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The Psychology Behind Financial Regret, and How to Avoid Costly Decisions

Libby Miles's profile
By Libby Miles
January 27, 2026
The Psychology Behind Financial Regret, and How to Avoid Costly Decisions

According to studies, money is a significant source of stress for more than 60% of people over the age of 18. In addition to the stress that comes from worrying about paying bills, many people deal with financial regret, especially after making an expensive purchase. What makes financial regret especially powerful is that it rarely comes from lack of information, but rather from how the brain processes risk, uncertainty, and hindsight.

Understanding the psychology behind financial regret is an important part of avoiding financial mistakes while also cutting down on the amount of anxiety that you deal with when it comes to your money. When you understand where regret comes from and how your emotions impact financial decisions, you can start making decisions that support your financial goals.

Why Financial Regret Feels So Intense

For most people, money represents security, identity, and freedom. This fact makes financial decisions incredibly personal, so when a financial decision turns out poorly, it doesn’t only represent a loss of money, but also a loss of very important feelings and emotions. In fact, a bad financial decision can feel like a personal failure. This reaction is amplified by hindsight bias, which convinces people that the “right” decision should have been obvious all along.

Regret also becomes more prevalent when you compare actual outcomes to what might have been. Seeing others succeed financially, or revisiting other alternatives, reinforces the feeling that a different path would have led to a better result. When you fall into this type of comparison loop, you will typically deal with regret long after the decision has been made. Over time, this type of negative thinking can leave you feeling like you’re not as successful as people you know, and that you have no one to blame but yourself for your shortcomings.

While personal responsibility is certainly a good quality to possess, a single financial miscue does not make you inferior to people you know.

How Emotion Affects Money Decisions

Credit: Stress can trigger retail therapy, and excitement can push risk taking, which can lead to spending that feels justified now and painful later. (Adobe Stock)

Emotional spending habits are at the heart of most financial miscues. Since money can represent security and freedom, when you find yourself feeling like you’ve lost control, you may resort to what many people call “retail therapy.” However, negative emotions aren’t the only feelings that produce poor financial decisions. Excitement can often lead to overspending and risk-taking.

Unfortunately, emotions can fluctuate from one minute to the next. This means that you should never let your feelings dictate your spending. What feels urgent or justified in the moment may no longer align with personal values or goals once emotions settle. Recognizing emotional influence is a critical step in avoiding financial mistakes.

Why Inaction Often Leads to More Regret Than Action

You may be surprised to learn that many people deal with regret over financial decisions they did not make more than those they did. Skipping opportunities, delaying investing, and avoiding financial planning can create a lingering sense of regret. This type of regret tends to get worse with time, since there is no clear resolution. For example, even if you start investing in retirement, you may deal with long-term regret for not doing so earlier.

Inaction certainly feels safer in the short-term, but the negative results can leave you feeling regret for years to come. Over time, avoidance can become a habit that reinforces financial insecurity rather than protecting against it.

How Expectations Impact Financial Satisfaction

Credit: When expectations are too high, even solid decisions can feel like failures, especially when comparison sets the standard for success. (Adobe Stock)

Behavioral finance psychology revolves around the relationship between expectations and financial satisfaction. Undoubtedly, you have a vision for your future, and money plays a big role in it. When you continually find yourself coming up short in the pursuit of those goals, it’s easy to point to moments where poor financial decisions were made.

However, it’s important to remember that your expectations need to be realistic. When people expect perfect outcomes or immediate results, even reasonable decisions can feel like failures. Unrealistic benchmarks, especially those influenced by social media, distort how you truly measure progress.

Be willing to evaluate and adjust your expectations. When you make financial decisions with realistic goals in mind, you can better handle outcomes that feel imperfect or slower than you had originally hoped.

Making Decisions You Won’t Regret

Ultimately, no financial decision is exempt from causing regret. However, when you align your financial decisions with personal priorities, those choices tend to feel more satisfying over time. When you analyze and understand why you made the choice that you made, you’re far less likely to judge that decision harshly later.

Creating decision-making pauses, setting clear criteria before acting, and reviewing choices periodically can all help reduce emotional reactions. Over time, these positive habits can help you create a healthy relationship with your finances.

While a certain level of financial regret may be unavoidable, you don’t have to let fear and shame be the driving forces behind all of your financial decisions. Instead of focusing on what a bad decision cost you in the past, shift your attention to the lessons that you learned and start making more responsible decisions in the future.


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