How Do I Let Go of the Person I Used To Be?

Letting Go of Who You Used To Be Is Harder Than Anyone Admits

Letting go of who you used to be is not a clean, quick process. It feels like losing a version of yourself you spent years building. It feels like failure, even when it’s progress. It feels like something ended, but nothing new has started yet.

If you’re stuck between the life you had and the life you want, you’re not alone. This is one of the biggest identity questions guys in their 20s deal with. I felt it heavily while talking to Jordan Litz, who plays Fiyero in Wicked on Broadway.

His story is one of the clearest examples of what it actually looks like to shed an old identity, grieve it, and slowly build a new one.

Here’s what I learned.

The Hardest Part Is Admitting Something Is Over

There’s a moment in our conversation where Jordan said something that hit hard:

“I was crushed, dude.”

He wasn’t exaggerating.
He wasn’t sugarcoating.
He wasn’t pretending he moved on quickly.

Swimming shaped his entire identity. His discipline. His community. His sense of purpose.

When it ended, he didn’t just lose a sport. He lost a version of himself.

That’s why letting go feels so painful. Your mind clings to the familiar, even when the familiar no longer fits. According to Psychology Today, identity loss often triggers grief responses similar to losing a relationship or major life role.

You Are Allowed To Mourn Your Old Life

One of the most important things Jordan shared was this:

“I loved the grind. I loved swimming.”

A lot of guys think letting go means pretending they never cared. It doesn’t.

You can love who you were and still outgrow him.
You can respect the past without living in it.
You can mourn what ended without sabotaging what’s next.

Letting go is not betrayal.
Letting go is evolution.

If your thoughts keep looping during this phase, How To Stop Overthinking Everything breaks down why your brain resists change even when it’s necessary.

Letting Go Creates Space for Who You’re Becoming

The moment things shifted for Jordan came years later when he said:

“I found musical theater at 26.”

That line matters.

He didn’t replace one identity with another overnight. There was a gap. There was confusion. There was a stretch where nothing made sense yet.

That space is where most guys panic.

But that space is also where new direction forms.

Research from Harvard Business Review shows that identity transitions often require periods of ambiguity before clarity emerges. That gap isn’t a failure. It’s a holding pattern for growth.

Your Old Identity Was Never a Waste

One of the biggest fears guys have is this:

If I walk away, does that mean everything I did before was pointless?

Jordan answered that directly:

“You can take the skill set you already have and apply it to something new.”

Starting over does not mean starting empty.
Reinvention does not erase your past.
It repurposes it.

Your discipline, resilience, work ethic, and experience still belong to you. How Do I Reinvent Myself in My 20s explains why reinvention works best when you build on what you already know instead of rejecting it.

Comparison Keeps You Attached to the Past

Jordan described stepping into a new world surrounded by elite performers:

“Those guys are superhuman.”

That’s comparison doing its thing.

It makes everyone else look untouchable and makes your old identity feel safer by comparison. At least there, you knew who you were.

But comparison isn’t clarity.
It’s fear wearing nostalgia.

If comparison keeps pulling you backward, How To Build Confidence When Your Life Feels Behind breaks down how to stop measuring yourself against versions of people you’re not meant to become.

Your Identity Is Supposed To Change

One of the most grounding lines Jordan shared was this:

“The stresses of your young life are so much smaller than you think.”

Who you were at 18 was never meant to be who you are forever.
Who you were at 22 wasn’t the final version either.

Identity is supposed to evolve.

Letting go of an old identity isn’t losing yourself.
It’s returning to yourself.

Fear Is Part of the Transition

Jordan didn’t step into his next chapter confidently.

“I was terrified.”

Fear doesn’t mean you’re not ready.
Fear means you’re standing in the doorway.

The discomfort you’re trying to avoid is often the entry point to the life you want.

Where You Go From Here

Letting go of who you used to be takes time. It takes honesty. It takes sitting in uncertainty long enough for something new to take shape.

Honor who you were.
Release who you no longer are.
Make space for who you’re becoming.

If you’re still searching for direction, How Do I Find My Purpose When I Feel Lost is the most natural next step.

FAQ

Why is it so hard to let go of an old identity?
Because it’s familiar and tied to self-worth. Letting go requires uncertainty, and uncertainty feels threatening.

How do I know I’ve outgrown something?
When it drains more than it fulfills you. When obligation replaces passion.

Is it normal to feel lost between identities?
Yes. That gap is where self-discovery happens.

How do I stop attaching my worth to my past?
Focus on transferable skills, not old labels. Your value isn’t limited to one chapter.

Will the fear ever go away?
It fades with movement. It stops controlling you once you start moving forward.