Reframing Loss: Why I No Longer Believe in Regret

David Meltzer
Reframing Loss: Why I No Longer Believe in Regret
Reframing Loss: Why I No Longer Believe in Regret
I once watched nearly a million dollars vanish during a flight to Vancouver. Before boarding, I was up $985,000 on a $60,000 investment. My wife urged me to sell, but I was convinced the stock would climb higher when news broke the following day. By the time I landed, my stop-loss had triggered, and I walked away with nothing but my initial investment. Back then, my reaction was predictable: self-loathing and regret. “I lost $985,000. I’m an idiot. I could have retired my mom,” I told my wife. I dwelled on what could have been rather than what was.Today, I see this experience through an entirely different lens. This shift in perspective has transformed how I view not just financial setbacks but all of life’s disappointments.

The Illusion of Loss

I no longer believe in loss or sacrifice. These concepts create unnecessary suffering by focusing on what we don’t have rather than what we do. When we frame experiences as losses, we create stories of deprivation that keep us stuck in a cycle of regret.

What if we eliminated the concept of loss from our vocabulary? Instead of saying “I lost money,” what if we simply acknowledged that our investment yielded a different return than anticipated?

This isn’t semantic gymnastics—it’s a fundamental shift in how we process reality. When I “lost” that potential windfall, I didn’t actually lose anything I already possessed. I simply returned to my starting point with valuable experience gained.

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Investment vs. Return

Every decision we make is an investment that yields some form of return. Sometimes that return aligns with our expectations; often it doesn’t. The key is recognizing that every outcome provides value, even when it’s not the value we anticipated.

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In my Vancouver experience, I invested $60,000 and received:

  • My original capital back (thanks to my stop-loss strategy)
  • A powerful lesson about timing and decision-making
  • The opportunity to develop a healthier relationship with money
  • A story I now use to help others reframe their thinking

Was this the return I wanted? No. But it was the return I received, and recognizing its value freed me from the trap of regret.

Eliminating “Could Have, Should Have, Would Have”

Perhaps the most damaging aspect of perceiving experiences as losses is how it traps us in alternative realities. I could have retired my mom” creates a fictional narrative that only serves to intensify disappointment.

If I truly want to retire my mother, I’ll make it happen when I have the means to do so. Creating stories about missed opportunities doesn’t serve anyone, least of all my mom.

This applies universally. How often do we torture ourselves with thoughts of what could have been if we’d made different choices? This thinking pattern keeps us anchored to the past rather than focused on creating the future we want.

Taking Ownership of Outcomes

The most empowering aspect of this mindset shift is how it places responsibility squarely in our hands. When we stop viewing outcomes as losses, we stop seeing ourselves as victims of circumstance.

I now understand that I didn’t “lose” $985,000—I made a series of decisions that resulted in a break-even outcome on my investment. Those decisions were mine, as were their consequences.

This ownership extends to future actions as well. Rather than lamenting what could have been, I focus on what can be. If retiring my mother remains important to me, I’ll create new opportunities to make that happen.

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Life rarely unfolds exactly as we plan. Markets fluctuate, opportunities shift, and timing often works against us. But by reframing how we view these experiences—seeing returns rather than losses—we free ourselves to learn, grow, and move forward without the burden of regret.


Frequently Asked Questions

Q: How can I start changing my mindset about financial losses?

Begin by changing your language. Instead of saying “I lost money,” try “My investment yielded a different return than expected.” This simple shift helps you focus on what you gained from the experience rather than what you didn’t receive.

Q: Isn’t this just positive thinking that ignores real financial consequences?

Not at all. This mindset acknowledges reality while refusing to add emotional suffering through regret. The financial outcome remains the same, but your relationship to it changes dramatically, allowing you to learn and move forward constructively.

Q: How do you balance this mindset with proper risk management?

This perspective actually enhances risk management. By viewing every outcome as a return on investment rather than a potential loss, you can make clearer decisions about which risks are worth taking and which protective measures (such as stop-losses) to implement.

Q: Does this approach work for non-financial disappointments too?

Absolutely. Whether it’s a relationship ending, a missed career opportunity, or any other disappointment, focusing on what you gained rather than what you lost transforms how you process and learn from these experiences.

Q: How do you handle the emotional impact of significant financial setbacks?

Emotions are natural and shouldn’t be suppressed. Allow yourself to feel disappointed, but then redirect your focus to what you learned and how you’ll apply that knowledge going forward. Remember that your worth isn’t determined by financial outcomes.

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​​David Meltzer is the Chairman of the Napoleon Hill Institute and formerly served as CEO of the renowned Leigh Steinberg Sports & Entertainment agency, which was the inspiration for the movie Jerry Maguire. He is a globally recognized entrepreneur, investor, and top business coach. Variety Magazine has recognized him as their Sports Humanitarian of the Year and has been awarded the Ellis Island Medal of Honor.