The Hidden Skill of Winging It (Day 11)

I still remember booking a one-way flight to Thailand, telling my friends I was going to become a professional poker player.

I had no idea what I was doing. I had $500 to my name and no backup plan if it failed. It was naive. It was reckless. Yet it worked out.

Not because I had it figured out. But because I was willing to figure it out along the way.

And that’s something I’ve come to see clearly, over and over again — not just in my own life, but in the lives of the people I coach, the mentors I’ve admired, and the friends I’ve looked up to.

We’re all just winging it.

The Myth of Having It All Figured Out

We live in a world obsessed with certainty.

We create five-year plans and milestones to work towards. We look to the experts and follow their frameworks for a successful life. We convince ourselves that one day, we’ll have it all sorted — and then we’ll finally feel safe and secure.

I used to believe that too. I told myself happiness would come once I ticked enough boxes:

• Financial stability

• Passive income

• A healthy body

• Total control over my time

I achieved most of that. And instead of happiness, I found confusion.

It wasn’t a breakthrough. It felt more like a breakdown.

Because here’s the truth: you can’t build your way out of uncertainty.

The big questions — What makes me happy? What’s my purpose? What kind of life do I really want? — they don’t have fixed answers.

They shift.

They evolve.

And most of the time, they only make sense in hindsight.

Everyone’s Winging It (Even the Experts)

At some point, you realise the people you admire are winging it too.

They might have mastery in a narrow domain, sure. But zoom out just a little and you’ll see they wrestle with the same questions, fears, and patterns as the rest of us.

Some are still caught up in games of status or acceptance. Others, the wiser ones, have stopped pretending they know. They’ve made peace with not knowing.

I love the story of Socrates. 2000 years ago, the Oracle at Delphi told him he was the wisest man alive. He thought this was ridiculous, as he believed he knew nothing.

But as he questioned others — politicians, poets, thought leaders — he noticed something: They all thought they knew, when they didn't. They spoke with confidence about about the answers to life’s big questions, yet when Socrates questioned them he realised they knew very little.

The fact that we was smart enough to know he didn't know, was what made him wise.

True wisdom isn’t having certainty.

It’s knowing that you don’t know — and being okay with that.

My Inner Conflict

This has been one of the hardest parts of my journey. As a coach, people come to me expecting clarity. They want answers and solutions to their problems.

And for a long time, I felt like I had to give them that. I had to present myself as someone who knew. Someone who had it all together.

So I hid parts of myself. The parts still exploring, still learning and still doubting.

But over time, that started to crack. Because the more I’ve grown — as a person and as a coach — the more I’ve realised that pretending doesn’t help anyone.

And actually, when I let go of trying to sound smart or always have the “right” thing to say, when I just show up, listen, and trust myself to respond from presence — that’s when the real shifts happen.

Often, the student already knows the answer. They just need the right space to find it. And I need to be comfortable enough to hold that space — even if I don’t have a perfect plan.

The Art of Winging It Well

Winging it has a bad reputation.

It sounds like being unprepared, sloppy, or lazy.

But that’s not what I mean.

Winging it well is a skill.

It means showing up with energy and and presence.

It means trusting yourself to handle what life throws at you.

It means preparing, yes — but not clinging to the plan.

It means responding instead of controlling.

For me, winging it well looks like this:

• Being well-rested, energised, and connected to myself

• Creating space to listen — rather than forcing outcomes

• Acting from curiosity, not fear

• Trusting that I don’t need all the answers to move forward

It’s less about knowing — and more about responding.

Less about control — and more about trust.

Why This Matters More Than Ever

We’re entering an era where certainty is becoming a myth. AI is disrupting industries. Traditional jobs are dissolving. Life paths are becoming nonlinear and unpredictable.

And as the pace of change increases, we’re going to have to face an uncomfortable truth:

You can’t plan your way to safety.

The world is shifting too fast.

The rules are being rewritten in real time. Trying to map it all out is a recipe for anxiety and paralysis.

Instead, we need to learn how to move in uncertainty. To retrain our nervous systems to find calm in the unknown. To trust ourselves to adapt, upskill, pivot, create, connect — even when the outcome isn’t clear.

That’s the future skill set.

Not mastery over outcomes — but presence in process.

Closing Thoughts: You Don’t Need to Know

You don’t need to know what’s coming.

You don’t need a step-by-step map.

You just need to keep showing up — honestly, fully, and with an open mind.

What if you dropped the need to know?

What if the goal wasn’t to figure it all out — but to get better at moving forward when you don’t?

That’s where the magic is. That’s where growth is. That’s where life is.

Because the truth is… we’re all winging it.

The ones who do it well? They’re just the ones who’ve learned to trust themselves in the unknown.

Adam