At some point in our lives, we've all experienced a woulda, shoulda, coulda, moment. You know… one of those incidents where if we had just done something different, the result would have been an entirely different outcome? What was it for you, who was there, and when was it? Because that missed opportunity made you…you!
Sometimes, when you're having a restless night and can't sleep, and your brain starts roaming over your memories, you usually lock onto some event you regret and simply wish you'd have done something different. I'm amazed at what my mind will think of at these moments of O' Dark Thirty in the middle of the night. Sometimes, it happened in the 4th grade in elementary school; other times, it was a job-related opportunity that passed by, and I didn't latch onto it. Then you began to wonder what your life would be like if you had just made that other choice. Hopefully, you learned a lesson from the incident and haven't made the same mistake twice.
When these things occur to me, I have learned to consciously redirect my thoughts toward some other memory that was a positive event in my life and start listing my blessings instead of dwelling on those negative vibes. A happy marriage for over 40 years, a wonderful daughter, all the beautiful memories of travel over the years, and the team at our office that is just plain fun to work with, to name a few. Trust me, if you give yourself a moment, you'll find the good outweighs the bad in your life by a long shot.
As we've learned these lessons in life, you'll eventually conclude that, good or bad, these missed opportunities have made you…you!
By David Edge
David Edge is a retirement lifestyle writer and contributor to the ARA monthly newsletter. His articles blend personal stories with practical insights on living well in retirement.
You Might Also Like
- Why Am I Me? Life's Milestones Shape Who We Become
Lifestyle & Mindset · David S. Edge - Why Am I Me? Good Luck! Reflecting on Life's Lucky Moments
Lifestyle & Mindset · David S. Edge - It's Pumpkin Time! Tips for Perfect Jack-O-Lantern Picking
Lifestyle & Mindset · David S. Edge
Easy Eddie's Take
David's reflection on those middle-of-the-night regrets really hits home for a lot of folks, especially as we get older. Here's the thing about retirement though – it's actually one area where you still have time to avoid those "what if" moments. A lot of people ask me, "What's the biggest retirement mistake I can still fix?" The answer is usually not starting Social Security planning early enough, or missing out on catch-up contributions to their 401k or IRA.
For 2026, if you're 50 or older, you can contribute an extra $7,500 to your 401k (that's $31,000 total) and an additional $1,000 to your traditional or Roth IRA (that's $8,000 total). Those catch-up contributions can make a real difference, and the IRS gives you until April 15, 2027 to make your 2026 IRA contributions. Most people are surprised when they learn they still have that flexibility.
The good news is that even if you've had some financial regrets along the way, small changes today can still have a big impact on your retirement security. A little preparation now means fewer sleepless nights later.