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Dealing with Crypto Regret: Missed Opportunities and Bad Trades

You had $1,000 sitting in a savings account earning 2% in 2020. You thought about Bitcoin at $9,000. You talked yourself out of it. You watched it hit $69,000 in 2021. You calculated what that $1,000 would have been. You felt sick. Or maybe you actually bought Bitcoin, held it all the way through 2022, panicked when it dropped below $17,000, and sold. Then watched it recover to over $126,000 by October 2025. You have a different kind of sick feeling, but it is equally real. Crypto regret is one of the most psychologically specific experiences in modern finance. This blog does not dismiss it. It explains it, contextualises it, and gives you a framework for moving through it without letting it destroy your future investment decisions or your peace of mind.

By CryptoAcademy Team | Published: 2026-04-04 | 18 min read time read | Category: Educational

You Are Not Alone: The Scale of Crypto Regret

Before anything else, it is worth establishing that what you are feeling is not unusual, not dramatic, and not a sign that you are doing anything wrong as an investor or as a person.

A study of 3,009 people in Australia found that over 40% of under-35s say they regret not investing in cryptocurrency over the past decade, with 80% of Australians under 50 saying they regretted the investment choices they had made over the last decade overall. This was the single most commonly cited missed opportunity, ahead of property and shares in major tech companies.

A 2024 Kraken survey of 1,248 US crypto holders revealed that 63% reported that emotional decisions had negatively impacted their portfolios. When asked about FOMO specifically, 84% admitted to making decisions based on it. When asked about FUD-driven decisions, 81% admitted to those too.

These are not statistics about people who are bad at investing. They are statistics about the normal human experience of participating in one of the most volatile, psychologically demanding, and socially visible asset markets ever created. The numbers are high because the market itself is designed, either deliberately or as an emergent property of its structure, to generate exactly these emotional responses.

There are two distinct categories of crypto regret, and they work differently in the brain. Understanding the distinction helps you work through each more effectively.

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Two Flavours of Regret: Omission vs Commission

Cognitive psychology has recognised for some time that many decisions are based on the desire to minimise anticipated regret, and that there is a fundamental asymmetry between two types of regret.

Regret of omission is the pain of not doing something. Not buying Bitcoin. Not adding more during the dip. Not moving to a hardware wallet before the exchange collapse. The psychological mechanism here is counterfactual thinking: you imagine the action you did not take and compare the outcome you missed to the outcome you have.

Regret of commission is the pain of having done something. Buying at the top. Selling at the bottom. Moving into a meme coin that went to zero. The action you took produced a bad outcome.

Research shows that people generally feel stronger regret over acts of commission than acts of omission in most contexts. However, crypto trading appears to be an exception that creates unusually strong regret in both directions. What they missed out on, a coin that has multiplied in value over months, and what coins they sold too early, are both sources of lasting pain that traders observe over extended periods.

Why does crypto amplify both types? Because the market never closes, the information is always available, and the counterfactual is always visible.

If you sold Bitcoin at $17,000 in late 2022, the Bitcoin price chart is still there to view at any moment. The distance between your exit and the subsequent recovery is a number you can calculate precisely and repeatedly, any time you choose to look. There is no soft-focus forgetting in a market that keeps its entire history on a publicly accessible chart.

This is fundamentally different from most other financial decisions. If you decided not to buy a property that subsequently appreciated, you do not see a live price ticker for that specific property every time you open an app. The visibility of crypto's price history makes the counterfactual constantly available, which means regret has fewer natural barriers to fading.

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The "I Should Have Bought Bitcoin" Regret

Let us address the most common form of crypto regret: the version experienced by people who never participated at all, or who participated too little, and watched from the outside as extraordinary gains happened without them.

This is the regret of omission. It is extremely common. It is also, when examined carefully, less meaningful than it feels.

The hindsight problem. Hindsight bias is the cognitive tendency to believe, after an outcome is known, that you should have seen it coming. You know Bitcoin went from $9,000 to $69,000 now. In 2020, you did not know that. In 2020, Bitcoin had also dropped from $20,000 to $3,000 in the preceding two years and the majority of financial media was describing it as a failed experiment. The decision you made in 2020 was made with 2020 information, not 2025 information. Judging that decision using hindsight is not fair to yourself.

The risk you would have needed to take. The people who held Bitcoin from $9,000 to $69,000 also experienced multiple 30% to 50% corrections along the way. They held through periods where every financial expert was predicting further declines. They held through regulatory attacks, exchange failures, and years of negative media coverage. The comfortable "I should have just bought and held" narrative erases the actual emotional difficulty of doing so. If you had bought, would you have actually held through all of that? The honest answer for most people is probably no.

