8 questions for what to do with your life


Hey Reader,

What would you do if you knew you couldn’t fail?

You’ve probably seen some version of this question before.

It’s a good one, though sometimes the answer isn’t immediately obvious.

That’s why I like Graham Weaver’s 8 questions for what to do with your life.

Graham founded the private equity firm Alpine Investors, and he teaches at Stanford. In Chapter 2 of my upcoming book, The Ladders of Wealth, I credit him with a principle he shared with his MBA students called "worse first", which is the idea that anything worth doing gets harder before it gets easier.

So when Graham posts something—like this reel on what to do with your life—I pay attention.

Here are his 8 questions:

1. What’s play for you that’s work for others?

Graham credits this one to Naval Ravikant. This is the kind of thing you’d happily spend a Saturday on that someone would have to be paid to do on a Tuesday.

2. Who do you admire? What do those people do?

Write the names down first. Then write down how each of those people spends a typical week. Because their typical week is what you’d actually be signing up for.

3. If you didn’t have to make money, what would you be doing?

Graham warns against using this one as a back-door way to wish for money. He says money is not a good place to start. Also, don’t give the answer your dad, or mom, or boss, or partner thinks you should do.

4. What would you wish for even if you knew it was going to take you 25 years to build it?

This rules out anything that you’d only do to reach the finish line. Whatever survives the question is something you’d want to do no matter the outcome.

5. What’s a problem that breaks your heart that you have to solve?

You may already have an answer before you finish reading the question. Write down whatever came to you first, even if you can’t yet explain why.

6. What would you do differently if you were reborn?

If you could start over and have another go, what would you do? Maybe you should still do it.

7. What do you really want to do but are too embarrassed to tell anyone about it?

Graham answered this one himself and said he wanted to be a motivational speaker like Tony Robbins. He said he had to push aside the fear of admitting it.

If an answer makes you wince, you should definitely write it down.

8. When you were most alive, what were you doing?

Think of a specific day rather than an era. What were you working on, and what made that day different?


Lastly, of all the things you’ve written down, come back and answer the original question:

What would you do if you knew you couldn’t fail?

The question works better now because you can run it against your answers to the other eight.

This helps you get past the obvious ones to find what's useful.

Then, as Graham says, go do that thing.


video preview

PODCAST

How the Author of Atomic Habits ACTUALLY Makes Money

I’m excited to have James Clear back on the podcast—this time on stage.

The last time James spoke at Craft + Commerce, Atomic Habits hadn’t come out yet. It has now sold more than 30 million copies.

I wanted to go beyond the book and unpack the business behind it. We get into what makes a product people keep talking about, and how he grew his email list past 4 million subscribers.

James also breaks down the publishing model he’s building with Authors Equity, then answers audience questions on simplifying complex ideas.

Someone also asks him what his life’s mission is.

Watch or listen to episode »

FREE TRAINING

How to write and publish your book (even if you haven’t started writing yet)

Writing a book is one of the hardest things you’ll ever do. I told people I was going to write one for years, then it took years more to finish it.

My friend Chandler Bolt built his career on helping people navigate that process. Through selfpublishing.​com, he’s coached thousands of authors to go from blank page to finished book.

He’s hosting a free workshop on September 8th where he’ll walk you through how to finish writing your manuscript and turn it into a published book.

Register now »

BOOK

Own or Be Owned: Build a Business So Good It Doesn’t Need You

My friend Codie Sanchez, founder and CEO of Contrarian Thinking and New York Times bestselling author of Main Street Millionaire, has a new book coming out September 18th.

Own or Be Owned is about owner dependency. If your business can’t survive without you, then what you own is a job. Codie’s test for that is simple—take a vacation and see what happens.

In addition to scaling your business and creating the freedom you really want, you’ll learn:

  • The 10-minute Owner Score: do you own your business or does it own you?
  • How to find your weakest links and double your profits
  • Pricing that turns underpaid owners into high-margin operators
  • The 12 Profit Levers & which one you need to make your business successful

Codie is hosting a virtual book launch event where she’ll be teaching all 12 profit levers live on September 18th:

Get your free ticket »

—Nathan

P.S.

This past week, I helped my son August sell ice cream at the local park, played lots of cards, and built a sauna a friend gave us.

Did you do anything fun?

Selling ice cream in the park
Building a sauna

Nathan Barry

I'm a designer who turned into a writer who turned into a startup CEO. My mission is to help creators earn a living. Subscribe for essays on building an audience and earning a living as a creator.

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