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.

How to Build a Wheelchair Ramp (During a Pandemic)


Every so often in life you have the opportunity to put whatever meager skills you’ve managed to cobble together over the years to work for a good cause. For me, in most cases that’s helping friends or family with the technology in their life: problems with their devices, issues with their broadband or trying to figure out how to get high speed access to an area in the foothills of the Sangre De Cristo mountains that has none.

Occasionally, however, I get called on to build something. Usually, and appropriately, I’m the option of last resort, because I seem to have inherited my grandfather’s fine carpentry skills, and he was an outstanding rough carpenter. This past weekend was one of those times, where I was tasked with building a ramp for a temporarily wheelchair bound family member who shall go unnamed in case they would prefer not to be included here.

Never having built a wheelchair ramp, or a ramp of any kind for that matter, I had many questions. Among them:

  1. How steep – or not – can a ramp be?
  2. How do I determine and cut the necessary angles?
  3. If I know the angles, how do I determine length?
  4. Can I build this solo?

The good news is that thanks to YouTube, I had answers to the first three questions inside of an hour. Specifically I relied on this one for the ramp construction and this one for the dark arts of using a speed square. As for the fourth question, that was the easiest to answer, which was that it didn’t matter because I didn’t have a choice. A number of people were amazing in their offers of assistance, but trying to social distance in the middle of a project being built in half the bay of a garage would be impossible, so as much as I appreciated the offers, this was on me.

If any of you find yourself in the position of having to build a ramp, then, hopefully the following is of some use. This is how I constructed the ramp in question. Before I proceed, because my wife is a lawyer, let me state here clearly that I am not a professional, and I offer no warranty on this advice whatsoever: use it at your own risk. Let me also be sure to thank said wife for watching our daughter the whole day so I could knock this out.

Step One: Determine the Height

The most important number you need to have is the height of your entryway. Everything will follow from that. In my case, this number was 31″, which was a lot higher than most of the videos I watched – they tended to be in the 16″ – 24″ range most often. The reason this is important is that the higher the entryway is, the longer your ramp will have to be because of the slope.

Step Two: Determine the Slope

Per the first linked video above, according to the ADA the maximum allowable slope for assisted usage of the ramp is 9.5 degrees. If you’re building a ramp for someone who will need to use the ramp on their own, unassisted, the max slope is 4.8 degrees.

Step Three: Determine the Dimensions of the Ramp

Originally I thought I was going to have to use the Pythagorean Theorem myself and do some actual math, but it turns out Googling “right triangle calculator” yields a large number of sites that let you skip the math. So I took advantage of this one because time was of the essence.

All you need to calculate the dimensions of a triangle are one side and an angle, fortunately. After providing height A and the opposite angle – 9.5 in my case – I had the dimensions that I needed. To come down from 31″ at 9.5 degrees, my ramp would need to be about sixteen feet long. The problem for me was that seventeen feet away from the door in question was a shop sink, so unless I wanted to rip that out from the wall, and I very much did not, I was looking at two ramps. One ramp down to a platform, and then a second ramp off that platform at 90 degrees.

Like so.


I know, I’m quite the artist.

Anyway, the first one would step it down about 10″ to a 40″x40″ platform 20″, and the second ramp would pivot 90 degrees to drop that 20″ to the floor.

Importantly, there’s some play in both heights because I had to account for the height of the plywood sheeting. Basically what I did on the ground was recompute my right triangle dimensions for 3/4″ less than the original height and build the ramps accordingly. This allowed me to fit the sheeting in without issue.

At any rate, I now had everything I needed to begin preparing a cutlist.

Step Four: Prepare a Cutlist

Unlike the right triangle thing, I have yet to find an app that can prepare a general cutlist outside of specific, common use cases like decks. So I had to prepare a list of the materials I needed.

In my case, I went with standard 2×6 dimensional lumber and 3/4″ plywood. I picked up, or was supposed to anyway, 11 2×6’s, 3 sheets of 8’x4′ 3/4″ plywood, some 2×4’s in case I needed a railing and a single 8′ 4×4 for the platform legs. All in, it cost a little over $200 for the materials (I had a lot of 1 1/2″, 2″ and 3″ fasteners lying around so I didn’t need that).

