There is a moment in your 20s where you look around and think, is this really who I want to be. Maybe it hits after a breakup, a job burnout, or watching someone else chase something you wish you had the nerve to try. Reinvention always starts with that uncomfortable moment of honesty.

That feeling shows up more often than people admit. It is the same internal questioning I have written about in How Do I Reinvent Myself in My 20s? because it is one of the most common crossroads guys hit during this decade.

And I learned that clearly while interviewing Jordan Litz, who plays Fiyero in Wicked on Broadway. His story makes one thing undeniable.

You can start over at any point in your life.
You just have to be willing to choose the path that actually fits you.

Here is what Jordan taught me about reinvention.

1. Reinvention Has No Timeline

In our conversation, Jordan said something that stopped me.

“I found performing at 26.”

That line changes everything. Because most guys think they missed their window, that they are too late, that the ship sailed.

Then he told me another detail that hit even harder.

“Wicked is your Broadway debut at 37.”

You hear that and something in you relaxes. Reinvention does not run on a schedule. You are not behind. You are simply earlier in a different story.

This idea is backed by research on nonlinear career paths. Harvard Business Review has published multiple pieces showing that career pivots later in life are not only common, but often lead to higher fulfillment Harvard Business Review on career reinvention.

2. Reinvention Begins With Loss

Most people skip the hardest part of reinvention. Jordan did not.

He told me openly:

“I was crushed… so I found a new dream.”

There is something powerful about someone admitting they reached a dead end and kept going anyway. Reinvention does not always feel brave. Sometimes it feels like grieving the version of you that no longer fits.

That grief is part of the process.
You are allowed to outgrow the old you.

If you are stuck replaying what did not work, this connects directly to How Do I Handle Rejection Without Losing Confidence?, because reinvention often starts right after disappointment.

3. You Bring Your Skills With You

One of my favorite moments from the interview was hearing Jordan talk about applying everything he learned from his old life into his new one.

He said:

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

That line is freedom.
It means you do not start over empty.
You start over experienced.

Career experts consistently reinforce this idea of transferable skills. LinkedIn regularly highlights how skills compound across industries rather than reset LinkedIn on transferable skills.

Nothing you have done up to this point is wasted. It just might belong to a different chapter.

4. Fear Is Not a Stop Sign

Jordan did not sugarcoat anything. There is a point where he admits:

“I was terrified.”

And yet he kept going. He even said:

“You have to be calm even when your heart rate is jacked.”

That is reinvention.
Not confidence.
Not certainty.
Not smooth sailing.

Just courage layered over fear, repeated until it becomes your new normal.

If fear is the thing holding you back, this pairs naturally with How To Build Confidence When You Feel Behind, because confidence often comes after action, not before it.

5. Effort Is Your Advantage

Jordan made something very clear during the conversation:

“You can control how hard you work.”

You cannot control timing or opportunity, but you can always control effort. Reinvention rewards consistency way more than natural talent. The guys who change their lives are the guys who keep showing up when no one is watching.

Psychologists often describe this as effort-based identity building, where consistency reshapes self-belief over time. Psychology Today has written extensively about effort as a driver of long-term confidence Psychology Today on effort and growth.

6. Comparison Will Kill Your Progress

There was a point where Jordan talked about the level of talent around him and admitted:

“Those guys are superhuman.”

And I loved that honesty.
Because that is how comparison works.
It makes everyone else look superhuman and makes you feel behind.

But the interview reminded me of something every guy needs to hear.

You are not competing against their path.
You are building your own.

If comparison spirals are taking over, reading How To Stop Overthinking Everything can help before you go further.

If comparison spirals are taking over, reading How To Stop Overthinking Everything can help reset your perspective before you go further.

7. Reinvention Requires Humility

Jordan told me about moments where he felt like he was starting from nothing. Literally nothing.

“I walked in there with nothing.”

That is the part no one glamorizes. Reinvention demands being new again. It demands being willing to be taught, corrected, challenged, humbled. It is uncomfortable, but it is also the thing that opens every door.

8. Pressure Is Not Reality

Later in the conversation, Jordan said something that has stayed with me.

“It’s just your career.”

And that line puts everything in perspective.
Your identity is bigger than your job.
Your worth is bigger than your timeline.
Your life is bigger than any one chapter.

The moment you stop treating every decision like a life sentence is the moment reinvention becomes possible.

Where You Go From Here

Your 20s are not about getting everything right. They are about learning who you are and choosing the version of you that feels honest. Reinvention is not a crisis. It is an upgrade.

You are not stuck.
You are not late.
You are in transition.

And transitions are where the best stories begin.

If you want the next step, read How To Build Confidence When You Feel Behind next.

FAQ

How do I know it is time to reinvent myself?
When your life feels too small for who you are becoming. When staying feels heavier than leaving.

Do I have to quit everything to reinvent myself?
No. You can build the new identity while managing the old responsibilities.

What if I fail?
Failure is part of the switch. You do not reinvent yourself without falling a few times.

What if I feel too far behind?
Jordan’s story proves you are not. Reinvention has no age limit.

How do I stay confident while starting over?
Anchor yourself in what you can control: effort, attitude, and consistent action.

Episode Referenced

For deeper insight, watch or listen to Episode 101 of the Guyset Podcast.