I spent the first 7 years of my “career” as a jazz pianist.
I spent the next 7 years as an English teacher, traveling the world.
After that, I spent 7 years building a $10M online education business.
I’m going to tell you the story of all this malarkey, what it taught me, and the very real consequences on the way I ended up designing my business.
(I'll tell you the meaning of the “7 years” thing too.)
Here’s the punchline:
Everyone who hears this story thinks the best bit is the part about the successful business.
But I don’t.
It’s not at all clear to me that the last 7 years I spent building a big business has been unambiguously good, healthy or virtuous.
At times, it's been downright miserable.
But luckily, my previous "7 year careers" have helped me understand what really matters when it comes to building a business that allows you to flourish ... not just survive.
For those who care to listen, this is the story of my various careers, and what they taught me about building a business I love.
1. The Jazz Musician
I grew up playing music.
I took classical piano lessons as a child.
When I was 16, I became infatuated with jazz.
So much so, that I ended up doing a degree in Jazz Piano at one of London’s top conservatoires.
I was obsessed with music.
I remember a time at university when I used to wake up at 7am... and put on a suit. I’d head over to the practice rooms stay there all morning long – in my f***ing suit – and practice. Why the suit? Because it made me more serious.
I formed a trio with my friends Simon (bass) and Dave (drums), and we would stay up till 4am drinking beer, smoking joints and playing jazz.
Later, I moved into a shared house in North London with six jazz musicians.
Those were great years.
I had no idea how lucky we were, living and breathing jazz for years on end, while my childhood friends were all stuck on the 26th floor of some City office.
I would do crappy gigs in smokey London pubs on Saturday night for £50 cash.
I had no money.
But I didn’t care.
What was there to care about?
"Rent is cheap, I'm living a life drenched in music, the alcohol flows liberally, and I have the best friends in the world!"
But trouble was lurking around the corner.
At music, I was good.
But I wasn’t that good.
Despite being naturally talented, I didn’t have the maturity to do what it took to be great.
I was watching other pianists on the scene pass me by like a freight train.
These guys weren’t any more talented than me, but they worked harder, and committed more earnestly.
Maybe I was too immature to commit.
Maybe I loved the music, but not the work.
Maybe I just wanted something else from life.
I don’t know.
Either way, I started to doubt that the jazz life was for me, and I started to drift away, leaving the riffs and rhythms behind.
Here’s what I learnt during that period:
- A life with art is a great privilege
- It’s possible to be broke and happy
- Community is priceless
- 95% of success is hard work (even for the naturally talented)
- Passion dies when it becomes work
2. The English Teacher
So, what do you do when you’re 28 years old, and totally lost?
Move to Japan, that’s what.
See, in my wayward years as a jazz musician, I had what would, in today’s terminology, be known as a “side gig”:
I learnt foreign languages.
In fact, I taught myself four languages in my 20s!
So, when it was time for a change of direction, I turned immediately to the obvious choice:
Teach English and travel the world!
While my contemporaries had long since established themselves in well-paying careers, little ol’ Olly decided to pack it all in and start from scratch.
“Reckless!” some said. (My friends and parents included.)
I just wanted to enjoy life.
Seriously – what was the point otherwise?
So, in August 2008, I took a CELTA (teacher training) course in London, and applied for a job in Japan.
Cos it sounded exciting.
I also thought I’d be more likely to find what I was looking for with a radical change, rather than a small shift.
(There’s a big business lesson in there, by the way, if you’re paying attention.)
So there I was…
28 years young, crammed into a tiny Tokyo pad, working a gig with conditions that’d be illegal back home, searching for a dream yet to unfold.
All in all, I spent 3.5 years in Japan.
During that time, I got a better teaching gig, earned a bit more dough, explored the country, learnt Japanese.
It was the thrill of my life.
And turns out, I freakin’ loved teaching.
It felt good to help people - seeing students week in, week out, watching them improve, being part of their journey.
But man… the schedule of an English teacher sucks!
I’d wake up at 6:15am, squeeze onto a rush-hour train for a 90-minute commute to a school on the other side of Tokyo for an 8:30am start…
Knackered before I even started the day.
After school, I’d often have an evening shift from 7-9pm, with a huge, pointless gap in the middle of the day.
I’d get home at 9:30pm and crash out.
But I loved the work, and I enjoyed learning just as much...
I did a diploma. (Where I got really good at teaching.)
Then, a master’s degree in applied linguistics. (Where I learnt to write and to think.)
By 2015, I felt like I could have done anything in the teaching world… academia, publishing, teacher training.
It was fascinating to see how it was possible to start an entirely new career (from scratch) and become “top 1%” in only 5-7 years.
Feeling ambitious, I took job in academic management and moved to the Middle East – finally, a career path!
There, I entered the depressing hierarchy of a huge, lumbering government organisation. The kind of place where you’re a number in a system, bureaucracy rules, idiots get promoted, and the fate of your entire career, salary and life, rests in the hands of said idiots.
(Image: me, not amused.)
Something wasn’t right.
I’d stopped teaching by this point. I was a middle manager in a suit and tie.
I’d swapped the jazz life for this?
How’d this happen?
My daughter was born in 2015, and that was the excuse I needed.
So I quit, and went back to London.
Back to square one.
Here’s what I’d learnt from all this:
- Teaching and helping others is a virtuous path
- Learning and development improves and inspires you
- You can become world-class at a new skill in 7 years
- Corporate hierarchy, wage caps and lack of autonomy are soul destroying
3. The Entrepreneur
With a newborn baby in tow, I moved back to the UK.
No job. No home.
I was 34.
