Welcome to One Thing Better. Each week, the editor in chief of Entrepreneur magazine (that’s me) shares one way to be happier and more effective at work — and build a career or company you love.
Today’s one thing: Letting your anxiety call the shots.
That one thing, better: Letting your regret call the shots.
You’re not taking the risks you should.
Sure, you’re an open-minded person, but your comfort zone can also be a trap. It’s too easy to stick with what you know. Why make yourself uncomfortable?
As a result, you miss out on a lot. Or at least, you feel like you miss out on a lot.
Today, I am not going to scream YOLO and FOMO at you. That’s unhelpful.
Instead, I’ll give you the trick that I’ve used to propel myself into the unknown:
I ask my Future Self.
It sounds weird. But it’s easy, helpful, and it drives results. And to understand why it works, you first need to know about my past self…
When new things are scary
I spent most of my 20s living with my college girlfriend, working as a small-town newspaper reporter in Massachusetts. It was fine, but it was also repetitive — same people, same activities, same experiences.
In 2008, at the age of 28, everything changed: My girlfriend and I broke up, I got a job at Men’s Health, and I moved to New York.
I arrived full of dreams and ambitions, eager to do the things I hadn’t. But… eek, that was scary! I didn’t know many people. Going out often meant going out alone.
I met some people like me. They spent a lot of time at home, watching TV. That seemed easy and tempting — to just retreat to a quiet life, firmly inside a comfort zone.
Then I had a revelation that changed everything:
I imagined my Future Self
I pictured myself in a future stage of life — married, with kids, full of responsibilities and limitations.
Then I imagined that guy looking back on his 20s, when life was simple and unrestrained. He could think one of two things:
Regret: “Why didn’t I do more in my 20s, when I still could?”
Satisfaction: “I’m so glad I did all of that.”
That helped me realize something: You don’t actually live just for today. Your decisions contribute to a whole life — fulfilling the dreams of the person you were, challenging and growing the person you are, and nourishing the person you’ll become. Tomorrow’s regrets are erased today.
So back then, I made a decision: I will do something every night. Sometimes it’ll be an adventure. Sometimes, just meeting someone for dinner. But I will not go home until an experience is had, Monday to Sunday.
This isn’t right for everyone, but it was right for me. I did amazing things. Dumb things. Weird things! I kept it up while dating, then after getting married (when my wife would often join me). And I kept going until we had kids at the age of 35.
Now I’m 44. I am the guy I imagined back at age 28, with more responsibilities and less free time. And I am deeply grateful for that younger version of me, who anticipated my life — no, our combined life! — and gave me the gift of experience.
Today, when I’m deciding whether to do something, I still ask myself: Would my Future Self regret missing this experience? It’s helped me join big projects, take big risks with my career, and go places I might not have otherwise gone.
Try it yourself. Here’s why I think it’s so powerful:
The “comfort zone” is a myth
People talk a lot about the “comfort zone”, but that’s not a helpful framing. It sets experiences up as binary: There’s comfort, or there’s discomfort.
Life doesn’t work like that. Experiences are more of a gradient. Here’s a better way to think of it — I’ll draw a chart with three zones:
Your comfort zone is where you start.
Your curiosity zone is where you’d go, if only you had the courage or energy. It might be great or terrible, but you’d be satisfied just knowing what happens.
Your hard pass zone is what you are genuinely not interested in.
These will be different for everyone, and that’s fine! I can’t say what belongs in your zones. But you can.
You know what you’re deep-down curious about. Out of fear, you might try to dismiss those things. You might say, “Oh, that’s silly and not worth trying.”
But today’s curiosity can become tomorrow’s longing. When you imagine your future self’s satisfactions or regrets, you get a fresh perspective. You see how important a decision really is. Is it worth passing on? Or is it worth following your curiosity?
Be kind to your Future Self
Stop for a moment and remember yourself 10 years ago. What did you not do, that you now regret? What did you avoid because of fear or nervousness?
Don’t you wish you could go back and do it?
You can’t.
But now imagine yourself 10 years into the future. Imagine the regret you’d have about not doing something today. Now realize: You actually can “go back and do it.” Because the opportunity still exists. It’s in front of you. Right now.
Use the time you have.
That’s how to do one thing better.
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