted from an active role on I’ve lost track of how many different local committees and boards to being a full time nurse, cook and patient advocate overnight. The next complaint I hear from her about this abrupt and unexpected turn her life took will be the first. When I talk to her every day, she’s cheerful, focused on what she controls and always more interested in hearing about what’s going on with our little family than in her own struggles.

These are the two toughest people I know.

If there is one thing I’m thankful for in 2020 it’s that my Dad was not taken away from me. My parents are, each in their own way, an inspiration and a standard that I will never live up to. Here’s hoping 2021 is kinder to the both of them than 2020 was.

February 21

Got out for a quiet birthday lunch at Slab. That’s not in the cards this year, but I look forward to the day when it’s possible again.

February 22

We had no idea at the time what a train wreck of a season the Red Sox, the sport and the country were about to have, but we enjoyed the first game of Spring Training anyway.

March 11

Things that had been gradually deteriorating in February finally fell apart during the second week of March. The suspension of the NBA season was perhaps the most shocking indication of how truly unprecedented the events were, but it was merely the beginning. Within a week lockdowns were spreading, we pulled Eleanor from daycare – permanently, as it turned out – and transitioned into bunker mode becoming part time schoolteachers in the process.

March 13

Shortages didn’t take long. It was probably four or five months before we could reliably get toilet paper, as but one example.

March 14

Having decided in late February to potentially list our house, we started preparing for a sale by getting a storage unit. We knew that the spread of the virus was a wildcard, but we thought at the time that it would be a couple of months at most.


March 16

We pulled Eleanor out of daycare the Monday after the lockdowns began. Kate’s work schedule exploded given the unprecedented challenges the virus posed to higher education, so I was mostly on duty in those early days. I thought I was doing pretty well until discovering at the end of literally the first day that Eleanor had cut off huge hunks of her own hair.

March 18

Didn’t take long for everyday experiences like going to the dump to get weird.

March 19

As so many educational and non-profit organizations did, bless them, the Atlantic White Shark Conservancy spun up educational videos virtually overnight. A couple of days a week, then, Eleanor and I would watch virtual shark classes as part of general enrichment activities with her out of school.

March 20

With curbside experiences a little rough around the edges in the opening stages of the pandemic, buying beer in bulk became a no brainer. Credit to Maine Beer Company for running a great contactless setup.

March 21

As we pondered moving in the wake of the outbreak, one of the decisions we made was to upgrade from shitty old foam core doors to newer, solid core doors. The idea was that if we moved, they’d show better, and if we didn’t, they’d offer some noise reduction while we were all crammed into a small house for months on end. The doors were picked up curbside, of course.

And while I always endeavor not to get injured, it’s amazing how much more careful you can be on a project if you know going to the ER might mean getting infected with a potentially deadly pathogen.

March 21

In the face of a global pandemic, we all had to make adjustments. Zoom’s not the same as in person, but we made do.

March 25

At the first hint that masks might be an effective deterrent – long before they were officially approved as such – my Mom leveraged her skills with a sewing machine and launched into action making cloth masks for the entire oncology unit at Maine Med where my Dad was being treated.

Per a text from one of the doctors, the masks plus the giant batch of chocolate chip cookies she baked and brought to the office, “put a smile on the face of everyone in here, one that was needed.” Many of the nurses apparently liked them so much they chose to wear the cloth masks over their issued N95’s.

Later, my Mom made masks for all of our local friends. When I relayed their thanks and appreciation, my Mom’s reply was “thank them all from us for helping to keep your father and I safe.”

March 26

Twelve degrees above freezing is apparently warm enough to pull the roof off if you’re in need of a smile.

March 29

Got some help stacking wood.

March 30

Even amidst the misery, it’s worth noting that 2020 featured its share of heroes as well.