Under normal circumstances, I’d just drive up to Home Depot, pick the stuff up and walk out. With the pandemic, however, we’re only doing curbside. I called the store to confirm, placed the order – though oddly only after it was nearly complete did it mention the curbside availability – and was done.

Step Four: Stage the Tools

Not having room in the truck for both tools and lumber, I ran the tools up the day before and set them up for usage. It’s nice having a pickup for things like this, I have to say.


Step Five: Pickup the Lumber

This was an ordeal. I ordered Saturday afternoon in two separate orders because I’d forgotten the 4×4 initially. Sunday morning I got an email that my order was ready to pickup, and they only brought out the 4×4. Kind of tough to make a ramp just from one eight foot piece of lumber. After some haggling back and forth through the car window, he went back in, found the other order, and brought it out – only there was no plywood. After communicating to him that without the sheeting the whole thing was moot, I finally was able to order 3/4″ OSB instead which he went back in again to get. And came out with an extra sheet – thanks mobile app!, that I could not return without going into the store.

At which point, I gave up, thanked him and started loading the truck. So the ordering part was complicated, thanks to the virus. Also complicated was having to turn down multiple very kind people in the parking lot who saw me loading a lot of lumber by myself and offered to help. One even offered to drive it over because he doubted it would fit in my mid-sized truck.

They were wrong, it did.


Between the messed up order and the loading, I was at the store for over an hour and then it took me twice as long as it should to get the project site because I had to stop every few miles to prevent the wood from sliding out.

Not good times, bad times.

Step Six: Unload the Lumber



Step Six: Build the Platform

Because I wasn’t sure of my angles yet and wanted something to physically test from, I built the platform. It’s just a frame of 2×6’s around 4×4 legs. Pretty straightforward.

Step Seven: Build the First Ramp

This is where the angles came in. I needed to determine what angles to cut on the joists to connect the platform to the entryway. With that, I turned to my speed square. You’ll notice on here that it has a table for common rafter conversions. This is how that works.


  1. Find your angle on the table: in my case, 9.5 degrees.
  2. According to this table, that equates to a 2″ rise every 12″.
  3. Place the square on your lumber, and pivot it “2” on the COMMON scale. That’s your angle. Make a line, and cut to that. If you’re like me, you’re wondering about the angle for the floor – but hold that thought, we’ll come back to it.


Once I had the angle process above worked out, I measured the distance of the platform to the entryway, and fixed the former to the back wall so it wouldn’t move. Then I cut 2×6 segments to that angle to the appropriate length and toenailed them to the entryway and the platform like so.


You can’t see it because it’s behind the drill drive in that photo, but I had to bird’s mouth – that is to say, notch out – the far joist to have it seat properly. The process for that is simple. Make a mark with the same angle you’re cutting the rafter at – 2, in my case – and then make a perpindicular line connecting to that at whatever height you need to remove for it to seat.

Step Eight: Built the Second Ramp

One thing I was unsure of before I started the process was the angle of the joists that connect to the floor. I understood the process as outlined above for determining a rafter angle like cut, but what about the pieces connecting to the floor? As it turned out, this couldn’t have been simpler: it’s the same angle as the rafters.

The only difference is that instead of pivoting on the long side of the joist, you pivot from its end, like so.


That gave me the long angle I needed to have the joists seat properly on the floor, as you can see.


I went back later and added some cross braces between the joists for extra stability, just in case.


Step Nine: Sheath the Ramps and Platform

Ideally, I’d prefer to cut my sheet goods on a tablesaw, but the cuts I needed to make here exceeded its maximum fence depth so that was out. Instead, I cut everything freehand with a handheld circular saw. The work wasn’t perfect, but for this project it didn’t need to be so long as it was workable. I worked from the entryway down, laying the OSB down on it as I went.

One other minor thing: I beveled the edge of the OSB where it met the floor to make it even slightly easier to get a chair up on to.

