image by Behnam Norouzi

Year in Review 2021

Well it was better than 2020. But that’s a low bar.

RailsConf 2024

I'm co-chairing RailsConf 2024 in Detroit May 7–9. Come and join us 


A second major, extended, lockdown hit in January/February. This torpedoed any efforts to run an in-person event in 2021 despite how optimistic I felt as New Year rolled around.

The kid’s school was set up well to do remote teaching and thus the burden of home tuition fell a lot lighter than in 2020. Whilst still being stressful and frustrating to be mostly shut in our homes, with the vaccinations on the horizon it wasn’t as destabilizing as the previous major lockdown. Although it was very annoying.

We even got a chance to join the art lessons on a Wednesday after lunch. I think (hope?) we were the art teacher’s favourite family. I guess once a teacher’s pet, always a teacher’s pet.

I also managed to restart, and maintain, the writing for One Ruby Thing after a pandemic hiatus broke my consistency. Twenty articles isn’t a bad haul for the year, although the writing of them tended to be in unmanageable splurges rather than a consistent pace.


One of home school benefits was that when snow hit we could make the most of it. The sheeting blizzard meant that even this close to the sea enough snow settled to skid around on sledges up at the golf course.

The best thing I did for myself this year was to email Jamie and Emma and suggest a weekly “CTO catchup” which has been completely invaluable. I hesitate to call it a “mastermind” because we’re all just puzzling through, but three minds are better than one in challenging situations.

CoverageBook, Podia & Consonance have different business models, sales patterns and ownerships (and our personal ownership stakes) but retain the same scale to a certain extent and let’s face it: humans need managing everywhere!

We’re able to take our learning from our own jobs and share it around, plus reassure each other that the approaches that we’re considering in our teams are the right ones. Or at least are a decent effort that have been sense checked.

Would strongly recommend anyone should set one of these up for themselves. All it takes is confidentiality, trust and a willingness to share.


Started doing a formal mentoring role for a brilliant human in an agency trying to do the “product thing”. It’s been super rewarding to examine the commonalities and differences with their organization and the genuinely difficult thing it is to do to to move and organization mindset from selling “things” from selling time. I occasionally say things accidentally that are perceived as worth writing on a post-it note and doing something about.

I’ve also done a couple of bits of ad hoc career mentoring for friends of friends over the year, but I’d love to do a little more. I’d encourage anyone interested to get in touch.


April saw Alan leave the business. Reducing our total team headcount to ten again. We didn’t replace him, as is our typical approach to team headcount. It has felt as though the balance and collaboration of the product team has worked really well in the remaining months of the year.

Jab one. Yay science.


May saw my regular-ish running come to an abrupt stop with shooting pain in the Achilles’ tendons of both feet. Plenty of ice means the symptoms seem to have stopped enough for me to continue weekly “dad football” but I haven’t restarted non-treadmill running.

I have, starting once the symptoms had abated, been pretty good about maintaining my fitness a mixture of regular weight lifting (using the StrongLifts app) and a bunch of Apple Fitness+ HIIT classes, included with my Apple subscription. While a little cheesy—and performed behind a solidly closed door—is properly hard and tickles whatever need my brain has to actually start and complete a class two or three times a week.


My therapist finished up all his clients in July and went off to spend time as a new parent. He kindly said that he was somewhat inspired by some of the stuff I had said about my making time, back in the day, to spend with my own very small kids.

It was probably about the right time after a few years. Although having that hour most weeks to talk things through was still useful I feel like I’ve worked through a bunch of stuff.


Spent a bunch of time holidaying in the UK in the early summer, having decided it was “too hard” to attempt travel to Europe (or further!) so we bounced around the UK.

We walked around the lower Peak District, some days quite large distances around Chatsworth House, eating the local delicacy of Bakewell pudding and adopting nuthatches from the garden of our accommodation.

We spent a long weekend literally on the beach at Camber, walking out of the back door in wet suits and straight across the beach into the sea. With evenings spent watching England over-achieve in the delayed Euros.

We travelled to the Isle of Wight, and got a handful of glorious “Mediterranean” summer days on the beaches of Sandown.

Jab two.


The launch of a new version of CoverageBook, eighteen months in the making. Three years in the planning.

In the end it was as simple as setting an ENV variable in our hosting platform of choice. And just like that a bunch of our trialing customers were in the new version. It didn’t explode the business (job one) and all we’ve had to do is manage a bit of support confusion.

Changing an ENV var

It looks as though we’ve fundamentally changed the patterns of sign ups. Before the change we would see the bulk of customers either sign up in week one, or never. The newer version (even without changing the marketing site and with zero focussed onboarding) seems to have a much longer tail of trial conversion and results in the same number of trials.


We had our first work away day for two years. In a massive, and slightly strangely laid out, country pad.

Was great to see folks in the team who don’t typically interact day-to-day spend time together and to spend extended time with folks who I haven’t seen enough of in the last two years. We did some, much needed, work on the company as opposed to the day-to-day head down work on the products.

One of the major outcomes was a rough internal handbook as to how we do things. I think my favourite principle was “winging it with style”, which truly captures the confidence that we’re not idiots and we can probably work out a decent path given a goal that we’re aiming at but that we leave plenty of room for improvement.


I finished up my four year tenure as a Governor of the kid’s infant school, eighteen months after they left for pastures new.

Over the period I went from “feeling like not having a clue” to “leading a battle with the local authority”. I feel like I was finally helpful in the last couple of years, even as we were expelled from the school during COVID, but I’m glad it’s over. The time commitment wasn’t massive but I never fully felt like I had the expertise or the time to assist very busy people rather than adding extra chores and difficulty to their lives. That sadly though might be a feature of how our public education system is run.