April 1

Well before Eleanor was born, I’d jotted down a long list of potential life lessons for her. The pandemic and more particularly its accelerating death toll was, among other things, incentive enough to finally complete this stalled project. The result was

Unexpectedly for what was literally a labor of love, some people actually read it. People not related to me. Some even had good things to say. Tough to say which was more of a surprise. The site even did more traffic than did for one day.

April 10

Kate, as usual, was way ahead of me in demonstrating our appreciation for some of the essential workers that kept our house supplied.

April 12

We did our first official socially distanced outing with friends out of the back of the Jeep in a driveway.

April 14

Among the limited benefits to the pandemic was vastly more time at home, spent doing things like watching Eleanor get more confident on her bike by the day.

April 14

Can’t even imagine how bad the past year has been for restaurants, those who own them and those who work for them. This was not a typical night at the River Grill.

April 20

It’s a sign of how bad things have been this year that this iconic image barely registers.

April 25

I am no foodie and as such am generally not snobby about food. But having grown up outside of NYC, I’m very particular about my sandwiches. For all of its other culinary talents, Maine’s sandwich game has, for most of the time I’ve been here, been woeful. That all changed when Ramona’s opened. The place is legit.

May 3

It may not be true that there “ain’t no laws when you’re drinking Claws,” but the pandemic did certainly cause people to rethink what was strictly legal about open containers versus what was more, say, a guideline.

May 10

The good news was that I put together a swing. The bad news was that it broke with her on it. Twice.

May 16

Got my first, but far from last, pandemic haircut thanks to Kate. Eleanor, predictably, spent the entire time looking for opportunities to spray me in the face with cold water.

May 23

I’d actually never had a margarita pre-pandemic.

May 24

If you need a break from everything that’s going on, there’s nothing quite like putting on a seventy year old ballgame – replete with seventy year old ads and news bulletins – and loading a woodshed.

May 24

Kate’s birthday present – an Ooni woodfired pizza oven – made its debut. Cooks a small 9″ pie in around ninety seconds, so we’re looking forward to the days when we can once again have people over.

June 2

Would that we could have been there.

June 7

After my Dad broke his leg, my parents were in need of a temporary wheelchair ramp, so I put my meager skills to work on one. For the curious, this how I built it. It’s not actually that difficult.

June 20

We missed a great many things in 2020, but not the annual First Day of Summer Jaws viewing.

June 21

It being summer finally, it was time for the doors to come off. And put a pin in that garage comment.

June 21

As part of our “we might sell the house” plan, we wanted to fix the railing on the deck. The good news was that while there were huge shortages on PT lumber due to the pandemic I managed to score the last few sections from Lowe’s. The bad news was that it fell out of the truck and all over the road on the way home.

I was able to jump out quickly to grab it thanks to not having any doors, at least.

June 28

Historically, we haven’t bothered with air conditioning given that there just aren’t that many hot weeks in Maine and we’ve all been out of the house during the hottest part of the day, whether at work or daycare. Between climate change and the pandemic-driven working-from-home situation, however, we invested in the only AC units we could find. Which turned out to need more clearance than we had, so I had to shoehorn them into the windows and build a false sill. Anyway, they went in eventually.

July 4

Did the only kind of fireworks we could – socially distant fireworks.

July 12

If I had to do it all over, I would just rip the entire deck off and rebuild it. Or maybe just burn it down and salt the earth so that nothing could ever grow there again. But instead we opted to sand it and refinish it. It was about as fun as you might imagine.

July 14

With our dishwasher already down, it was the stove’s turn. And while it’s next to impossible to get anyone to service appliances that they didn’t sell here, it is literally impossible during a pandemic. Off to YouTube I went.

July 24

I was not of the opinion that MLB should have been playing, but seeing as they were we had tradition to hold up. This was us on the much delayed Opening Day.

July 27

Having eventually wrestled all that PT lumber home, I finally got the railings replaced, a job that whoever built the deck originally made nearly impossible by using railroad spike-sized nails.

August 1

It took two tries, but I eventually figured out what was actually wrong with the stove and fixed it. Good times.

