7 Lessons From People Who Actually Started Over

Most People Talk About Starting Over. Very Few Actually Do.

Starting over sounds clean when people talk about it from the other side.

They frame it as courage. As clarity. As a single decision that changed everything.

What they rarely talk about is how uncertain it feels while you’re inside it. How much doubt exists before anything works. How often it could have gone the other way.

That’s why this conversation stayed with me.

I sat down with Simon Gervais and Ryan Steck, two men who rebuilt their lives from the ground up. Simon walked away from a six-figure career in counterterrorism to become a thriller novelist. Ryan went from reviewing authors as The Real Book Spy to becoming one himself.

Both took leaps that could have failed.

They didn’t.

But not because they were fearless. Because they understood something most people miss.

You Don’t Feel Ready First

One of the biggest myths about starting over is that you’ll know when it’s time.

You won’t.

“It took me seven years to write my first novel. When I signed a contract, I had another book due a year later. I told my wife I wanted to try it full-time, and she said absolutely.”

Simon didn’t wait until the fear went away. He didn’t wait for certainty. He moved when the pull became impossible to ignore.

Most people tell themselves they’re being responsible when they wait. In reality, they’re waiting for permission that never comes. I’ve written about this same pattern before in What To Do When You Feel Stuck.

If the same idea keeps showing up, the same urge, the same what-if that won’t leave you alone, that’s usually the signal. Not clarity. Not safety. Just persistence.

Awareness always comes before action.

Discipline Outlasts Motivation

People love to talk about motivation. It sounds good. It feels good. It makes change feel exciting.

But motivation fades quickly.

“I’m not lazy. Whatever I need to do to get to my objective, I will do. It doesn’t matter if I’m at the end of a deadline and need to work twenty-hour days.”

Every big change has a honeymoon phase. Then comes the quiet stretch where no one’s clapping, progress feels slow, and self-doubt creeps in.

The people who make it through aren’t more inspired. They’re more consistent. This is something I break down more deeply in Why Consistency Feels So Hard Even When You Care.

Discipline is what carries you when motivation disappears. It’s what turns a risky decision into something sustainable. James Clear makes a similar point in Atomic Habits, where he explains how systems matter more than bursts of motivation.

Pressure Doesn’t Go Away. It Just Changes Shape.

A lot of people assume pressure ends once you “make it.”

It doesn’t.

“When you’re at the top of the pyramid, it’s a fight to stay there. There are ten thousand people who want your spot.”

Before the leap, the pressure is whether you’ll succeed. After the leap, the pressure is whether you’ll keep it.

Ryan talks openly about this. Early wins don’t mean you’ve arrived. They mean expectations increase. Standards rise. The margin for error shrinks.

That’s why humility matters more than confidence at the next level. Confidence can make you careless. Humility keeps you working. You see this echoed across creative careers, especially in publishing and film, where success resets the bar instead of removing it.

Progress Beats Perfection Every Time

One line from this conversation kept echoing for me.

“You can always edit bad pages. You just can’t edit blank pages.”

That applies to everything.

Careers. Creative work. Reinvention.

Most people don’t stall because they lack talent. They stall because they’re waiting to get it right the first time. But clarity doesn’t come from thinking harder. It comes from doing something imperfect and learning from it.

Progress creates feedback. Feedback creates direction. Direction builds confidence.

You don’t think your way into momentum. You move your way into it. I’ve seen this same truth show up again and again in How Do I Know What Job Is Right for Me?.

Every New Chapter Resets the Mountain

This is the part nobody warns you about.

“It’s like you just climbed Everest and then blinked and you’re back at the bottom. You don’t even get to come down. You just have to climb again.”

Every leap puts you back in beginner mode. New rules. New standards. New pressure.

Feeling like you’re back at square one doesn’t mean you failed. It usually means you leveled up.

That disorientation is not a sign you chose wrong. It’s a sign your identity hasn’t caught up to your growth yet.

Confidence Comes After the Risk

Most people think confidence is a prerequisite for change.

It’s not.

“I never doubted myself. I didn’t know the business very well when I did that. Maybe if I knew everything, I would’ve done something different.”

That line flips the whole equation.

You don’t wait until you feel confident to take a risk. You become confident because you survived the risk.

Every leap teaches you something permanent. I can handle more than I thought.

That lesson sticks longer than any single outcome ever will.

Don’t Do It Alone

Reinvention is hard enough by yourself. It’s even harder surrounded by people who don’t understand what you’re building.

“Make yourself a group of friends and grow with them. In publishing, I have friends who started at the same level, and we grew together.”

The people you spend time with quietly shape what feels possible. Find people climbing their own hill. People who can talk honestly about doubt, discipline, and pressure without pretending they have it all figured out.

That’s where momentum compounds.

The Real Truth About Starting Over

Starting over isn’t about being fearless. It’s about being honest.

Honest about what no longer fits.
Honest about what keeps pulling at you.
Honest about the work it’s going to take.

Most people never start because they’re waiting to feel ready.

The people who actually change their lives move first and trust themselves to figure it out as they go.

And that’s the difference.

FAQ: Starting Over and Reinventing Your Life

Is it normal to want to start over in your career or life?
Yes. Wanting to start over usually means something no longer fits, not that something is wrong. That feeling often shows up before you have clarity on what comes next.

Do I need to feel ready before making a big change?
No. “You’ll never feel ready” is the reality most people don’t admit. Readiness usually comes after you move, not before.

What if I make the leap and it fails?
Every leap teaches you something permanent. Surviving the risk builds confidence in a way preparation alone never can.

Why does starting over feel so uncomfortable even when it’s the right move?
Because “every leap resets the mountain.” New chapters put you back in beginner mode, which can feel disorienting even when you’re growing.

How do I know if this urge to start over is real or just fear?
Fear comes and goes. The pull that keeps showing up, the idea you can’t shake, is usually the signal worth listening to.