How to Know When It’s Time to Bet on Yourself

If you’re stuck between staying safe and taking the leap, here’s how to tell when it’s time to finally trust yourself and what it actually looks like when you do.

By

Josh Felgoise

Nov 4, 2025

Q: How do you actually know when it’s time to take the leap?

You never really know. You just reach a point where staying safe feels worse than trying.

That was true for both Simon Gervais and Ryan Steck. Simon walked away from a six-figure government career protecting world leaders to become a full-time novelist. Ryan left ten years of success as a top book critic to write his first thriller.

“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.”

There’s no perfect plan, no magic number, no formula. The right time is when you can’t stop thinking about the risk. That’s when it’s already begun.

If you want to see what that looks like in real time, read The Risk That Changes Everything: Why Starting Over Is the Real Test of Confidence.

Q: What if I’m scared I’ll regret it?

You probably will at first.

But regret cuts both ways. There’s the regret of failing, and the regret of never trying. One teaches you something. The other just lingers.

Ryan once said something that stuck with me:

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

It’s the same with life. You can always adjust your path, learn from it, pivot, or restart. You just can’t grow from doing nothing.

Fear isn’t a reason to wait. It’s proof that you care about what’s on the other side.

Q: How do I stay disciplined when motivation disappears?

Motivation fades fast. That’s normal. The question isn’t whether you’ll feel like it every day — it’s what you’ll do when you don’t.

Simon’s answer to that question was simple:

“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.”

That’s not about being superhuman. It’s about commitment.

Discipline is what keeps you grounded when everything else feels shaky. It’s how you rebuild confidence after a leap.

If you need a reset, check out How to Build Confidence from Scratch.

Q: What happens after you take the leap?

Everyone thinks the hardest part is starting. It’s not. It’s staying consistent once you’ve started.

“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.”

That’s how Simon described what happens when your risk pays off. Success doesn’t end the pressure. It changes it.

You climb one mountain, and suddenly you’re standing at the bottom of the next. The real work is learning how to keep going without losing your balance.

If that’s where you’re at right now, What to Do When You Feel Lost in Your Career is for you.

Q: What if I fail?

Then you’re already ahead of most people.

Failing means you tried. It means you took a swing when everyone else was too scared to pick up the bat. You learn something about yourself that safety can’t teach you.

“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, but I didn’t know the odds. So I just went at it.”

That’s the mindset. Don’t wait to feel ready. Just start.

Q: How do I rebuild after starting over?

Start by doing one thing consistently, every day, even when it feels pointless.

You’ll be shocked by how much momentum that creates. Confidence doesn’t show up first. It follows repetition.

And remember what Ryan said: “

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

If you’re rebuilding, you’re already on the right page.

Q: How do I surround myself with the right people while I’m doing it?

You don’t need a massive network. You need a handful of people who get it.

Simon put it best:

“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. When you exchange about challenges, they understand.”

Find people who challenge you and understand the grind. People who want more for themselves, not just from you. That’s how you keep your energy clean when you’re climbing something hard.

My Favorite Quotes

“You can always edit bad pages. You just can’t edit blank pages.”
“Whatever I need to do to get to my objective, I will do.”
“There are ten thousand people who want your spot.”