August 5

Did not have the same luck with the dishwasher, so after attempting to get our local appliance place out with a new one – they literally laughed at me saying it’d be six weeks best case – I finally gave up and just ordered what was available from the internet and got it installed. Installing it was miserable, but having a working dishwasher for the first time in weeks was so worth it.

August 12

Having tried to stain the deck twice only to have the prior paint show through – honestly, who paints a fucking deck royal blue? – we finally gave up and just painted the whole thing.

August 12

Running out of time to get the house ready to list, took to working nights.

August 27

During a pandemic, there is nothing better than an empty playground.

September 1

When the playground wasn’t empty, we showed adaptability.

September 9

I didn’t get to San Francisco this year, obviously, but it was terrible to see what the wildfires did to it.

September 14

Having not seen him since the previous summer, my brother made a quick strike visit to my parents. He came down one night for a few socially distanced beers out by the fire pit. Have not been able to see him since.

September 18

The closing for our old house was complete, though not without issue. We ended up having to hang a u-turn just out of the parking lot flagging down the buyers in the process because the title company had so badly screwed up the paperwork and check. Our buyers were great about it, however, and we’re very happy to hand the property over to people who clearly valued it the way we did.

September 24

Eleanor may not have been going to school, per se, but I sincerely doubt that she would have learned as much about sharks at daycare.

September 24

As parental roles go, I’m more the one who roughhouses and gets jumped on than does crafts, but she asked me very nicely to make this.

October 1

We held out hope as long as we could, but eventually we conceded to the inevitable and cancelled the Monktoberfest, our beer & tech conference here in the great state of Maine. We held an online toast with alums, and all of us here have our fingers crossed things are better by next fall.

October 14

The process was absolute hell – more on that here – but much as we loved where we used to live, we eventually made the decision to move one town south to a house that gave us much more room to maneuver. Hopefully those of you not in our pod will be able to see it in person at some point, eventually.

October 15

There was no chance I was going to miss the opportunity to vote this year, so first opening in our quarantine window I popped in. I was met by our realtor, in fact, who was working the polls, bless her.

October 16

Hauled the last of our precious cargo out of the old house and down to the new.

October 31

We knew we couldn’t give the kids a normal Halloween, but we all did the best we could.

November 1

We didn’t buy the new house with the intent of setting up a movie theater in the basement, but it didn’t take that long for us to do just that either.

November 7

First faint signs of hope in a long while.

November 9

Some people started baking bread during the pandemic. I tried my hand at hot sauces, several of which rendered my food inedible. One of them is really good, though.

November 10

My non-traditional pre-school curriculum continued.

November 18

We bought the house in part because of its size, which gave us all room to breathe. The downside was that I had to physically run cabling everywhere. Absolute nightmare.

November 30

Spent her birthday at the playground.

December 4

When your ability to work at home depends on having power, generators acquire a new importance. The only problem was that they shipped it to me with a massive dent, so I had to take it apart and “undent” it. Doesn’t look pretty, but works now.

December 5

December 9

In case you were wondering how Eleanor got so good with her shark identification skills, let’s just say she works at it.

December 17

The forecasts originally all said the storm was going to pass south and miss us. Over thirty-six hours or so the predictions went from an inch or two to a foot. We ended up getting something like sixteen inches, and much higher in spots where the snow had drifted.

The good news was that having a garage now meant that a) we could pull our cars in out of the storm, b) I could just roll the snowblower out of the garage rather than pushing it up the hill in the back like at the last house. And as a bonus: c) I now had a place to hang the Jeep’s doors when I took them off (see 21, June).

December 25

Making this was an absolute disaster and I was up until two in the morning – and then got woken up by Eleanor at 5 after she had a nightmare – but we got to have Christmas with Kate’s family who’d quarantined for two weeks for us, bless them. Also great was the fact that all three of us napped that afternoon, a Christmas miracle.

