Finding the Courage to Make a Big Leap in Life

There’s something terrifying about big leaps. The moment before jumping feels like standing at the edge of a cliff, staring into the unknown.

It’s nerve-wracking. It’s exciting. It’s a mix of emotions that make you wonder whether to step forward or retreat to safety.

I’ve taken one major leap in life – leaving home to work on a cruise ship.

The second, working for myself, is still in progress. It’s messy. I started multiple projects at once, drawn in by shiny object syndrome.

I thought they would complement each other, and maybe they will, but right now, I’m not making any income.

In fact, I’m currently in the negative due to the costs of building something new.

I haven’t fully jumped – I’m still in the process of jumping.

The Fear That Holds Us Back

I hesitate when it comes to risks. Fear creeps in, whispering doubts: What if you fail? What if you’re not good enough?

It’s easier to stay in the familiar, in the routines that feel safe. But I also know that without change, life becomes stagnant.

Looking back, I regret the small leaps I didn’t take – like not singing at karaoke, not dancing when I wanted to.

They may seem minor, but they were moments when I let fear win. And on a cruise ship, where work and life intertwine and eyes are always watching, the fear of judgment is amplified.

Every decision – big or small – shapes the life I live, and I remind myself of that constantly.

Navigating the Unknown

How do you take a leap when fear grips you? Here’s what works for me:

  • Imagining the worst-case scenario. What’s the absolute worst that could happen? If you can survive that, then the risk may be worth it.

  • Writing out the pros and cons. Seeing things on paper helps sort emotions from logic, though I admit my method isn’t always the most structured or logical.

  • Taking time to process. I tend to avoid thinking about it for days, then suddenly – when it feels right – I jump.

  • Accepting that the unknown is part of the journey. The best stories come from the unexpected.

Not every leap goes as planned.

I once applied for a more exciting cruise line, only to be turned away due to medical reasons. The whole process cost me money, time, and energy.

A failure? Maybe. But I learned something valuable: not every opportunity is meant for you, and that’s okay.

I ended up getting rehired by my original company, and that experience shaped how I now approach big decisions.

If You Feel the Pull, Try It

There’s no perfect timing for a leap. If you feel the urge or passion for something, try it.

You don’t have to commit for life – just see where it takes you. Some leaps are permanent, but many are not.

And often, the first step is smaller than you think.

Sometimes, small leaps prepare us for bigger ones.

I’m still figuring out what mine are, but maybe it starts with saying yes to things that scare me.

Maybe it’s speaking up more, pushing myself into new challenges, or simply allowing myself to be seen.

Because in the end, the biggest regret isn’t the leap itself – it’s wondering what could have happened if you had taken it.

I also know this: I struggle with traditional employment and have anarchist instincts that resist rigid structures.

Being told what to do, when to eat, what to wear – it grates on me.

That’s part of why working for myself is so appealing, even if I’m still figuring out how to make it work.

Freedom isn’t just a luxury; for some of us, it’s a necessity.

Perhaps this leap I’m taking – this leap in progress – makes less sense than my previous one.

Back then, I was a broke student, and entering employment was the natural path forward.

Now, I’m stepping away from structured work into uncertainty, without the financial safety net I once thought I needed.

I’m not leaping into financial freedom just yet, but I am stepping away from a life that never quite fit.

Even later in life, taking a sabbatical feels like an unconventional but necessary step.

At least I’m in a somewhat stable, though not ideal, financial position to make this choice.

It’s an opportunity to figure things out, to embrace the uncertainty rather than fear it.

If you’re in a reasonably stable financial position, taking a sabbatical can be a way to rediscover yourself.

I guess this is a nicer way of saying it.

Otherwise, it could be seen – especially by the elders – as a midlife crisis.

Perhaps this is simply a transitional phase – one that others might label a midlife crisis.

If you're standing on the edge, wondering whether to jump – know that you are not alone.

And maybe, just maybe, it’s time to take that step.

 

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Joanne Tai

An adventurer, and former seafarer.

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Earning a Living on a Cruise Ship and Sending Money Home

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