Letting Go (When You Don’t Know How)

If you’re reading this, you’ve probably held on to something too long. Maybe it’s a person, a place, a regret, or even a version of yourself that doesn’t fit anymore. And maybe, like me, you’re not great at letting go.

Here’s the thing: Nobody teaches you how to do it. There’s no manual on how to move on from things that mattered, no step-by-step guide on how to stop replaying memories like a song stuck in your head. People just tell you to “move on” like it’s as easy as flipping a switch. It’s not.

I’ve held on to things way past their expiration date—old friendships, old mistakes, old ideas of who I thought I’d be by now. And every time I tried to force myself to let go, I ended up gripping even tighter, like somehow the tighter I held on, the less real the loss would feel.

But life doesn’t work that way. Holding on doesn’t stop things from ending. It just makes it hurt more when they do.

The Weight We Carry

Think about the last time you carried something heavy for too long. At first, it’s fine. Manageable. Then, the longer you hold it, the more it burns, the more it digs into your skin. Letting go isn’t about pretending something didn’t matter. It’s about realizing you can’t carry everything forever.

Some things—some people, some memories—are meant to be put down.

That’s not easy. Letting go feels like giving up, like losing a part of yourself. But the truth is, it’s not loss—it’s space. Space for something new. Space to breathe. Space to become someone who isn’t weighed down by the past.

Why We Hold On

If letting go is so necessary, why is it so hard? Because even the things that hurt us can feel safe. Familiar. Even regret can feel like home when you’ve lived in it long enough.

We hold on because:

  • We’re scared of emptiness. Even pain feels like something. Letting go feels like walking into the unknown with nothing in our hands.
  • We want closure we’ll never get. Sometimes we wait for a perfect goodbye that will never come. The right words. The right ending. But life doesn’t work like movies. Sometimes you have to create your own closure.
  • We tie our identity to the past. We think, If I let this go, who am I without it? But you are not your past. You are not your mistakes, your failed relationships, or the dreams that didn’t work out. You are who you choose to be now.

How to (Actually) Let Go

I won’t lie and say there’s an easy way to do this. If you’re looking for a shortcut, there isn’t one. But here’s what I’ve learned:

  1. Acknowledge it. Whatever you’re holding on to—name it. Say it out loud. Write it down. Admit to yourself what you’re afraid to release.
  2. Sit with the discomfort. Letting go feels like grief because it is. There’s no shortcut through that. You have to sit in it. Feel it. And then, slowly, it starts to loosen its grip.
  3. Stop rehearsing the past. You know those mental replays? The what ifs and should haves? They keep you trapped. When you catch yourself going back, remind yourself: The past is a place you can visit, but you don’t have to live there.
  4. Find something new to hold onto. Letting go isn’t just about releasing—it’s about replacing. A new habit. A new goal. A new dream. Give your hands something else to carry.
  5. Forgive (yourself and them). This one’s the hardest. But holding onto resentment, even at yourself, is like drinking poison and expecting someone else to suffer. Letting go means choosing peace over punishment.

The Aftermath

Letting go isn’t a one-time thing. It’s a process. Some days, you’ll feel free. Other days, the weight will creep back in. That’s normal. The important thing is to keep choosing release. Keep choosing to move forward, even when it hurts.

One day, you’ll wake up and realize the grip has loosened. The thing you thought you could never let go of? It won’t feel as heavy anymore. And in that space, something new will grow.

You are not what you’ve lost. You are what you build from here.

So take a deep breath.

And let go.

Jesse “J” Calloway Avatar

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