Accidental career
Careers always look much more intentional in retrospect.
Mine definitely wasn't.
Here are 10 moments that, looking back, probably shaped my career more than I realized at the time.
1. Growing up around my mom's photography business
My mom ran a photography business out of our house. My dad had his regular job, but would help her nights and weekends. We helped too.
So entrepreneurship wasn't some glamorous thing involving pitch decks, venture capital, or the word "founder." It was just work.
And through all of it, my dad had a phrase he'd repeat to me: "Work for yourself, son."
2. Working Sunday brunch when nobody else wanted to
When I was waiting tables, everyone hated Sunday brunch. The checks were smaller, which meant smaller tips. But the tables turned over much faster.
Everyone else was optimizing for tips per table. I started optimizing for tips per hour.
It was probably my first lesson in looking at a problem from a different angle.
3. Building Blackjack in Excel
In my first week at PNC, I was tasked with building a working Blackjack game in Excel. The managing director plopped a heavy book on Excel VBA on my desk.
That was when I learned I could just try (and try again) until I made it work.
4. Accidentally shaving a stripe into the back of my head
I was working in investment banking and desperately trying to look like I belonged. Then one morning I screwed up cutting my own hair and shaved a very noticeable stripe into the back of my head.
I spent entirely too much time worrying about what other people would think. In the end, it didn't matter.
An early lesson that other people spend significantly less time thinking about you than you think they do.
5. Moving to Japan to teach English
Investment banking to teaching English in Japan isn't exactly the traditional career ladder. At the time, it felt like I was stepping off the ladder entirely.
I've now lived in Japan for almost 20 years.
Sometimes the most important career decisions are the ones that don't look like career decisions.
6. Trying to build a miniature golf franchise business
I decided Japan needed better miniature golf. Naturally, I wrote a 234-page business plan.
Putter King never became the miniature golf empire I imagined. But it forced me to learn about building products, hiring developers, marketing, customers, and outsourcing. It also taught me that if you're spending that much time writing a business plan instead of talking to customers, you're just playing house.
It failed as a business. I'm increasingly convinced it succeeded as an education.
7. Doing the same Ruby on Rails tutorial 10 times
When I decided to learn programming, I did the same Rails tutorial over and over. The first time, I understood almost nothing. So I did it again. And again. Around the tenth time, things finally started clicking.
There's probably a lesson in there about persistence. Or stubbornness. I've never been entirely sure where one ends and the other begins.
8. A friend buying a pediatric therapy practice
A friend bought a pediatric therapy practice and needed help with technology. I knew basically nothing about pediatric therapy. That seemingly random conversation eventually led me deep into speech, occupational and physical therapy software.
Some of the biggest opportunities in my career never arrived looking like opportunities. They arrived as, "Hey, can you help me with something?"
9. Realizing I needed to learn how to sell
For most of my career, I was much more comfortable building things than selling them.
So I decided to lean into something I wasn't particularly good at. I read Matthew Dicks' Storyworthy. I started writing consistently. I got back on LinkedIn. I took Darren's social selling class. I started putting myself and my ideas out there a lot more.
I'm still much more comfortable sitting behind a computer building something. But I've learned that avoiding the things you're bad at is a pretty effective way to make sure you stay bad at them.
And sometimes the skill you least want to learn is the one your business most needs you to learn.
10. Having my own teammates stage an intervention
I literally wrote a book called The Problem-First Method about understanding problems before jumping to solutions. Then my own teammates had to tell me I was jumping to solutions too quickly.
Turns out writing the book does not make you immune to the problem. This was both humbling and objectively pretty funny.
Looking back across all of these, there are probably three things that have helped me more than anything else.
1. Having a memory like a goldfish
There are plenty of downsides to having a terrible long-term memory. But one benefit is that I'm pretty good at forgetting when I screw up. Mess something up. Feel bad about it. Learn something. Forget about it. Move on.
2. Hard work
Yes, work smart. But somewhere along the way, "work smarter, not harder" started sounding like you shouldn't have to work hard. Sometimes you do.
A lot of the opportunities I've had came because I was willing to put in the hours when something mattered.
3. Not worrying about whether something was officially part of my job
If something needed doing and I could help, I generally just did it. I didn't worry too much about whether it was technically my responsibility, whether it was in my job description, or whether someone had explicitly asked me to do it.