MW These are my biggest investing regrets - and how I'm hitting reset in retirement

By David Conti

For retirees, missed opportunities can feel extremely painful. Here's how to move forward.

By trying to avoid regret, we create more of it.

'I held my biggest stock winner too long and missed crypto at the bottom.'

If you've ever sat around a dinner table with fellow retirees or what I call "honest friends," you know how the stories go. Someone leans back and says, "I sold too early." Another admits, "I never bought when I had the chance." And pretty soon, you're trading stock-market tales of near misses, missed opportunities and what might have been.

These stories aren't really about money. They're about regret. More specifically, what behavior experts call "regret aversion" - our tendency to avoid choices that might someday leave us second-guessing ourselves.

In retirement, this hidden force can feel even stronger. Every decision feels weightier. Every missed chance feels sharper. And yet, my own investing history shows that regret is simply part of the journey. The trick isn't to avoid it - it's to learn how to live with it.

Adobe: Riding a winner too long

I've been holding Adobe $(ADBE)$ stock for more than 25 years. What began as a $1,500 investment grew to almost $90,000.

By late 2021, the stock was trading close to $700 a share. It was my biggest winner by far. That was my chance to sell half, lock in life-changing gains and redeploy the rest into other opportunities. But I didn't. (Adobe shares closed Monday around $337 - the stock is down 30% in the past 12 months.)

Why didn't I sell? Regret aversion. I was afraid I'd regret selling too soon. I told myself, "What if it doubles again? What if I miss out?" So I held on. And when the stock inevitably pulled back, my paper profits shrank.

The regret wasn't that Adobe shares fell - stocks rise and fall all the time. The regret was that I didn't have the discipline to take some gains when the moment was right - because I enjoyed the feeling of holding a winner. By trying to avoid regret, I created more of it.

Missing out on 'crypto winter'

My other big regret is the opposite. In January 2023, bitcoin (BTCUSD) was at around $16,500. Ethereum (ETHUSD), too, was deeply out of favor. It was the depths of "crypto winter" - when negative headlines about crypto bankruptcies and fraud dominated the news. Most investors, myself included, stayed cautious.

But that was the opportunity. By mid-2025, bitcoin had soared past $100,000, a sixfold increase. Ethereum surged as well. Those who bought when fear was highest were rewarded handsomely.

And me? I dipped a toe into crypto with small investments - Kraken, Gemini and the Fidelity Wise Origin Bitcoin Fund FBTC - but I didn't commit more. Once again, regret aversion held me back. I didn't want to risk being wrong. I didn't want to feel foolish for buying "too soon." So I hesitated - and missed a chance to build real gains.

Why retirees are especially vulnerable to regret

The danger is letting regret aversion push us into extremes - becoming paralyzed and too conservative, or overreacting and chasing returns.

As we get older, we tend to become more cautious. Some of that is rational - we don't have 30 years to recover from market downturns. But behavioral research shows that regret looms larger in later life. Here's why:

-- High stakes. Every decision feels like it could affect lifestyle, healthcare or legacy.

-- Limited do-overs. Unlike younger investors, retirees don't always have decades of earnings power to rebuild after losses.

-- Memory bias. We remember regrets vividly and replay them, often with a harsher self-judgment than the situation deserves.

-- Peer comparison. Retirees talk. Hearing that a neighbor "got out at the top" or "bought Bitcoin at $20K" can amplify our own feelings of having missed out.

The danger is letting regret aversion push us into extremes - becoming paralyzed and too conservative, or overreacting and chasing returns.

What I've learned

Did you miss out on gold (GC00)? Do you wish you had bought Costco $(COST)$ in 2020 at $300 a share? Or Nvidia (NVDA), Meta Platforms (META), or any of the "Magnificent Seven" tech stocks?

How do we manage regret - especially when the margin for error feels smaller in retirement? Here are a few lessons I've taken from my own experiences:

-- Take partial action. You don't have to go all in or all out. Selling part of a concentrated position or buying a modest slice of a beaten-down asset can give you balance.

-- Make rules ahead of time. In a calm frame of mind, decide what you'll do if a stock doubles - or drops 50%. That way, you're not making emotional calls in the heat of the moment.

-- Think portfolio, not position. Regrets tend to focus on single trades. But your retirement security rests on your whole plan - diversified, balanced and aligned with your goals.

-- Don't carry regret too long. Forgive yourself. Learn the lesson and reset. Wasted energy doesn't compound, but investments and experiences do.

-- Understand risk capacity. Keeping debt and spending in check, you can boost your ability to comfortably take calculated and appropriate investment risks.

Regret beyond the markets

The key isn't to avoid regret. It's to process it, reset, and keep going.

The truth is that regret aversion doesn't just shape our investing. It also shows up in life:

-- Putting off a dream vacation because "what if the timing isn't right?"

-- Holding back from moving closer to family because "what if I regret it later?"

-- Avoiding new hobbies or "active retiree" communities because "what if I don't fit in?"

These are all forms of regret aversion. We freeze up because we're afraid of the wrong choice. But the reality is that life itself is a portfolio. Some choices will pay off, some won't. The point is to stay engaged and keep moving forward.

Hitting the reset button

If there's one thing retirement has taught me, it's that regret is inevitable. We all have stories of what we should have done differently - in money, in work, in relationships. The key isn't to avoid regret. It's to process it, reset, and keep going.

Life is constantly changing. Markets are constantly changing. We all take risks in different ways. Some of us play it safe, some of us swing for the fences. Either way, regret is part of the game.

So acknowledge it. Learn from it. Then hit the reset button. Because every day in retirement is a fresh chance to choose, to act, and to live fully.

David Conti is a financial writer and retirement coach at RetireMentors.

More: 3 ways to make sure the 'great wealth transfer' enriches your family

Also read: Are your parents afraid of investing in crypto? How to talk with them so they'll actually listen.

-David Conti

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November 05, 2025 08:12 ET (13:12 GMT)

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