Who is Lost Harry?

Playing finders keepers with my ability to do anything.

3 years ago, I wanted everything to change.

I remember waking up to the ocean next to me. It was January 24th 2020, and I was at an AirBnB 2 hours south of Perth, WA.

I was tired. For the first time in a long time, I felt like I was fuelling up. Fuelling up my passion, my creativity, my self-care tank.

It was a glimpse of the life I wanted to live.

I grabbed it with both hands, made a bunch of (loud) proclamations and changed everything. I was determined to live a creative life and I had a vision of what that felt like.

Then, it slipped through my fingers. I was floundering in my own scattered ambition. I call this version of me Lost Harry.

Shortly afterwards, the pandemic hit and, just like that, the ground shifted again under my feet.

3 years later, I don’t live in Perth and I’ve become a variation of the person I always wanted to be.

So how did I get here? And who is Lost Harry?

Let’s wind back the clock

What the heck was going on in my life prior to this crisis?

The short answer is: a lot. That’s for another blog so let’s recap it in dot-point form.

I was:

  • Travelling the country working at a youth leadership not-for-profit

  • Building a skateboard business

  • Freelancing in photo, video and web design

  • Just dropped out of my law degree

I had ambitions to live and work as a full-time creator. I was rapidly approaching the part of the bell curve in my creative journey where I thought I knew far more than I did.

I think they call it the Dunning-Kruger effect

I had this desire to uproot my life and shed what people thought of me; to start fresh. It was a mid-life crisis, except I was 20 years old, broke and had no credible life experience.

Then everything changed.

The world put up its ‘Back in 5 Mins’ sign

You know when you go to a store and you see a sign sticky-taped to the door saying they’ll be back in 5 minutes so you decide to wait it out but after 20 minutes, no one’s turned up?

That’s what the intro to Covid felt like for me.

Upon returning to Sydney in January, I broke up with my girlfriend, told my bosses my plans to move to the other side of the country, got 75% of the way into a $50K video client contract, and (this part’s important) told anyone who would listen about my plans.

In March 2020, I was back in Perth seeing friends and scouting areas to live in. There had been rumblings of this ‘coronavirus’; I didn’t think much of it at the time.

On one of my last mornings, I hopped on a zoom call at 6am Perth time with my work team.

“Everything’s closing up. This virus is going to have some significant impacts on us. We’re going to make everything we do digital.” That’s what I heard come out of my laptop speakers and I realised: we could be a bit screwed here.

I made it back to Sydney with a day to spare before the border closed between states.

As one of the few people at the organisation who knew how to man a camera, edit footage, and build digital systems - I got drafted to build our digital programs. That started me down a path that I’m super grateful for even though it put a dent in my dreams.

It created Lost Harry (someone you’ll meet properly in our next section) but it gave him the path he needed to turn the frenzy in his head into a dream with legs.

I call him Lost Harry

4 weeks ago, one of the best humans I know - Nic Hurrell - DM’d me with a proposition.

He was running Sprouter: a four-week program of learning, accountability and encouragement to do the things that terrify you.

I was pot-committed before I even finished reading the text he sent me.

Honestly, I just love Malkovich’s accent in Rounders

In one of the week’s sessions, he asked me to think about the version of me that believes all the doubts I have about myself.

Coincidentally, this workshop was around the same time that I had one of the best chats with Ellen, a person I absolutely cherish who just gets me.

We landed on a defining moment that stopped me in my tracks.

After my dream of moving to Perth died, I had a series of conversations with people I really trusted and respected. The same message came out of 4 different people’s mouths.

“We knew you weren’t going to do it anyway.”

This is the moment a new version of me came to life. Suddenly, I was terrified of putting myself out there in my creative projects because I didn’t want to stare down the barrel of possibly not following through.

This is the person I named Lost Harry.

Taylor never lies (don’t fact check me on this)

He’s me if I relied on others for self-belief instead of backing myself.

Ditching that guy for good

“I saw your video” or “I read your article” is one of the most common things I hear at the moment.

And everyone who’s said it has done so with excitement or pride. It’s electric.

All of this is a conscious decision to ditch Lost Harry for good, to make what I want and trust myself to execute what I know is possible for me to do.

Every time I hit publish, I cringe at myself a little but I make myself do it anyway. I don’t want to look back at myself in three years and feel like I lost my passion again.

So, as a summary of this deeply innate part of my life - I strung together 5 lessons I’ve learned along the way that you can take with you.

The 5 lessons learned

1. You’ll have to be patient; whether you like it or not.

Patience has a way of hitting you, especially when you don’t want it. Don’t stop moving and shaking but know that everything you do will be cumulative, you’ll only notice the progress in time.

2. Be along for the journey, but make your own path.

There’s a fine balance between relentlessly pushing yourself down a path and forcing an outcome to occur. Know the balance and be open to going where the journey chooses to take you.

3. Set your foundation as wide as you can.

Your journey is going to push and pull you in a million directions. Set your foundation of skills, networks, and experiences wide so you’re equipped with something more valuable than specialty: adaptability.

4. People will support you just as much as they’ll judge you.

Find your cheer squad and create a very open, very direct dialogue around boosting each other through the difficulty. For me, it was Sprouter and some of my best friends who knew my ambitions and support it 110%.

5. You’ll never know the alternative.

You can spend forever wondering if you should have done something differently. The truth is, you’ll never know the difference. Make a call and run with it. If it turns out to not be what you hoped, change your mind and go another way. You’ll never have a time machine to see what could have been.

If you’ve read this far, shoot me a message saying “Orange Quesadillas” and I’ll shout you a coffee.

Hey, I’m Harry 👋🏻

I’m a creative generalist with a pinball machine for a brain.

I'm passionate about building creative communities and reinstalling creative intelligence in our rapidly updating humanOS.

My work has taken me through a bunch of arenas. From delivering leadership workshops across the country to building communities in startups and VC (with a few fun pitstops along the way).

I share stories of things I’ve learned, wild theories I’ve tested, and random pieces of information I need to get off my brain to clear the hard drive.

Follow for more and if you ever wanna get a coffee (in-person or virtually), hmu. I’m always keen. ☕️