My Business Failures: The Hero’s Journey Part II

This email I'm sharing my business failures! Should be fun!...

A closer up look following from my last email: A decision to build boring software.

Fifteen years, one lesson, learned the expensive way.

Firstly...
Thank you for the replies to the last email! They were real and human. Best thing that happened all week.

Second only to Coco learning to stick her tongue out and laugh at the same time.

(Proud dad photo at the end.)

It validated something: writing my authentic feelings beats “look what I did with AI”.

Off the back of that, it felt right to continue the hero's journey theme…

The Trials and Failures.

The point in the film where our protagonist gets beaten by the bad guy.

In my case the bad guy was life.

Or my own stupidity.

Said a little kinder: inexperience.

Business failures.

First, let's wind back to me never getting a job...

At 22, after four summers working on a sailing beach, I looked at the end of university and a job with ~20 days of paid holiday a year.

And thought: fuck that. I want to go kitesurfing.

So I made a promise. I'd do my own thing, and buy a boat within five years.

I remember the exact thought — it could be a kayak or a superyacht. Either one counted as success.

In the hero's journey, this is crossing the threshold.

This was the boat. It did actually happen. Small, brilliant, perfect.

#1 — Online marketing

With little — ahem, no — experience, I started doing companies' social media marketing from my university bedroom.

It was 2012. Getting a few clients worked, because nobody knew what they were doing and I was young and cheap.

It turned into making content, with some cool video projects.

The failure: selling my time, not building a business.

Note: when you're inexperienced you also can't sell your time for much! 😅

#2 — Yoga retreats

Financially, hugely successful. 40+ retreats a year, split between skiing and yoga in the French Alps, and a retreat centre in Ibiza.

The failure: not sustainable. Not for my yoga teacher girlfriend, not for me, not for the relationship.

#3 — Deep Work

Huge success.

A leading web3 design studio, very cash-flow positive at its peak with a team of 30+ designers.

Over-focused on the team, not the market.

Never solved distribution.

The market moved.

Failed.

Lots of fun — in Paris, March 2020, before the world closed down.

#4 — Freelancing again

Not really a business. But worth calling out, because two problems survived it intact:

Time = money.

No distribution channel.

Basically, since leaving Deep Work in 2023, I've been freelancing for a calmer life. It doesn't always remain calm — there's a cap on the time available, and also the next client to find.

#5 — The recent ones

A therapy app I built. No channel to distribute it.

Design Canvas — I emailed about it before — genuinely great app. No way to sell it.

Consulting — still needs distribution. Still needs awareness.

Zebra Sprints — “One PMF bet, one critical flow, one week. Charlie designs it, ships working code to your repo, and validates it with real users.”

I keep counting things as failures.

Honestly, everything has been a success in experience and skills.

Building apps into a void meant I have the skills to build more!

The lesson underneath all of it.

Yoga Retreats. Deep Work Studio. Freelancing.

Every single one worked when distribution was solved.

Ads for the retreats. Word of mouth for the studio. Referrals for the freelancing.

Channels I rented, never owned.

Every single one failed when it wasn't.

All strategies need distribution.

That's it. That's the whole audit.

Fifteen years, one lesson, learned the expensive way.

Where I actually am.

The last email ended on the up — passion arriving, a well-trodden path ahead.

Reading it back, I made it sound like the hard part was done.

That was a bit of a lie.

I'm probably here.

At the rebirth. Choosing the path forward.

Consulting/freelancing still exists — call it the barbell strategy — cash-flow consulting, building software as the bet.

Four roads:

Sprints and consulting
Build a content channel for micro-SaaS / my canvas app
Get a job
“Boring accounting software”

Where I hope this goes.

That building accountancy software — where there is a real, proven need — whilst also solving the distribution, is the best option available to me.

Not the coolest. The best.

And that it creates the best life for this one.

The photo I promised at the start.
Twist: she's not smiley — incredibly upset there are no more blackberries.

The well-trodden path.

I said this was a well-trodden path.

I researched it, and found some others with eerily similar stories to success.

I was going to make that the whole email content — but then decided it was a better long read for someone interested, rather than an email summary.

Here's the link!

(AI-written, not Charlie-written.)

Final words.

A shout out to my own Dad. For his support.

Most kids get pushed towards careers. I got a weird route and no judgement.

And then he trusted me again — to build the software his practice now runs on.

And to you reading: I do realise what a privileged position I'm in.

Much love,
Charlie

P.S. If you've done your own version of this audit — the one where every failure turns out to be the same failure — reply and tell me. I love getting email.

This is email six. Previous emails: ellington.design/emails. Part one is email five.