August 3


Secrets to Living Regret Free at Midlife

The Problem with Regret

Every human makes mistakes. Some mistakes have small consequences and others have large consequences. When the outcome of any situation is not as desired, thoughts and feelings of regret commonly occur. Regret can be emotionally painful causing a lack of motivation, fear of failure, and even depression. Regret can be damaging to self-esteem and can negatively affect your future performance.

Learning to recognize and effectively handle regret is an important life skill. Frequently thinking about regret or trying to ignore regret a destructive force that retards motivation. It also damages self-esteem that leads to feelings of being unworthy to succeed.

Common Scenarios of Regret

An impromptu poll on Twitter with over 300 people responding found that regrets typically fall into one of the following categories:

  • Not doing the right thing when someone died
  • Not getting out from under a bad situation or relationship sooner
  • Not getting the education they wanted
  • Making the wrong career choices
  • Not pursuing love or telling people they loved them
  • Letting self-doubts such as fear, anxiety, and worry dominate thoughts
  • Lost or wasted time
  • Opportunities not taken, and dreams not pursued


These responses come from people of all ages and reflect where they are currently in their life. Which of these areas hit home with you? Do any specific situations come to mind? If you were asked what was your greatest life regret right now, what would you say?

It’s very interesting to note that no one said that their biggest regret is something that happened to them. Instead, all of the regrets were based on what people chose to do or didn’t do. True regret and sorrow do not come from things beyond our control. Instead, they come from consciously making poor choices or unconsciously not being aware of what we are doing.

Common Questions About Regret

Here are the most common questions about regret and living a regret-free life that will be covered in this success skill:

  • What is regret and why do we experience it?
  • Is regret inevitable?
  • Is regret useful, neutral or destructive?
  • What are the different aspects of regret?
  • How do our brains process regret?
  • How can we manage current regrets?
  • How can we avoid regret in the future?

Psychology of Regret

Decision-making and Regret

Regret is uniquely tied to decision-based situations, and the decision can be action or inaction. The assumption of decision-making is that there is a choice to be made, and regret comes when the choice results in an outcome that is not optimal. We experience regret when we realize or imagine that our present situation would have been better had we decided differently in the past.

The purpose of regret is to motivate us to maximize outcomes in the short term and maximize learning in the long term. While this sounds like a healthy psychological process on the surface, regret is a comparison-based emotion. We compare what happened with what could have been. A little regret can be good to motivate positive changes in behavior and decision making. However, regret also has the power to take us down a deep spiral of self-blame, self-loathing, anxiety, and fear of taking future action.

Thought-driven and Emotion-fueled

Regret is powerful because it is both thought-driven and emotion-fueled. As we think more about the situation, the decision we didn’t make, and the outcome that might have been, we create stronger and stronger negative emotions of self-blame. The stronger the emotions, the more we remember it and the more it affects our future behavior. The negative thoughts lead to negative feelings, and the negative feelings lead to more negative thoughts. The thinking and feeling become a vicious circle that can easily become destructive.

Distinct from Other Emotions

Regret is distinct from related other specific emotions such as anger, disappointment, envy, guilt, sadness, and shame and from general negative effect on the basis of its appraisals, experiential content, and behavioral consequences. Regret is different from sadness, sorrow, anger, frustration or other negative emotions. The emotions and thoughts are related but distinct. Regrets with higher amounts of emotion and fewer thoughts can lead to poor mental health. Regrets with a high component of thought lead to more learning.

Tied to Feelings of Self-Responsibility

Individual differences in the tendency to experience regret are reliably related to the tendency to maximize and compare one’s outcomes. Regret is tied to a feeling of self-responsibility for the situation. The more self-responsibility, the greater for potential regret. For example, you may regret how you voted in the last election. However, realizing that the change of one single vote would not have changed the outcome reduces the feeling of regret. On the other hand, if you are the leader of a team or organization and your decision negatively affected the members of your team, it is likely you will feel greater regret.

Regret from Action or Inaction

Regret can stem from decisions to act and from decisions not to act: The more justifiable the decision, the less regret. Regret can be experienced about decision process (“process regret”) and decision outcomes (“outcome regret”).

