The 3 Regrets of Retirees—and How to Dodge Every One Like a Damn Pro

Because you didn’t come this far just to become a cautionary tale.

Let’s get one thing straight:
Getting older isn’t the problem.
Living small is.

There’s a video making the rounds from a financial planner who works with retirees and it stopped me cold. He said there are three things retirees regret most. And let me tell you—they aren’t about the stock market. They’re about how we live. Or don’t.

Let’s break them down—and more importantly, let’s flip the damn script.

1. I Spent My Whole Life Saving… and Now I Don’t Know How to Spend.

Oh honey. The number of women I’ve met who saved their entire lives only to feel guilty buying a nice handbag or booking a flight to Italy?

You built a life around caution. Around safety. Around “just in case.”
And now, with time and money finally on your side—you’re afraid to enjoy it.

This isn’t just about finances. It’s about worthiness.
Somewhere along the way, you learned to see spending on yourself as indulgent. Wasteful. Maybe even selfish.

Let me fix that for you:
Spending money on joy, on adventure, on beauty, on you—is an act of rebellion. Of healing. Of finally, fully living.

Don’t die with money in the bank and unlived dreams in your gut.

2. I’m Afraid I’ll Run Out of Money.

The fear is real. But let’s talk about what you’re actually afraid of:
Running out of security. Of comfort. Of options.

Here’s the truth no one tells you:
You don’t need to spend recklessly to live fully. You need to spend intentionally.

That means deciding:

• What matters most to you now?

• What do you want to experience before your knees give out?

• What memories do you want to create before the lights go down?

You’ll never feel “ready.” Not financially, not emotionally. So stop waiting for the math to feel like magic. Make the plan and make the move.

Fear doesn’t deserve to be your financial advisor.

3. I Waited Too Long to Enjoy My Life.

Read that again.
That’s the one that haunts people.

They were “too busy.”
Too tired.
Too worried about what people would think.
Too stuck in shoulds.

And now? They’ve got the time—but not the same fire. Or health. Or maybe they just feel like the moment passed them by.

Let me be blunt:

If you woke up today, the moment hasn’t passed. It’s here. It’s now.

You don’t need to go skydiving or buy a yacht. You just need to say yes to things that make your heart race a little.

Say yes to the solo dinner.
Say yes to the trip, even if you go alone.
Say yes to the damn lipstick.

And say no to the lie that it’s too late.

Final Word:

No one regrets being bold.
They regret playing it safe for too long.

So here’s your permission slip, signed with love by this Old Broad:
Spend the money.
Take the risk.
Live the life.

Graceful aging is for the faint of heart.
You? You're aging with teeth, spark, and champagne in your carry-on.