Four Great Decisions per Year

Spontaneous, not Forced

Created using Midjourney

You only need to make four great decisions per year. 

The first version of this idea I heard was attributed to Peter Theil as advice for founders and CEOs. As the head of a company, you only have to make one big great decision per quarter, and the company will be on the right track. 

I’m not sure if he actually said it or not. I can’t find a source. But the idea stuck with me. 

When you reflect on the last few years of your life, how much has been determined by a few great decisions? 

To commit to, or separate from, that one person? 

To start, or quit, that job or business? 

To focus on, or deprioritize, that area of your life? 

Four decisions per year might even be too many. I can capture the major inflection points in my life in one or two choices each year. 

It’s obvious when I zoom out like this that slowness, patience, and giving great opportunities the time to bubble up has slowly compounded into a life I’m extremely grateful for. But in the day-to-day rush, it’s hard to keep this in perspective. It feels like we need to always be doing something, deciding something, starting something, changing something, or scrambling frantically across the Internet in search of whatever piece of information will salve our frenetic anxiety of the day.¹

But if one to four great decisions per year is all it takes, when and how do we make one of these decisions? Each decision is a change, a reaction to something in our lives that kicks us out of the steady track we’ve been on. And those decisions seem to arise out of two circumstances: 

First: Something in our lives is not working and needs to be changed. 

I can see this in pursuing entrepreneurship after realizing how miserable I’d have been in a corporate job. 

Cosette and I’s relationship wasn’t working for the first two years, so we decided to stress test it and determine if we wanted to be together.

The Medley was getting boring, so I started this blog instead. 

We often need some sort of stressor that we keep struggling against to make us say: “something needs to change here.”

Second: We’re suddenly presented with a new opportunity we hadn’t previously anticipated.

I started blogging and content marketing because I was a decent writer, and it seemed like a quick way to make money while I figured out entrepreneurship. 

My first job in Austin, the first time I sold SEO work, and starting Growth Machine all came from other people approaching me for help and me realizing there was a bigger opportunity there. 

Getting into crypto in 2021 was a lucky combination of being suddenly underemployed and the market starting to rip. 

But perhaps the best decisions arise from a combination of the two: a nagging problem in your life that you suddenly recognize an opportunity to solve. 

If that’s what drives the best life-changing decisions, then we might be approaching goal setting, lifestyle design, and self-improvement incorrectly. 

None of the major decisions that have shaped my life were lengthy deliberations. They were each slowly building momentum for months or years, and then the decision was suddenly obvious. A certain amount of energy had built up behind it in my subconscious until one day, the dam burst, and the choice was clear. 

We clearly cannot sit down and decide to make life-changing decisions. They seem to pop out of our subconscious in moments of surprising clarity. 

If you are constantly trying to find yourself or change your path through retreats, conferences, books, podcasts, or TikToks, then you might recognize on some level that you have a thing that needs to be changed, but if the answer isn’t obvious, then maybe it isn’t time to change it yet. It might be more productive to take long walks without headphones and finally give your subconscious the space and quiet it needs to process instead of constantly inundating it with new lists of goals and inspiration.² 

Considering how many great ideas seem to pop out of nowhere, it may even be harmful to attempt to force yourself to make one of these decisions. You might be better off asking yourself a question like “what would make my kids proud?” in the morning and then try to be extremely bored for the rest of the day.³ That will kick off many more great ideas than any structured exercise because the good ideas come from that spontaneous fermentation of experiences inside you. 

And maybe you don’t need to do anything at all right now. If you’re constantly making big decisions, those decisions will never have time to compound into anything meaningful. Most of the time, you should just be following through on the big decisions you already made.

Four, two, or even one a year is certainly enough to lead you somewhere interesting over the decades. 

You just need to create the space for those decisions to appear. And once they do, follow them through until it’s time for the next one.

1. See also: Addicted to Speed

2. Another framing of the idea that you need a more internal Locus of Entertainment

3. If you don’t have kids, my other favorite question is, “what would an 80-year-old me regret not doing?” I also like the questions from “When the Money’s Just Too Damn Good” and thinking about if you might have it backwards.