The two kinds of regret
One starts with a big "R" and the other with a little "r"
I’ve written before about regret minimization:
Live now, avoid regrets later (Feb, 2025)
A financial fork in the road (June, 2024)
Can you save too much? (July, 2019)
But I’ve come to realize not all regret is the same...
My client Lisa shared something with me the other day.
“I wish I’d spent more time with my kids when they were little.”
She said it with real pain in her voice. I could see it in her eyes.
Like she had failed somehow.
But then I asked her a question.
“What were you doing instead?”
She thought about it and said,
“Working. Building my career. Saving for their college. Trying to give them a good life.”
“And did you?” I asked.
“Yes. They both graduated debt-free. They’re doing great.”
Here’s what I told Lisa: Not all regret is the same.
There’s big “R” Regret
These are the things we truly wish we had done differently.
The times we acted out of fear. The words we didn’t say. The dreams we gave up for no good reason.
Big “R” Regret means something. It points to a real mistake. It deserves our attention.
Then there’s little “r” regret
These are the things we missed because we chose something else. Not mistakes.
Lisa didn’t neglect her kids.
She made a choice.
She traded some time together for their future security.
That’s not a failure. That’s life.
Every choice has a cost. When you say yes to one thing, you say no to something else.
I’ll forever regret giving up on piano lessons when I was in middle school. But at the time, I’d rather have been doing anything instead of practicing my arpeggios.
An idea this brings to mind is “you can do anything, but you can’t do everything.”
That’s not regret. That’s math.
The problem is, we often mix these up.
We treat every missed opportunity like a mistake. We carry guilt for trade-offs that were actually good decisions at the time.
So how do you tell the difference?
Ask yourself: If I could go back, would I truly choose differently?
Or was I doing the best I could with what I had?
Big “R” Regret says: “I was wrong. I need to learn from this.”
Little “r” regret says: “I chose something else. And that was okay.”
Here’s why this matters for your retirement:
You have choices ahead of you. Some will feel big. Some will feel scary.
If you try to avoid all regret, you’ll never choose anything. You’ll stay stuck.
But if you know the difference between Big “R” regret and little “r” regret, you can move forward.
Focus on avoiding Big “R” Regrets.
The stuff that really matters.
The trips you’ll wish you had taken. The people you’ll wish you had called. The life you’ll wish you had lived.
This is exactly the regret minimization I help my clients with.
Let go of little “r” regret. You can’t do everything. No one can.
The goal isn’t a perfect life with no regrets.
The goal is a life where you chose what matters most to you.
On purpose.
That’s enough.
Links & things
Some things I’ve been reading that I encourage you to check out:
Take Retirement in Little Batches by David Baker
Some gems in this article even though he frames it from the perspective of building and running a business
Somewhere Down There by Jeffrey Ptak
Another example of why to be wary of “alternative” investments. The one he highlights costs over 7% a year in fees
Oh, Go On by Rubin Miller
Good investing isn’t simply about being right; it’s about building systems that protect you from yourself
Five Pearls of Wisdom From a Legend of Financial Writing by Ron Lieber
Mr. Lieber honors Jonathan Clements by sharing some of his best ideas
I recently stumbled across this and love it:
“Protecting your family wealth from predators, creditors, and senators.”
Maybe I should adopt as my business tagline?
Thank you for reading!
If you’re not a client and would like my advice, simply reply to this email with your questions and I’ll be happy to respond with my thoughts…
Until next Wednesday,
Russ