Step Ten: Install Edging

While the slope is gradual and ADA approved, I would prefer to not be responsible for someone careening off a ramp I built and therefore installed 2×6’s around the edges of the ramp. Where necessary, the angles were cut using the exact same process outlined in Step Seven.

Here’s the finished product.


There are some rough parts, for sure, which I expect that one friend in particular will find and point out, and I would not expect this to last forever. But as a temporary measure to meet an immediate need, it should be serviceable.

Step Eleven: Shower Beer

The best reward for a completed project is a shower beer – Maine Beer Company’s Lunch in a travel mug, in this case. And as it turned out, the hot shower itself was necessary because having to crouch over for the better part of a day left my back pretty stiff.

Step Twelve: Takeaways

The net is that a ramp is not a hard thing to build. The angles are the only tricky part, but once you figure that out with a speed square it’s very straightforward. Some of the cuts – specifically the long cross grain cuts using a circular saw – were a bit of a pain in the ass, but those notwithstanding there’s nothing particularly complicated about the build.

Total project time was from maybe 10:30 in the morning working straight through to around 4:30 in the afternoon, and the cost as mentioned was in the $215-$225 range assuming you don’t actually buy an extra sheet of OSB you don’t need.

Bonus: The Only Injury


Unusually, I had almost no worksite injuries on this project. Apart from some nicks and scrapes on my arms and legs from the OSB, the only notable problem was the blister I got on my index finger. Word to the wise: if you are having a tough time driving a screw in and the driver has worked on it for a while, do not touch that screw. Damn thing burned the hell out of me and hurt like hell while it blistered.

As my injuries in these thing go, however, I’ll take it.

Like Guac? This Will Change Your Life

With the rather large caveat that you may not want to take advice on kitchen gadgets from someone who, left to his own devices, would eat all his meals directly over the sink, let me recommend a kitchen gadget that will change your life.

If you like guacamole, anyway.

Which I do. But while I enjoy guacamole more than any other food that doesn’t involve raw fish wrapped up in some combination with rice, I am very particular about the taste of the guacamole. The nationally distributed artificial, ersatz packaged stuff is a non-starter. I’m more forgiving of local packagers, who can sometimes do a nearly adequate job but still tend to over-rely on preservatives. And even the fresh made onsite varieties such as at Whole Foods or our local super market, while night and day versus the abominable artificial stuff, are still not my cup of tea. Usually it’s the ingredient mix: some turn the guacamole into a veritable salad with peppers, onions and tomatoes all competing with the avocado for pride of place. Others use enough lime juice to make a half dozen gin rickeys.

I am not, in general, a food person in that I’m a lot happier eating whatever seems edible at a dive bar than I am at the kinds of restaurants where presentation matters and people take pictures of each course as it comes out. There are very few foods, therefore, that I care enough about to get snobby about. Guacamole is one of them, which is why I prefer my own.

My recipe is the opposite of fancy; it’s stripped down and simple, letting the flavor of the avocado do the work. For base ingredients, I use nothing but avocados, sea salt and a bit of garlic. If I know Kate’s going to be eating it as well, I’ll use a tiny bit of lime juice because she prefers that, but otherwise I skip it.

The only other thing I toss in which is admittedly non-traditional is a drop or two, depending on the batch size, of sesame oil. Years ago I was eating at my favorite Mexican joint in NYC with my parents and raving about the quality of their guac. My only complaint was that I couldn’t quite pin down what set it off. My Mom’s an excellent cook, however, and called it immediately: they use, or used to at least, a tiny, barely detectable amount of sesame oil. And so, after that revelation, did I.

By now you’re probably wondering what all of this rambling about guacamole snobbery has to do with a kitchen gadget, so let me explain.

For Christmas, Kate got me one of these.


Technically it’s called the Prepworks Guacamole Prokeeper, but basically it’s just a plastic container you can vacuum seal. The idea is simple: you angle the top down, forcing out any trapped air thereby vacuum sealing whatever you’re storing in there – the guacamole, in this case.

I was skeptical, not least because most of the miracle kitchen gadgets I’ve seen are not exactly miracles. And to be fair, this one takes a bit of trial and error to get the angle right, and it can be tedious to clean. But the damn thing actually works, and works well. What that means in practical terms is this: I can have guacamole – my guacamole, made myself to my exacting specifications – all week with only one prep. On sandwiches, on eggs, on toast, even on actual Mexican food if that happens to be available.

