You Won't Regret the Risk. You'll Regret Playing It Safe.

The regret that keeps you up at 3 a.m. is never the thing you did.

Regrets hit harder as you get older because time stops feeling abstract.

In 2005, I walked away from a sales career that paid well to go back to school for a counseling degree. On paper, it made no sense. My first job paid a fraction of what I’d earned.

It’s one of the best decisions I’ve ever made, and I almost didn’t make it, because the safe version of me had a very convincing argument.

Cornell psychologists Thomas Gilovich and Victoria Medvec found that in the short run, people regret the things they did. But over a lifetime, the regrets that stick are the things they didn’t do (1994). The risk you took and botched fades. The thing you never tried is the one that keeps you up at 3 a.m.

These are the eight I hear most.

1. Not taking your own ambitions seriously while there’s still time.
You treated your own goals like a hobby you’d get to later. Later kept moving. The ambition didn’t die from failure. It died because you never gave it a real shot.

2. Never learning to be alone.
You went from your parents’ house to a roommate to a marriage and never once lived inside your own company. So you stayed in rooms you’d outgrown, because the alternative felt like a void. Being alone is a skill. Nobody teaches it to women.

3. Apologizing for things that weren’t your fault.
Sorry became a reflex. You apologized for taking up space, for having needs, for other people’s bad moods. That word, said ten thousand times, is its own slow erosion.

4. Letting your body become a source of shame instead of a home.
You spent decades at war with the body that carried you through all of it. I stopped apologizing for it a long time ago. Your body kept its end of the deal. The shame was never yours to hold.

5. Choosing the safe version of yourself for too long.
Safe feels fine right up until you notice you built a whole life around not being seen. The safe version doesn’t fail. It just quietly disappears. Plenty of women hit 60, 70, or 80, grieving a person they were too scared to become.

6. Not resting without guilt.
You earned the rest and then couldn’t take it because somewhere you learned your worth was measured in output. So you ran on empty and called it being responsible. Guilt is a terrible substitute for a nap.

7. Spending so many years caring about what people thought.
You let the opinions of people you didn’t even like steer decisions that were yours alone. Most of them weren’t thinking about you at all. They were too busy worrying about what you thought of them.

8. Not understanding sooner that you were enough.
This is the one sitting underneath all the others. You kept auditioning for a part you already had. The proof was never going to arrive from out there. You just needed to stop waiting for someone to hand it to you.

The regret women carry as they age rarely comes from the risks they took. It comes from the years they played it safe.

So if you’ve reached midlife and your stomach just dropped reading this, good.

It means there’s still time to keep a few of these off your own list.

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If you've been waiting for permission to stop playing it safe, this is it. The Midlife Clarity Roadmap walks you through the five stages I take my clients through, from grief to actually moving. Begin the Roadmap.

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Ellen Scherr is a licensed clinical professional counselor and midlife transition coach for women over 40. After her 18-year marriage ended at 50, she left her career and rebuilt her life from the ground up. She writes Life Branches, a Substack on divorce, identity, and starting over for women.