The art of letting go: 10 things people hold onto decades longer than they should

Have you ever caught yourself replaying a conversation from 2003, wondering what you should have said differently?

I have. Just last week, I found myself thinking about a project presentation I bungled at my old finance job. The meeting happened over a decade ago, yet there I was, mentally rewriting my slides while brushing my teeth.

We're funny creatures, aren't we? We can lose our car keys in five seconds flat, but somehow manage to hold onto emotional baggage for decades. The grudge from high school. The career path we didn't take. That perfect comeback we thought of three years too late.

After experiencing burnout at 36 and spending countless therapy sessions unpacking why I was still carrying so much unnecessary weight, I've learned that letting go isn't just an art. It's a survival skill. And most of us are terrible at it.

Here are ten things I've noticed we cling to way past their expiration date.

1. The version of yourself from your twenties

Remember who you were at 25? Full of energy, maybe a bit reckless, probably surviving on four hours of sleep and terrible coffee?

That person was great. But that person is also gone.

I spent years trying to maintain the same pace I had when I first started in finance. Wake up at 5 AM, work until 9 PM, squeeze in social events, repeat. When I discovered trail running at 28, I'd push myself to run faster and longer every week, thinking more was always better.

But bodies change. Priorities shift. What worked then might be destroying you now.

Yet so many of us keep trying to squeeze into that old version like it's a pair of jeans from college. We compare our current energy levels, our Friday night preferences, our metabolism to that ghost from the past. Stop it. You're not supposed to be the same person you were two decades ago. That's called growth.

2. Other people's definitions of success

When I walked away from my six-figure salary at 37, my former colleagues thought I'd lost my mind. "You're throwing away everything you worked for," one said.

But whose definition of "everything" was I using?

Success to my parents meant a stable corporate job. Success to my MBA cohort meant climbing the ladder. Success to society meant a bigger house, fancier car, more impressive LinkedIn title.

It took me until my late thirties to realize I'd been chasing someone else's dream. Maybe your parents wanted you to be a doctor. Maybe your college friends measure worth in square footage. Maybe Instagram makes you think success looks like yoga retreats in Bali.

Ask yourself: What does success actually mean to YOU? Not your mother, not your peers, not some motivational speaker on a podcast. You.

3. Guilt over boundaries you set

"Am I being too harsh?"
"Should I have just said yes?"
"Maybe I'm being selfish."

Sound familiar?

Setting boundaries is hard enough. But the guilt that follows? We carry that for years. You said no to hosting Thanksgiving in 2015 and still feel bad about it. You stopped lending money to that friend in 2018 and wonder if you're stingy. You quit the volunteer committee five years ago and still feel like you let everyone down.

Here's what therapy taught me: boundaries aren't cruel. They're necessary. That guilt you're carrying? It's just proof you're a caring person. But caring doesn't mean sacrificing yourself indefinitely.

4. The "perfect" life you planned at 18

At 18, I had it all figured out. Career by 25, married by 28, kids by 30, early retirement by 50. Life would be a neat checklist, each box ticked on schedule.

How's that working out for any of us?

Yet we hold onto these arbitrary timelines like they're sacred contracts. We feel "behind" because we're not where our teenage self thought we'd be. We judge our actual life against this fictional timeline created by someone who hadn't even lived yet.

Your 18-year-old self didn't know what they were talking about. They'd never experienced real loss, real love, real challenge. Give yourself permission to want different things than that kid wanted.

5. Resentment toward people who've moved on

They hurt you in 2008. They probably don't even remember it happened. Meanwhile, you're still having imaginary arguments with them in the shower.

I've filled at least ten of my 47 journals with variations of the same resentments. People who got promotions I deserved. Friends who disappeared when life got complicated. The ex who moved on too quickly.

But holding resentment is like drinking poison and expecting the other person to get sick. They're living their life. You're the one suffering.

6. The belief that struggle equals worthiness

"I'll sleep when I'm dead."
"No pain, no gain."
"If it's not hard, it's not worth doing."

We've turned suffering into a badge of honor. If you're not exhausted, you're not working hard enough. If you're not stressed, you're not taking life seriously.

This mentality nearly killed me. Literally. The burnout that hit me at 36 was my body's way of saying enough. Yet even in therapy, I felt guilty for resting. As if ease somehow meant I was cheating.

You don't earn your place on this planet through suffering. You're already worthy. Stop holding onto the idea that you need to prove it through pain.

7. Anger at your younger self

"Why didn't I save more money?"
"Why did I waste time in that relationship?"
"Why didn't I take that opportunity?"

We can be incredibly cruel to our past selves. We judge them with information they didn't have, wisdom they hadn't earned, experience they couldn't possibly possess.

When I look back at some of my choices, especially in my twenties and early thirties, I cringe. But that person was doing their best with what they knew. They were learning. They were human.

Forgive that person. They got you here.

8. The fear of being seen as difficult

"I don't want to rock the boat."
"I don't want to be THAT person."
"I'll just go along with it."

How many times have you swallowed your opinion, your needs, your truth because you didn't want to be labeled difficult? And how many years have you been doing this?

Being agreeable isn't a virtue if it means constantly betraying yourself. Having standards isn't difficult. Having opinions isn't problematic. Having needs isn't high maintenance.

The people who matter won't be threatened by your authenticity. The ones who are? Let them go.

9. Relationships that ended years ago

Not just romantic ones. Friendships that faded. Professional relationships that soured. Family dynamics that shifted.

We hold onto these connections, analyzing what went wrong, wondering if we could fix them, keeping them on life support in our minds long after they've actually died.

Some relationships are meant to be chapters, not entire books. They served their purpose. They taught their lessons. Holding onto them doesn't honor what they were; it prevents you from seeing what's possible now.

10. The idea that it's too late to change

"I'm too old to start over."
"It's too late to try something new."
"This is just who I am now."

Says who?

At 37, I thought it was too late to become a writer. At 36, I thought it was too late to address my mental health. Now, in my forties, running 20-30 miles a week and living a life I actually chose, I realize how young I still was.

You're not too old. It's not too late. That thing you want to try, that change you want to make, that dream you've been sitting on? The only thing making it impossible is your grip on the belief that it is.

Final thoughts

Letting go isn't about forgetting or pretending things didn't matter. It's about choosing what deserves your energy now.

I met Marcus, my partner, at a trail running event five years ago. If I'd still been carrying all my old baggage, convinced I was too damaged from past relationships, too set in my ways, too whatever, I would have missed him entirely.

The art of letting go is really the art of making space. Space for growth, for joy, for possibilities you can't even imagine yet.

What are you ready to release?