I’ve never bothered to make much in years past, because it goes bad so quickly. Even if you use the trick of saving the pit with the guac, it doesn’t last more than a day or two in the fridge without developing a nasty brown skin. With this little gadget, it will literally last a week.

Most Saturdays, then, I now cut up four or five avocados rather than the one or two I’d normally use for a single meal.


Then I grind up a week’s worth of guacamole à la sog, like so.


And here’s what it looks like in the miracle kitchen gadget four and a half days later. First from the top.


And then from the bottom.


With the exception of some crust around the edges where it sealed, the guac is basically perfect even days later. If you like guacamole, then – like it enough to make large batches of your own – you should definitely grab this or one of the dozens like it.

It’ll change your life by adding more guac to it.

Disclosure: As always, the Amazon link above is an affiliate link simply because I enjoy seeing whether people take any of the recommendations made here.

My 2019 in Pictures

As has become custom, I’m late with my year end wrap-up this year – but not as late as I was last year, so there’s that.

As always, these are the moments – significant or mostly not – that characterized my year personally. So not much about work, and as little as possible about airports. Before we get to the pictures, however, a quick check-in on travel.


While it had some brutal stretches, travel was much more manageable this year. After ballooning in 2018, my travel came back down to a more or less manageable level – even with some unanticipated personal travel thrown in.

Notably for me, this was the first year since it was introduced that I did not qualify for JetBlue’s Mosaic program, as 2019 marked my first full year flying Delta. With the exception of a single New York to Portland segment after a Delta flight got cancelled, I didn’t fly JetBlue at all.

Delta, meanwhile, has been something of a revelation. I actually get upgraded to First Class now, for one, and every so often the cost to upgrade to one of those seats is reasonable enough that I can justify it. Throw in the lounge access – including showers for post red-eye flights – and the jump to Delta has been a huge improvement in my overall travel comfort. Big thanks to Kate who was the one who actually kicked me to do it.

In the meantime, a few other tidbits courtesy of and

  • Distance: Clocking in at 69,312 miles I was off 19% on the year, which was excellent news.
  • 100K: This was the sixth time in nine years I failed to reach 100,000 miles. I will continue to try and keep it up.
  • Carrier: As mentioned above, I cut fully over to Delta this year. 52 of 56 segments were Delta; 3 were Norwegian to and from London, and one was the aforementioned JetBlue hop.
  • Airport: For the second year in a row I reversed last year’s trend, and spent more time this year in Portland (22) than Boston (9).
  • First Time: Visited Memphis, TN for the first time as you’ll see below. It’s fun, but I have no idea how people live past forty with that food.
  • Where To: San Francisco narrowly edged out New York this year as the destination I visited the most for the second year in a row. Here’s hoping the city that’s only 45 minutes away by plane makes a comeback this year.

With that, on to the pictures.

January 1


Spent New Year’s morning helping my brother-in-law cut up a tree that fell on and crushed his car. The good news is that it was overnight and no one was hurt. The bad news is that the tree fell in several inches of ice cold slush.

January 30


In London for the Monki Gras, learned to my surprise that the other investor in Mikkeller London is…well, I’m never gonna give that up.

February 1


James continues to reset the bar every year. Biggest thing the Monktoberfest stole from its sister show this year was closed captioning.

February 14


You know you’re in trouble when you’re getting ready for a talk – or in this case a panel with the IBM CEO, hence the abnormal attention to my appearance – and the makeup person looks at the scar on your nose and says “oh…oh no.” Ten minutes later and they made me as pretty as I was ever going to be.

February 23


The Red Sox were back and someone was excited.

March 12


Speaking of being excited, we ended up at the 21st Amendment in Boston due to every other restaurant laughing at us for not having reservations during Restaurant Week.

It is really weird to take your kid to a bar you used to close down regularly with your friends in your twenties. Cool, but like, really weird. Twenty something sog would not have expected this development.

