This is especially true when holding a concentrated position in a single stock. During periods like the current correction in tech, when certain names have pulled back 20 to 30 percent from recent highs, many investors find themselves questioning what to do next.

But this isn’t just a discussion about losses. In other cases, investors may be holding a stock that’s up 30 percent and are unsure whether to lock in gains, continue holding, or rebalance into other opportunities. The common thread is uncertainty, and the fear of making a decision they’ll later regret.

That’s where regret minimization comes in.

This concept was famously used by Jeff Bezos when deciding whether to leave his job in finance to start Amazon. He asked himself:

“When I’m 80, will I regret not having tried this?”

It wasn’t about maximizing expected value—it was about minimizing future regret.

This simple shift in mindset can also apply to how we manage investments. Rather than asking, “What’s the right answer?”, we can ask:

“What decision will I regret the least, regardless of how things turn out?”

When the future is unknowable (and it always is), this framework helps bring clarity to emotionally charged decisions—especially around concentrated stock positions.

Three Paths Forward and the Pros & Cons of Each

If you’re sitting on a significant position in a tech stock that’s declined meaningfully—or has become a dominant share of your portfolio—you’re likely weighing your next move. Regret minimization helps you understand the emotional consequences of each path before making a decision.

1. Hold the Position and Wait

• Why it appeals: You believe in the company. You see the dip as temporary. Selling now feels premature.
• The risk: If the stock continues to underperform—or stays flat while others rebound—you may miss broader opportunities.
• Potential regret: In hindsight, doing nothing might feel like a costly delay.

2. Reallocate Into a Basket of Diversified Tech Stocks

• Why it’s compelling: Rather than relying on the fate of a single company, reallocating into a carefully selected basket of diversified tech names can help spread risk while maintaining exposure to innovation and long-term growth trends.
• The strategy: Some quality tech companies—particularly in growth-oriented sectors like cloud, cybersecurity, or AI—may have corrected more than your current holding. By reallocating into a group of 10 to 15 well-researched, fundamentally strong stocks, you may capture greater upside in the eventual rebound.
• The benefit: You stay invested in the sector you believe in, but with better diversification and potentially stronger return prospects than holding one name.
• Potential regret: If your original stock recovers faster than the others, you may feel you moved too soon—but you’ve reduced downside exposure and improved overall portfolio resilience.

3. Shift Into a Diversified Portfolio

• Why this works: It reduces single-stock risk and aligns your investments with long-term financial goals, not just short-term stock moves.
• You’re exchanging: Volatility and uncertainty in one name for a broader, more resilient structure.
• Potential regret: Missing a sharp rebound in your former position—but gaining peace of mind and more balanced exposure.

There’s no perfect choice, only the one you’re least likely to regret. But regret minimization isn’t meant to stand alone. The most effective way to make these decisions is by viewing them through the lens of your overall financial plan, specifically, the Wealth Allocation Framework.

This framework breaks your wealth into different “buckets” of risk:

• Personal Risk Bucket: designed for stability and essential needs
• Market Risk Bucket: built for diversified exposure to long-term growth
• Aspirational Risk Bucket: concentrated positions or high-upside opportunities

If the concentrated stock you hold today falls into the Aspirational Bucket, a reallocation might involve moving that capital into the Market Bucket, or staying within the same risk category, but diversifying into a better mix of assets. That’s where planning intersects with behavior: understanding not just what you can do, but what makes sense for your specific goals and risk profile.

The Emotional Fallacy of Waiting to Break Even

One of the most common behaviors during drawdowns is waiting to “get back to even” before taking action. It feels like a responsible decision. But it’s often just a way to delay discomfort.

The market doesn’t know—or care—what you paid for your shares.

Ask yourself:

• If I didn’t already own this stock, would I buy it at this price today?

• If I had this cash available now, is this where I’d allocate it?

If the answer is no, then “waiting to break even” is just another way of saying you’re hoping the market will make the decision for you.

Anchoring: The Illusion of the “Right” Price

Another common trap is anchoring, fixating on a specific price point as your mental reference. That anchor might be:

• The stock’s previous high

• Your cost basis

• A recent valuation or IPO price

• A number mentioned in a company update or media story

Once an anchor is established, it can distort how you interpret new information. Even when circumstances change, that number can keep you emotionally locked into a target that no longer makes sense.

Anchoring can lead to inaction, missed opportunities, or unjustified confidence in a rebound.

Letting go of anchors, just like letting go of break-even fixation is part of building a forward-looking mindset that leads to more rational decisions.

This Isn’t About Buying or Selling. It’s About Clarity

The goal isn’t to tell you to sell your position—or to keep holding it. In fact, for some investors, the right decision might be to buy more. For others, it might be to trim or fully reallocate.

The point is: you can make a proactive, intentional decision, rather than one based on fear, habit, or indecision.

When you use regret minimization, you weigh each path based on how it aligns with your values, your risk tolerance, and your long-term goals.

That’s real clarity and it often leads to better outcomes than any “perfectly timed” trade.

What Comes Next

We don’t pretend to know when tech stocks, or the broader market will bounce back. But based on history, we believe:

• Corrections are temporary
• While the path is never linear, markets have recovered from every downturn
• Returns tend to be strongest after periods of fear and decline

What no one can predict is the timing, whether that rebound comes in a week, a month, or a year. But the more important question is whether your portfolio, and your mindset, are built to hold steady until it does.

At Prospera, we work with tech professionals, executives, and entrepreneurs who often find themselves navigating concentrated stock decisions during uncertain markets. We combine behavioral tools like regret minimization with a structured planning process. That way, the decision isn’t just emotionally manageable, it’s aligned with your bigger picture.

If you're facing a concentrated stock decision and want to explore your options with experienced guidance, talk to us.