More Writing from Me

April 22, 2012 — 11 Comments

I was going to keep this writing separate but the posts have turned out to be pretty good so I decided to linking to them here. I’m writing for Forbes now and you can subscribe to my posts via RSS here or you can just follow it on Twitter for links. Initially, writing on Forbes it was a bit of an experiment but it seems to have stuck and I have enjoyed doing it.

H.L Mencken & Jack London: How to Pitch Editors, Agents and Book Publishers
9 Timeless Leadership Lessons from Cyrus the Great
Why Wouldn’t Planned Parenthood Take $500,000? (this controversy was awesome and got picked up everywhere)
The Marketer’s Dirty Secret: Exploiting Perception vs Reality
What the Failed $1M Netflix Prize Says About Business Advice

It’s a different kind of writing for me but still good practice and I write there more often. The weightier material is all going to stay on this site and I’ll be posting on Forbes just the stuff that I couldn’t make work for this format. It’s also not a bad seque into my book, which is a mix of both. Stay tuned for that announcement next month.

Anyway, read them or don’t. Either way, stay tuned for regularly scheduled programming.

Some weirdo says something to you in the grocery store and you smile and nod your head, “Yup!” Just to avoid a scene right? You have a meeting with a sales rep and indulge the friendly but pointless chitchat even though you hate it. But a friend mispronounces a word and we leap to correct them. Your girlfriend tells a boring story and you’ve got to say something about it, you’ve got to get short with her. What kind of bullshit is this? We give the benefit of courtesy to everybody but the people who earned it.

Think of how much patience we have for total strangers and acquaintances. But what a short fuse we have for the actual people in our life. In the course of our everyday lives, our priorities are so very backwards. We do our best to impress people we’ll never see again and take for granted people we see all the time. We’re respectful in our business lives, casual and careless in our personal. We punish closeness with criticism, reward unfamiliarity with politeness.

On some days, deep down, I think we’d rather just be an asshole to everyone. But we can’t, so on those days we take it out all the harder on the people we can. When kids are misbehaving, it’s the one within reach that the parent slaps. Just because you can call someone out (or hold them accountable) doesn’t mean you should. The fact that you can certainly shouldn’t count against the person. As though being your friend or co-worker costs them your patience.

Not that I’m saying to flip the ratio and be less tolerant to people outside your circle than those inside it. Instead, see if you can give everyone the graciousness of meeting them fresh each time. Ask yourself: how would I treat this person if we weren’t so familiar? If it’s more generously, do that. Don’t use history against people, don’t slap just because you can. Sure, be friendly to everyone but bend over backwardsbecause they’ve earned itfor the people who put up with your shit on a daily basis.

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.