December 28

With the Lego table out of the way, I got to organizing the new shop, which is maybe twice the size of the old shop.

December 31

More socially distant fireworks to close the year.

So We Moved

When Kate and I bought our first house together seven years ago this past May, we bought purely because it was on the water. We knew the house needed a lot of work, and the best that could be said of it aesthetically is that we wouldn’t get rained on. Our bet was that the house itself could be fixed, and that the location – and especially the view – were worthy of the effort.
So we got to work.
We repainted the whole thing. We redid the kitchen, but on a budget. The budget meant that I did the tile work, which was mostly acceptable because I started on the section that would be hidden by the range so my initial mistakes were largely out of sight. At one point the budget also involved me ripping out our kitchen sink and counters so that the stone counter people could measure, then putting them both back in for a week until the counter folks came back to install the counters they’d custom cut. That sounds crazy, even to me right now, but it actually happened.
We did a ton of other work. One year I dug a french drain in the back yard so that the basement stopped flooding. Another year it was installing a new maple fireplace surround and mantle. Whether it was ripping out inconveniently placed closets or patching the holes in the hardwood floors caused by ripping out inconveniently placed closets, or building organizers for the closets we spared, it became a thing over time. The bulk of my summer vacation each year would be spent on home improvement projects.
Many of these projects left me with injuries of varying severity. I got shocked at one point and couldn’t move my arm for an hour. I almost lost the tip of my index finger when a saw horse collapsed and two heavy sections of melamine plywood crushed it. I ended up in the emergency room because an unfortunately springy piece of corner bead sliced open my leg and had me pulsing blood with each beat of my heart.
As an aside, in my defense on that, I wanted to just seal it up with duct tape and the doc who stitched me up agreed that that would in fact have worked. But my efforts to hide the severity of the problem failed when Kate caught me turning large sections of our deck red. After our friend Ryan took her side, it was off to Midcoast in his Jeep with my leg in a trash bag so I didn’t turn his back seat into a scene from CSI.
Point is, the blood, sweat and tears thing is true quite literally true with our old house. We worked hard to make it better.
Which we were happy to do because our plan all along was to be there for a long time. To that end, we engaged a designer to draw up plans to expand the house and give ourselves more breathing room. Three things then happened in succession, each of which changed our calculus with respect to staying.
  • First, our designer ghosted us. We liked him and his work very much, and his initial draft plan looked great and we were good to move to phase two where he delivered final construction ready plans. Except that he didn’t. He didn’t return calls, he didn’t return emails. For the better part of a year he was MIA, to the point that I’d started to worry that he’d passed away. At that point, he turned back up, said he’d taken on too much work and was ready to re-engage. The problem was that in the interim, the President of the United States had decided to pick a fight with, well, everyone. Between the trade wars with Canada and China alone, our projected costs for building had spiked dramatically. Building, suddenly, looked a lot less attractive.
  • Second, we had a kid. Besides making us really, really tired, our daughter’s arrival changed our calculus considerably. Suddenly school systems mattered, and as she grew so too did her impact on our livable space. What was a livable space for us as a couple was more and more cramped as a family of three. A living room overrun by stuffies and kid’s tea sets makes for some long days.
  • Lastly, there was the global pandemic our country is still in the midst of thanks to incompetent leadership. As it has for everyone, COVID-19 has dramatically complicated our lives. Both Kate and I were suddenly at home full time. So was our daughter, who we pulled out of daycare in March.
I remember volunteering to go get takeout in February solely because I wanted to get out of the house after working from home three straight days. If only I’d known.
The first two factors were enough to get us to at least entertain the idea of moving. So I did what I always do when I need help, and I turned to our local tech Slack. One of the folks in there – thanks Dan! – connected us with a local realtor (who was, as an aside, incredible). We met with her for the first time on February 13th. That meeting was encouraging, and she saw more promise and possibility in our little property than the other brokers we’d spoken with, and we decided to move forward.
Then came March, and COVID-19.
All thoughts of moving went right out the window as we struggled, like the rest of the country, to adjust to lockdown conditions and trying to juggle two full time jobs with a third job of being full time preschool teachers. We were doing the best we could to keep our heads above water, and the idea of adding additional burdens to our plate was just unthinkable. And even if we were ready to list, the market cooled considerably in the early stages of the outbreak.
That is where things sat until late July. By that point, we were still out straight but at least we had our routines down. After seeing so many people in our tech Slack refinance at bonkers interest rates, I pinged my ex-CFO little brother and asked for his opinion on re-financing or even, if such a thing could be accomplished, selling. After a few days of watching market numbers, he came back with a bunch of charts that I didn’t understand but a message that I did: that if we wanted to sell anytime soon, we should do it now and do it quickly.
The last time he gave a family member this advice it was to my parents in the run up to 2008.
So it was that we met in proper socially distanced fashion with our realtor out on our back deck the Monday of July 27th. She talked potential numbers, they worked for us and we asked about timing. She said the sooner the better. Kate and I, much to my later regret, agreed to list in just shy of three weeks.
For some homes, and in non-pandemic times, this would be a perfectly reasonable ask. For us, it was insane. The next three weeks were easily my worst in recent memory, as might have been inferred from my tweets at the time.
I spent my two weeks of summer vacation moving half of the items in the house over to storage using my hand truck and my actual truck. We had so much that needed to be moved we outgrew one storage unit and expanded into a second, much larger one, nearly filling that one too. Nor did we have time to pack properly; the night before the photographers arrived, in fact, we were basically pulling things off counters and throwing them into boxes (and when they were unable to shoot due to poor weather, I ran around the house shouting “DEUS EX MACHINA!”).


