Letting go of regret and guilt

This is Part III of a series of articles sharing what I learned from the book, Expectation Hangover by Christine Hassler.

She has some very helpful advice on how to deal with feelings of guilt and regret.

Click here to read Part I about how to feel your feelings.


When you spend a lot of mental energy in the past it often leads us to feelings guilt or regret.

When you spend too much time thinking about the future it fuels anxiety, worry and fear.


Regret is one of the most common and painful mental activities that we all engage in by replaying scenarios over and over in our head.

When you’re lost in the past, you are usually either beating yourself up or having a fantasy about how much better things used to be.

You think of all the things you could have or should have done, which makes you miserable.

Here is how it goes: 

Something happens.

You react by making a choice and taking action.

Time passes.

You start analyzing it, obsessing over it and talking about it to others.

You gather information and then take that to beat yourself up, because you did not know the knowledge you now have then.

This is both unfair and unreasonable!


You experience guilt when you believe you did something wrong or made a huge mistake.

dealing with regret and guilt

Regret and guilt keep you in the past.

When you are consistently looking behind you, it is very difficult to move forward.

What if you drove your car by only looking in the rearview mirror?

Would you ever get to your destination?


Having the expectation of forever – a career path, someone to share your life with or anything else you believe will never end – puts you at risk of judging yourself as failing if it ends and leads to feelings of regret.

Some relationships, jobs and situations have an expiration date and when you reach it, it is time to move on.

This can be especially difficult if you were expecting it to last forever, but you cannot allow your need for certainty to keep you in situations that have reached their expiration date.

Just as you moved from one grade to the next in school, you may have to move from a job, a relationship or a situation to fulfill your life’s purpose and learn the lessons you are here to learn.


Our minds often play tricks on us – completely altering our memories.

We recall things from our past as much better than they actually were, forgetting the truth and romanticizing “the way things were.”

I am always astonished at how people forget how miserable they were in a relationship or a job once it is over.

Perpetual thoughts about how great things were keep you from thinking about how much better things are or could be.

Stop romanticizing about what was and tell yourself the WHOLE truth, not just the things you miss or liked.

I recommend writing out a detailed and accurate assessment of what you did not like regarding the situation or the relationship.

Use your logical side of your brain to get you out of your fantasies and into a reality check.


To let go of guilt and regret, you must learn from your past and take those lessons into your present and future.

Let Go of the Guilt

We all make mistakes!  It is part of being human.

So stop expecting yourself to get it right all the time.

Rewinding time is impossible and what happened is now over.

Beating yourself up, feeling guilty or wishing it was different is not going to change it and is a waste of time and energy.

You are in charge of guiding your thoughts back to the truth:

“You did the best you could with what you knew at the time.”


This process will help you let go of the past rather than to continue to rehash it in your mind.

Follow these steps and answer the questions:

1. Bring to mind an experience where you feel guilty or regretful about.

2. Write a confession that includes all the details, your reasons, your thoughts, your beliefs about the experience.  Get the guilt and regret out of your head and onto the paper.

3. Steer your thoughts away from self-judgment and toward investigation by answering these questions:

  • What did you learn about yourself?
  • What did you learn about someone else or the situation?
  • How would you behave differently in the future?

4. Based on what you learned, what commitment would you like to make to yourself about how you will respond in the future?  Avoid “always” and “never.”  Instead consider what agreement would feel encouraging instead of punishing.

Here are some examples from clients:

I vow to tell the truth even if it is scary.

I promise to speak up rather than hold something inside.

I promise to only pursue romantic relationships with available people.

I plan to listen to my gut/intuition.

I will honor my word and the agreements I have made and be honest if and when I cannot.

I vow to not gossip.

5. Once you have made your commitment and start to feel a sense of relief than you are on the right path.

6. Write out your commitment (you can have more than one.)  Say it out loud and then sign and date it.

If and when your thoughts drift back to guilt and regret, redirect them toward your vow instead.

Clarity Session with Wendy Lynne, Life Coach


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