How to Get over 20s (or 30s, 40s, 50s…) Regret

When reaching a “breakthrough moment” in creating positive changes in their lives, many of my clients say things like,

“I just wish I’d figured this all out sooner.”

“If only I hadn’t wasted that time in my 20s, I’d have it all together by now.”

“Why did it take me so long to see this?”

When you’ve hit upon a discovery and/or finally taken action that makes you much happier than you’ve ever been, it’s only natural to wish that you could have made that discovery or taken that action in the first place!

Of course, the truth is that it’s those past events—the risks, the accidents, the stumbles, the perceived failures—that cumulatively got you to this moment, with the insights, experiences, and resources you need to take this action that feels so right to you now.

You get to decide how you frame the twists and turns of your path. You can choose to look at your past experiences as wasted time or one mistake after another, or you can choose to believe that there are no mistakes, really, and every “wrong” turn you took helped you grow and taught you more about who you are and what you want.

These “mistakes” or “failures” gave you the information you needed to figure out who you really are, as well as what you don’t want and what you do want.

What’s more, if you had taken a given action or made this breakthrough choice earlier in the game, it may not have had the same impact on you. In many cases, we appreciate “right” only after experiencing a suitable variety of “wrong” (just ask Goldilocks!).

Or maybe you’re not at that breakthrough, take-action stage yet. If you’re STILL not sure where you’re going or how to get there, you can mine the “trial and error” of your past for gold, using it to get the data to create the roadmap for the life you want. My clients make the most amazing discoveries when we do just that.

If you have been carrying around the belief that your 20s, 30s, and so forth were “wasted time,” ask yourself: how well does that story serve you?

If the answer is that it’s holding you back, here are some new beliefs for you to try out.

1. It’s okay that you experimented or jumped without planning.

First, congratulations on having the courage to do that! There is a place for planning, and you may be ready now to create a vision for your life and make an intentional plan to achieve it.

But don’t overlook the great qualities that you’ve demonstrated along the way up till now. People often blame fear of commitment or poor planning for their own or other people’s experimental paths—while overlooking the positive qualities that could also be behind the story.

For example, if you have had a tendency to leap without a plan, sure, your choices could have been impacted by an inability to commit or resistance to planning—but it’s possible that you are ahead of the game with regards to one particular tool: your intuition. Being able to tap into your intuition is crucial when it comes to making big decisions, and you can reap great rewards by learning to access your intuition intentionally, now that you’re ready to make a plan.

Your experimental path may indicate an adventurous spirit, above-average adaptability, and a willingness to take courageous risks. If you have hopped and experimented, you have likely gathered rich and diverse experiences that you’ll be able to draw on for the rest of your life.

On your side of the fence, you may see the people who appeared to have a plan and think, Why couldn’t I do that? Whether or not you’re aware of it, know that many of the people who seem to have “settled down” earlier in the game are looking at you and admiring the risks you took, and may even be jealous of the time you took to explore and jump around, and of the freedom they perceive that you have now.

2. It’s okay that you stayed in the wrong relationship for too long, or dated the wrong people.

For many people, dating is a series of experiments with the “right wrong” people. You attract people into your life who have something to teach you, or who can help you grow, change, discover more about yourself, or resolve issues that you have. You stay with them as long as you do for a reason (maybe not what you now see as a good reason, but a reason that can teach you about yourself, nonetheless).

Looking in depth at these “failed” relationships, you can learn so much, including:

  • what you want and need in a partner
  • how you show up in a relationship
  • what your patterns are—communication, conflict, triggers, pursuing/distancing, etc.
  • what you don’t want in a partner
  • what qualities you want to further cultivate in yourself
  • what tendencies you want to curb
  • what inner work you still need to do before you can attract the partner (and other things) you want

By looking at your past relationships individually (what did this particular person bring out of me that no one else has?) and together (hmm…there’s a pattern here…), you can learn so much—and use what you learn to achieve tremendous growth.

What’s amazing is that the learning from a relationship can happen months or even years after a relationship has ended! You may not be ready to receive a particular lesson or insight from a particular person until a Tuesday afternoon two years, five months, and three days after last seeing that person, when something else sparks the “Ohhhhhhhhh!” in you and makes it click into place.

