Make That Bold Move Now -- and Avoid Looking Back With Regret

Entrepreneurs live to push boundaries, but fear can cause us to second-guess our gut. Don't. Act now.
Make That Bold Move Now -- and Avoid Looking Back With Regret
Image credit: Nigel Parry
Magazine Contributor
4 min read

This story appears in the November 2018 issue of Entrepreneur. Subscribe »

Get a bunch of people in advertising together, and they’ll complain about the same thing: Their clients are wimps. The clients keep saying they want innovative ideas -- they want to do something big and bold, something nobody else does. So the ad folks dream up a ton of ambitious stuff. The client reviews it and winces. Not what they’re looking for, they say. And they steer the ad firm toward a campaign that’s safe and timid and very, very familiar.

Related: Stop Planning and Take Action

I’ve seen it myself, in my own industry. At a magazine where I used to work, a boss kept telling me he wanted the magazine to be funny. Frankly, this magazine was not funny. It had never been funny. But, I agreed, this was a good way to shake things up. So I hired comedy writers. I added jokes to stories. I made it funny! Then he and my other superiors took all the jokes out and killed the stories by the comedy writers. “Too off-brand,” they explained. What they really wanted, it seemed, was the idea of the magazine being funny. But they didn’t want to sacrifice the comfort of familiarity -- of doing things exactly as they’d always been done.

People say they like to push boundaries, but they rarely push those boundaries. They like the idea of change more than they like change. They call themselves risk-takers but always play it safe. You know the difference between successful entrepreneurs and everyone else? They don’t just flatter themselves with talk of their bold hearts and daring intentions. They make hard, necessary, real decisions. They produce things nobody has seen before. They push and they scrape and make holes in the wall. They act.

Related: 12 Motivation Hacks From the Best of the Best

I’ve always struggled to understand the disconnect. Why do so many people think of themselves as daring but fail to live up to their own self-­conception? I suspect it has to do with fear. An idea is easier than execution. It’s easier to imagine jumping out of a plane than it is to actually stand there, the ground a bazillion feet below you, and take the leap. That moment -- the moment when it’s real, when it’s right there in front of you, when you either act or you don’t -- is when we really learn about ourselves. That’s when we see how we fare against fear.

I’ll admit: I’m not perfect. I’ve stared down the precipice and backed slowly away. But at least a few times -- when it really counted, when it changed my life -- I’ve taken the leap. I’ve heard people say that, in moments like these, it helps to imagine the ultimate outcome. Rather than get lost imagining the long road ahead, you think of the great job, or product, or life you’ll have at the end of that road. It’s a fine method, and maybe that works for people. For me, however, I tend to think the opposite way. I think about what happens if I don’t take the risk.

I’ve regretted the moments when I backed away from a bold, exciting risk. Regret makes you feel like you don’t belong somewhere; you’re here now, but you keep thinking, I should be over there. And so, when it comes time for me to take another risk, I force myself to relive that regret. I imagine feeling it again, a regret plastered to my body. I hate that feeling. I don’t want it ever again. So then I give myself an option: Feel that awful regret, or be free of it. Take a leap, and be free.

Related: 6 Surefire Ways to Stay Constantly Motivated

This is also why I love talking to entrepreneurs who take big risks -- and I encourage you to surround yourself with the same kind of people. They are living proof of positive outcomes, and we can and should set the same example for others. We all can exemplify what it looks like to not live with regret. We’ll still have problems, of course -- and some will be of our own making. (Not every bold move works out, after all!) But let’s give everything we have. We have an idea of ourselves. We think of ourselves as bold. All we have to do now is live up to it.


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