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.
Whenever my young or old friends tell me they are getting married, I just say "good luck, you'll need it." "Congratulations" would be dishonest. Half of all marriages fail in a few years, half of the remaining half are stuck out of miserable loyalty or "for the kids." In my 70 years, I have met very few of the remaining fraction. So, good luck, dude.
Looking at your list, it's hard for me to connect that to this statement, "Around half of mine were time sensitive and would have been more difficult or impossible if I deliberated too long." I don't see a one that had time pressure. In my experience, most people screw up when they allow emotions into a decision. That makes for quick, unrealistic, irrational decisions. I often go to the decision tree system, quantifying the positives and negatives of a decision and, once I've done that I stick with the numbers for the decision. If it isn't strongly positive, I pass.
How'd you move away from strong anti-marriage views learned in pickup, and how does marriage benefit you?
Tynan, I agree with much of what you say, but question the pickup bit helping you keep such an amazing woman. I’m not familiar with your pickup work, but I like to think that you are able to keep such an incredible person in your life because of who you are. You are a good person. And authentic. Plus, you have interests that pair well with hers. I will agree that mastering pickups helped you gain confidence. But it only goes so far...
Interesting to see the criteria in which you define "biggest" decisions. I deduced:
And it looks like it can't just be one of those. Surprised to see "starting a business" not in there, as well as "marriage" being in there.
I do hesitate to extrapolate too much from your mentality "acting fast" versus "not acting at all." I think a lot of this is particularly suited to your highly nonconformist, entrepreneurial and analytical mindset. Frankly, most people are not this.
I do agree that many people would benefit immensely from this, but many would probably also suffer immensely from this. They may not have the same skills or temperament to rebound from failure as you do. This tends to be a problem with self-improvement advice: what worked for Tony Robbins actually worked for Tony Robbins - it just may not necessarily work for someone else. Said otherwise, I can't disagree the advice (on the whole, I completely agree), but I do think it requires a little footnoted disclaimer.
Last night I was in the Las Vegas airport, waiting for boarding to start on my flight. I went there an hour early because I didn't have time to play poker, so I figured I could get on wifi and get some work done. I knocked out a couple small SETT bugs, and then remembered about getgoing.com, the YC-backed discount flight site. The way it works is you pick two deeply discounted flights that you'd be willing to take, put in your credit card, and getgoing picks one for you. You don't know where you're going until after you've paid. When I first got invited to the site I mucked around with it and found some really great fares to both Beijing and Shanghai.
Maybe I should go to China, I thought. Twenty minutes later my flight to Shanghai was booked.
I like making impulsive decisions like this. My past is filled with them, and none that I can think of have ended in regret. Actually, if I were asked what I thought my biggest strength is, I would probably say that it is making good decisions very quickly.
I wasn't always good at making quick decisions. Twelve years ago I had the opportunity to fly on the Concorde for $1000. It was usually over $10,000 round trip. I really wanted to do it, so I called a few friends to see if anyone else was interested. There was some hemming and hawing, but no one was ready to commit. Well, I thought, I'll wait until tomorrow and buy a ticket then if I still want to go. The next day came and the deal was gone. Now the Concorde is decommissioned and I'll never have the chance to ride it. Strange is it sounds, this is probably one of the bigger regrets in my life. I really wish I got to ride the Concorde before it folded.
We are planning creatures. We plan our weekends, vacations, and lives to a greater or lesser extent. Some of us pick out every detail and polish perfectly while others are on a plan that involves not having any plan. We build our time so that we can get the most out of it. On weekends we structure our time that we might do what we want to do and get done what must get done. On vacation we plan to see new things and plan relaxing activities. For life, we plan where we will be in five years, ten years, etc.
"The plan" has been one of the biggest things in my life. As a young person I feel that everyone really wants to know what your plan is. Where are you considering going to school? What are you studying? What do you want to do with that? What do you want to do with your life?
These are all big questions and it sounds quite nice to have big answers. Yet, for all of our planning nothing is more certain than the fact that something will go wrong. There is an issue in planning inherent to the fact that things are ever changing. I had the firmest of plans to go to law school after I graduated from college, but I didn't anticipate an intense feeling of burn out. I had a plan all lined up and everything that I did was able to be tied back to the plan.
I had my eyes on the prize yet I, as many do even with plans of lesser severity, got tunnel visioned. Frankly, I had tried too hard and ignored my limits. Like a guy in a bar defiantly having a good time I went past my limits without even realizing it and found myself sitting, wondering why things just wouldn't fit with the plan. Yet the thinking in that is backward. Life will never fit your plans. Plans can, however fit life. Life is in constant flux and so too should be our plans.
I had a friend in college who got a lot of guff for being a planner. She would thoroughly plan her weekend, picking out the interesting stuff to do around town and building a group with whom to do it. When it came time for the festivities she lead the charge, but sometimes the charge did not happen. People would flake, things would change, and plans would fall through but that was not a problem.