3. It’s okay that you let yourself get hurt.

It takes tremendous courage to open your heart and make yourself vulnerable, to another person or to the pursuit of a dream. If you let down your protective walls enough to let someone in (or to go after an audacious career goal), good for you. It means you’re choosing to experience relationships and follow your passion, opening yourself to some of the most rewarding parts of life.

Of course, if you are getting hurt again and again in the same way, or if you notice that you are attracting the same type of person over and over again with an undesired result, it’s time to do the work to figure out how to attract the love you want. And when you’re ready to do that work, you’ll have lots of information to help you (see number two).

4. It’s okay that you hurt some people.

Our greatest regrets often concern things we said or did that, intentionally or unintentionally, caused another person pain. Hard-but-true: if you choose to engage in human relationships, it’s inevitable that you will hurt others. What you can do is learn from these experiences, and grow in your ability to communicate with compassion, integrity, and generosity. You can improve how you handle it when you learn that you have hurt someone, too.

Furthermore, your experiences of hurting someone else help you develop empathy that can be helpful in situations when someone else hurts you. Knowing that you, too, are capable of causing pain, you’re better able to believe and accept that someone else could have hurt you and not meant to, or that someone else could have hurt you and yet still be a good person.

5. It’s okay that you job-hopped.

I have worked with sooooo many people who feel frustrated and even ashamed that they haven’t “figured out” one clear, linear, upwardly mobile career path by (fill in the blank with whatever age they happen to be now).

Many people look around at their friends who appear to have more stable careers with seemingly predictable growth paths. They tell themselves a failure story—“I just never figured it out” or “There just isn’t a perfect job for me.”

Just as your relationships can provide huge insights into yourself and the road map to the relationship you desire, so can your previous job experiences provide the raw material from which to glean key data that will help you zero in on the career that’s right for you.

Your “right wrong” jobs can help you determine:

  • what skills, talents, and qualities you have
  • what patterns there are in work you like and don’t like
  • where your “growing edges” are
  • what tasks and contributions make you feel “on purpose”
  • what your greatest achievements have been
  • what environments cause you to thrive (or wilt)

…and other key pieces of information that will help you get clear on the kind of work you want to do and where you want to do it.

You may think you’ve just been aimlessly hopping, but the truth is that no matter what you have been doing, you have been developing transferable skills that can be repurposed in your future career. And who knows—your diversity of experience may end up being one of your greatest assets.

6. It’s okay that you messed up.

It’s a total cliché, but it’s true—we learn so much from our mistakes. Thank goodness you’ve already made a bunch! That’s part of what your early adulthood is for! (Be assured, the mistakes don’t stop here…)

If you’ve made a lot of mistakes, you’ve had a ton of opportunities for growth. And chances are you can trace many good things that have happened in your life back to a “mistake” that you’ve chosen to regret.

What’s more, your missteps help you to empathize with others who feel off-track. Somebody out there is going to benefit from the wisdom you have to share—wisdom you gained from the so-called mistakes so far.

You can choose to let go of regret and, from right where you are now, reap the greatest possible benefits from the choices that are already behind you.


What benefits do you see in the time you took to explore and experiment? What did you learn from your own “right wrong” relationships or jobs? What’s your greatest lesson learned or gift received from a so-called mistake? Tell us in the comments below. And then share this article with the thirtysomethings in your life!

Get free articles, tips and tools sent straight to you.

1 thought on “How to Get over 20s (or 30s, 40s, 50s…) Regret”

  1. Even though you don’t include “60s” in the title of this post, I think it will be OK for me to respond! I’m now almost midway through my 60s, and one thing I wish I had been able to do sooner is to accept the points you list above, particularly point 4–which, for me, is the most difficult. I remember well the moment that I first came to terms with the fact that I had deeply, selfishly, blindly hurt a person I cared about–in a way that I might, had I tried harder, have avoided. I recall feeling so shocked and thinking, “Oh, no. I’m not at all the person I thought I was. This is not something that the person I’ve thought I was would do, and yet I’ve done it.” Acceptance of one’s serious imperfection requires perspective, however, and for me it took this long. What I hope your post will do for readers younger than I is to give them a jump on gaining that perspective. I try to allow myself 5 minutes to regret “messing up,” and then I try to move forward, applying whatever lesson I’ve learned from my error. Very valuable post–thanks, Carrie.

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.