Risk-taking and regret in the coffee shop

September 13, 2021

She’s in line at the coffee shop. In front of her, a handsome man. He’s muscular, has a great smile. He flashes that smile at her; she smiles back.

“I love your shoes”, he says. She blushes. “Thank you! I got them in Tokyo.”

He’s been to Tokyo as well; they chat about their favorite places there. When he speaks, she’s only half listening. The other half of her brain wonders.

Will he ask for my number? Should I ask him? What if I ask and he rejects me? That would be so embarrassing. This is a public place. There are so many people around. I’d die of shame.

His coffee is ready. He got it to go. The two smile at each other one more time. An awkward pause. He breaks the silence: “Have a nice day then!”


He hasn’t even left the coffee shop and she’s already berating herself. Argh! She should have just asked for his number! Why is she so scared? Should she run after him? No, she can’t get herself to do that. Anyway, she’s waiting for her coffee.

Outside, the handsome man with the great smile is thinking the same.

Taking risk is necessary to advance your goals. Whether your objective is to go on a fun date, to enter into a new business niche, or to win a dance competition, you need to take risk.

By definition, taking a risk means you can fail. You might screw up, you might get rejected, or you might simply not be good enough yet.

Do these possibilities make you uncomfortable? They sure make me uncomfortable. But you can act despite the fear of failure. Even when you’re awfully worried about the risk, you can still act. It takes practice, but that practice is oh-so-worth-it.

You might not get someone’s number, but you might also meet your future husband. Your new business venture might flop, or it might make you a multimillionaire. You might fall flat on your face at the dance competition, or win it and make the memory of a lifetime.

Imagine you are hiring an external consultant to evaluate your personal strengths and weaknesses. In their report, what would they write about your risk tolerance? Would they say you are comfortable taking risks, which propels you forward? Would they say you are sometimes too reckless?

Or would they say you tend to shy away and miss out on opportunities?

Getting rejected when asking someone out in a coffee shop is a good thing. It’s not the best outcome, of course—that’s meeting your future husband—but it’s still a good outcome. It’s taking the risk you need to take to get what you want, eventually.

Which risk should you be taking?

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