How to Turn Regrets into Life Lessons

I see a lot of motivational quotes and memes on the internet about how one is not supposed to live their life with regret. My reaction to that is: how is someone supposed to correct course in life or make sure they’re not on their death bed with a list of regrets if they’re not going to at least acknowledge their regrets?

I think our culture has a few problems in this regard. First, many have a sort of “just don’t think about bad stuff ever” mentality. These people can’t handle regret or other negative emotions at all simply because they refuse to think about them. I believe this breeds immaturity and a “coddling” culture which prevents a person from learning and growing as a person. You can’t really correct course if you are not critical of yourself at all (basic self awareness). This is sort of a lobotomized denial of reality which I don’t think is healthy. 

On the other hand, some people seem addicted to their emotional pain to the point where their expression of regret, guilt and other negative emotions is almost pornagraphic and completely defines who they are. They’ve dedicated their lives to identifying traumas, misery, guilt and other negative emotions to the point they’re so fragile they can barely function. Many times these are people with a completely normal upbringing in a middle-class (or higher) family who have actually probably never really experienced what would be considered by most to be a genuinely traumatic life (certainly not the violence, abuse or even war that many poor and 3rd world humans experience daily). The explosion of antidepressant usage amongst otherwise healthy and wealthy people is a concerning indicator of this. 

Sure, you can view anything as a trauma but I believe this can also be viewed as a certain immaturity: you’ve identified with your negative emotions and it’s defined you but you haven’t learned anything from them and taken action to correct course. Worse, some use this to trauma obsession to prompt sympathy or low expectations from others (so you don’t have to take responsibility or even participate in life). 

Regret is Just Feedback

Surely, there is a balance between these two extremes (balance is a common theme in many areas of life). The negative feeling of regret is probably not helpful beyond the initial prompt for you to examine your decisions. However, I think you should definitely process your regrets and make steps to make sure you have actually learned why you are feeling regret and how to minimize that in the future. Tragic people don’t learn from their mistakes, the most effective people use mistakes to learn and grow. 

Remember that regret or any negative (or positive) emotion is just feedback. Remove the negative association and it’s simply a reminder of what didn’t work out before, just a signal that we should examine and take action. Feedback is how you improve your thinking, decisions and actions. It’s simple: you process the negative feeling and think “hmm, that makes me feel bad, I wonder why that is and what can I do differently next time?”.

Yes, I do think regrets are usually a waste of energy and a “sunk cost”, but only if you ruminate on them, don’t process them and don’t learn the lesson. Process them, release their negative energy and resolve to do better or make better decisions. Regret can be a powerful way to improve the direction of your life. You can either think that regret is a debilitating source of depression or simply feedback – I prefer framing them as feedback. 

How to Turn Regret into Lessons

I don’t know if it’s the general increased availability of information and knowledge but I now see people that seem to have things figured out in their 20’s which took me well into my 40’s. I don’t see a lot of denial or rumination in these people, they seem to be dramatically more effective at life because they’ve learned (or were taught) these lessons early in life. 

After recently turning 45 and having a son now old enough to learn valuable lessons, I thought it would be a good exercise to purge the regrets and mistakes I’ve made and turn them into life lessons which I review regularly. 

These are commonly framed as “advice to your younger self” as well. Don’t get me wrong, things are great for me now, but I could have saved an enormous amount of grief by just correctly processing regrets and learning the proper lessons. 

A “good” or “bad” thing can be largely a matter of perspective and if you learn the lesson. A famous story is of the twins that were raised by an abusive father. One grew up to become abusive to his children and the other became a wonderful father. When asked why, they both answered the same: “How else would I have raised my child given my upbringing?” One learned the lesson, the other did not.

There’s even anecdotal evidence that many high-performing people have huge chips on their shoulder or other negative experiences that actually drive them. Certainly this reminds me of a few US presidents and other wildly successful people (I’m not saying they’re happy though!). 

Step 1: List Your Regrets

The methodology is simple: brainstorm a list of every regret, screw-up and mistake. If you’re serious about processing your regrets then you’ll actually write them out. Here’s some ideas to prompt you: 

  • The famous “deathbed regrets” that people regret the most:
    • I wish I’d had the courage to live a life true to myself, not the life others expected of me. 
    • I wish I hadn’t worked so hard. 
    • I wish I’d had the courage to express my feelings. 
    • I wish I had stayed in touch with my friends. 
    • I wish that I had let myself be happier.
  • Other “regret lists”
  • Bad Habits: drinking, smoking, drugs, not having a good sleep schedule, not exercising, eating poorly, etc.
  • Emotional control: anger, fighting, ruminating, not being able to relax, poor interpersonal skills (bragging, berating), etc.
  • Fear: fear of failure, fear of others opinions, fear of confrontation, fear of looking silly, fear of asking a person out, fear of calling an old friend, etc. 
  • Ignoring intuition: not trusting your gut, ignoring “bad feelings” about someone or a situation, etc. 

Step 2: Group Your Similar Regrets

You will probably start noticing some very similar items in this list. I can almost guarantee the most common thread will be some variation of “fear”. Notice how many times “courage to X” or “others expectations” is listed in the various lists of regrets above? That’s just fear. A lot of people are afraid to assert themselves and their desires and that can be a huge source of regret. Some will be the opposite: you were reckless or abusive in how you wanted things and that damaged people or relationships (note this is also fear, fear of not being respected, fear of not being in control, etc.). Some sample categories:

  • Fear or lack of courage (risks you should have taken)
  • Habits (bad habits started or good habits abandoned)
  • Friends and family (not reaching out, not treasuring them while they’re alive, etc.)
  • Work and career (working too hard, doing what others want, etc.)
  • Health (not taking care of it)

We want to group them so we can come up with some simple lessons we can learn. 

Step 3: Create Your Lessons

You will be fully able to dismiss the regret once you’ve created the lesson you need to learn. For example, if one of my big group of regrets is that I started bad habits that affected my health then I will simply resolve to:

  • Adopt better and more consistent habits that promote health. 

If I regretted not asking for the promotion, asking for the date or asserting myself.

  • Politely make my desires known and others can simply accept or reject them. 

Do this to create a handful of lessons you can easily review and remember. 

Step 4: Reinforce Your Lessons

I’m a huge fan of reinforcing new habits in a very systematic way. I will have much more to write about this in future articles but I believe that new habits, thoughts or routines require a regular (even daily) reminder until they become an integral part of your life. 

Seriously, a lot of people do the work, do the exercises, then the lesson is forgotten in a week. Set a recurring reminder, task or calendar item to review your lessons. This is when the magic happens, you’ll soon start to make these lessons part of your daily decision making. 

Step 5: Dismiss Your Regrets

What do you do with the list of regrets after you’ve created your lessons and reinforced them? I recommend you delete the document or print and burn the list. Regrets won’t be holding us back any longer. 


We all have regrets, it’s how we use and process them that will improve the quality of our lives. After you’ve created, learned and internalized the lessons, you can dismiss the feeling of regret and simply take the lessons learned as feedback. It’s silly to expect that we won’t continue to screw-up, however we can live confidently knowing that we’ll learn lessons from our screw-ups. 

  • The best news is you can work to change negativity in your life right now. It is never to late. I recommend you read The Four Agreements. A book short and sweet.

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