Nathan Bashaw

@nbashaw

How to make hard decisions

Every choice you make fits somewhere in one of these four boxes:

Learning to deal with Type 4 decisions (those in the bottom-right box) is one of the hardest parts of growing up.

As life goes on, your responsibilities grow and the stakes only get higher. Plus, as you gain experience and wisdom, you get better at seeing both sides of an issue. Your battle scars teach you to be humble about your own ability to predict the future.

No matter how much you spin your wheels analyzing and debating the logic of a particular decision, sometimes it feels impossible to pick a side.

So, how do you deal with it?

While there is no silver bullet, I’m a big believer in thought experiments. There’s nothing like a well-designed question to help your mind (and heart) gain conviction about a tough call.

For example, last year I decided to leave my job and start a new company. We’ve face our share of existential decisions along the way:

  • Should we create our own stories or just focus on attracting other people to do it?
  • Should we simplify our format to make it easier for others to create stories, or should we focus on making the best stories we possibly can?
  • What kind of stories should we make?
  • How much effort should we spend trying to attract advertisers? Should we just charge users directly instead?

There are no easy answers.

Here are some questions me and my cofounder Joe asked ourselves to help us make those decisions:

  • Even if we fail, will it still have been worth trying if we do it this way?
  • If we do it this way and we succeed, will we be proud of what we’ve done?
  • When I’m old, how will it feel to explain to my future grandchildren what we did?
  • If one of my heroes from the past were somehow able to come back and have dinner with me, what would I want to be able to say to them?
  • If it were my kid in this exact situation, what would I advise them to do?

These questions all have one thing in common: they help you step outside your fear and cut to the moral core of the decision at hand. They force you to decide what’s most important to you, and guide you towards the choice that best reflects your values.

The thing about most Type 4 decisions is that either choice will probably be fine. There is no one “right” way to navigate the world. There are a myriad of ways, and it’s up to us to find the one that best reflects our values.

Finding moral clarity in decisions like these is important, because the only thing worse that making a bad decision is waffling about your decision for too long. Or questioning yourself too much when someone with more experience than you comes along and says that they would do things differently.

Because, after all, Patton was right:

A good plan violently executed now is better than a perfect plan executed next week.

The End

(If you liked this, check out Hardbound, where you can see more stories like this, but even better: they’re visual and animated!)

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