March 22


Went to Memphis for the first time for a Bachelor’s Party, and it’s a fun town. I could never spend much time here or the food would kill me, but it’s got a bit of a New Orleans vibe to it and the first place we went to randomly had goats walking up a jungle gym.

April 8


A famous San Franciscan establishment in RedMonk lore, I hadn’t been back here in years. It’s changed, but still a quality venue.

April 15


Was crushed to see Notre Dame – easily the most impressive human construction I have ever seen in person – nearly burn down.

April 16


Finally bit the bullet and got a battery powered chainsaw. You can read the review at the link, but the short version is that it’s great.

April 26


Took Kate to see the Avengers:Endgame for her birthday, and while it’s no Alamo Drafthouse, you can get a beer – or cocktail, in her case – while you watch. Totally worth it for the Captain America scene alone.

April 30


Didn’t manage to get down to the Sangre de Cristo’s this trip, but always good to see the BFF.

May 18


Our friends take rehearsal dinner beers seriously.

May 19


Said friend got married in a beautiful spot up the coast, and thanks to me it was raining. Sorry buddy.

May 27


Lot of firsts this year, including the first Memorial Day parade.

May 28


After years of neglect due to having a tiny human to care for, we finally bit the bullet and tore up our sad, tired lawn and put down seed.

June 3


With the exception of my parents and grandparents, no one ever had more influence on who I am today than my coach. He died on June 3rd, and he is missed.

June 30


We managed to a) get to the Blessing of the Fleet and b) keep the various cousins from tumbling into the water and c) race back to the cars seconds before a massive thunderstorm rolled in.

July 3


Lawns get better if you pay attention to them, it turns out.

July 4


Fireworks at Bean’s.

July 10


The last time I was in the Blind Tiger in NYC I lived there. In NYC, I mean, not the Blind Tiger. Not most of the time, at least.

July 27


We got hops.

July 28


Nothing better than a secret, locals only beach.

July 29


Got a new truck, one with a removable roof and doors that can come off and actually be put back on. More on that here.

August 3

IMG_20190809_134905 (1)

This vacation week in this place is what gets me through the year. And yes, that unicorn is exactly as comically oversized as it looks.

August 20


Annual pilgrimage complete.

August 22


Vacation isn’t just waterfalls. It’s putting in new entry lights and trying not to get electrocuted.

August 23


Vacation is also tearing apart your stove to replace the igniter without getting electrocuted or blowing up the house. So far, so good.

August 30


First ride on the ride on with my Dad.

August 31


First time camping. Ish.

September 6

IMG_20190906_172330 (1)

This was for sale literally on my way to daycare, and I neither bought it nor stole it. Somehow.

September 18


On behalf of four generations of Kate’s family, I said goodbye to a beloved Boston institution closing its doors.

September 26


En route to Vermont for Monktoberfest related activities, stopped by another institution.

September 29


It was time, at least according to the friend who called the old hat “gross.”

October 3


Survived this, once again.

October 12


Said goodbye to a beloved aunt. Marcia, you are missed.

October 13


I would have killed for something like this as a kid when I spent weeks on the Cape, but better late than never.

October 17


Big storm, power goes out, generator kicks on, all is well. Until 5ish because, as it turns out, we were out of propane. Because the folks responsible for auto-filling our propane tanks hadn’t filled our propane tanks in a year. “Yeah, I know it’s late, but we’re going to need you get over here with some fuel.”

October 31


Puffin randomly flew into our house, thanks to Kate’s handiwork.

November 8

IMG_20191108_163912 (1)

Opened my wallet at the store and was very confused to find none of my cards.

“Did you take daddy’s credit cards?”
“Yes! I put them in here because they were tired.”

In here = the paper drawer in the printer. Could be worse, I guess: she could know how to use them.

November 9


Biggest little game in America.

November 16


Wood dropoff.

November 17

IMG_20191116_135108-ANIMATION (1)

Woodshed loaded

November 30


Can’t believe it’s been four years.

December 14


First ballet recital went great until she tried to take off her leotard “because it was itchy” and almost pulled down the Christmas lights of the set.

December 24

There was a viral video going around this year about how to wrap your presents diagonally.