Regret in Specific Areas of Life

Regret most often occurs in the areas of education, career, consumption, and romance. One area not mentioned in the research is the area of character. Character spans across all life domains and thus could be in any of the areas of education, career, consumption, or romance. When a poor decision negatively affects our character, there is both shame and regret. Shame is considered the lowest form of emotion and the most damaging to self-identity. The late Zig Ziglar used to say, “All great failures are a failure of character.”

Past and Future Regret

Regret can be experienced about past (“retrospective regret”) and future (“anticipated or prospective regret”) decisions. Anticipated regret is experienced when decisions are difficult and important and when the decision maker expects to learn the outcomes of both the chosen and rejected options quickly. Regret can be experienced over past events but can also be experienced prior to an event. Prior regret is called anticipated regret. A study showed that in daily decision making, people can feel an average of 70% anticipated regret, but experience actual or past regret only 30% of the time. This difference between the anticipated and experienced regret is likely due to the regret prevention of strategy of preparing for the worst. It could also be a regret management strategy of making the best of a poor outcome.

Immediate Regret vs Delayed Regret

Regrets have a temporal aspect meaning they can be short-term or long-term. Making a bad decision today may cause considerable regret. However, given enough time one can usually learn and recover from the experience. In addition, regret can occur immediately, delayed or even after significant periods of time. The consequences of many events do not occur or are not evident for quite some time. Sometimes, regret only comes after self-reflection when we think about another choice that wasn’t considered before that could have provided a better outcome.

Avoiding Life Regrets

Life regrets are a different kind of regret. These are regrets that are not experienced immediately after the decision and often they are not just one decision. Life regrets are the result of many small decisions made over time.

In her book, “The Regrets of the Dying” Bronnie Ware describes the 5 most common life regrets. 1) I wish I’d had the courage to live a life true to myself, not the life others expected of me. 2) I wish I hadn’t worked so hard. 3)I wish I’d had the courage to express my feelings. 4) I wish I had stayed in touch with my friends. 5) I wish that I had let myself be happier.

These 5 life regrets have a common theme. The theme is a lack or misplaced set of priorities that allowed the habits of everyday living to determine the life that was lived. The tombstone or deathbed exercise can be a useful one. Imagine you are old and know you will die soon. How would you look back on your life? What things would you have done? What relationships would you have developed and maintained? What experiences would you have created for yourself and others? How would you have impacted others? Answering these questions and living that life now is the secret to avoiding life regrets.

Factual vs Counterfactual Regret

Regret can be based on real facts or believed facts. Some outcomes are based entirely on our decisions and our decisions alone. However, other situations are not as clear. And, still, other situations are entirely out of our control. And yet, our feeling of self-responsibility and the vicious circle of what-if thoughts and self-blaming emotions can twist the facts in our mind causing regret. In fact the greater the loss, the easier it is to twist the facts and blame ourselves creating regret.

For example, a wife blames herself for the husband’s heart attack. While the wife has some influence on the husband’s health, the husband was ultimately responsible for his own health and lifestyle choices. In blaming herself, the wife is being counterfactual. Her sorrow is normal and healthy step in her grieving process. However, her regret is unwarranted and unproductive and could prevent her from living well the rest of her life.

Intensity of Regret

Some regrets are small like I should have ordered the fish instead of the steak, and some regrets are life changing like I shouldn’t have cheated on my wife. The intensity of the regret that is felt is dependent upon the magnitude of the decision and the level of self-responsibility both perceived and objective.

In addition, the intensity of regret tends to increase with age as people feel they have less time and opportunities to correct or undo past situations. This feeling of “it’s too late” keeps people from taking action and engaging with life. In most cases, this is simply a case of self-limiting beliefs. Colonel Sanders was 62 years old when he started Kentucky Fried Chicken. Louise Hay, the founder of Hay House Publishing, wrote her first book when she was 57 years old. Interestingly, both Colonel Sanders and Louise Hay lived to be 90. Perhaps their longevity was related to their living a regret-free life.

