My last day at GitHub was at the beginning of June 2025. I started my next job on June 2, 2026—almost exactly a year later. Then I took a job at Google that begins August 3. Professionally, it’s been a “gap” year. But that gap was not empty, and that’s the whole point of this post.
In between was a sabbatical: a full year away from corporate work, for personal and family reasons. It’s the second time I’ve done this. In 2018 I took five months as a stay-at-home dad to move our family from San Francisco to Denver. This one was longer, and there was a lot more going on.
My wife is a CEO, and for the year I was Head of DadOps, running the household fully to make her life tolerable. That meant the kids’ summer and school activities, college prep for one of them, an extended health issue for another (that’s all the detail I’m going to share), and, since she works from home, a constant supply of tea, snacks, and lunches.
Decompression and Calibration #
The first part of the year was decompression. Running a TPM organization through major product and platform shifts is not a job you switch off from overnight, and I needed time to wind down before I could think clearly about anything else.
Once I could, I realized I was not mentally healthy. I was actually quite anxious. The tech industry is going through big shifts—layoffs, cutbacks, radical rethinking of priorities—and there’s plenty of fear, uncertainty, and doubt within the TPM profession. (I’m glad to say TPM work has gone the same way as software engineering: the work has shifted from the mundane to the complex and interesting. But that wasn’t a given 12-18 months ago!)
So decompression was one thing. Then came realizing that a shift in attitude and perspective was needed as well: mindfulness practice, and paying attention to anxiety rather than ignoring it. Seeing a therapist helped me develop a much healthier relationship with my own idea of work, and of worth. I’m not ashamed of that. The recalibration was overdue, and I’m running smoothly again. (I sound like an old car!)
Hitting the Road #
Speaking of cars, we traveled a lot this year. In between the big trips, I also got out on overnight bike-packing trips on my own.
Japan with My Son #
What made Japan special was that the itinerary wasn’t built around business. It was built around the interests my son and I share. Funky old-school gaming hardware shops and arcades were high on the list, along with the Nintendo and Studio Ghibli stores; museums were not. Trying all kinds of food that’s “hot on TikTok” was a blast, and having my son order “the best wagyu on a stick in Japan” was great. There was also knife shopping.
Sticker shopping, with a basket sized for the job.
Sushi at the train station.
Visiting an onsen was definitely my idea, but walking through an absolute blizzard to see the snow monkeys was a shared experience we’ll never forget. The best part? Probably eating Japanese junk food for dinner after sitting in an exquisite public onsen in Shibu and being cooked alive. I’ve never slept so well!
The UK with My Daughter #
The UK trip was in the summer of 2025: university scouting, and just fun. We visited family, reconnected with my friends, and spent a few days in Cornwall for beach time and looking up the family history of mining. (If you want to learn more about that history, my aunt wrote a book: One Cornishman’s Children.)
It was also the first time I’d driven in the UK. For extreme excitement, try a stick shift on Dartmoor, on a narrow country road wide enough for one vehicle, meeting a large lorry coming the other way. Reversing for a third of a mile in a car I’d just rented was quite an experience. I’m proud of myself.
Hiking on Dartmoor with my daughter.
A lane in the Yorkshire Dales, rain on the way.
The yarn fairies below were at the Ribblehead Viaduct in the Yorkshire Dales, and we saw at least five similar crocheted scenes around England. So whimsical and fun.
Yarn fairies at work near the Ribblehead Viaduct.
The Western US with My Son #
The road trip was my son and me camping our way across the western US: Mesa Verde, the Grand Canyon, then San Diego, where a broken car led to three days of hanging out in a friend’s backyard pool (rough!). On the way back we came through Utah—Bryce Canyon, Moab, and home to Denver. We ate a lot of campfire-cooked burritos. Taking nighttime photos of the Milky Way in Bryce was a highlight: 2AM, with a red light to see by.
Road trip lunch: the cooler doubles as a kitchen counter.
Niagara and Montreal with Margaret #
With my cousin Margaret I went to Niagara Falls on the Canadian side…
On the Niagara Falls boat with Margaret. The ponchos only sort of work.
…and on to Montreal: tons of sightseeing, late-night walks, classical music, and one of the best museums I’ve ever been to, Pointe-à-Callière. The exhibits are superb at painting a compelling picture of first peoples and Europeans coming together in one place.
The mounted police were out in Montreal, rain or not.
Dealing with Surprises #
Not everything went perfectly; far from it! I had everything planned for the Erie Canal ride from Buffalo to Rochester: eight days, fully self-supported, camping the whole way. Four days before the ride I got a herniated disk in my spine and had to cancel everything.