Do not believe it. Do not trust it.

December 25


This is how you do Christmas morning correctly.

December 31


“It’ll mostly be rain on the coast” apparently translates to a foot of snow.

What Even is a Jeep Gladiator?

A little over a month ago, I drove home from Westbrook in a brand new truck. It was not, as I would have assumed a year or two back, another Tacoma. It was instead the first generation of a brand new truck, a sort of franken-truck that was relatedly the first pickup Jeep has sold since the sixties. The truck I drove home was a Jeep Gladiator.

I got a lot of questions when I originally leased the Tacoma three years ago; I’ve gotten an order of magnitude more about the Gladiator. For those confused about why I picked one up, or even what it is, this is for you.

What Even is a Jeep Gladiator?

This is the first question that people ask. The day I picked one up, some rando in a parking lot literally asked “what in the hell is that?” Someone else walked by, did a double take, nodded once and just asked, “is it awesome?” – but we’ll come back to the reactions this thing provokes.

Anyway, while Jeep’s answer to the question of what a Gladiator is involves lengthy discussions of parts borrowed from other truck lines the parent company owns, the simplest and also correct answer is that the Gladiator is exactly what it looks like: a Jeep Wrangler with a pickup bed pasted onto the back of it.

That also, helpfully, explains why I bought one. But before we get there, why a pickup?

Why a Truck?

Much as it may seem otherwise if you’ve driven up here, you are not in fact legally required as a resident of the great state of Maine to drive a pickup. You can drive an SUV, a Subaru or anything else that has four wheel drive. Probably some other cars too. All of which implies that I am driving a pickup voluntarily, a fact that is likely to baffle the many sports car enthusiasts at a minimum.

Three years ago, I became convinced that – based on our lifestyle and more particularly the state of our house – a pickup was more need to have than nice to have. As someone who’d always driven sports cars or at least sportier sedans, however, I had less than no interest in driving one. So I set about convincing Kate that she should be the one to drive a pickup. That plan went about as far as you think it would, and she ended up driving a Volvo and I ended up with a Tacoma.

The good news was that the truck was every bit as useful as anticipated. The Tacoma conveyed plywood, sheetrock, 2×4’s and 2×6’s, 10 foot sections of walnut, 12 foot sections of hard rock maple and more. It picked up firewood (more than once). It picked up a tablesaw. It picked up a lawnmower. It emptied our house on trash day. It even got pressed into service for the Monktoberfest. And that’s just the special event stuff; the truck also did basic blocking and tackling like picking up mulch, mulch and more mulch in the spring or our weekly runs to the transfer station, recycling and bottle redemption places – it’s really nice to not care if your trash or bottles leak because you can just hose out the bed.

Point is, the truck got used as a truck all the time, and a truck had become indispensable. With Kate not having changed her mind about pickups, then, I was in the market for one.

Why a Gladiator?

This whole thing began with a single text from my brother – the car person in our family – from last November. It included a picture of the not-yet-on-sale Gladiator with the minimalist caption, “next truck.”


That kicked off a long, winding road leading here which careened between extremes like “they’re reportedly going to sell them for $10K over list so I’m out” to “wait, they’re leasing it for what?” In the end, the reality was closer to the latter, and I got the truck for below invoice and within a couple of grand of what the Tacoma had cost three years ago.

But that’s just the logistics that made it possible; it doesn’t get at the actual why.

Back in high school, when I was approaching the age I would be taking my driving test, I spent hours upon hours pouring over used car classifieds (for my younger readers, that’s like Craigslist printed on sheets of thin, black and white paper). I had two preferred options: a Wrangler or a sports car. The results were disheartening. Wranglers hold their resale value absurdly well, so they were a non-starter. Sports cars were similarly spendy, unless they had some near fatal flaw. The good news was that I ended up with a sports car, a ’73 Mustang bought off a coworker of my Mom’s that was, well, let’s just say not one of the classics aesthetically speaking. But it was my car and I loved it, and from that point forward I drove fast cars right until the time I ended up with the Tacoma.

