5 Ways to Channel Your Biggest Regrets into Even Bigger Wins

Mining wins from regrets is easier said than done.

But we’re all human. We all make mistakes.

And here’s something we don’t often think about—the successful people we admire and idolize are the ones who were able to successfully turn their regrets into opportunities for self-improvement and motivation.

Did you know Bill Gates was a Harvard dropout? And Steve Jobs was fired from Apple, the very company he founded? And Oprah Winfrey lost her job co-anchoring the news after only 7.5 months? What kinds of regrets do you think kept them up at night?

There are plenty of famous failures who prove that regrets can be turned into big wins with the right mindset, motivation, and determination to push forward.

most common regrets in life


Key takeaways:

  • Accept that you can’t change the past.
  • Learn how to identify and break obsessive thinking about your regrets.
  • Forgive yourself.
  • Make amends when you need to.
  • Use your greatest regrets to identify your most important goals, and then take action.


Find wins from regrets with these 5 tips to encourage positive change

Just as it’s human nature to make mistakes, it’s also human nature to dwell on those feelings of regret.

We have a tendency to look back on actions that we wish we hadn’t taken, as well as missed opportunities (either real or imagined) that we should have acted upon and didn’t.

The most common causes of regret can usually be traced back to decisions we make about:

  • Romance
  • Family
  • Education
  • Career
  • Finances
  • Parenting
  • Health
  • Friendships
  • Spirituality
  • Community

But ruminating on the past too much has a negative impact on our present and future. If you want to transform those regrets into wins, here are 5 tips to help you accomplish that.


1. Accept that you can’t change the past

It’s important to learn from the past. But no matter how many times you run through scenarios in your head, that isn’t going to change what happened.

Instead, you need to acknowledge the past, learn from it, accept that it happened and that life doesn’t have any redos, and then move forward. Take the lessons you learned with you. But don’t lose yourself in an endless time loop repeating the same hypothetical “what if” situations over and over again.


2. Interrupt yourself from an obsessive regret spiral

When you catch yourself in a time loop of regret, learn to take back control. You need to interrupt the pattern, instead of wasting precious energy and mental health feeling bad about something you did or didn’t do.

If you’re having a hard time breaking free, focus on a different project or set of goals instead. This can be productive and relevant to you, such as mentally running through your to-do list or thinking about what you need at the grocery store. Or, maybe you’re trying to sleep at night and those regrets creep in. Try an unrelated distraction, like identifying an object for each letter of the alphabet.

The goal is to regulate your emotions and break the obsessive train of thought. Don’t be held hostage by the past—you can always come back to the situation with a clearer and more analytical mindset.


3. Forgive yourself for transgressions, both real and imagined

Stop beating yourself up.

Forgiving yourself is just as important as forgiving others when they wrong you. Did you make a mistake? You learned from it and won’t make that same mistake again.

Did you miss an opportunity? It’s not the end of the world. Have faith that another opportunity will come. Carrying around shame and blame won’t help you move forward.


4. Make amends, if necessary 

If the regret that’s eating at your conscience happened because you hurt someone else, the greatest act of healing you can do for yourself is to reach out, apologize, and make it right. Don’t burn bridges if you can help it.

That being said, be mindful of the fences you choose to mend. Sometimes, a dangerous, decrepit bridge is better off burned to ashes.

You may reach the difficult decision to cut out toxic relationships from your life. And that’s okay. Gardeners have to prune away the dead and diseased branches to make sure there’s room for healthy growth. Take the time to tend to your garden.


5. Focus on your goals and start taking action 

Regrets are a distraction in the rearview mirror—they distract your eyes from the road and, ultimately, your final destination. If you want to turn your regrets into wins, you can’t do that looking over your shoulder.

Once you’ve accepted that you can’t change the past, learned to break obsessive thoughts, forgiven yourself for any perceived mistakes, and made amends when needed, it’s time to direct your time and energy toward your goals instead.

Identify what is most important to you. Understand why you felt regretful and how you can avoid feeling that way again. Regrets won’t turn into wins if you simply think about them long and hard enough.

If you regret not spending enough time with family, prioritize your time with loved ones.

If you regret your career choice, start looking into educational courses, internships, job openings, and other opportunities to change your career path in the direction you want it to go.

If you regret not traveling more, start a proactive plan to save money in a travel fund so you can make those trips happen.

If you regret not following your gut instincts, start listening to them moving forward.

The secret to getting wins from regrets is to use those regrets as a motivational roadmap to create an actionable plan.

Wins from regrets quote by Marlon Brando – Regret is useless in life. It’s in the past. All we have is now.


Our best potential to win often lies in our deepest regrets

Regret is a painful yet powerful teacher. It gives us a unique insight into what really matters to us as individuals and can help us reflect on our goals, dreams, and values.

It’s tempting to try and shove regret to the back of our minds, but that doesn’t help us grow. Identify your regrets, understand them to understand yourself, and then harness those lessons to move forward in pursuit of your goals. And if you can do that? You’re already winning.

Are you ready to turn your regrets into wins and experience personal growth? Join our team.