October half-term saw a family holiday to a very fancy hotel in Crete, I managed to not only hugely overeat at the buffet, but also to exercise every day at the open-air gym. I’m gonna call that a score-draw physically.

We’d arranged two different hotel stops to make the most of the flights and COVID paperwork hassle, but when we arrived at the second hotel to the resort was basically shut, the weather had turned and I’d experienced my first ever (very painful) aura-warned migraine. So we pulled the holiday parachute, paid the hotel for one night plus their booking.com commission and headed home a couple of days early.


While we’d quietly launched a new version of CoverageBook it was a big deal to announce the new incoming version to all of our existing customers. The main thing we’ve been spending all year doing is ensuring we don’t break too much for folks. That means their old data as well as their primary workflows.

This is a lot of work. We (mostly Emma) have attacked this from multiple angles, migrating a bunch of accounts in the background and making sure it all works correctly. We’ve tried small, new accounts as well as our oldest, crunchiest, accounts… it’s boding well for January. Post-that the deletion of a lot of old code. A brave new era.

There’s also been a migration to a new video hosting provider, mux. And ongoing improvements to areas of the application to ensure we have (mostly) feature parity before moving folks over.

The feedback has mostly been of the “give this to me NOW” variety which is reassuring, plus we have managed to move a handful of teams who were willing to start afresh with ‘clean’ accounts.

Early in November I finally managed to pin Vaidehi down after contacting her in July about chatting to me about an article about burnout that she wrote. So we’ve agreed to do a “low hassle” podcast where we just have an unplanned, half-hour chat about a work-related topic and then I do the least amount of editing to get it live. And Chats in the Cupboard is now a thing.

Managed to squeeze in editing & releasing the four episodes of the cupboard chats pre-Xmas, I hope we can record a bunch more in the new year. They’re fun, people have said nice things and the low-key process means it feels sustainable. Plus it’s a great excuse to talk to a brilliant human every week.

Jab three.

The seasonality of CoverageBook (and our defensive engineering culture) means we have busy application in December that falls off marvelously as Xmas nears. So the period at the end of the year is a great time to take stock, hang out with the kids with no plans, reflect and refresh.

Stuff I’ve…


I PS5-ed this year. The instant loading times alone are worth the queuing time on the Game website.

Loved the (throw-in) Astro’s Playroom and Spider-man: Miles Morales. And went back to properly play the previous Ratchet & Clank and Horizon: Zero Dawn as they received PS5 performance patches.

Getting into Deathloop alongside my continuing commitment to Fortnite, which remains a way to hang out with folks as well as hugely ambitious, impressive and on some level a way to add more chores to my life.

I continue to buy games and not play them, misjudging the amount of solo free time I have, which is a bad habit. And neglect my Switch other than to play Smash Bros. with the kids.


More and more inseparable, all that seems to change is the time investment, damn TV with it’s low initial barrier and secret long commitment.

Brooklyn Nine-nine’s six seasons got us through lockdown as a palette cleanser while paired with more dour material. Mare of Easttown, Chernobyl and Peaky Blinders.

Returning favourites Succession, The Witcher and What We Do in the Shadows continued to be great at what they’re great at.

I found The Last Dance to be completely magnetic and given my lack of basketball knowledge I think might be the best way to watch the highlights of the greatest team ever.

The Morning Show badly fumbled it’s second season.

Marvel’s best year? Wandavision was a delight, as were Loki and Hawkeye. The movies were patchier. Shang Chi was delightful and then wonderfully bonkers in the second half, Eternals looked beautiful and grew on me, but Spider-man: No Way Home had Avengers: Endgame levels of plotting skill and “woah” moments.

The Father and Promising Young Woman were probably my two favourite movies of the year, but it’s clear TV has had its claws into me. There’s a bunch of backlogged “good stuff”. I should watch more movies. I’ve signed up for Odeon’s “all you can watch” plan, despite the pretty shabby venue in town, to get myself there more often in the daytime.


Recorded my reading for the first time, using The StoryGraph. It’s a joy to see Nadia’s baby grow from strength to strength.

The book that blew me away was Neil Gaiman’s The Graveyard Book. A decade old, a kid’s book, utterly packed with imagination and melancholy.

Uncanny Valley was terrific and confirmed all of my biases about “big tech”. Small Fry did the same about Steve Jobs, albeit with a excess of lyricality.

I also enjoyed the cinematic-feeling, alternative future in The Power by Naomi Alderman and Neil Stevenson’s Fall: Or Dodge in Hell was another crunchy science fiction tome.

I finally cracked open an NK Jemisin saga. In this case her debut Inheritance Trilogy was was as super as it’s reputation suggests. The Broken Earth Trilogy awaits me next year.

Not a good year for the “business-y” non-fiction I read. Possibly just I was coming to books too late after their lessons were filtered through a bunch of later works. Obviously Awesome, What the CEO Wants You To Know and Traction all fell into nodding in agreement while speed reading. Not bad, just not new information.

The best “book about work” I read all year was Spelunky, a story of the creative process behind a classic Indie game, by the genius behind the game itself. The clarity of direction through the iterative uncertainty, inherent to the creation of a game with a tiny team was hugely inspiring.

2022 Plans

Feels like I’m doing the right things most of the time for family, health, happiness and my work. And side work. I’m not doing too many things I can’t stand and I’m continuing to focus on helping myself and other folks achieve a balance and a level of contentment.

Consistency of good personal stuff. Maintenance of a calm work environment. Power to nudge things in ever improving directions.

And restart a conference after two years out of the “in person” game.

Brighton Ruby 2024

Still running UK’s friendliest, Ruby event on Friday 28th June. Ice cream + Ruby 

Last updated on December 31st, 2021 by @andycroll