When my brother sent me that text, however, I was faced with an interesting proposition. If I had to drive a truck rather than a sport car as circumstances seemed to dictate, what if that truck was a Wrangler at the same time? What if I could get a truck that was also a convertible? What if there was a truck whose doors and roof would come off in ten minutes?

The answer to these and other questions is sitting outside in our driveway as I write this.

Oh, and as an aside, if you own a Tacoma whose doors were not remotely designed to come off, I highly recommend not confessing to your significant other that you’ve been Googling about how to do that.

Why Did I Order One?

Once people get beyond the shock of the thing – it’s a Wrangler, but it’s a pickup? – one of the other questions people had is why did I order one? Most people, after all, buy off the lot because dealers are more incented to move those. I had certainly never ordered a car previously.

Part of it was the fact that I wanted a stick, and part of it was timing.


Since 2005, I’ve driven nothing but a manual transmission and had no intention of changing that. The good news was that the Gladiator’s default transmission was a standard. The bad news was that – default or no – virtually none of the early models that shipped out were manuals, and the few that were were far more richly optioned than my budget allowed for. Seriously, you wouldn’t believe what some people will pay for a pickup truck.

Under other circumstances, I’d simply bide my time and wait for manuals to start shipping. In my case, however, the Tacoma lease was up in June and even automatic-equipped Gladiators were few and far between at that point. I was able to extend my lease on a month to month basis, but the clock was ticking on the still expensive state registration. If I could get a new truck quickly, I’d be spared the hundreds of dollars necessary to register the old one that I’d be turning in anyway. If I waited for a suitable manual Gladiator to arrive on its own, meanwhile, I’d have to register the Tacoma for a full year, the majority of which I didn’t plan to own it – a waste of money.

Once I got one of the four Jeep dealers I was working with down to a workable number, then, I called it good.

What About the Environmental Impact?

Like every other reasonable, rational human being on the planet I’m desperately concerned about climate change, and its impact on the planet both near term but more for my daughter’s future. And while the Gladiator’s average mileage so far is a tick above what I was getting with the Tacoma and light years ahead of my old Mustang, there’s no way around this: the Gladiator is not in the least an environmentally friendly vehicle.

But for where we live and what we do, a pickup is a must have as discussed. Which is why part of the reason I leased the Tacoma was my hope that by the time that lease was up, hybrid or EV pickups would be available. The good news is that EV pickups exist now. The bad news is that they cost seventy grand, which is not only not in the ballpark of what I’m willing to spend, it’s not in the same league.

My hope with the Gladiator, therefore, is that three years from now, I’ll be able to get one that is an EV, or at worst a more efficient hybrid – something that looks increasingly plausible. Or failing that, that a Rivian, a Tesla or something similar has a pickup at a price point that is close enough to work (and has a dealership that is closer than several hundred miles away).

What About it Being a First Generation Vehicle?

A couple of people have asked whether I have any concerns about buying a first generation vehicle. The answer is an emphatic yes, and this is another reason I’m leasing. If Jeep’s first go round with the Gladiator turns out to be fatally flawed, I’m only on the hook for the early years and I can hand them the keys at the end of it and walk away.

How Does it Drive?

It drives like what it is, a truck. It’ll never be mistaken for my beloved old Volvo S40, let alone a true sports car, but it’s perfectly well mannered for a truck. One of the complaints about the Wranglers, from what I understand, is that because they’re short in wheelbase, they don’t track all that well, particularly on highways. The Gladiator, being a lot longer, has no such problem.

The manual transmission, for its part, is a lot closer to my Volvo than the Tacoma; the clutch is softer, and the throws are shorter and much more car-like. Once I got over the initial adjustment of not being able to feel the clutch engage because it wasn’t as hard as I was used to, it’s more pleasant to drive.

All in all, the driving experience is consistent with every other truck I’ve driven, and similar to at least the bigger SUVs.

How Big is the Bed?

It’s big enough for giant inflatable unicorns, at least.

More empirically, it’s slightly shallower, and thus easier to reach into, than my old Tacoma bed. Otherwise it’s a basically a standard midsize pickup bed.

The bed has one thoughtful little trick, though: you can suspend the tailgate halfway down to make it easy to carry full size sheets of plywood, sheetrock, etc.

