Ryan Holiday:

A CEO calls her staff into the conference room on the eve of the launch of a major new initiative. They file in and take their seats around the table. She calls the meeting to attention and begins, “I have bad news. The project has failed spectacularly. What went wrong?”

The team is perplexed: What?! But we haven’t even launched yet…!


The technique that the CEO above was using was designed by psychologist Gary Klein. It’s called a premortem. In a premortem, a project manager must envision what could go wrong—what will go wrong—in advance, before starting. Why? Far too many ambitious undertakings fail for preventable reasons. Far too many people don’t have a backup plan because they refuse to consider that something might not go exactly as they wish.

Tom Bilyeu:

“Paul, we’re here to answer exactly one question: Why am I going to fail?”

And if you start with that, instead of “Tell me how to succeed” — which is what most people do — you can start to eliminate some of the obvious paths, or at least understand why they’re dangerous paths, why most people fail as they go down those.

Looking at that, what I’m trying to do is rapidly iterate through all the possibilities. There’s a 1000 doors before you. 999 of them aren’t going to work. So the question is: how do you find the one that’s going to work?

And the answer is, you go through one — “Did this work?” No. Back up. Next one. Back up. Next one. Over and over and over. The goal is to fail rapidly. The question is, what are you learning when you’re failing?

Scott H. Young:

If you can endure the worst case, the best cases take care of themselves.

All of my plans are pessimistic. I focus on what might go wrong, not speculating about what might go right.

This may seem like a mindset doomed to fail, but I’ve found quite the opposite. When you manage and control the worst case, fear and anxiety are less likely to overwhelm your thinking. Since you know you can endure the worst outcome, then anything becomes tolerable.

Part of this is asking whether I could sustain a failed outcome. What if a new project completely goes bust? What if I make no progress? Could I keep going, or would failure to reach a certain outcome be a disaster with my plan as it is now?

But an even bigger part of this is expecting a certain amount of behavioral failure. What if I get sick? What if this takes me longer than I had anticipated? What if this turns out to be harder than expected?

When you take this mindset, you start to feel a lot luckier. Why? Because when you’ve planned and prepared for the majority of negative possibilities, then the “random” events you tend to encounter are biased towards the positive. You get a lucky break, or something succeeds more than you had expected.

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Your Life Strategy

Scott H. Young:

When in doubt, build assets.

Often it’s not clear what needs to happen in order to succeed in some area of life.

In these cases, my default mode has always been to try to build generally useful assets. This is to switch out the question of “what should I do?” with “what would be useful, generally speaking?” The former question may not have a clear answer, but the latter usually has many things which could probably help. Sometimes success is simply answering this question enough times that the accumulation eventually breaks through.

For instance, if you’re luckless in love, you might decide to start working on your communication skills, start building a deeper social network, improve your fashion/appearance or learn improv to become funnier. It’s not clear any of these projects will bring success, but if you build enough assets in this direction, you’ll probably improve your chances.

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