You have a decision to make. One option feels clear and familiar. The other seems riskier and harder to picture.
If you’re like most people, you’re tempted to choose the safe one. But before you do, consider this piece of advice, given recently to a teenager facing a huge life choice — because it might lead you toward a bigger life.
A young friend of my family, Lucia, was recently deciding which college to attend this fall. She narrowed it down to two options. The first is comfortable and familiar, in a city she knows well. The second is exciting but far from home, in an unfamiliar city, and unlike anything she’s known before.
Lucia told an adult she was leaning toward the first school. Here’s why: “I can picture myself at the first school, but I can’t really picture myself at the second one,” she said.
The adult replied, “If you can so easily see yourself there, maybe it’s not a big enough adventure.”
That line changed her thinking. She chose the second school. I think we should all tell ourselves the same thing.
We like to reduce risk. That’s natural. And it’s often how we make decisions: We choose the knowable option because it limits our downside.
But consider what else you might be limiting.
If you only choose the things you can already picture, then you are mostly living inside the edges of your existing experience. You revisit what you already know, or what sits one degree away from it. Your life expands slowly, or not at all.
When I think about the most meaningful turns in my own life, I realize I could not picture them in advance.
For example, I’d never heard of Entrepreneur magazine when I began my career. Even when I first applied for a job here, I didn’t take it especially seriously and didn’t think of myself as entrepreneurial.
But I got the job, took the leap, and spent years absorbing how entrepreneurs think. It changed me. The version of myself from 10 years ago could never have pictured the version of myself today. My life is bigger, richer, and more fulfilling. This only exists because I pursued the unfamiliar.
I see this same pattern in my own kids, who are 7 and 11. My wife and I often encourage them to try a new activity, like a class or sport, and they say no.
“I don’t like that,” they say.
“You’ve never tried,” we say.
“That’s because I don’t like it,” they reply.
It’s terrible circular logic, and yet adults trap themselves in a version of this all the time. We dismiss ideas because they don’t resemble the decisions we already know. We confuse unfamiliarity with wrongness.
As parents, we can force our kids out of their comfort zones. But as entrepreneurs, we must do it for ourselves.
So here’s a useful question to ask the next time you’re deciding between two paths:
Can I picture this?
If the answer is yes, pause and wonder why. Maybe it’s because the option is genuinely right for you. But maybe it’s just because it resembles what you already know.
Then ask the opposite:
If I can’t picture this, is that a reason not to choose it?
Sometimes the answer is yes. The unknown is not always the right fit. I’m not suggesting that you always choose the hardest path, or the one most designed to make you uncomfortable.
I’m simply saying: Don’t confuse familiarity with correctness.
Sometimes the thing you can’t yet picture is the thing that expands your life. Sometimes, “I can’t see myself there” is not a warning sign, but an invitation. And sometimes the best way to live a bigger life is to stop choosing what feels safest, and start choosing what feels like an adventure.
You have a decision to make. One option feels clear and familiar. The other seems riskier and harder to picture.
If you’re like most people, you’re tempted to choose the safe one. But before you do, consider this piece of advice, given recently to a teenager facing a huge life choice — because it might lead you toward a bigger life.
A young friend of my family, Lucia, was recently deciding which college to attend this fall. She narrowed it down to two options. The first is comfortable and familiar, in a city she knows well. The second is exciting but far from home, in an unfamiliar city, and unlike anything she’s known before.