What Don’t I like?

Let’s start with the bad stuff. The mileage is fairly standard for a midsize truck, but that’s another way of saying not good. While the Gladiator can tow an impressive amount of weight, the gear ratios are more oriented towards offroad usage than winding yourself up the gearbox. And even with the optional liners for the hard top, the road noise at highway speed is noticeable. A lot quieter than it would be with a soft top, but the truck is never going to be cathedral quiet.

The last thing to mention is not so much intrinsically bad as something that takes getting used to, and probably dependent on what you’re used to driving (and/or your personality). In my case, apart from my old Mustang which elicited comments – many of them not terribly complimentary – I’ve never driven a car or truck that was in the slightest way noticeable. They’ve all been fundamentally unremarkable, at least in terms of their outward appearance.

The Jeep, thus far, is the inverse of this. I have not driven anywhere without someone making some gesture or comment.

  • “Is that the new Jeep truck? How is it?”
  • “My husband really wants one, but I wanted to see one first.”
  • “My husband and I had one like that in the sixties; we had a great time with it.”
  • “I’m sorry, I just have to check it out.”
  • “So do you call it a Juck or a Treep?”

Then there are experiences like the following.

I was in our local hardware store picking up some caulk to seal up a new front entry light when I noticed that one of the staff members appeared to be furtively stalking me. This isn’t totally unusual, because they tend to assume you don’t know how to find what you’re looking for. Anyway, he poked his head around a corner, looked back and forth almost as if afraid of getting caught at something, then walked over. While I got ready to tell him I was all set and had found the caulk, he stammered out a question like he had to work up his courage to ask: “I, uh, sir, I…is…is that your truck outside?” Allowing that it was, we chatted a bit about it and I answered a few questions. 

Outside in the truck queuing up a podcast for the ride home, I happened to look up. The kid had pulled over two of the other kids working in there, and they were standing in the doorway gawking and pointing at the truck. They at least had the sense to be embarrassed when I caught them at it, however.

On the one hand, it’s nice that people are so enthusiastic about something you drive, but as someone who’s not generally in the habit of making random conversation with strangers, it’s also deeply weird. People really do seem infatuated with it, though.

What I Like?

Way more than I can list here, but as mentioned it drives well and predictably, the manual transmission is solid and the interior is both comfortable and can be hosed out and drained through plugs in the floor if necessary.


I’m really enjoying Android Auto, meanwhile. At the time I leased the Tacoma, Toyota was still trying and mostly failing to compete with both Apple and Google on user interfaces (they’ve since given that up). Android Auto isn’t perfect, and I’ve submitted a bunch of bugs ranging from trivial (the steering wheel track advance hardware buttons occasionally don’t work) to actively irritating (phone calls routed to the handset instead of the in-car audio mic/speakers), but overall it’s a lot more functional than Toyota’s old interface. From the Google Maps native integration to the mostly reliable voice operation of Google Play Music, Pocketcasts, and so on, Android Auto’s been an upgrade in my experience. It’s also a timely upgrade because as of Thursday Maine is going to begin ticketing drivers using their phones and I can now navigate the entire entertainment system with the Google Assistant’s voice interface.

The interior of the Jeep is also surprisingly roomy. The back seats fit adults capably and even our off-the-charts tall soon-to-be four year old has plenty of room. Kate’s primary complaint with the Tacoma was that she felt claustrophobic in it; no such complaints with the Gladiator, and that was with the roof on.

Speaking of Kate, for those trying to sell significant others on a Gladiator, the spousal approval factor in our house is far higher than I had anticipated. The no roof experience was such a hit, in fact, that she requested an extended evening drive out in the country the day I brought it home.

There are a hundred other things I could mention here, but honestly the thing I like best is the reason I bought it in the first place: the roof and doors come off. The first time you’re driving around on a hot day in the summer in the open air, well, if that doesn’t put a smile on your face I don’t know what could.

What’s it Like in the Winter?

I’m about to find out. Check back with me next spring, could be I’ll have a Jeep truck to sell you, cheap.

So, Is it Awesome?