Regret Management and Prevention

Regret aversion is distinct from risk aversion, and they jointly and independently influence behavioral decisions. Regret regulation strategies are decision-, alternative-, or feeling-focused and implemented based on their accessibility and their instrumentality to the current overarching goal. Fortunately, regret prevention strategies and management strategies have been developed and tested. Both approaches are effective at turning regret from a painful debilitating experience into a learning experience.

Neuroscience of Regret

When people experience regret, a number of areas of the brain light up showing activity. One of the most important areas of the brain involved in regret is the amygdala. The amygdala’s function is to gather personally relevant information for the stimulus-reward association to guide future behavior. In simple terms, the amygdala quickly processes whether something is pleasure or pain. If it’s painful then avoid it in the future. If it’s pleasurable, seek to do it again.

The amygdala’s involvement in regret highlights the complex nature of regret that comprises both emotions and thoughts. Thoughts and emotions often operate in a cycle where emotions bring up past memories leading to negative thoughts. Negative thoughts of past or future events can trigger negative emotions.

Understanding that the amygdala’s function is to help us learn at both an emotional and thought level provides insight into managing regret. Namely, preventing and managing regret are learned strategies. Just as the amygdala produced initial learning, cognitive strategies emanating from the neocortex can retrain the thinking and emotions for future decision making. Just because we burned our hand on the stove, doesn’t mean we will never cook again. Instead, we retrain ourselves to use the stove without getting burned.

Reducing Regret

Now that we know what regret is and what the most common areas of regret are, how do we go about transforming our lives into a regret-free life?

Managing Current Regret

If your regret is based around not achieving goals, then choose to decrease your goal level. If someone else is giving you an unachievable goal, let them know what you think is achievable and work to reach that goal instead.

If your regret is decision focused, then explore if the decision can be undone. If it cannot be undone, then work on justifying your decision by gathering additional facts that supported the decision you made at the time. If the decision was not entirely yours, take responsibility for your portion of the decision but acknowledge that others had a hand in it too.  Remember, the decision you made was based on the knowledge and experience had at the time. You can only resolve to get more information and utilize your experience in future decisions.

If your regret is centered around choosing between alternatives, you can reverse your decision and switch alternatives. This can often occur with buyer’s remorse. If you are unhappy with your choice, determine what you can do to switch to another option. In addition, you can re-appraise the alternatives looking for the good qualities of the alternative you chose.

If your regret is oriented around feelings, then do some psychological repair work. Acknowledge your feelings and determine where they are coming from. Ask what are your feelings trying to tell you? Don’t suppress or deny your feelings because they won’t go away. If you don’t want to deal with your feelings now, you can put them aside temporarily but make sure to make time to deal with them soon.

Preventing Future Regret

If your anticipated regret is related to a goal, then consider decreasing the goal. Again, if someone else is setting a goal for you, choose what you believe is an achievable goal and let them know that is what you will be working towards. If a 12-month or 6-month goals seems overwhelming, then break it down into smaller pieces such as monthly, weekly or even daily goals. If the goal is outcome oriented that feels intangible, try turning it into an activity goal instead. You can control your activity, but you can’t always control your outcomes.

If your anticipated regret is about an upcoming decision, there are a number of ways to reduce regret. You can increase your decision quality by making sure you have enough time to gather all the information, consider the options and possible consequences, and even get the advice of others. You can also spend more effort into justifying the decision you are making. Justification is not for others, but rather your peace of mind in knowing that it was a decision based upon facts.

If you don’t have to be the person making the decision, then consider empowering someone else to make the decision instead. And, if there’s not a hard deadline on the decision, consider delaying the decision to a later day.

If your anticipated regret is associated with alternatives, then either restrict or enlarge the choice set. If you are feeling overwhelmed with the choices, begin by narrowing them down. If you feel there aren’t any good choices, then search for additional alternatives. If possible, make sure the decision is reversible. Instead of making a final decision, consider doing a 30 or 90-day trial with whatever alternative you are considering. Finally, after a final decision is made, forgo the feedback about the other alternatives. It’s water under the bridge and potentially causes regret.

