13. Living With The Consequences

The biggest decisions of my life never felt like choices.

That’s a weird sentence because it seems to break everything I believe about deciding. When I look back at the forks that made my life, I don't remember standing at them. I remember being partway down one road and understanding—with something closer to recognition than decision—that I was already on it.

The clearest one is leaving New Zealand. I had it sweet there, and I mean genuinely sweet. Mountain biking from my front door, sometimes at lunchtime from work on legit single track. Kids who walked themselves to school. Work I liked, senior enough to matter. Great friends. Family close. If you sat down to design a life for contentment, it would look a great deal like the one I had. There was no problem to solve. Nothing was wrong. And that's exactly why no list of pros and cons could ever have decided it. Staying and going were really two different people.

For a long time this pattern bothered me. If the biggest decisions never felt like deciding, what exactly was I doing? Chasing that question is how I ended up examining my relationship with regret, and with the stories I tell myself—and those two things, regret and stories, are where this whole part about decision making has been heading. Because you're about to hand more of your deciding to machines than any generation of humans has handed to anything, ever. And regret and stories are the two parts of deciding the machine cannot live for you, no matter how good it gets.

So I want to take them in order.