38 and Grateful

It’s been a while since I’ve written an update – 2.5y! – and a long time since I wrote very frequently. On top of all the crazy ways the world has changed in the last five years, a bunch has changed for me personally in the last five years as well, along a bunch of different axes.

I think part of the reason it’s been hard to post is wanting to avoid coming across as bragging about the high points of this journey and also not really wanting to admit some of the low points, but I feel I’ve had a lot on my mind that doesn’t really make sense in blog form without the greater context; I’ve decided that I’d rather just share a lot of what’s been going on in the hopes that some part of it is relevant to someone out there or gives them some fortitude for whatever low spot they’re going through or can learn something from it.

In neither increasing nor decreasing importance — or, both, if you’d rather! — some of these changes and some reflections on them:

1. became an engineering manager of my team at Square, got overwhelmed and burned out, and returned to life as an individual contributor. This came along with a bit of a roller coaster in job level, from over-performing L6 IC to underperforming L6 EM back to L6 IC to principal at a new company to “member of the technical staff” somewhere else to L7 IC back at Block. I learned a lot about making technical decisions that impact an entire engineering department, a bit about what business-to-business software sales looks like, and perhaps not quite enough about how to run an effective team.

2. left San Francisco, returned to Illinois, and bought a house. We live in a Chicago suburb called Glenview, a former naval base “village” of 50k people with pretty easy access south into the city or north to Wisconsin but with tons of forest preserves, parks, and gardens. It’s hard to measure up to SF’s incredible Golden Gate Park & Bridge & the Presidio and Twin Peaks and Muir Woods and the Pacific and Highway 1 & all of the greatness that is California … but the move also affords us a quality of life improvement that would have been hard—or outright impossible!—to attain in SF or the Bay Area. Home ownership has been completely overwhelming at times (I’m thinking of when we thought we had bats or of all the work we did this summer), but 2020 seems to have been an objectively time to buy. I’m proud of how we’ve really made it our home and how it has become a destination for our families and think it’ll serve us well for a very long time.

3. left Square to join a small fintech startup (which granted me the principal title but I abandoned after two rapid-fire “RIF”s that I wasn’t a part of, but significantly changed the outlook of the company as a whole), and then a small infrastructure startup (which laid me off), and then came back to CashApp to work on fraudsy things. Getting laid off was immensely humbling. Coming back to Block has also been very humbling in a pretty different way, just trying to wrap my head around the massive scope of this thing that’s 20x larger than when I first joined in 2014 and the dizzying amount of different things a 20x larger org can do.

4. let my alcohol intake get out of hand, had a moment of clarity, and have systematically removed alcohol consumption from my life for the last (nearly) two years — 663 days as I’m writing this. I’ve made a lot of friends that did the same and motivated at least a couple people close to me to also cut back. Perhaps interestingly, the layoff happened after the sobriety journey started; turns out that processing feelings and emotions when out of practice is pretty exhausting… especially when also abruptly terminating ADHD medication.

5. ventured into residential real estate investing with two small multifamily properties, then added property self management when my PM company gave notice 2, then took on a commercial office building to work out of. I now self manage 7 apartment units and 30 office suites. This was intended to be a diversification away from the tech industry at peak burnout, but it turns out there’s a fair bit of joy from the tangible nature of operating and improving these properties that really balances the abstract nature of software engineering. It has also been pretty capital intensive to get into & even more so to operate, especially when still climbing the learning curve — I’ve spent a lot of money making these improvements and I’m not sure I’ll really see a great (or any) ROI on it for a long time, but at least I’m a bit more proud of my assets.

6. Traded in the KLR 650 for a KTM1290 SAS, rode it with Paul while social distancing on the deserted California highways of Covid. When we moved to Illinois, I bought myself a pickup (still my daily), then a porsche 911 (which I eventually gave up), then a subaru wrx sti (project car). I’ve taken the 911 and the STi to Grattan Raceway for three autocross track days, once each solo, with my longtime mate Beals, and with Allison).

7. became a dog-dad to a labradoodle named Ripley in 2021, then a double-dog-dad to Karma (the sweetest goldendoodle ever) in 2022, then a human-dad to my son Ryan. Ryan just turned 1 and seems to be growing every day. We adopted Karma in part trying to keep Ripley occupied – she makes focusing on work objectively harder – but it turns out dog distraction scales nonlinearly. Oh well… who else is gonna drag me all over the neighborhood?!

8. let my weight get out of hand, started on Zepbound, and lost around 40 pounds. This is one of the more recent changes — the last 6mo or so — but my blood pressure and several blood of my lab test values have all already improved pretty markedly.

9. Spent time with Allison in Lake Tahoe & Lake Geneva, spent one week in Joshua Tree & another in Maui. We drove across the country from SF to Illinois and we took a family jet-boat tour of the Snake River in Washington. I flew to Utah for motorcycle trips twice, drove solo from Chicago to Louisiana to meet Karma, attended a Christmas on-site in NYC, and a real estate seminar in Scottsdale.

I’d really like to dive into each of these deeper, but that’s going to be another – or some more – blogposts in the future. Stay tuned!

Phew – writing this out makes it feel like quite a lot. I don’t think I could have foreseen ending up living this exact life 5 years ago. Allison and I often joke about (or admit to) “throwing ourselves/each other into chaos”, and we certainly have… but that seems to be how to push your own limits and understand what you can really accomplish!

I’m very grateful for what the chaos has made me: a father, a bit healthier, a bit less busy at work, and a bit busier at life.