How to Do Hard Things and Win Big

One of the secrets to legendary investor Bill Gurley’s success was asking, “What could go right?”

In his world, there’s a lot of emphasis on knowing which deals to say no to. Of course, if you say yes to too many bad deals, you will lose all your money and be out of the game. So you have to avoid bad deals.

But that’s not how you win. That’s just how you don’t lose. They aren’t the same thing.

Winning big can happen by stroke of dumb luck, but more frequently, it starts in the least expected place: in your imagination.

If you see what can go right in your imagination, before anyone else sees it, you can say yes to it before anyone else does. If it turns out to work, you’ve won big. 

Or, you can do what many shrewd investors do. Look at a goal or an option presented to you, and you can call out 20 things that could go wrong. You can say no, and avoid failure all your life. Hey, it’s better than failing.

But to do hard things and win big at them, search for the best possible outcome in your imagination. What’s the best possible thing that could happen? Once you hold that image in your mind, ask how can it become reality? Then work your way to it.

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Thanks to Krystal Black for the photo.