How Do You Make Life-Changing Decisions?

First, you get rid of the notion that anything about your life is really at stake. Whatever happens, you’ll be fine. You’re not deciding whether to opt for chemo or not.

That is to say: calm down. We, the young and ambitious, deal almost exclusively with rich white people problems. We’re not going to starve if we make the wrong decision.* There is very little we can’t undo.

Of course, that doesn’t make life-changing decisions any less intimidating or take away the fact that the adults in our lives did next to nothing in the way of preparing us. I think that’s why since I dropped out of school (and wrote about it as it was happening) people have been coming to me as though I have some special insight on making these kinds of calls. Since I did it then and have done it several times since, they think I know the secret. I don’t, but I do have some tricks.

When I get these emails I almost always ignore the specific details and respond with a few simple questions. Stuff like: “What’s the absolute worst thing that could happen?” “What would you miss out on if you did it?” “Are you fighting for a piece of a shrinking dying industry or are you getting something whose value will hold up over time?” I never tell them what to do. I just pose questions.

These are no rhetorical questions, though I am sure they seem that way to someone just looking for advice. I intend for the person to answer them. Think about like a math equation for a second. It seems like a jumble of symbols and unknowns at first, but when you stop, breathe and break it down, the process basically takes care of itself. Isolate the variables, solve for them and all that is left is your answer.

Answer the questions and the right choice becomes clear.

This strategy gives you the single most important tactic when you’re trying to make life-changing decisions:

Get information, not advice. See most people—no matter how wise or successful—give horrible advice. They’ll send you astray. So don’t ask for advice. Ask them for information that you can translate into advice.

Isolate the various issues that will influence your decision and then ask people about that. By zeroing in on specifics rather than the big picture, you avoid the trap of their (distorted) picture. Simplify your decision into [If this] then [x] or [If that] then [y]. Then use the smart people in your life to help solve for the variables.

It’s the difference between asking: “What should I do?” and “Do you know anyone who ran into problems taking some time off from school?” To me, this difference was the world. I asked the latter question to someone when I was dropping out and their answer was brilliant. “Problems?” he said, “I got really sick when I was in college and had to spend a year in the hospital. Do you think that matters at all to anyone 20 years later?”

So try it: What is the worst thing that can happen? Well, it could cost me some money. Ok, well money is replaceable so that’s a stupid reason not to do something with so much potential upside. Is this a once in a lifetime opportunity? Yes. Really, never again? I don’t know… Then you haven’t thought about this enough. And so and so on.

After that, this is what else is important:

• Think about where you want to go, back out your decisions from there. Let’s say you want to be a politician way down the line. Well, what does the biography of a politician look like? Probably some military service, success in the private sector, multiple degrees, clean private life, good connections, rich benefactors, a public profile, one or two key (untouchable) stances, sense of style, etc. Ok, now when you make decisions all you have to do is ask yourself: Does this help me check off any of those boxes? If it doesn’t, it’s probably not the right thing to do.
• Remember to consider opportunity costs.
• “Enter Action With Boldness” and sometimes, you may have “Act Before You Are Ready”
• It doesn’t matter how much other people “get” you, they’ll never fully understand your aspirations so don’t go around expecting them to. It’s too hard for them to see past their own experiences. Prepare to be misunderstood, both when you ask for advice and when you finally take action.
• Scared about making the wrong choice? You won’t ever know if you did. Cognitive dissonance won’t let you.
• Strategy is a matter of options. Generally, the aim is to act in a way that leaves as many possible options open as possible (remember, opportunity costs). Keep this in mind as you make your decision. What gives me the most options? What gives me the most freedom and creates the most opportunities? Do not discount the things you do not yet know are important.
• Books. Books. Books. People have been doing [whatever it is you’re deciding about] for a while now. They’ve been moving West, leaving school, investing their savings, getting dumped or filing for divorce, starting businesses, quitting their jobs, fighting, dying and fucking for thousands of years. This is all written down, often in the first person. Read it. Stop pretending you’re breaking new ground.

Finally, don’t feel guilty for asking for help. There is NOT A CHANCE that the successful people you know today didn’t rely on the successful people they knew in order to get where they are. That’s the cycle. It’s why I respond to these emails and do my best to walk people through it however I can. So if you don’t have anyone else to ask, you can also come to me as a last resort. You know where to find me.

 *When I made the decision to leave my life behind and write my book, I asked Tucker: “Is there anything I should be worried about when I’m doing this?” His answer: “Nothing about any of this should worry you. It’s all upside.”