Training with the full loadout on a ride from Denver to Fort Collins.
Very sad, but there was a silver lining: that’s exactly when my kid needed full support with health issues, for the better part of three months. Doing that while holding down a job at the same time just would not have been possible.
Learning Like It’s My Job #
I treated professional development as a real workstream during the year, starting with software. I love writing it. I’m far from the best, but it truly gives me joy to build and express creativity. So the heading above isn’t quite right: this wasn’t just “like it’s my job.” It’s an itch I love to scratch.
I took an AI engineering course and published notes as I went. I went very deep hands-on with Claude and other tools—enough to develop opinions about how to bookend agentic work and compound engineering.
And I built open source: CalcMark, a language for structured calculations in Markdown; GH Velocity, a CLI for engineering delivery signals from GitHub data; and Jobs4Me, which I’ll get to in a moment. I also rebuilt this website from scratch, including a proper portfolio of my work.
Just as much, I got a lot better informed about the history and application of lean: how to think about estimation (and when it’s good versus a waste of time), what it means to truly focus on throughput, and how even old(er) management advice from folks like Deming and Goldratt applies today. I’m really proud of flowmetrics as a way to summarize what I learned, and how lean has filtered into my industry on the back of folks like Vacanti. This was a return to fundamentals, through the lens of experience, and it’s why AlwaysMap LLC exists as a consulting company.
The Monte Carlo forecasts in flowmetrics: when will it be done, and how many will be done in 7 days.
The Job Search #
Through AlwaysMap LLC I did consulting work, including overhauling an engineering hiring pipeline with AI for a SaaS company. When I started exploring the market again, I remembered how much I dislike the mechanics of a job search, so I built an agent to do it and open-sourced it at jobs4me.org.
That search landed me a really great role at a fintech company, for about a month. I like to think I had great impact, and the people are all wonderful. Plus, the solutions to their challenges felt very much Dylan-shaped. It was great to be back in the saddle, so to speak.
In a case of awful timing, my old team at Google reached out just as I was starting that new job. Ultimately my wife and I decided that Google in San Francisco was a case of good timing for our life plans. So my first job was the result of a rigorous and structured search, and the pending Google gig is relationships (and matching skill set and needs!) all the way.
The People #
A lot of the year went into maintaining, refreshing, and building connections, and I’ve come out of it with better friendships and better professional relationships. Some of that is the everyday kind: Signal chats, WhatsApp groups, and one-off conversations with interesting people via LinkedIn. Some of it came from being out in the world: meeting Michael for dinner in Tokyo, almost meeting Nobu in Shibu Onsen, crashing at Jen’s house after a hot day on the bike, and sending James my live location as I flew over his house near Heathrow.
Dinner with Michael was at a neighborhood izakaya. My son wasn’t very hungry, but I was, and Michael had organized an incredible meal. I’ll eat anything once; I won’t be trying shirako again.
The “almost” with Nobu: we spoke on video chat, and then he tried to meet us in Shibu Onsen. The weather was crazy, and he slid off the road, had to recover his vehicle, and turned around to head home. He’s OK, but that’s what the weather was like.
With the pending move back to San Francisco for the Google job, I’ve been reconnecting with folks there, and with my Googler network—in some cases after many years.
None of this is “networking” in the career-advice sense. It’s human connection, and even for someone who typically keeps a small and curated friend group, it feeds my soul. It really is about the people.
Why Do It at All #
A few things I keep coming back to:
- None of this works without the finances to support it, and I don’t take it for granted that we could swing a year without my income.
- Having more stuff is nice, and I like my comforts. But I have so many more experiences and memories to draw on now, and so do my wife, kids, family, and friends.
- It’s all about timing, and this is the big one. My wife and my kids really needed me more this year, even though none of us actually knew it in advance. My family and my relationships won’t wait for me to be ready. The college prep, the health issue, the kids being the age they are right now—none of that was going to wait.
Consider taking a sabbatical when it’s right for you. It will feel like the most magical time, and somehow the timing will work out to be just perfect. You just don’t—and cannot—know it yet. A sabbatical is a gift, and if your career and your finances can support one, I can tell you from doing it twice: I have zero regrets at all. None.
And the balancing act doesn’t end here. The move to San Francisco is complicated: my family will stay in Colorado through June 2027, until the kids are done with school. After twelve months of one working model, we’re on to eleven months that will be challenging in different ways, with different trade-offs and different opportunities. It’s always a balance, and yet another reason I’m glad I took the time.
Making memories at Terry Bison Ranch Resort, Wyoming.
P.S. Thank you Maria. Twenty years in and she’s still my rock and my best friend. She makes it all possible.