It would be very easy, very easy, for me to say that one of my biggest regrets is not leaving my corporate job sooner.

People love that line. It rolls off the tongue nicely. It sounds brave and self-aware. It fits neatly into Instagram captions and dinner party conversations, usually delivered with a sigh and a glass of wine.

“I wish I’d started earlier.”

But here’s the thing. That sentence only works if you ignore who you were at the time. And hindsight is very good at doing exactly that.

Looking back now, with distance, confidence, a life I genuinely love, and proof that everything didn’t fall apart when I finally walked away, I can absolutely see that I could have left sooner. I wasn’t doing myself any favours. I wasn’t doing the company any favours either. I was restless, disengaged, quietly unhappy, and already halfway out the door in my head.

But none of that means I was ready. And this is where we need to stop being so cruel to our past selves.

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The Problem With Hindsight Is That It Deletes Context

Because hindsight has a nasty habit of stripping away context. It removes fear. It deletes uncertainty. It conveniently forgets the very real risks you felt at the time: financial, emotional, social, existential. It judges your past decisions using information and self-belief you simply didn’t possess yet.

It’s a rigged game.

We look back and say, “I could have done it.”
But what we really mean is, “If I had been who I am now, back then, I would have done it.”

Which is… not how time works.

At the time, I didn’t feel ready. And that’s the only thing that actually matters.

We talk about regret as if it’s some great moral failing. As if not taking the leap sooner means you lacked courage, ambition, or vision. As if everyone who stayed in a job too long, a relationship too long, or a life that felt too small simply didn’t have the guts to leave.

That narrative is rubbish.

Readiness isn’t about logic. Or intelligence. Or even desire.

Readiness is about whether your nervous system believes you’ll survive the consequences.

Readiness Isn’t Weakness, It’s Capacity

You can want something deeply and still not be equipped to hold the fallout of choosing it. You can crave freedom and still be paralysed by responsibility, identity, fear of judgment, or the very real possibility of failure. That doesn’t make you weak, it makes you human.

We love to talk about “deathbed regrets”. You know the ones. Not travelling enough. Not taking risks. Not living more boldly.

But those lists always miss something crucial.

They never ask why people didn’t do those things.

It’s very easy, from the outside, to say someone should have travelled more. It’s much harder to sit with the reality that maybe they didn’t feel safe enough to leave. Or confident enough to go alone. Or financially secure enough to risk it. Or emotionally intact enough to break away from expectations, obligations, or a version of themselves they hadn’t yet outgrown.

Regret doesn’t always mean you failed to act.

Sometimes it means you survived long enough to become someone who finally could.

Why Beating Yourself Up Helps No One

That distinction matters.

Because when we frame our lives as a series of missed opportunities, we turn growth into shame. We convince ourselves we’re behind, late, or broken, when in reality, we were simply still becoming.

And here’s the uncomfortable flip side of this: hindsight is brilliant, but it’s also useless if all you do with it is beat yourself up.

What actually matters isn’t what you wish you’d done. It’s what would make you feel ready now. That’s the question nobody asks.

Instead of “What will I regret one day?”
Try: “What do I need in order to trust myself with a different choice?”

Sometimes that’s money.
Sometimes it’s skills.
Sometimes it’s therapy.
Sometimes it’s space.
Sometimes it’s seeing other people do it and realising the world doesn’t end.

And sometimes, quietly, unexpectedly, it’s just one small step that cracks the door open.

You Don’t Need a Leap, You Need Permission

Not a grand leap. Not quitting your job tomorrow. Not blowing up your life for the sake of a motivational quote.

Just enough movement to remind yourself that you still have agency.

This is why I’m deeply suspicious of advice that tells people to “just go for it”. That sort of bravado sounds inspiring until you realise how alienating it can feel to someone who is exhausted, scared, or carrying far more than you can see.

You don’t need more pressure. You need permission.

Permission to move at your pace.
Permission to stop romanticising earlier versions of yourself.
Permission to recognise that the version of you who stayed was doing the best they could with the tools they had.

And if you’re reading this thinking, Okay, but I don’t want to be here forever, good. That matters too.

Readiness isn’t static. It’s something you build.

Sometimes the First Step Isn’t a Decision, It’s Space

Sometimes that looks like trying something adjacent rather than jumping straight into the unknown. Sometimes it looks like stepping into environments that stretch you without overwhelming you. Sometimes it looks like seeing what it feels like to be a slightly braver version of yourself, just for a week or two.

This is where travel can be quietly powerful, not as an escape, but as a mirror.

Not the glossy, box-ticking kind. The kind that slows you down, puts you somewhere unfamiliar, introduces you to people living differently, and gently asks, Is this still the life you want?

I’ve watched people arrive on my tours burnt out, stuck, grieving, curious, or quietly dissatisfied, and leave not with a five-year plan, but with clarity. Not answers, but better questions. Not a new identity, but a deeper trust in themselves.

And that’s often the real first step.

Not deciding what you’re going to do with the rest of your life, but creating enough space to hear yourself think.

You Didn’t Start Late, You Started When You Could

I didn’t start late.
I started when I was finally able to hold the consequences of starting.

If you’re still where you are, that doesn’t mean you’ve failed.
It might just mean you’re still becoming the person who can leave.

And when you’re ready, really ready, you won’t need hindsight to tell you.

You’ll feel it.

If you’re not looking for a dramatic leap, just a chance to step slightly outside your normal life and see yourself from a different angle, then consider joining one of my tours.