The Pirate Life

I’ve been drawing a lot of inspiration from Steve Jobs recently. One quote that’s been bouncing around my head quite a bit is this one from 1983:

“It’s better to be a pirate than to join the navy.”

I’m sure there were many meanings tucked away inside that simple phrase, but the story I’ve seen attributed to Andy Hertzfeld (who was at Apple in 1983) centers around resisting the bureaucratic nonsense that was increasing in the Mac group at Apple as they were growing. Don’t give up your scrappy, win-at-all-costs, counter-culture identity just to conform to “the system”.

That message resonates with me.

I’ve always been a little resistant to bureaucracy or extra process. I’m much happier when I’m able to focus on getting the job done without the need to check extra boxes or jump through hoops. To build on the Navy metaphor, there’s a time and a place for that sort of process and chain of command. How is an aircraft carrier going to operate safely, smoothly, and efficiently if no one is handing down orders? Without some process and structure, there’s no guarantee all of the stations will be manned or all the jobs will be done.

But if you’d rather have more control over everything that goes in to manning the boat, it may be better to be on a smaller more scrappy boat, or as Steve Jobs put it: “be a pirate”.

Time to be a Pirate

When I wrote about joining Apple at the end of last year, I had no idea I’d be writing this followup post so soon, but I’ve made the difficult decision that it’s time for me to leave Apple and be a pirate again.

I’m not leaving Apple for any one specific reason, but I do want to touch on a few things that led to my decision.

Remote Work

I’ve worked on distributed teams for over six years, and while I was originally planning on relocating to Austin, Texas to join part of my team later this year, half of my immediate team would have been distributed at other Apple campuses around the world. I was looking forward to continuing to embrace distributed work while being colocated with some of my team in Texas.

However, over the last eight months, many things have changed that caused us to reconsider whether moving was the right decision. I won’t go into all the details, but by the end of our deliberations, we felt very strongly that it was no longer a good move for our family.

I discussed the situation with my manager and although he was sympathetic to my circumstances, Apple has taken a stance against new remote work exceptions for anything other than approved medical exemptions. Since my reasons were not medical, it was decided that I would not be able to continue in my role without relocating.

The Pirate Life

Apple works at a scale that few companies on this planet ever have, and being a part of that massive operation is a huge learning opportunity, but there are also trade-offs. In many ways, Apple is the Navy now: tons of process, a massive number of people involved in most projects, high communication overhead, and much more.

When the decision was looming and it started to look like we’d decided against relocating, the potential of returning to the pirate life was invigorating to me. I thrive in work environments where I have a high level of ownership and trust and have the freedom and flexibility to mix work and life instead of being at a desk from 9-5.

As I started to explore new teams and opportunities with those things in mind, I found several that were chasing the same goals and working on some pretty interesting challenges. The pirate life was calling.

Personal Projects

Apple famously doesn’t allow people to work on side projects. In practice there are many employees that take a “better to ask for forgiveness than permission” approach, keeping any side projects (including blogging) to themselves. I knew the rules when I joined, but as the months went on I kept wanting to dive back into projects and work on fun things outside of my day job.

While this wasn’t a major reason for my departure, it was something that added to the pros list of leaving Apple.

Setting Sail

I’ll be sharing more about what’s next for me soon; I’m excited to be joining a great team at an early-stage startup working on some fun challenges.

In closing, here’s a tweet I sent last month that sums up how I’ve been feeling over the last few months as I’ve grappled with this decision:

Sometimes growth is achieved through the process of making your dreams reality. Other times, growth is achieved by letting go of dreams that are no longer serving you.

It’s ok to change along the way and adjust what you’re looking for.

Joining Apple and being a part of the incredible group of people that ship some of my favorite products year after year has been a longtime dream for me. Leaving that dream behind and acknowledging that it’s no longer the right fit for me has been difficult, but very freeing. I’m looking forward to future growth opportunities as I set sail into the unknown with a Jolly Roger on the mast.

🏴‍☠️