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What’s Your Biggest Regret?

Published on August 17, 2020

When I read about Daniel Pink’s latest endeavor, I was eager to participate. His one question: What’s your biggest regret?

I didn’t have to think long about this one. My biggest regret, I wrote, is not taking a gap year after graduating high school. To be fair, it wasn’t really a thing back in 1981. I was programmed, along with everyone else, to move steadily from one achievement to another—high school to college to grad school to career to marriage to kids.

When I hear of someone my age who consciously chose to deviate from these purported steppingstones to success, I’m impressed. Impressed that they defied the norm and withstood the pressure from family or peers or society.

I wonder how my life would have turned out had I taken that gap year. I was so lost and fearful at 17 and needed time to find myself and ask those big existential questions: Who am I? Where do I belong? What is the meaning of my life?

That regret has fueled my desire in midlife to ask those very questions. To get clear on who I am and what I want for the rest of my life. I’ve got a second chance and I’m not wasting it. Call it a second adolescence.

YOUR TURN: What do you wish you’d asked yourself when you were in your teens or 20s? Why not ask now?


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Hélène Stelian, the Midlife Empowerment Coach

I’m Hélène, the Midlife Empowerment Coach. I help women who are struggling in midlife—who wonder if their best years are behind them and what’s next for them. I show them how to put themselves first, reclaim their identity, figure out what’s next, and feel excited about their future.


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