Worried You're Going to Fall Flat on Your Face?
Me too - here's why you should do it anyway!
What if the thing holding you back from going for your dreams isn’t failure, but your fear of feeling foolish for even trying?
You know what I’m talking about.
That idea that won’t leave you alone. The dream you’ve shelved because… what if it flops? What if no one cares? What if you look like a right idiot for putting yourself out there?
Left unchecked, that fear turns into regret. Quiet at first. Then louder with every year you delay.
Instead, what if you chose to try anyway?
For the joy, for the learning, for the life you want, or just for the hell of it!
What might happen then?
The Question That Changes Everything
Most self-help books love to ask: What would you do if you knew you couldn’t fail?
It’s meant to inspire, to remove fear from the equation and open up possibility.
But in her awesome book Big Magic, Elizabeth Gilbert asks something far more powerful:
“What would you do even if you knew you might very well fail?”
That’s a different question entirely.
It removes the safety net. No guaranteed wins. No admiration. No applause. Just you, your idea, and the choice to follow it anyway.
The fantasy disappears, and what’s left is what matters to you. What you’d show up for, even without the shiny rewards.
And that’s what makes it powerful. It forces you to face your own reasons, rather than the filtered, polished ones we say out loud. The real ones that sit quietly in your chest and whisper, “Go on. Give it a go.”
Most people don’t. Because failure is one thing. But looking like an idiot or getting judged by peers or family members, is another thing altogether.
And yet… choosing to do it anyway is where all the good stuff begins.
Why I’m Writing This (and why I’m scared too)
Right now, I’m working on a new travel gear brand under The 50+ Nomad. It’s something I’ve been talking about for years. A stylish range designed for grown-up adventurers. Gear that works, lasts, and feels like it was made for us older travellers.
My first product will be packing cubes. Then comes the crossbody bags, the backpacks, the travel journals, the sleep kits. Eventually, I want to create thoughtful pieces for everything from hiking to house sitting.
And long term, I want it to mean even more. I’d love to partner with local makers, support remote villages, and use the platform to tell their stories and give back.
That’s the dream.
But I’m scared shitless. I have all the doubts.
What if no one buys it.
What if it all falls flat.
What if people think it’s naff.
What if I put myself out there and it just doesn’t resonate.
The idea has lived in my head for a long time. I’ve scribbled sketches, collected samples, pinned swatches. I’ve opened browser tabs I never closed and bought domain names I haven’t used. Something about it won’t leave me alone.
And now I’ve decided to go for it.
I’m going to post the photos, share the designs, and start building the thing I’ve been dreaming about. Even if I get it wrong. Even if no one’s watching, and even if I need to freelance to fund it along the way.
Because I’m already a 50+ nomad. I live this life. I love travel gear. I care about the stories behind the things we carry. So I’m doing it. Even if I might fail.
So What Would You Do Anyway?
Forget the usual question. The one that asks what you’d do if you couldn’t fail. That version tends to bring out the big silly stuff.
Start a billion dollar business.
Win an Oscar.
Become a pop star.
Climb Everest.
Star alongside Ryan Gosling. (Just me?)
All of those are bold, glittery dreams that sounded brilliant when we were 13, but are most often totally out of reach.
Now we're older and wiser, let’s get real.
What would you do just because you want to? What are you curious about? What keeps nudging you, even if it scares you a bit?
Maybe it’s writing a book. Maybe it’s launching a tiny online shop. Maybe it’s packing a bag and trying a month in Mexico, just to see.
The result isn’t the most important part. What matters is how it feels to follow something that feels true to you. To spend time doing something that brings you energy, focus or even just a quiet sense of satisfaction.
This isn't about perfectionism, impressing anyone or doing something because somebody else said you should. This is just you my friend, following your dreams. (And why the hell not!)
Your Dreams Might Be Buried, But They’re Still There
Somewhere along the way, we've been taught to shrink a little.
As we grew up we apparently needed to be sensible, to stay in our lane, to 'stop daydreaming!', and to swap imagination for practicality and call it maturity.
We learned to be realistic. Take the job, pay the bills, raise the kids, do the decent thing. And there's nothing wrong with that. But in the process, some of our dreams got quietly packed away.
It wasn't because we didn’t care, but we ran out of time. Responsibility took over, life happened and our aspirations got stuffed in the box in the loft.
They’re still there though. Maybe a bit dusty, and maybe a little harder to hear under the noise of daily life. But they haven’t vanished.
And you don’t need a dramatic reinvention either, or to start from scratch. Sometimes you just need to remember what used to light you up before everything got so serious.
As Liz Gilbert says so perfectly:
“What else are you going to do with your time here on earth — not make things? Not do interesting stuff? Not follow your love and your curiosity?”
Exactly.
Give Yourself Permission To Try
You don’t need to overhaul your life or shout your dreams from the rooftops. You just need to get started.
Here are five simple things you can do this week to reconnect with what you’d do anyway, just for the joy of it.
1. Write a “would-do-anyway” list
Grab a notebook, a scrap of paper, or the the back of a receipt. Jot down three to five things you’d happily do even if no one applauded, liked, or paid you for it. No filtering. Just write what comes.
2. Pick one tiny action
It doesn’t matter what it is. A quick sketch. A messy blog post. Ten minutes tinkering with an idea. Just one small move that signals to yourself, I’m doing this.
3. Detach the outcome from the effort
Try showing up for 30 days without tracking, measuring, or expecting results. Give yourself the space to create or explore without needing it to be a thing. See how that feels.
4. Find your fellow dreamers
Surround yourself with people who get it. Join a Facebook group, pop into a Substack chat, message a mate who’s doing their own weird and wonderful thing. It’s easier to stay brave when you’re not doing it alone.
5. Read Big Magic (or any book that inspires you)
Sometimes one sentence is all it takes to spark something again. Go find it. Let it remind you what you’ve always known.
Big Magic is More Than Just a Book. It’s a Permission Slip
Elizabeth Gilbert didn’t write Big Magic to help us be fearless. She wrote it to help us move forward even if it’s with fear.
The book encourages us to live with more courage and curiosity. That might mean starting something new, speaking up, moving across the world, building a different kind of life, or simply saying yes to an idea that’s been quietly tugging at your sleeve for years.
It’s time to give yourself permission to try, even if the outcome is uncertain.
You don’t have to be brilliant or bold. You don’t even have to have a plan. You just have to begin with what feels real to you.
Elizabeth doesn’t pretend the fear will vanish. Because it won’t. Her message is simple: bring it along for the ride, just don’t let it drive.
Join in The Fun!
If you’d like to support me on my journey to bring smart travel gear to grown-up adventurers (and snag some free stuff), sign up to the packing cubes early bird launch list here!
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Great article and motivating!!
I'd love a easy way to pack small, light spices and herbs. ❤️ Great article, very motivating.