How To Deal With Your Biggest Regrets In Life

Pinterest Hidden Image

It is very common for midlife women to look back on their lives and experience regret. Regrets are normal. Everyone struggles with the idea that they should have done things differently.

Wondering How To Move On From Regret?

Regrets in life can be simple, such as: “I regret buying a little dog that barks insanely!” Or maybe you are trying to forgive your 20-year-old self for getting eyelid tattoos.


My Biggest Regret Is Losing You

For many of us, our biggest regrets happened when we were feeling pressure and lacking the emotional maturity to help us navigate our mistakes.

Sometimes, our regrets are based around relationships and the choices we made in the past. Some of my coaching clients express regret about “the one that got away.” It’s very common for us to end a romantic relationship and then, years later, experience regret. Ending a romantic relationship can often bring us to a place of self-reflection, and a decision to pursue personal growth.

Dealing with regrets? You can learn to move on and forgive yourself.

How To Deal With Regrets In Life

Main ideas in this article:

  • · Everyone has regrets: choose to avoid identifying or feeling like a victim.
  • · Regrets can result from feeling pressured by others or being emotionally immature.
  • · As an adult, it is critical that you forgive others’ potential influence on your mistakes.
  • · Practice acceptance and forgiveness for yourself and those who might have influenced you.

Regrets can be difficult to cope with and it’s easy to become mired in the cycle of negative emotions they can trigger. There are some simple steps that you can take to help overcome any regrets or painful mistakes you might have made in life.

Regrets Can Be The Best Teacher

The best way to learn from a mistake you have made is to accept that you can learn from regrets. Are there any lessons that will help you make better decisions in the future? Additionally, think about how your regrets could help other people avoid making the same mistake.

As We Age We See Our Regrets More Clearly

Last year, in one of my grad school classes, we did a project that was based on interviewing senior citizens about their lives. The class was called “Life Span Development” and was directed at the major developmental and cognitive milestones in every humans life. We were asked to choose a time frame of life and interview a person currently in that time frame. I choose senior citizens (age 75 +) and interviewed a lovely woman who was 80-years-old.

She was a black artist, who had recently begun to accept commissions for her paintings. As we spoke, she shared important moments in her life with me. Her first job, her first marriage, her children and her re-marriage to a neuroscientist.

At the end of our interview, I asked her about her “soft regrets”. After thinking for a bit, told me that she regretted not continuing with college. She had enrolled, but life became too complicated and she let that dream go. Despite being happy with her life, there was a sting of regret about her missed opportunity for more education.

Easing The Pain Of Your Life Regrets

Do You Have Soft Regrets?

My classmates and I came up with the term “soft regrets” for our interviews. We called it “soft regrets” because we wanted choices that altered life paths, things that were under a persons control and experiences that could be measured. The most common responses were regrets of not pursuing more education and wishing romantic relationships had been different.

Do Women and Men Struggle With Different Types of Regret?

In our class research project, we found some differences between male and female life regrets.

Regrets about romantic relationships are common in midlife.

Women often express regret over not having put their own mental health and happiness first, not pursuing a dream or talent, failing to stand up for themselves more, not forming meaningful relationships, and not taking risks earlier in life.

Some of the most common regrets among men include not pursuing higher education or career goals, not taking better care of their physical health, and not having meaningful connections with family members and friends.

End Of Life Regrets Are Very Similar

That small sample of classroom data supports that idea that at end of life people are focused on relationships and experiences, both achieved and those seemingly lost. There is well known research that was done with people who were dying. The studies done on the regrets of the dying are clear, no one wanted more hours at the office!

Regrets can be disheartening, but it’s possible to learn to live with them and make peace with the past. If you want to move forward in life and stop feeling haunted by your mistakes, there are a few key strategies to help you come to terms with your biggest regrets.

Don’t Let Your Regrets Last A Lifetime

Just as with any other emotion, regret has the potential to be a powerful tool for growth and learning. Recognizing regret’s role in helping you make sense of a situation and move forward can be powerful.

Examining your regrets can be helpful in accepting your life experience and increasing your capacity to create more positive outcomes in the future. Acknowledge what caused you pain or disappointment and use it to gain insight into yourself and identify areas of improvement.

In my life, I have experienced both types of soft regrets. An early love relationship that I left under pressure from family, and the realization that ” younger me” should have pursued more education to develop a career.

There have been hours, that have turned into days, where I have mourned the choices I made both in love and career. Sure, those were important feelings to experience and express, but in the end, I can’t go back. And you can’t either.

Creating A Road Map For Moving On From Your Life’s Regrets

So, How Do We Deal With Regrets In Midlife?

First, admit you have regrets- some of us hate to consider the idea that we were wrong! Our egos want to protect us from saying we made a bad choice. Give it up people! We have all made bad choices, from fashion to finances to fiancées. Give yourself permission to admit you made a bad choice.

Name Your Regret

Name it: I feel sorrow because I didn’t marry ________ when he/she asked me. I wish I would have had the confidence to ______________ when they asked me to. Allowing yourself to verbally OUT LOUD state your regret is part of the healing process. In the coaching world, we call it “Name it = Tame It”.

The world will not stop spinning when you say what is really in your heart and thoughts! Actually, when we speak difficult things out loud, it often loses its power over us. Our thoughts about the mistake become more manageable and then we can begin to process the regret.

