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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 do 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 decision 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 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 peopleno matter how wise or successfulgive 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 ask then 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.”

You Won. Now What?

March 14, 2012 — 21 Comments

To readers of PaleoHacks, Lifehacker, Get Rich Slowly, 37 Signals, StevePavilina, Quantified Self:


You’ve found the perfect…

[diet, productivity system, way to save money, workflow, source of inspiration, regimen]

You’ve done it. We all agree. Now what?

Remember, it’s bad strategy to go past the mark you aimed for. When we look at our health, our money, our productivity or anything else that takes our time and energy, the metric that matters is ROI. Nature has given us a wonderful guide to help with that: the law of diminishing returns. Yet, you stuck with it long past then.

You spent so many hours slaving over improvements at the margins. So many pedantic debates on the internetbecause you had to be right. How much time did you spend trying to be a better person? A better father? A better friend? You know definitively whether legumes are good for you or not, but whether you are good or not remains less clear.

What should you focus on instead? Start with the things that matter: Philosophy. Empathy. Goodness. And from there, proceed to basically just about everything else. You know, stuff that matters.


Return to Philosophy

March 4, 2012 — 33 Comments

I have written this post before, but it remains a common theme. The busier we get, the more we work, and learn and read, the further we drift. We get in a rhythm. We’re making money, being creative, we’re stimulated and busy. It seems like everything is going well. But we drift further and further from Philosophy.

So we must catch ourselves and return to it. Pick up Meditations, Seneca, Plutarch, Hadot, our notecards of quotes and reminders or, anything from the shelf of “Life” books. Stop and evaluate. Read something that challenges, instead of informs.

No matter how much learning or work or thinking we do, none of it matters unless it happens against the backstop of exhortative analysis. The kind rooted in the deep study of the mind and emotion, and demands that we hold ourselves to certain standards. We must turn to the practical, to the spiritual exercises of great men and actively use them. It’s the only way we’ll get anything out of the rest of our efforts. It’s simple: stop learning (or “working”) for a second and refine.

Put aside all the momentum and the moment. Tap the brakes. Return to philosophy.

You’re Not a Genius

February 22, 2012 — 39 Comments

Your most self-destructive impulse: believing that thing it took you two seconds to come up with was a genius idea. That you’re some creative mastermind who can brainstorm gold. Get over it. The first thing that pops into your head is not revolutionary. It wasn’t, it couldn’t be. So we hold ourselves back when we fall in love with the narrative that we will walk into a room full of people who have done this longer than we have and dazzle them with our ideas. Or not even ideas, but dazzle them while spitballing.

I wish it was cool like that, but it never seems to be.

No. Contributions come from taking the time to develop a deep understanding of everything at play and more often than not, coming up with gradual improvements and suggestions. They come from the rigor and discipline of really knowing something. Half your ideas get thrown away. More than half deserve to be thrown away. Maybe there is some vaunted genius out there whose every thought is mind-blowing but that person is not you.

This bitter little pill does not change another hard reality, however: most people accepted ‘the way things have always been done’ with equal flippancy. Whatever is wrong or broken about the field you’re working in probably will be incredibly and instantly obvious. That is, you are not a genius but most people and practices are really dumb. When you can wrap your head around that paradox, you’ll have the whole package.

The key to doing it is this: trust your instincts as you survey what’s wrong, ignore them as soon as what they tell you starts to make you feel superior. Make your evaluations but shut your mouth. Why replace flippantly accepted ideas with new flippantly created ideas? Think about your idea for more than two seconds. Don’t fall in love with the image of you as the artist or the wunderkind or the hired gun or intuitive expert. These are chimeras.

What you can be is the person who gets things done, the person whose ideas are better. And changes people’s minds, slowly, over time.

The Next Step

February 11, 2012 — 36 Comments

The first level is easy. You get a sense for what people seem to do. That this guy will make himself the center of attention. Or that he needs you to know how smart he is. Or whether status is important to them or whether they value freedom or being loved or being in control more than other things. Or you see that they’re the type to set themselves up to fail. You become hyper-aware of patterns of behavior. You uncover their inner-motivations and anticipate the results. Read them, know them, outmaneuver them. It is a powerful ability that comes with all sorts of advantages. People might even pay you for it.

The second level is harder. You think about why they act that way. He needs to be the center of attention because it was hard having parents who didn’t seem to care. Maybe she wants you to know how smart she is because nobody ever thought she was. Maybe they want status because they think it will get them what they want. Or they like control because it feels so different than how they felt at a point in their life when someone should have been looking out for them but fell down on the job. But instead of exploiting this like you did at the first level, at the second level you understand it. You begin to see them for what they really are: a human being. A human being doing the best they can as best they’ve been taught. You see them with empathy and compassion. You don’t hold any of it against them.

People hurt. People are messed up. People are stuck in patterns and don’t even know they are pattens. Most of what we do is not malicious, not stupid, not selfish or ignorant. Is is, instead, a response to events whose significance we often don’t even recall. The next time you look down on someone else’s behavior—the next time you think, Oh, here we go again or _________ always does this—try to remember that. Remember that these aren’t just little personality quirks, but real feelings masked by annoying actions. These are people in pain, like we are in pain—even if it makes them act like a dick. Don’t hate or pity or pander to them. But let it remind you that they’re human.

The first level is in your self-interest. And so is the second. Because when you can start to understand other people, accept them as they are and forgive them for what they do, you can start to do it to yourself. You can expect it for yourself.