thoughts from the red planet

Most people flee uncertainty. Yet being able to think well under uncertainty can be very rewarding, and I've come to realize it's a skill that can be learned. Here are some tips for thinking under uncertainty.

1. Think in terms of ranges of scenarios

In many situations, you only have limited information. Our brains are quick to make conclusions and don't consider all the scenarios.

Don't let this happen.

You have to realize that given the information you have, there is a range of scenarios that could account for it.

Talking to someone who seems cold and aloof? Maybe the person is unfriendly, or maybe the person is just shy.

Is your boss micromanaging you lately? Maybe he doesn't trust you, maybe he's under increased pressure from his boss, or maybe it's just a random event.

You need to avoid tunnel vision. It's easy to become focused on one scenario - because you're afraid of the scenario or really hopeful for it - and ignore information that points to other possibilities.

For each decision you can make, consider the consequences in each scenario. Which decision maximizes your "expected benefit"¹ across all scenarios?

2. Acquire more information

One of the best ways to deal with uncertainty is to reduce it. What options do you have available to acquire more information?

If you're deciding whether or not to take a job offer, learn as much as you can about the company. What's the turnover rate? Talk to current employees and question them on what it's like to work there.

3. In general, taking action is better than being passive

It's easy to be overwhelmed by uncertainty and be afraid to take action. Nothing comes to you in life, you have to be willing to take action without certainty.

I had a friend in high school who asked out 8 girls in a two week period and got rejected by each one. Did this stop him and cause him to question himself? No, the 9th girl said yes, they were a great match, and now they're married.

I love this anecdote about taking action in an uncertain situation.

4. Control your emotions

Uncertainty makes people anxious. And that anxiousness can lead to frustration and rash decisions.

Emotions come into play when you don't know what action to take. Having a disciplined approach to thinking through the information you have and analyzing the possibilities avoids this feeling of haplessness.

5. Learn to play poker

Poker is a game of making decisions under uncertainty. Good poker playing is an unnatural skill; it must be learned. It's interesting how the skills you learn in poker translate into the real world.

To be a good poker player you have to consider the ranges of possibilities for the cards in your opponents' hands that fit the betting so far. You have to control your emotions or you'll make bad decisions and go broke. And being aggressive is crucial².

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¹ Expectation is a statistical concept. Your expected value is the sum of each scenario's value multiplied by its probability.

² Don't take the analogy too far though. Life is not a zero sum game like poker, and there's no concept of cooperation in poker.

Spencer Fry wrote a great post on "Why entrepreneurs should write." I would further add that the benefits of writing are so extraordinary that you should write a blog even if you have no readers (and regardless of whether you're an entrepreneur).

I have over 50 unfinished drafts. Some of them are just a few ideas scribbled down arguing with myself. Most of them will never be published, yet I got value out of writing all of them.

Writing makes you a better reader

Blogging has changed how I read other people's writing.

In struggling to find the right ways to structure and present my posts, I am much more attuned to what makes a good argument and what makes a bad argument. I am better at seeing holes in other people's reasoning.

At the same time, when reading I am less likely to fall into the trap of discrediting a post with weak counterclaims. In most any post, there are likely to be counterclaims that are based on exceptional cases. Internet commenters love to point these out. However, these exceptional cases miss the main thrust of the post, and by understanding the implicit backdrop behind a post's argument, I get a lot more value out of reading.

I'm also more aware of the style of good writers. I mentally take note of the ways good writers phrase their ideas. I'd always enjoyed Paul Graham's writing, but now I really appreciate how he organizes his posts. He has an awesome ability to suck you into his world and show you what it looks like from his perspective. I've learned a lot about good writing from reading Bradford Cross's blog; his posts have a clear arc and make excellent use of short paragraphs to keep the posts flowing.

Writing makes you smarter

Writing reveals holes in your thinking. When your ideas are written and looking back at you, they're a lot less convincing than when they're just in your head. Writing forces you to mature your ideas by thinking through counterarguments.

Writing helps you organize your thoughts in a coherent way. This makes you a much better conversationalist when these topics come up. I can't count the number of times I've had deeper conversations with people because I had matured my ideas offline.

Consider anything else a side benefit

Everything else writing gives you -- personal branding, networking, inbound opportunities -- are just side benefits. They're potentially very large side benefits, but they are not the main reason you should write.

You should write because writing makes you a better person.

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