even the darkest moments spark goodness

Transforming Regrets into Valuable Life Lessons

We all have some regrets—those little and big decisions in life that we wish we could undo. It’s human nature to dwell on our past choices, labeling them as “mistakes” and berating ourselves for the paths we took. A bad marriage that ended in a contentious divorce. A career move that turned out to be a poor fit. These moments often haunt us, but what if they weren’t really mistakes at all?

What if those so-called “mistakes” were actually necessary steps that brought us to the life we’re living now—a life that might, in its own way, be just right?

Every decision we make informs the next one. Each choice, whether it feels right or wrong at the time, teaches us something invaluable about ourselves. Through every experience, our preferences become clearer, our understanding deepens, and our future decisions are made with greater wisdom. Yet, we don’t always know the best course of action at the outset. Life, by its very nature, requires a certain amount of trial and error.

The beauty of this process is that even our perceived missteps play a critical role. While it’s easy to isolate a single decision and criticize it harshly, when we zoom out and view it as part of the larger picture, its value often becomes evident. What initially seemed like a detour or a disaster might have been the very thing that set us on the path toward a better, more fulfilling life.

Think about your first relationships. They might not have been the healthiest or the happiest. They may even feel like mistakes or wasted time now. But didn’t those experiences teach you what to look for—and what to avoid—in future relationships? Didn’t they train you to be more discerning and self-aware?  Are you now in a better relationship and does that have at least a little to do with your previous relationship misteps?

The same goes for your first jobs. Maybe you couldn’t stand the work, the environment, or the role itself. Perhaps you counted the minutes until you could leave and regretted chasing the opportunity. But wasn’t the next opportunity all the sweeter for it? Didn’t you approach it with clearer priorities and a deeper understanding of what you truly wanted?  The previous ‘mistakes’ made you much better at looking for and, importantly, asking more exactly what you now know you need!

This isn’t a coincidence—it’s growth. Every experience, even the difficult ones, advises and trains us, offering the perspective and relativity we need to thrive. Without those “mistakes,” we might never arrive at the clarity required to make better choices.

So, instead of dwelling on our history of missteps with frustration or regret, what if we reframed them as essential stepping stones? These moments, however challenging, are often the very catalysts that lead us toward our happiest and most authentic lives.

Of course, it’s unrealistic to expect ourselves to celebrate when things go wrong. Mistakes hurt. But perhaps we can offer ourselves a bit of grace. Perhaps we can acknowledge that those tough moments—the failed relationships, the wrong turns, the less-than-ideal jobs—are not failures at all. They’re part of the process, essential in shaping who we are and guiding us toward what’s next.

In the end, our so-called “mistakes” make us smarter, stronger, and better equipped for life. They are not just setbacks; they are vital lessons. And in that sense, mistakes are not only inevitable—they’re essential. 

(**Disclaimer:  I am not suggesting impetuous or reckless behavior that will increase the likelihood of silly mistakes.  In fact, just the opposite — be careful and as disciplined as possible when making life decisions applying all the information, knowledge, intuition and third party advice to make the best decisions possible no matter what.  But, if /when you make a mistake, know that it’s all part of life, adds strength and character and, when used correctly, brings you to an increasingly informed stage in life.  And, don’t be too hard on yourself along the way.  Nobody is perfect.)

Finding the Wins amidst the Losses

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In the summer of 2006, at the absolute top of the housing market boom in the SE and literally weeks before one of the biggest housing crashes in history, I purchased my new lakefront house!   The housing market was booming and everyone was making money. Timing was perfect! I figured I’d get a great house, have fun using it and then make a bundle selling it whenever I wanted. Well, things didn’t quite work out the way I wanted. I, like so many, had no idea how wrong I was and how the looming risk was so imminent and so substantial.

As you would expect I grossly overpaid for the house and, today, I’m suffering the consequences as I try to sell it. Twelve-years later and the house is finally under contract to be sold for 30% less than I paid.  Didn’t our parents tell us that real estate is supposed to be a good investment and appreciate ~5% /year?   Well, I guess, like anything, there are good real estate opportunities and bad ones, and so many factors impact the transaction. What makes it worse is that the loss in value of the house is not the only loss. Think of the opportunity cost for the money that has been stuck in a depreciating asset for 12-years. I could invested the money elsewhere where it would have compounded interest for years. Well, enough about the loss.

Interestingly, my misfortune turns out to be a boon for the new buyer who is getting an amazing lake house for tens of thousands less than I paid. One man’s suffering is certainly another man’s fortune. I guess that creates balance in the universe. Furthermore, I’ve learned that I cannot expect to win every time. Other people have to win too!

As I reflect on the lake house transaction further and focus differently, I realize I had substantial intangible gains on the house.   My friends, family and I shared dozens of weekends relaxing, cooking, boating and chatting at the house. It was (and is) a special place that that created indelible memories.   And, if I had not bought the lake house, I would never have met my wife (longer story). Those are some big wins!

When I look back on my life 30-40 years from now, I trust that I will not regret my lake house purchase, despite it being a financial loss. I realize that winning and losing is totally relative. I am grateful for the opportunity to own a lake house and to have shared that with my friends and family. In the scheme of things, I now recognize this as more of a win and great learning experience. Don’t get me wrong… For now, I’m happy to rent a lake house from time to time when the urge arises (and won’t be buying a second home any time soon).

The Smarter Sooner takeaway: be sure to look closely at all of life’s events as there usually are wins (sometimes tucked away) that may just overshadow even the most prickly financial losses. Good luck!