Some of those boxes even got labeled, if you can call these labels.

I also spent vacation out in the blazing sun sanding our house’s long deck, then staining it twice before giving up and painting it once. I replaced the deck railings, a task which was substantially complicated by the fact that due to the pandemic there were massive shortages of pressure treated lumber, and when I finally found some I spilled it all over the road transporting it home.
I installed a new dishwasher, spraying myself with disgusting bilgewater in the process. I replaced parts on the range, it worked for two days, broke again, after which I took everything apart again and found the actual problem. Kate and I painted the sun room in our house, including the cathedral ceiling, in spite of the fact that I couldn’t figure out how to work our borrowed paint sprayer and almost doused a floor and two cabinets with Benjamin Moore Decorator White.
It didn’t help that all of that sanding took place in August, which was the hottest month on record, ever, in Portland. It also didn’t help that I badly tore a muscle in my left rib cage less than a week into prep, and when I Googled how long that recovery would be the answer was 4-6 weeks.
Anyway, I could go on, but you probably get the point: this was not my favorite start to August ever.
The worst part of all of this, however, was the uncertainty. We were fairly confident, based on our understanding of the market, that we’d get offers. We had no idea whether they’d be acceptable offers, however. And even if we were able to successfully sell the place, we had no idea where we were going to be living, first because there were less than ten houses available in the four or five towns we were looking in combined and second because all of the available rentals had been snapped up by out-of-towners fleeing COVID.
The good news was that our effort, and the wise counsel of our broker both in terms of how to prepare and what to list at, paid off. We ended up listing late on a Thursday night, and were under contract by Sunday to a nice couple from Boston. Our broker – bless her – even managed to wrangle a rent-back from our buyers, so that we had up to two months to look before we had to move.
The better news was the miracle that was our purchase.
During one of the showings of the property we were selling, we were casting about for somewhere to be. These days, after all, you can’t just clear out to a restaurant for lunch because COVID, or visit with friends and family, also because COVID. The process of selling violated our respective quarantine protocols, so we were on the outs with our pod for the duration.
On a whim, then, we decided to go look at two properties.
The first was a rabbit warren and felt smaller than our then current house in spite of being almost three times as large. The second, on the other hand, was interesting. Really interesting. It ticked a lot of boxes for us. Right town, gigabit bandwidth, attached garage, and it was much larger than we would have wanted pre-COVID but perfectly sized in a world of pods, lockdowns and quarantine protocols. Even better, it was on a quiet, private street where kids can wander and ride bikes and families can walk out the driveway and make a left into nature or a right onto a rocky beach across the street. And did I mention that it was on an island?
The second property might not have been perfect, but it was as close to it as we were likely to find – certainly in this market.
The problem was that a lot of other people saw the same attributes we did, and we were outbid. Sad news, but expected because we, alas, were not paying in cash and needed to actually have our sale close first. Thanks to our broker’s relationships, however, and some serious coaching on her part regarding our offer, we ended up as the backup offer. Which we originally agreed to not out of any sense of real hope, but more because we had nothing better on tap, and by nothing better I mean nothing else period.
