Regret in Midlife: What to Do When You Wish You’d Chosen Differently

I could hear it in her voice. She tried to hold herself together, but as her eyes filled with tears, she whispered, “I’ll be 50 years old tomorrow and I have so many regrets.”

I knew exactly what she meant.

The week I turned 50, I remember looking around my life and barely recognizing it. I was unhealthy—physically, emotionally, financially, and relationally. I wrote about that season here if you want to read more of my story:  A life I love felt impossible....

As my client talked about trying to celebrate her birthday while carrying the weight of regret, I reflected on how many women I’ve spoken to who feel the same way. At midlife, so many of us quietly ask:

“How in the world did I get here?”
“This is not what I planned.”
“Is it too late to change things?”

If you’re here, you’re not alone. And more importantly—you’re not stuck.

Here’s what I told her, and what I want to tell you too:

1. You were doing the best you could.

It's easy to look back with today’s clarity and judge yourself for past choices. But most of the time, you made decisions with the knowledge, resources, and capacity you had at the time.

2. Write down your regrets—not to punish yourself, but to release yourself.

Name them. Get them out of your head and onto paper so they lose their power.

3. Do something symbolic with the list.

Burn it. Tear it up. Shred it. Throw it in a river or the garbage. Create a visual moment your brain can return to—an anchor of self-forgiveness.

4. Let regret become a doorway, not a dead end.

Ask yourself:
How do I want life to feel from here? What do I want more of? Less of?
Midlife isn’t a wrap-up—it’s a reset.

5. Don’t carry it alone.

Talk it through with a trusted friend, a counselor, or a coach (I know one). Learn from women who have been in the trenches and rebuilt something beautiful. Their stories are proof that you can, too.

Regret is part of being human—but it doesn’t have to haunt you. Now is the perfect time to work through it, release what you’re carrying, and move forward with hope.

You Don’t Have to Do This Alone

If you’re ready for support, here are a few ways I walk with women through this season:

• 1:1 Coaching – Personalized guidance for your specific season and story

• The Midlife Roadmap – My 10-week program that helps you rebuild with clarity, confidence, and purpose

• Midlife With Purpose Facebook Group – A safe, encouraging community of women navigating midlife together

You can take your next step whenever you're ready. I’m here when you are.