The comparison is unfair to everything else. Bitcoin from 2020 to 2025 was one of the best-performing assets in the history of global financial markets. Comparing your actual portfolio returns to the absolute best possible outcome in the most exceptional asset of the decade is a recipe for permanent dissatisfaction. Nobody does this consistently with traditional assets. You do not calculate what your savings account would be worth if you had put it all in Nvidia in 2020. But with crypto, the visibility of the missed gain makes it impossible to look away.

You can participate going forward. This is the most practically relevant reframe. The regret of missing early Bitcoin is largely backward-looking. But the asset still exists. It is still trading. The institutional adoption that is driving long-term demand is still accelerating. The supply dynamics from the 2024 halving are still playing out. Regret about the past is only useful if it informs action going forward. The question is not "why did I not buy in 2015" but "what do I want to do now with the information and context I have."

> Real-world example:

> "Spent about two years being genuinely upset that had not bought Bitcoin in 2019 when a friend recommended it at $8,000. Watched it reach $69,000 and felt genuinely sick. The turning point was calculating that the Bitcoin story was not over: it had just reached $69,000 for the first time. At that point started actually researching and eventually bought during the 2022 correction when it was under $20,000. The opportunity was not gone. It had just changed shape. The regret about 2019 eventually became useful because it made sure of actually acting when the next good entry arrived instead of waiting for the perfect entry that does not exist."

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The "I Sold Too Early" Regret

This is the regret of commission: you owned the asset, made a decision about it, and watched the outcome of that decision play out unfavourably. This is often more painful than never having participated because you came so close to the outcome you wanted.

Bitcoin's journey provides the clearest example. The investors who bought at various stages through 2021, held through the crash to $15,500 in November 2022, stayed through the slow recovery of 2023, and ultimately saw the all-time high of $126,272 in October 2025 experienced an extraordinary multi-year payoff.

But many investors along that path made what seemed at the time like entirely reasonable exits. Some sold in mid-2022 after holding for months and watching losses accumulate past 50%. Some sold in late 2022 after the FTX collapse when the news was catastrophically bad. Some sold in early 2023 when there was no obvious catalyst for recovery. Each of those exits was made with the information available at the time. Each of those exits felt like rational risk management in the moment. Each of them looks, in retrospect, like a costly mistake.

The painful reality of this type of regret is that the exit you regret was almost always made by a version of yourself operating under conditions of genuine stress and genuine information uncertainty. That version of yourself was not stupid. They were scared and exhausted and responding to real signals in the environment.

The disposition effect trap. Research shows that investors hold losing positions too long and cut winning positions too early, a pattern called the disposition effect. But crypto creates a specific variant: investors often hold through the worst of a decline, eventually sell at the point of maximum pain when the narrative is uniformly negative, and watch the recovery happen without them. This is almost the mirror image of the disposition effect. They held longer than they should have given their emotional capacity, then sold at precisely the worst moment.

What the exit actually was. When you sold Bitcoin at $17,000, you were not making a permanent decision about Bitcoin's future. You were making a decision about what you were going to do with your capital on that specific day. You cannot know what Bitcoin's future holds any more than the person who bought from you knew. The person who bought your Bitcoin at $17,000 took a risk. They were right, this time. If Bitcoin had continued lower, they would be the one looking at a loss and you would have avoided it.

The regret is about the story, not the number. Much of the pain from selling too early is not purely about the financial loss of the unrealised gain. It is about the narrative: the story you tell yourself about having been right about an asset but having failed to benefit from being right. That narrative feels like personal failure in a way that simply not having been exposed to the asset does not. This is why commission regret tends to be more acutely painful than omission regret in most contexts.

> Real-world example:

> "Sold a significant Ethereum position in June 2022 after holding through a 65% drawdown. The decision felt rational. The FUD was everywhere, the project had not shipped the Merge yet, the broader market was destroyed. Watched the Merge happen in September 2022, watched the subsequent recovery, watched the ETH ETF approval in 2024. The financial gap between my exit and where Ethereum eventually went is something spent a year being unable to think about without pain. The thing that eventually helped was accepting that the decision was made correctly given the information and emotional state at the time. The June 2022 version could not have known any of what happened next. That version made the best decision available with what was known."

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The "I Bought at the Top" Regret

There is a third form of crypto regret that combines elements of both. You bought an asset. It subsequently lost significant value. You are now holding a position you wish you had never entered.

This is the most acute form because it combines financial loss with the knowledge that you made an active choice that produced a bad outcome. The omission regret is about things you did not do. The commission regret after an exit is about something you did that turned out well but could have been better. This version is about something you did that turned out badly.

The research on this is sobering. 63% of crypto holders in a major 2023 study reported that their emotional decisions had negatively impacted their portfolios. The most common pathway to this outcome is exactly this: buying at or near a peak during a period of maximum excitement and social validation, then holding through a significant drawdown.

There are several cognitive traps that make this version of regret especially difficult to work through.

The sunk cost fallacy. Once you have a loss, the instinct is to hold until you recover your original investment. "It's only a loss if I sell." This reasoning is psychologically understandable but logically flawed. The

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