One Thing Better

Say Yes to the Things That Scare You

Welcome to ​​One Thing Better​​. Each week, the editor in chief of Entrepreneur magazine (that’s me) shares one way to achieve a breakthrough at work — and build a career or company you love.


“If your teenage self could see you now, would they be proud?”

My friend Rah just asked me that. It’s his favorite question; it helps him step back and see how far he’s come.

But I never think about my younger self, I told him.

Instead, I think about my older self. And it’s a terrifying, motivating, and clarifying thought. It feels visceral. It drives me to take risks. It helps me say yes when I might have said no.

And I believe I live a better life because of it.

It’s part of something I call the Future-Self Test — and today, I’ll show you how to use it.

It’s a small, simple way to make decisions… and I think it’ll light a fire under you too.

Meet your older, future self

Whenever I hesitate to take a risk, or to do something rewarding but potentially uncomfortable, here’s what I do:

I imagine myself at 90 years old, sitting on a couch, my body aching, and reflecting on all the things I didn’t do when I was young and able.

Then I ask myself: “If I say no to this risk today, will that 90-year-old man regret it?“

This is the Future-Self Test. It’s a question of what your future self would want.

Whenever I think this way, I’m filled with a sense of urgency. Because I do not want to be an old man full of regrets. And that means I must take action now.

I am currently 46. I am young and able, in a way I’ll one day be wistful for. Time is (hopefully) still on my side. But it won’t be forever.

So today is the time to erase future regret. The window is right now.

Forwards, not just backwards

I was just telling my friend Alice about this idea. Then she said something that really struck me:

“You’re being conscious that you have a duty to someone else — and that someone else is you,” she said.

That’s exactly right.

Our actions today don’t just impact us now. They impact all the future versions of ourselves. Our risks today are tomorrow’s gift of experience. Our failures today are tomorrow’s wisdom.

That makes my decisions today feel more active and purposeful. It gives my daily choices more weight and responsibility. And it makes me think of life as an endless accumulation — that we are the sum of all our choices and experiences, and that a fulfilling life means always adding to that sum.

Maybe this is why I’m less interested in thinking about my younger self. He contributed something to me, but I cannot contribute back to him. He’s gone. Stuck in time.

But my future self? His story is being written right now, and I have the pen.

Which made me realize:

In a way, I am already that older self

I started thinking about my “future self” in my 30s, as my wife and I were deciding when to have kids.

Back then, I wasn’t imagining myself at 90. I was imagining myself in my 40s, as a father with less flexibility and more responsibilities. So whenever I hesitated to do something, I’d ask: “If I say no to this risk today, will the future dad version of me regret it?”

In 2012, for example, a friend asked if I’d join him at the Bonnaroo music festival. I hesitated. I love live music, but I don’t love being hot and sweaty and sleeping on the ground in a stuffy tent for days. So I almost said no.

Then I imagined being in my 40s, without the flexibility to do something like that. So I said yes.

It was fantastic. I discovered new bands. I spent days with a friend in a way that adult life rarely allows. I saw Ben Folds, one of my favorite musicians, and got to meet him afterward. And hell, sleeping in the tent wasn’t half bad!

Caption: Me and Ben. Definitely worth it.

Three years later, my first child was born. Now my kids are 7 and 11. My life is less flexible, just as I imagined. Going to a multi-day festival today would take a small miracle of scheduling.

But I have those memories. I am so, so happy I said yes.

This isn’t about saying yes to everything

An important caveat: The Future-Self Test isn’t permission to be reckless, or to fill every hour of your calendar. Your 90-year-old self won’t thank you for being stupid or burning yourself out.

The test is for a specific kind of no: It’s the one you say because something is uncomfortable, unfamiliar, or a little scary.

I’ve been saying this a lot lately: Just because something is hard, that’s not a reason not to do it.

I aspire to say yes to things that make me nervous. New business opportunities. New social opportunities. Going to that place, and trying that thing, and being in that situation, and challenging my notions of what I like, and what I want, and what’s comfortable, and what’s worth doing.

Try it this week. Think about something you’ve hesitated on recently — an invitation, an opportunity, a conversation you’ve been avoiding. Then picture yourself at 90.

You have a responsibility to that person.

Do not leave them with regrets.

That’s how to do one thing better.

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and build a career or company you love.