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

How You Know It’s Time to Take the Leap

There is a moment before every real leap where nothing has changed yet, but everything already feels different.

Your life still looks the same from the outside. Same job. Same routine. Same sense of safety. But internally, something has shifted. Staying where you are starts to feel heavier than the risk of moving.

You do not suddenly feel ready. You just reach a point where trying feels less painful than not trying.

That moment showed up in different ways for Simon Gervais and Ryan Steck, but the feeling was the same.

Simon walked away from a six-figure government career protecting world leaders to become a full-time novelist. Ryan left more than a decade as one of the most respected thriller critics in the world to write his first book after running The Real Book Spy.

Neither waited for certainty.

“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 was no perfect plan. No guarantee. Just a pull that stopped being ignorable.

That is usually how it starts.

When You Stop Asking for Permission

Most people believe taking a leap comes after clarity. In reality, clarity usually comes after movement.

You do not wake up one day knowing exactly how things will work out. You wake up realizing you cannot stop thinking about the risk. The idea keeps resurfacing. The question keeps lingering. The what-if refuses to leave.

That is when the leap has already begun.

The leap does not start when you quit your job or announce the change. It starts when staying safe feels worse than trying. And once you cross that internal line, it becomes hard to go back to pretending you do not feel it. This same internal shift shows up again and again in How To Get Unstuck in Life When Nothing Feels Right.

The Fear That Actually Stops People

The fear that holds most people back is not failure.

It is regret.

What if I look back and wish I had not done this?

The uncomfortable truth is that you probably will feel that way at some point. Not because the leap was wrong, but because every real change comes with friction. Growth is rarely comfortable in real time.

But regret cuts both ways.

There is the regret of trying and stumbling. And there is the regret of never trying at all. One teaches you something. The other just lingers.

Research from Psychology Today backs this up. Long-term regret is usually about what people did not try, not what they did.

Ryan said something that reframed this completely for me.

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

That applies to writing and to life. You can pivot. You can adjust. You can start over again. What you cannot do is grow from standing still.

Fear is not a reason to wait. It is often proof that what is on the other side matters to you.

What Happens When Motivation Runs Out

Motivation does not last. That is not a flaw. It is reality.

The real question is not whether you will feel inspired every day. It is what you will do on the days you do not.

Simon’s answer 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 is not about being superhuman. It is about commitment.

Discipline is what keeps you moving once the excitement fades. It is what grounds you when doubt creeps in. And it is how confidence actually gets built after the leap, not before it. This connects directly to Why Consistency Feels So Hard Even When You Care.

Confidence follows action. It does not precede it.

The Part Nobody Romanticizes

Everyone assumes the hardest part is starting.

It is not.

The hardest part is staying consistent once the adrenaline wears off.

“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 is how Simon described what happens when the risk pays off. Success does not remove pressure. It replaces one kind with another.

You climb one mountain and suddenly find yourself standing at the base of the next. New expectations. New standards. New fear of losing what you built.

Ryan described it even more bluntly.

“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.”

Starting over does not mean pressure disappears. It means you learn how to carry it differently. You see this constantly in creative and entrepreneurial careers where success resets expectations instead of easing them.

What Failure Actually Means

Failure is not the opposite of success. It is evidence that you showed up.

If you fail after taking a leap, you are already ahead of most people. You chose motion over comfort. You learned something about yourself that safety never teaches.

“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 mindset matters more than outcomes.

You do not wait to feel ready. You move, learn, adjust, and keep going. This is the same mental shift behind What Should I Do If I Have No Idea What I Want To Do With My Life?.

Rebuilding Is About Repetition

Starting over does not require a grand plan. It requires consistency.

Do one thing every day. Even when it feels small. Even when it feels pointless. Especially when no one is watching.

Confidence does not appear first. It follows repetition.

And if you forget everything else, remember this.

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

If you are rebuilding, you are already doing the work.

Who You Climb With Matters

You do not need a massive network. You need a few people who understand what it feels like to be in motion.

He puts 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 climbing something of their own. People who do not flinch when you talk about doubt, pressure, or starting over.

That is how you protect your energy while you are building something that might not work.

And that is how you give yourself a real shot at making it work anyway.

FAQ: Knowing When It’s Time to Take the Leap

How do I know if it’s really time to take a leap?
When staying where you are starts to feel heavier than the risk of moving.

Do I need to feel ready before I take a risk?
No. “You’ll never feel ready” is the reality most people experience.

What if I regret taking the leap?
Some regret is part of growth. “You can always edit bad pages. You just can’t edit blank pages.”

What happens if the leap works but feels harder than expected?
That is normal. “You just climbed Everest and then blinked and you’re back at the bottom.”

What actually builds confidence after a big change?
Repetition. “Whatever I need to do to get to my objective, I will do.”