If your anticipated regret is oriented around feelings, try anticipating what these feelings of regret will feel like. Then, think of ways that you can deal with them in a positive manner. Anticipating regrets allows you to prepare for them and handle them more effectively when they come.

Tenets of Regret-free Living

Be intentional about your life priorities both in the short-term and long-term. Structure your life to match your priorities. Some things can be changed immediately, and others will take months or years to change. Be patient and make the changes anyway. Life regret is a bitter pill that is not necessary.

Practice self-forgiveness and self-acceptance to process the negative emotions of regret. Look for the lesson in regret use the negative emotion to strengthen the lesson learned. The greater the emotion, the greater the lesson will be remembered.

Utilize regret prevention techniques prior to making a decision, and regret management techniques after making a decision. Making these strategies a habit ensures less regret and more learning over time.

Develop the mindset that everything in the past has led you to who you are today and the current realization of how you want to live your life going forward. Love and accept yourself for you who you are today. Then, be mindful of the changes you want to make in your life.

Develop the practice of mindfulness where you can choose to be the best you in any given moment. Become intentional about all areas of your life. It’s not about doing more. Instead, it’s about doing what matters to you and only you.

Answers to Common Questions About Regret:

  • Experiencing some amount of regret is both natural and inevitable as humans. It doesn’t matter whether the regret comes from action or inaction.
  • Regret is both a judgment of the outcome (positive or negative) and attribution of fault that is internal. Removing judgment from the outcome and honestly assessing self-involvement reduces the negative emotions of regret.
  • Looking for the lesson and the bigger picture (broader perspective) reduces regret.
  • Acknowledging the negative feelings of regret can prevent them from causing inaction or fear of failure in future situations.
  • Learning from mistakes is positive. Brooding on them is destructive.
  • Honest self-assessment and self-forgiveness
  • Reframing the past as a learning and growth experience for all involved and refocusing attention on future desires and intentions with the wisdom gained from the experience.

Action Steps:

“Two roads diverged in the wood and I – I took the road less traveled by, and that has made all the difference.” – Robert Frost

Take the road less traveled. Decide to complete these action steps so that you can begin living a regret-free life:

Step 1: Reducing Current Regret

  1. Write down both a personal situation and a professional situation that you feel regretful for.
  2. What action or inaction do you regret having taken, and what action would you have preferred to take?
  3. List the emotions you feel about the situation (sorrow, shame, sadness, anger, frustration, etc.)?
  4. Let go of any judgment and take a few moments to truly forgive yourself and others for their actions surrounding the situation.
  5. What lesson(s) can you learn from the experience?
  6. Write down three reasons why you are grateful for having lived through the experience.
  7. Determine how you will implement what you have learned for the future that will make you stronger and wiser.

Step 2: Preventing Future Regret

The best technique deciding how to live a regret-free life is to imagine the end of your life and look backward to now.

  1. What advice would your future self give you?
  2. What aspects of your life would they tell you to change?
  3. Who would they tell you to reach out to build better relationships?
  4. Who would they tell you to say, “I love you” to?
  5. How would they tell you to re-balance your life between work, family and personal time?
  6. Would they tell you to express your feelings more and in what way?
  7. How would they tell you to live in more alignment with your true self?

Skill Summary

Experiencing some amount of regret is inevitable. Regret from inaction grows over time where regret from action is more easily overcome. Becoming mindful of the feelings and thoughts of regret is useful to both process the emotions and learn from the situation. Removing judgment from the experience and reframing it as a growth experience removes the negative emotional charge. Refocusing on implementing the wisdom and knowledge learned recharges and motivates for future action.

Life is a series of choices. In some cases, we make active or conscious choices. In other cases, we don’t choose or choose by default. In either case, they are still choices. Living without regret means accepting the past and choosing to make better choices in the future. If it feels like a lot of pressure, don’t worry. Being human is not about perfection. It’s about progress.

“All is well. You can’t get it wrong, and you will never be done.” – Esther Hicks


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Bruce Fleck, PhD

About the Bruce Fleck, PhD

I help professionals overcome a health, career, or relationship crisis and make it a turning point for building a better life.

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