The Scariest Question Ever (and the only right answer)

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As adults (gasp), we face dozens of questions everyday:

  • What should I wear?
  • What should I have for breakfast?
  • What route should I take to work?
  • What should I listen to on the way? (hint: try a podcast)

Most of these questions are pretty small and trivial. The answer you choose probably won’t have any lasting long-term impact on your life.

I mean, Cheerios vs. toast, not exactly a game-changer.

But what about the deeper questions? The ones we don’t like to ask or answer because they require some serious soul-searching?

Questions like:

  • What do I fear most?
  • If I didn’t have to worry about money, what would I do?
  • What’s the point of all this?

These kind of questions are scary — at least to me — because I don’t have an immediate answer. And that’s an uncomfortable feeling.

I aced all kinds of standardized tests as a kid. Give me multiple choice any day.

Even when I didn’t know the answer, it was there on the page. It made not knowing a little bit easier; I could at least make a guess.

So what’s the scariest question ever if you don’t know the answer?

Here it is:

What do you want to be when you grow up?


As a kid in school, my answers included football player (um, never even played one down of organized football — not sure where that came from), teacher (hey, I liked school), baseball player, firefighter, journalist (sportswriter, really), and doctor.

The truth was I had no idea.

And if you asked me again today, I’m still not sure I have a good answer. So if you don’t know either, you’re not alone!

Professional online-shoe-salesguy and podcast host was never an option.

I would wager a good percentage of jobs today didn’t even exist while I was in school. Social media expert? SEO specialist? Web developer?

“Don’t feel guilty if you don’t know what you want to do with your life…the most interesting people I know didn’t know at 22 what they wanted to do with their lives, some of the most interesting 40 year-olds I know still don’t.”

–Baz Luhrmann

I think the thing that bothers me most about the question is that the expected answer is always a job of some sort. Does that really define us as what we are? I mean, the question is what you want to be?

What do I want to be when I grow up? Um, myself, just older. Is that cool?

But while the question is still scary to me — and I’d love to decouple our jobs from our beings — it’s really not all bad.

There are 2 things I love about the “what do you want to be” question.

The first is its open-endedness. There’s no wrong answer.

After all, it’s what YOU want. Sometimes I think first-grade teachers ask it just to count how many future Presidents they have in their class.

Aim high, little ones.

The second part of the question I like is the “when you grow up” portion. This implies that whatever you’re doing now, whatever you are now, you have the power to change it.

Sure, I’m still a little uncomfortable with the whole being a grown-up thing, but I like the fuzzy future-tense of it in this context.

At some hypothetical point in the future, when your robot butler is bringing you a cold one on the patio of your lunar vacation home, you can be whatever you want to be.

And like I said, there’s no wrong answer — but there is only one right answer:


What do you want to be when you grow up? Happy.

That’s all. So the challenge becomes to figure out what makes you happy and reverse engineer your life to get there.

Challenge accepted!

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

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