Life As a Series of Inflection Points

No matter how interesting my life is — and right now, it’s extremely interesting (I’ll explain below) — it is dotted by occasional inflection points.

Inflection points are points on a chart that mark where a curve changes direction.

But in life, they represent points of distinct change.

I’ve had many inflection points in my life. That’s why I think of life as a story that’s still being written.

So I’ve come to be able to identify them. There’s almost a thickness in the air. I feel like “From here on, things are going to be different.”

On Not Joining the Air Force

The first one of these I ever had was when I decided not to join the military as a kid. I started down the course of joining the Air Force as an engineer. Seemed to marry several things I enjoyed: being a nerdy engineer, having money in my pocket, someone forcing me to get fit, and getting a cool-sounding job.

But the downside, for me, was committing myself to something for nine years (4 years study + 5 years work). I had only recently gained consciousness, as an 18-year-old. I definitely had no idea what I’d be like when I was 27.

I ummed and ahhed about it for months. I went through all the interviews and tests. I passed and was admitted.

On day one, I showed up with a packed suitcase, said “Um… I don’t think I’ll be signing up.” They crossed my name off the list. I went home.

That was a turning point in my life. I had turned my back on structure, and committed myself to chaos. And a life-long commitment it has been!

On Quitting my Job at Lyft

Yes, during my life there have been other inflection points. But that’s a longer story for another day.

My most recent inflection point was definitely the time I decided to quit my job at Lyft.

Don’t feel bad, Lyft… This wasn’t about you. To be fair, the inflection point prior to this was getting the job at Lyft in the first place! (It was actually my first meet-and-greet, with one of your recruiters. You know who you are. That was when I was sure.)

I had been hatching a plan to become a nomadic blogger with my partner for months. I knew my last day, so I decided to resign three months prior, to give myself enough runway to get there.

I quit during a meeting with my then boss. I told her: “I’m leaving. In three months.”

She said: “Are you fucking kidding me???”

This was the best reaction ever. I had no idea what she was upset about! It seemed like she was upset about me leaving, which was nice.

But it got better — on that day, I also won an award, “Employee of the Fortnight”. It’s kind of a big deal at Lyft.

The best part was that I had planned, that same afternoon, on buying a new motorcycle, a Honda CB900F, which I was going to use to tour California before leaving the country.

What a hat trick! Quitting, an award, and a new bike. That day was definitely an inflection point.

Identifying Inflection Points in Life

Once I had been through a few, I began to sense that I could “feel” an inflection point in life.

There’s a palpable thickness in the air when one occurs.

Usually, it’s because I’m prevaricating over something, like moving to another country, changing a career, or starting a company. Something happens that spurs a decision, even if it’s unrelated.

For example, the way in which I decided to leave the US had nothing to do with my actual job. My job was fine. I was well-respected, on an upward trajectory, and found it easy. It was actually getting easier over time, too.

One day, I was offered a job in Germany, working for an old boss/friend, helping with a new, ambitious project. I was quite excited at the prospect, and said yes. I psychologically geared up to leave, and was even surprised to see that my partner was game.

We decided that we were done with San Francisco, where we had many friends, but where high taxation and cost of living mean that you have to make six figures just to break even with a modest life. We were happy to move on.

But then the project fell through. All that emotional preparation for nothing! So we thought: “Well, we already decided want to leave. But now that we’re not going to Germany, we can go anywhere. So: Where to?”

That was the inflection point. We realised we were done with San Francisco, and that it was time for a new project.

Sometimes you do need a kick in the pants, though. Especially in the beginning. Someone I know decided to leave the city they grew up in after a trifecta of signs: a break-up, a job redundancy, and a lease expiry. They thought: “Well, I can take a hint, city.”

But as time goes on, I find that I’ve become more and more used to inflection points.

What Next?

It’s easier to see inflection points in the past, just as it is easier to write career stories retrospectively.

It’s also safe to say that when you’re looking for an inflection point, you’re more willing to notice opportunities. I think of it as beign emotionally ready, and also making sure I’m ready in practical ways to make fundamental changes.

Right now, my inflection point is that I need to get ahead of AI, before it gets ahead of me. I work in media, which means I own media properties and continue to build more.

The threat of AI is that it’ll take traffic from my current sites, and that it’ll make it easier for people to make competing sites, as well.

So I’m trying to immerse myself in AI. If something comes my way, I’ll find it easy to say “yes”. Everything has to change, and soon. I’m just looking for the catalyst to do it.