How To Overcome Regret and Not Create Them Again

If you have lived more than 20 minutes, you have regrets.

It could be that time where you did not swing at the 3-2 pitch and struck out.

Maybe it was the girl you never asked out, or the risky job that you turned down.

Life is full of regrets – and if we let them, they will destroy us.

But you are reading this blog; so chances are, you are NOT someone who is going to let them take you down.

Let us look at the possible ways on how to overcome regret so you don’t repeat them.

5 Tips on How To Overcome Regret

1. Remember that things will look better in the morning.

General Colin Powell famously pointed out that things will look better in the morning.

As you reflect on your regrets, it is likely that you will be kicking yourself.

Everything inside you is calling you every name that you can imagine that rhymes with dummy. The General’s advice was to take a break from the difficulty.

Sleep, rest, watch a movie, or play a game – just do something for a short season to get away from it all.

If you stay on it for too long, you will grow despondent.

“Success is to be measured not so much by the position that one has reached in life as by the obstacles which he has overcome.”

Stepping away will enable you to begin looking at the regret from a different angle (e.g. maybe it was a good thing that you never took that job).

Who would you not have met, what opportunities would you have missed out on, if you had taken that risky job?

Was she really the right girl for you?

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Whatever the regret is, you somehow believe that life would have been better if you would have done something different.

That is NOT always true.

Take time to look at the negative results that could have taken place if you pursued your original plan.

(*I can’t believe that I just recommended negative thinking.

But in this case, it will help you on how to overcome regret.)

2. Make things right.

It is possible that your regret is something that can still be fixed.

Maybe taking a risky job now might help.

If you are single and the girl is available, you might be a better match now than you were back when you were a teenager.

It is never too late to go apologize either in person or in a letter.

Do what you can to go make things right.

I have two guys that in my younger life I was highly disrespectful to and I regret my words and actions towards them.

I hope to find them someday and make things right.

In the meantime, I look for them on Facebook from time to time and I rehearse the words I will use.

The truth is that these two guys were able to positively impact my life.

I do not know where they are today, but eventually, I will find them and get this regret off of my plate.

Do what you can to make things right.

3. Help someone else.

Zig Ziglar used to say that if you help enough people get what they want, you will get what you want.

If you are reading this, you want to know how to overcome regret – so why not help someone else to succeed?

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It will make you feel awesome.

It might be too late for you to be in the big leagues.

But what if you helped someone else get there? 

That would help you get over the pain of not taking that swing.

Coach a little league team or mentor a young person.

Helping other people achieve their dreams can be awesome!

Put in the time to help someone else live without regrets.

Mentor a young man on how to ask a girl out on a date.

Inspire someone to live their dreams.

Helping someone else is my favorite way of getting past my regrets.

Once you get past the pain of having made a mistake, it is good to figure out how NOT to do so again.

4. Do an after-action review.

During my time in the military, the most powerful learning lessons happened after the training event.

We would conduct a battle and sometimes, from my angle, it seemed that we either did really well or really poorly.

However, the after-action review where we would look at nearly every moment of the operation step by step would often reveal small victories or minute failures that led to our ultimate collapse.

Oftentimes, these inches would lead into miles of mistakes.

Learning how to avoid giving up those inches was a powerful learning lesson.

You can do this yourself on a daily basis.

End your day by reviewing the choices and decisions of your day.

Who did you talk to? Why were you afraid?

Take time to examine all that you did.

When you learn from your mistakes, you will learn how to overcome regret and you are less likely to repeat those mistakes.

Invite others into this process from time to time for even greater effect.

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How are others seeing you?

I have been surprised when I have honestly invited others to evaluate my actions.

Regularly conduct after-action review on major events in your life and take notes.

5. Evaluate yourself frequently.

You make thousands of choices everyday without ever really thinking about it.

You decide what to wear, where to go, and even the route to take to those places.

You decide to look left or right.

Why did you do that?

Now there is no way that you can examine all of your choices, but taking a handful each week can be very beneficial.

Here are the questions that I ask myself when I look at my choices:

  • What is the choice that I am evaluating?
  • What was I thinking when I made that choice? (You were thinking. It is impossible not to be thinking. You just may have been thinking of dinner when you should have been thinking of crossing the street safely.)
  • What did I want?
  • What was the impact on the world around me by that choice?
  • Was that a choice that honors the man that I desire to be?

Now that I have been doing this exercise for a few years, I find myself often evaluating choices BEFORE I make them.

I am confident that it has prevented me from doing things that I would regret today.


It seems lately that I hear people say things like, “No regrets.”

They are bold and powerful statements – but the truth is, few people I know have NO regrets.

But what is true is that we can learn how to overcome regret.

We can learn not to repeat the mistakes that got us into trouble in the first place.

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  1. Filip

    September 26, 2019 at 1:26 PM

    I wish parents were taught all of the above and then fostered all of it in their children. Sadly, that is not the truth.

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