How to Choose a Challenge to Take - Expanding Your Capacity

You need to constantly move out of your comfort zone and take new challenges. Otherwise you will just stay where you are as years go by.

One question you might have is: what challenge should I take? 

This is an important question to answer. Why? Because working on a challenge could take months or even years. Nobody wants to spend years working on the wrong thing, so you should choose your challenge wisely.

I’ll share with you how to choose a challenge, but before we start, you may want to list all your possible challenges first. Look at your dreams and desires. Look at the possibilities in front of you. Just write whatever comes into your mind.

Now, having known the options you have, the first step is to filter them to get only the most promising ones. To do that, ask yourself this question for each option:

Is it something I love doing?

Here is another way to ask the question:

Suppose I didn’t have to worry about money, would I gladly spend my time doing it?

Think about it for a moment. You don’t need to worry about money. You can do whatever you want. In such a situation, will you gladly do it? Or perhaps you will never do it if you don’t need the money?

This question helps you see your true motivation. Having the right motivation is important because working on a challenge isn’t easy (it’s a challenge, after all). If you aren’t passionate about it, it will be difficult for you to stay motivated in the long term. You will stop before you achieve success. This is especially true if the motivation is money. These people, when they can’t see financial results in relatively short time, become discouraged and stop working on the challenge.

There is another reason why having a “yes” here is important: Don’t just try to reach the destination; you should enjoy the journey as well. Why should you torture yourself along the way if you can do something you enjoy?

So look at your list and cross the items that don’t pass the filter.

Now, for those things that are left, you need to choose one of them to work and focus on. How? Here is a question I’ve found useful for this purpose:

Which one would give me the most regret if I didn’t do it?

This is what Jeff Bezos called “regret-minimization framework”. The idea is, you should choose a challenge that helps you avoid as much potential regret as possible.

To answer this second question, imagine yourself years from now. Imagine yourself looking back at the possibilities in your life that you didn’t take. Which one would make you regret the most?

That’s the challenge you should take.

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Buxone How To May 08, 2020