Making the Biggest Decisions

I wanted to write a post about making the Biggest Decisions. Before doing so, I thought I’d jot down some of mine and look for commonalities. What surprised me most was how few decisions of this magnitude there were. Depending on where I set the bar, I’ve probably only made 10 huge decisions in my entire life. I made the first about 20 years ago, so I make one every two years.

Here are some of what I consider to be the biggest decisions:

1. Dropping out of school
2. Deciding to travel around the world for an extended period of time
3. Moving to Las Vegas (as well as other moves)
4. Living in an RV
5. Focusing entirely on pickup for 1-2 years
6. Getting married

It was interesting to realize how few there were, especially while keeping in mind the enormous changes they’ve made in my life. In other words, they are even higher leverage than I had subconsciously considered them to be.

You may be surprised at some things that aren’t on that list. I consider my group real estate purchases to be relatively small decisions. While they’ve had a big impact, none of them were huge investments or difficult to decide. I don’t count starting or stopping various businesses because I just assume that if I didn’t start CruiseSheet, for example, I would have started something else. And those decisions are also easy.

I’m not actually married yet, so we can discount that one for the sake of discussion. If you’re familiar with my work, though, you probably know about the others. They were all pivotal points in my life that radically changed my results.

It is, of course, impossible to know if any of them were the right decisions. To me they feel like they are, because I’m 100% satisfied with my life and all of them were major contributors. But perhaps if I didn’t travel, something much better would have happened during that time. Hard to imagine, but I would have never imagined my life as it is anyway.

The thing is, this is always how these decisions are. You never know whether you made the right ones or not. It’s important to be comfortable with that, because if you aren’t then you will be scared to make the decisions. Big decisions can be scary, and that’s how they’re sometimes supposed to be. Part of the skill in making these decisions is being comfortable with that discomfort and having faith in yourself to make the best of them.

The biggest mistake I see people make with big decisions, ironically, is thinking too much about them. Around half of mine were time sensitive and would have been more difficult or impossible if I deliberated too long. In the same way that debt insidiously siphons money out of your bank account without you really noticing, excessive deliberating siphons away your years. I think we all know plenty of people who stayed at a job or in a relationship for years too long, or waited years to start a project or make a move they should have done years ago.

If you look at my list, I literally did not take more than a day to think about any of the big decisions I made. I always had it in the back of my head that I would probably drop out some day, but I did it on the same day that I seriously considered it for the first time. I bought my place in Vegas the same day I found it, without even seeing it. Within fifteen minutes of seeing a spot open up in the Project Hollywood pickup house, I committed to move. The first time my fiancée and I talked about getting married in the near future, we set a date three months out.

I tried very hard to come up with a big decision that I consider to have worked out poorly. I can’t think of any. The closest I can come up with are a few investments I’ve made, but overall my investments have drastically outpaced the market and as an ex pro gambler, I know it’s the nature of the game that not every bet will pay off.

I can, however, think of times where I made a mistake by not making a decision fast enough. There were relationships that I knew should end, but I put off by months. There are several businesses I should have started early or ended more quickly.

This isn’t so much about me as much as it is about the nature of these sorts of decisions. With the right attitude and a little bit of grit, I think that very few of what we see as Biggest Decisions actually end up poorly.

In most cases, these decisions fit the mold of having very large potential upsides and very small potential downsides. We are often more scared of the uncertainty of the situation than we are with the actual worst case scenario.

For example, it might be scary to drop everything and travel around the world, but at the end of the day you can always fly back. If it turns out it’s not for you, you’ve paid for a plane ticket or two more than you should have. If it IS for you, then maybe you’ve changed your whole life.

Focusing on pickup was the one from my list that had perhaps the biggest potential downside. If it didn’t work, I would have given up a year or two of productivity. And I would have felt like an idiot, which is probably the more visceral and emotional downside. The upside was enormous, though. While some alternative paths are unclear, I’m completely certain that I would not be in as good a relationship with as excellent of a girl as I am now. I simply didn’t have the skills to find that person, let alone keep her.

A fundamental bargain in life is the trading of discomfort for gain. We all do it, and the most successful among us do it a lot. With the asymmetry of big decisions, having huge tangible potential upsides versus moderate fear-based emotional downsides, it’s important to build the habit and skill of taking the less comfortable path.

Eventually you get to the point where you are conditioned to enjoy the discomfort because you associate it with an eventual reward. This doesn’t happen quickly, but it does happen. And when it does, you make even faster progress because these Biggest Decisions become hills rather than mountains.


Photo is the giant spider sculpture at Roppongi Hills, Tokyo

Sorry for the big delay on the gear post. I’m still waiting on some items and still trying to evaluate a few. It will be worth it! Lots of good stuff this year.

Also, I still haven’t sent out more information and payment requests for Superhuman Event #1 attendees. As you can probably gather, I’ve been extremely busy. I believe the event is full now, but feel free to e-mail to be on the waiting list and I’ll give you a spot if anyone changes their mind.

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