But remember how I said miracle? Late in the afternoon on Sunday, August 30th, we got a call from our realtor. Given that we were still finalizing a bunch of the details with regard to the closing on our old house, this was not unusual. The news was, however. The original buyers for the property we wanted, who were from California, had decided to renege on their offer and stay in California. The exact scenario, in fact, that our friend Corey had mentioned as a possibility of days previously. This left us, as the number one backup, as the prospective owners of the house that would have been – and is, in fact – such a good fit for us across a number of dimensions.
That closing was last Tuesday, and the movers arrived on Wednesday. Almost a week and a half later, we’re still living out of boxes, which is half us being totally depleted from the entire process and half the reality of working from home with no daycare thanks to the pandemic. But we’ll get there. Eventually. I hope.
In the meantime, I need to thank a few people:
  • First, a big shout out to our local tech community: we honestly wouldn’t be here if it wasn’t for the Computers Anonymous Slack crew. They got us curious about selling, found our realtor and our mortgage broker, and took everything from a broken dishwasher to an old electric log splitter off our hands so we didn’t have to move it. They also had to listen to venting about how miserable the prep was, poor things. 
  • We also owe an enormous debt to our realtor, who was the reason we decided to sell, the reason we sold for what we did and the reason we were in a position to land the house that we did. My experience with realtors has been less than stellar, generally, but she’s outstanding. If you’re in Maine and need a realtor, get in touch: this is who you want to work with.
  • My RedMonk colleagues, meanwhile, were incredibly patient with me. Already limited by my part-time childcare responsibilities, I added to that random and unpredictable absences for house prep, moving, closing and other responsibilities. And more specifically, as someone who’s self-employed, the documentation asks for the lender were incredibly broad, and Marcia got everything I needed efficiently and never griped once about my – or more accurately their – repeated demands. Couldn’t have done this without our team.
  • My wife’s family was amazing. With my parents out of action temporarily due to a medical issue, Kate’s parents went so far above and beyond the call of duty it can’t be properly conveyed. Kate’s Mom helped us pack, move and watch Eleanor. Kate’s Dad was a machine whether scraping and painting the side of our house or loading and unloading two and a half cords of heavy firewood with me. Kate’s brother-in-law, meanwhile, served as courier for our closing papers sacrificing a Sunday afternoon to get them executed.
  • Mom and Dad if you end up reading this, I know you would have been here if you could, so please no apologies. You’ve never shirked a job in your lives and you obviously didn’t here. Also, thanks for the advice that led us to pick the realtor we did, and for your support and guidance along the way.
  • To my brother for goading us into doing this. 
  • Our pod friends Shawn and Ryan for taking time that they didn’t have to come up and help us pack, but more importantly distract our kid so we could pack. Also for keeping us sane along the way. 
  • To Kate and Eleanor. The past few months have been incredibly stressful mentally and physically debilitating, but we got through it in one piece together.
  • Lastly, to our old house: you were good to us, and you will be missed. Here’s to many more fine years with your new family. 
And for my part, here’s to never moving again.