itshalfempty

Yesterday was my last day at Square. I thought I’d write a little about why I decided to leave - if nothing else to serve as a reminder for myself when I inevitably question myself in a few months.

I worked at Square for just over 4 years, and I served in a number of roles:

• As team member on a payment engineering team
• As an interim manager for that same team for a year
• As a member of an engineering tiger-team focused on identifying and making long-term improvements to payments
• As the Tech Lead across payments

It was a wild ride for me. I had never before worked on software as critical to a business and customers. Going on call for the first time was nerve wracking. Being aware that every minute of downtime cost the company (and our Sellers!) a lot of money was both a source of constant anxiety and a huge source of job satisfaction. In my time at Square, I focused a lot on reliability across payments, but also on reliability across the entire product ecosystem.

In many ways, my job at Square was my dream job that I have worked hard to get over the course of my career, and the decision to leave was not an easy one. Ultimately, it came down to several factors.

1. Life

To say I’m a workaholic would be an understatement. But my wife has also become a workaholic. I don’t know if I am the culprit, or if her career growth led her to the same destination as me. But either way, with both of us so focused on our careers, it’s made our day-to-day life a lot worse.

For the past few years, we’ve kicked a lot of things down the priority list, like house projects, planning vacations, building a social calendar, and so on. We both don’t like that we are frantically researching what to do on a vacation while we are traveling to our destination. Or that we’ve done very little on our house post-covid. Or that we end up eating out more than we eat at home.

It got to a point where we talked about moving to a new house that is upgraded and problem-free, or hiring a personal assistant, or maybe even a personal chef. And while we could those things….why? We’ve both done a pretty good job of minimizing lifestyle creep, and that would be a huge step in the wrong direction. Besides, I actually enjoy doing everything on that list - especially when it doesn’t feel like it interferes with work.

We’re fortunate enough not to depend on my income, so why not have me step away from my career for a bit and learn what’s its like not to pour 110% of my time and mental effort into a job, while also catching up on everything we’ve been putting off for years.

2. Community Service

I got involved in a lot of community service in high school, in part because that’s just what you do to flesh out a college application. But that didn’t really stop when I got to college. I was a member of the Residence Hall Association at Georgia Tech and not only helped plan and run events for my local hall, but I was pretty heavily involved in the larger RHA community across the campus. I also organized and ran a collectible card game club at Tech, and ran Friday Night Magic for a card shop.

When I left Tech, I joined the Civil Air Patrol and the Yellow Jacket Flying Club. But I dropped everything as my career as a software engineer picked up.

I realized earlier this year how much I missed those kinds of activities. Aside from being around a bunch of people who are decidedly not in the software world, it was a great way to foster communities. Nothing about my career really forbids me from participating, but it’s not something I felt like I really had the mental capacity for – and the day-to-day demands of my job definitely would make it hard to be as engaged in some activities as I’d like to be (you know, because I’m a workaholic).

3. Purpose

Something I’ve learned about myself is how important the mission is to me. At the end of the day, what you’re trying to solve for determines the optimal way to do everything - organize people, operate an organization, build software, etc. But even more important is how much good to society as a whole you are providing.

I vividly remember a conversation I had with someone many years ago. I asked them something along the lines of, “what is the purpose of this company? What are we trying to do?” They responded pretty immediately, with a chuckle, “to make money.” And while that’s technically the correct answer for any for-profit business, that never really sat right with me.

Ultimately at Square, I felt like Alyssa Henry helped create a clear shared understanding of Square’s goals and purpose across the entire organization. Since taking over, in my opinon anyway, Jack Dorsey has not. I feel like that is evident across the entire organization - with mismatched priorities and the lack of a clear framework to understand what is important and what isn’t. What I do get is a clear understanding of is how important the Rule of 40 is for Block, and how specific projects and initiates will help us reach those financial objectives.

Financials are definitely important, even more so for a public company. And maybe my perception is muddied even more by the fact that Square’s product is inherently to help companies make money. But at the end of the day I just didn’t find myself motivated by what Square and/or Block are trying to achieve.

4. Bitcoin

Jack has long been an outspoken supporter of Bitcoin. Block has several business units focused on Bitcoin-related products, and CashApp is a very popular platform for consumer purchases of BTC. I was able to compartmentalize those aspects because they weren’t part of Square, but both with Jack’s leadership of Square and the dissolution of Business Units, it’s hard to imagine a future where Square continues to stay out of the Bitcoin world. Whether consumers ask for it or not, this is just not the future I want to see, nor do I want to help enable it.

I don’t know if I would have joined Square 4 years ago if I knew how influential Jack was in the Bitcoin space.

The future

This has been one of the rare moments in my life where I’ve made a big decision without a full plan. I have a fairly loose outline for what the next few months might look like, but it’s all question marks beyond that.

In the shorter-term – I’ve already re-joined the Civil Air Patrol and I do plan on spending time getting trained to participate in Emergency Services missions. That said, I can only progress so far on my own, and my ability to get trained will be bottlenecked by the availability of training opportunities.

I’m also planning on getting my private pilot’s license, and maybe continuing on to get my instrument license. It’s something I’ve wanted to do for a long time. I got about 20 hours of instruction over a decade ago, but it was one of the things I dropped when I became very career-focused.

I also plan to establish some habits in my daily life, including spending more time outside, playing piano, and maybe learning a (non-programming) language. I’ve done all of those very sporadically over the last few years, but I think it should be a lot easier to build and establish the habit when I’m not feeling the pull to get on my computer and get to work at all waking hours of the day.

In the longer-term though, I’m not sure what I’ll do when I decide to resume my career, nor do I know when that might be. I think I’m content right now to kick that decision down the road a bit longer, and maybe just collect a list of possibilities that sound appealing.