On Retiring from Tech

“NOT Working From San Francisco”

The software industry in the United States is certainly a lucrative one. I’ve been fortunate to have worked in many great companies and with many great teammates – and I’m beyond grateful to everyone for helping me get to where I am now.

After 10 years of working in software product management, I realized I’m at a point where I can comfortably pursue other interests and develop other skills. Here I’ll walk through my thought process and hint at what’s next…

The lead-up

I’ve always had a bit of a love-hate relationship with the tech industry. On one hand, I believe strongly in the power of software to improve lives and create limitless opportunities. On the other hand, our industry has a tendency to generate negative externalities and augment some of the worst human behaviors when misguided. I rationalized this in my career by avoiding the sectors I found morally questionable and staying focused on delivering value in my area of specialty – relatively harmless productivity software. ☺

Our industry is also known for not solving enough real problems – ones affecting the broadest base of people and on the lower levels of Maslow’s Hierarchy of Needs.

Safety – is there an app for that?

Despite knowing all this, I continued working in my field for several key reasons:

  1. Skill: My educational background is rooted in software, and it’s not clear what other options I had where I could have performed as well.
  2. Money: As mentioned, this industry is extremely lucrative, particularly at pre-IPO companies that grant equity…
  3. Passion: I derived a lot of meaning from my craft, and I always got a thrill out of shipping experiences and delighting customers.

The end of October 2019 was technically my 10-year anniversary as a full-time Product Manager, and it was a great milestone to pause and reflect on my career thus far. So what has changed?

Peak of Skill

I’m not saying I’m the best Product Manager in the world (far from it!), but I definitely felt that I was reaching the limits of where I could go in a role that I would want to be in. I never had any interest in becoming a people manager, and there were very few opportunities I could see myself growing in as an individual contributor.

More importantly, the skills that I want to develop for myself have changed – and they are no longer tied to software product management. In fact, stepping away from this career may be my only path to continued personal growth.

Less Need of Money

This may sound ridiculous to many folks, but money has never really been high on my list of values. My discretionary spending is limited to budget travel, experiences, supporting my family, places to live, and charitable contributions. Beyond that, I live frugally and save aggressively – a way of life I learned from my upbringing and the FIRE movement.

Typical budget for a month (fortunately all mortgages are covered by rent)

The tech industry has been blessed with abundance over the past decade, and I will forever be grateful to have shared in some of that wealth creation. That being said, I have no intention nor compelling need to become a billionaire here – there is a sense that I now have enough.

Finding New Passion

I’m still passionate about software, but over the years I have developed several interests outside of this sphere. Some of those interests have clear paths to becoming whole new careers, with arcs similar to my product management career. The prospect of exploring these paths has now become more exciting to me than product management itself, a revelation both exhilarating and nerve-wracking.

Knowing that the average person has about 2-3 careers in their lifetime gives me conviction to do this exploration. Not sure I’ll make it to three (life is short!) but I know I want to at least try my hand at a second.

Next Steps

By December 2019, it was clear I needed to make a move. I made preparations to leave my job and created a plan to structure how 2020 would go. Part of the plan was this announcement to hold myself accountable. 😉

I’m not yet ready to share my longer-term plans as I’d like to get a few more pieces set in place first. However, I expect most people will be able to guess what I’m exploring based on my previous posts

For the next few months though, my priorities are clear:

  1. Rest & relaxation (it is a retirement after all!)
  2. Getting my house(s) in order, financially speaking
  3. Preparing my taxes (it usually takes me ~3 weeks)
  4. Catching up with friends & family – feel free to reach out if you want to learn more!

When I look back at my tech career, I am filled with both pride and gratitude for all the experiences and learnings. Not saying that I’ll never go back to tech, but now is the ideal time for charting what my second career could be.

Retirement is an accomplishment, but too often it is seen as the end of the road. To me, it is just the start of another – to new beginnings! 😁

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