Regret-Proofing Your Retirement: 5 Key Insights to Stop Looking Back and Start Living Now
By Dave Smith, The Ultimate Retirement Coach
One Big Idea:
Regret is a backward-facing emotion that steals forward momentum.
Most of us hit retirement with a suitcase full of “what-ifs.” Regret over career choices, missed family time, lost opportunities, or financial decisions can haunt the peace we long for. But here’s the truth: regret isn’t about the past. It’s about how we’re choosing to relate to the past in the present.
We can’t change our history, but we can change the story we tell about it—and how much power we give it over our current joy.
One Powerful Question:
What am I still holding against myself that’s keeping me from peace right now?
One Simple Exercise:
Try this:
Write down one regret you frequently think about—just one. Now answer this:
What was I truly needing or hoping for at that time?
Did I know better? Could I have done better with what I knew then?
What strength did I gain because of what happened?
Now reframe that regret into a message of growth. For example:
“I regret not being there for my daughter when she was young” becomes
“I didn’t know then how fast time would go. But I now prioritize deep presence with her as an adult—and that’s healing for both of us.”
✨ Free Worksheet: 5 Insights to Overcome Regret in Retirement
Download or print to complete your own reflection.
🧠 Insight #1: Regret thrives on comparison.
We imagine alternate lives that look better—but those lives are fantasy.
Take Action: List 3 things in your life now that wouldn’t exist if you’d made a different choice.
🧠 Insight #2: Regret comes from not honoring our past selves.
You did what you could, with what you had, and what you knew.
Take Action: Write a short letter of compassion to your younger self. What would you say to them if you were their coach?
🧠 Insight #3: Regret magnifies what we lost, not what we gained.
Even painful choices often lead to strength, resilience, or wisdom.
Take Action: Name 1 way you’ve grown because of a past decision you regret. How has that helped you today?
🧠 Insight #4: Regret deepens when we stay stuck.
If we keep reliving the past but take no action in the present, the story never changes.
Take Action: Identify 1 thing you can do this week to resolve, repair, or release the regret.
🧠 Insight #5: Regret fades with purpose.
When your why is strong, the past loses its grip.
Take Action: What legacy do you want to create in your retirement years? Write one sentence that describes it.
Closing Thought:
Regret doesn’t mean you failed—it means you’re still learning. Retirement isn’t the end. It’s the beginning of your wisest, most intentional chapter yet.
Let’s make it one you don’t regret.
– Dave Smith
The Ultimate Retirement Coach