Two Years of UpSkillion: What I’ve Actually Learnt About Speaking Up

Two years. Officially.

Looking at photos from this year — speaking at events, in conversations with people, with the team, moments I thought were tiny at the time — I’m struck by something: I look more myself in them. Not more polished. Not more “speaker-y.” Just… more real.

And that’s the whole story, isn’t it?

It’s a strange milestone to hit. Not huge, not tiny — just enough time to look back and actually see things clearly. To spot the patterns. To notice what changed.

And if I’m honest, what’s changed isn’t what I thought would change.

The Worst Moments Get All the Airtime

Here’s what I’ve learnt: we remember the worst experiences even though they’re rare.

I can tell you exactly how I physically reacted the first time I got a pitch slightly wrong. I can replay the awkward pause. I can still feel the moment I realised I’d said something that didn’t land.

But you know what I can’t remember? The hundreds of conversations that went fine. The pitches that worked. The client calls where we actually connected. Those moments just… happened. They were normal. So my brain filed them away.

We do this all the time. We focus on the one meeting where we stumbled, and convince ourselves it proves something about us. Meanwhile, we do okay most of the time. We just don’t notice because “okay” isn’t dramatic enough to remember.

Two years has taught me that “okay” is actually the norm. And “okay” is actually enough.

What I Actually Stand Out For (Spoiler: It’s Not What I Expected)

I don’t stand out for being a great public speaker.

Look at the photos — I’m not delivering perfectly polished pitches. I’m having conversations. Listening. Laughing. Sometimes slightly awkward, always real. That’s what’s actually happening.

The people who’ve come to UpSkillion didn’t come because of a flawless presentation. They came because we had a real conversation. Because I asked genuine questions. Because I actually cared.

I spent year one thinking I needed to be more polished, more professional, more “speaker-y.” Then I realised: the thing actually working was the opposite. It was showing up as myself.

So I stopped trying to be great and started being genuine. And that’s what people connected with.

The Scary Moments That Stopped Being Scary

Year one: last-minute speaking request = panic. Heart racing. Convinced it was a mistake.

I still need a list of points. (I’m not winging it — I’m not that person. Structure helps me think clearly.)

But the fear? It’s different now.

I’ve shown up enough times — at events, in conversations, in moments I wasn’t sure about — and discovered the same pattern: I stumble a bit, find my footing, say something real, and people respond to the realness. Not the perfection.

The growth wasn’t becoming fearless. It was becoming experienced enough to trust the pattern. Fear doesn’t mean anything will go wrong. It means I care.

The Speaking Up That Really Matters

Here’s what surprised me: the speaking up that transformed my business wasn’t about overcoming nerves to say something hard.

It was about learning to celebrate.

Saying out loud: “This is going really well.” Sharing wins instead of playing it safe. Being visible about what I’m enjoying, not hiding behind professional distance.

Early on, I thought confidence meant handling scary moments. Now I know it means claiming the good ones too.

There’s something vulnerable about saying “I’m really enjoying this” or “We’ve had amazing conversations.” It feels risky compared to the safe, neutral version.

But it’s not risky. It’s honest. And honest is what people actually respond to.

The Real Confidence

Two years in, I know this: confidence isn’t about being a great speaker. It’s not about polish or perfection.

Confidence is knowing that most of the time, you’ll do okay. And okay is actually enough.

It’s showing up as yourself, not as who you think you should be. Having conversations instead of delivering pitches. Celebrating wins and acknowledging hard parts.

It’s speaking up — whether that scares you or delights you.

And here’s the wild part: you don’t wait until you feel confident. You build it by doing it. By showing up imperfectly, surviving it, and realising you’re still here. Still standing. Still okay.

Shared photos? That’s what it looks like. Not perfect. Just real.

For You

If you’re thinking about speaking up — in meetings, at networking, about your business, about what you want — here’s what two years has taught me:

You don’t have to be polished. Just real.

You don’t have to be a great speaker. Just genuine.

You don’t have to wait until the fear is gone. You just have to do it and notice you’re okay.

The fact you’re reading this, thinking about how to show up differently? That’s proof you will be.

Most of the time, you’ll do okay. The moments when you stumble teach you something.

Two years in, I’m not a different person. I’m just more myself. More willing to be heard. More willing to celebrate the good stuff.

That’s the real win.


Here’s to two years of learning that okay is actually enough. And to whatever comes next.