Feel Your Regret

Feel the grief: Part of any healing process is allowing yourself to grieve real or perceived loss. Love lost, opportunity that you walked away from, jobs you didn’t get, bad legal decisions, apologies unspoken, the times you didn’t stop and think about anyone but yourself.

Grief is part of our operating system for a reason, it serves the purpose of releasing the inner anguish we all have. Each grief process looks different, please don’t get attached to the idea that you have to cry to be grieving! Grief is often expressed as anger toward yourself and at times, directed at others.

Be aware that grief can look like depression, and at times, can open the door to a depressive season. Check your emotional responses, be aware of your thoughts and make sure you get some professional help if you find yourself stuck in grief.

Forgive Your Regrets

Last, and the most important part- Forgive yourself. We all know the expression about bitterness: Bitterness is like drinking rat poison and hoping the other person dies. Well, if you don’t forgive yourself you will find parts of your life dying.

Unforgiveness against yourself affects every area of your life, love relationships, work and at times, your finances. Everything! When you don’t forgive yourself, you hold yourself hostage to an earlier, less mature version of you.

Basically you trade all of todays joy for constantly living in the past, perpetually bathing yourself with a bucket of pain, never feeling the freshness that self- forgiveness brings.

Understanding the Reasons for Feeling Sad about Life’s Regrets

Regrets can be a difficult emotion to address because it is usually compounded by feelings of guilt, sadness and shame. It is important to understand why we feel sad about having regrets in order to learn how these emotions can help us grow as individuals. By acknowledging our regrets and understanding their emotional root, we can strive to make more conscious decisions going forward and transform regret into positive growth.

Accepting and moving forward with life’s regrets takes time, intentionality, and a lot of self-reflection. Start by acknowledging and accepting your regret without berating yourself or becoming overly emotional. Then, identify the areas of your life that need to change in order to move forward. Finally, take active steps to implement these changes and make the most of your present situation.

Moving Forward with Life’s Regrets

We All Have Regrets In Life

Here’s the thing about life: we all have regrets. We regret actions, words, idea and choices. And for some of us, we convince ourselves that participating in self-punishment will somehow right our wrongs.

The following questions might be useful as you process your regrets. We all make decisions that are regrettable. For most of us, these decisions are made with the best information we have at the time. Those decisions are also based on the earlier version of ourselves. As we mature and begin to understand ourselves, it might help to evaluate the circumstances and influences we experienced during the decision making process.

Some Questions That Will Help You Process Your Regrets

Each of these questions must bring you back to a place of acceptance and forgiveness. First for yourself and then for any person who might have influenced your decision. Processing your regrets is not about staying in a place of “victimhood” but it is a choice to mourn, forgive and let go of the past.

How to Forgive Yourself for Regrets And Move On

The best way to work through these questions is to find a quiet space to write and reflect privately on a single regret at a time.

  • How old where you?
  • Did you feel that you had more than one option?
  • Was there pressure from family or friends to make a certain choice?
  • Did your gut tell you to choose something else?
  • Why didn’t you listen to your gut?
  • Have you ever shared this regret with a safe person?
  • Have you been able to identify the parts of you that wanted to please others?
  • If your regret involves other people, do you need to make an apology?
  • And most important, have you forgiven yourself?

Below is a simple six step framework for dealing with regrets. Forgiving yourself for past mistakes can take some time and effort. However, it is important to remember that everyone makes mistakes and learning to forgive yourself will help you move forward in life.

You can let go of regrets when you begin to accept and forgive yourself.

Six Steps To Dealing With Regrets In Life

  • Acknowledge your mistake
  • Take responsibility
  • Talk to someone
  • Reframe your thoughts
  • Learn from your mistakes
  • Make amends with those affected

Let me save you hours of therapy, please choose to forgive yourself! Have mercy on the younger self who made dumb decisions based on a faulty operating system. Release the shame that you might be carrying about some of your choices, you are not that person any longer.


Regret will steal the best years of your life you let it. It is so easy to waste time and energy wishing that you had made a different choice! Remember, every single person has regrets. You are not uniquely flawed or unusually weak, you are human. Staying stuck in regrets can cause you to miss some of the most important moments of your life. Instead use your energy to love, forgive and create the live you wish to have.

Use the questions listed above to help you process your regrets. If possible, talk it out with a safe person to benefit from their perspective. If needed, make amends with anyone that was affected by your regrettable decision/actions. And lastly, choose to forgive yourself.

Forgive Your Mistakes and Embrace Your Best Life

Turn your focus and energy into discovering the best parts of yourself, bringing them forward in relationships and in your community! As always, I am here to help you when you are looking to make changes. I specialize in helping midlife women create balanced relationships with themselves and their families.

Click here to read the details about my individual coaching.

Website | + posts

Melane Ann is a writer, blogger, and life coach. In 2020, she turned her experience in midlife divorce and creating a new life for herself into midlifeismagical. With a master's in Marriage and Family Therapy, Melane focuses on helping women over 50 navigate their relationships and commit to healthy aging. She and her new husband share 7 children between them. Melane jokes that she has a black belt in blended families! In addition to her writing, Melane works virtually with her coaching clients from her home office.

Similar Posts