(Only parents can truly appreciate how terrifying this kind of situation is.)
The one thing I did have going for me was a fledgling blog about language learning that I’d started while in the Middle East.
The blog was earning a bit of money already. Not a lot – enough for groceries.
Could this really work?
Was I really going to pack it all in to become... a blogger?
It seemed crazy, but I decided to make a go of it.
- I knew people were making money from blogging
- I’d learned not to be afraid of starting from scratch
- I had faith in myself to learn what I needed
In theory, it all stacked up.
So I got to work.
I invested all my money into training and paid masterminds. I knew that education was going to be the biggest ROI.
“If I fail at this, it won’t be for lack of knowledge!”
Man, did I hustle.
I wrote blogs, I wrote books, I did podcasts, I made products, I ran webinars, I sold.
Things grew – as they have a habit of doing when you focus on them.
“I” became “we”, and we started making real money.
(You know the story – it’s all laid out in my $10MM Case Study.)
Before I knew it, I’d walk into bookstores and my name was everywhere:
Our income statements now had 7 figures on them, our CAGR was north of 30%.
It was a real thrill to see all this stuff happening before my eyes.
For the first time in my life, I had money. Eventually, I gave myself permission to spend it...
The nice house, the nice car(s), the blowout meals, the business class travel.
I ain't gonna lie...
As an ex-jazz musician and English teacher, I really did enjoy having money to spend.
So, all rosy, right?
See, from the outside all you see is the money.
What you don’t see is the mind games that go on beneath the surface…
- I had no idea how to use handle money, and as the stakes got higher this caused anxiety.
- I made terrible hiring decisions that led to personal conflict.
- I burned out, because I never learned how to slow down.
The life of a jazz musician or English teacher doesn’t prepare you for the psychological rough and tumble of managing a business.
That stuff can only be learnt in the school of hard knocks.
I spent a large amount of the last 7 years worrying about stuff I probably didn’t need to…
- Waking up at 2am thinking about work.
- Taking calls at the weekend.
- Looking at my phone over dinner.
(Come on… you know what I’m talking about.)
And then when the money finally came, I discovered, to my horror, that it never really mattered in the first place.
And what the cost?
I don’t know.
Perhaps I should’ve been Jack Kerouac climbing the Matterhorn instead.
Or just kept playing jazz with my friends.
Life would’ve been simpler.
On the other hand, entrepreneurship taught me everything I know, and I emerged a wiser, stronger person as a result, today able to do stuff like this newsletter and continue my passion for teaching.
So who’s to say whether it was worth it or not.
Does the end justify the means?
There is no answer to this.
But my point is:
It ain’t all sunshine and roses, my friend.
Here’s what I learnt from all this:
- You can create any life you want (really)
- Entrepreneurship is a vehicle to create the highest version of yourself
- Time, money and freedom can inspire and crush you in equal measure
- Money is just a game you were never taught to play
So What’s It All For?
Now don’t worry…
I’m not about to tell you that the business, money, or entrepreneurial journey isn’t worth it…
(No fake-enlightenment guru here. Money is great. And I do love that champagne in business class.)
But I will tell you that you must build a business that serves you.
Not the other way round.
It’s not at all clear to me that the last 7 years building a business has been unambiguously good, healthy or virtuous.
I spent a long time pushing:
“More! Grow! Scale!” (said every single business coach)
As a consequence, I’ve spent far more time feeling stressed and anxious, when I could have simply been enjoying the fruits of my labor.
Your mind will sabotage you if you let it.
It takes serious work to break free from decades of societal and parental conditioning, which controls you far more than you’d like to believe.
What saved me, I think, were my previous 7 year careers…
Thanks to my earlier careers, I deeply understand my own values:
- Total autonomy over my time and schedule
- The value of teaching
- The importance of art and creativity in life
Having experienced these different ways of living, I've developed a certain confidence when it comes to making business decisions.
In the face of any given opportunity, I've long since learned to declare:
“I don’t care about making more money if it means compromising on the good life!”
And so, I deeply believe that you must...
Have The Courage To Say No
The right way to build your business it to bow down and worship at the alter of your own preferences – and cheerfully raise a middle finger to the Instagram guru who is tempting you with their “Proven 3-Step Formula" to do whatever the f***.
I frequently say “no” to all kinds of business opportunities because…
I simply don’t want to.
In fact, the entire product ecosystem and sales methodology that I’ve created for StoryLearning (see Case Study) is based on the premise that I want to own a business that leaves me free to go wandering the hills of Hobbitshire to my heart's content...
Go flying whenever the inspiration strikes (and weather permits)...
And generally have a calendar emptier than a doughnut box in a police station.
That’s how I get to work on StoryLearning only 5-6 days a month.
(Wait - you thought that was luck?)
Sales calls? Forget it.
Live webinars? Nada.
Social media? Surely you must be joking, sir!
And so, turning to you...
That big dilemma you’ve been wrestling with…
- Should I add a 1-to-1 option on that new course?
- Should I hire more people?
- Should I run a live webinar on launch week?
I’m here to tell you that it’s perfectly acceptable to say “no” to all these things simply because:
You simply don’t want to.
When I mentor business owners, I start with getting clear on their values, and then drill down many layers deep.
No growth strategy is worth the paper it’s written on without a clear picture of the life you want to build.
Here's why --
Because if you submit to doing stuff you don’t like when you’re small, what do you suppose happens when you scale?
If you try scaling a business you don't love, you'll know all about it, and it won't be pretty.
On the other hand, build a business that works for you, and you won't just live...
Have the courage to build a business that works for you.
Have the courage to say no.
Be skeptical of the lure of money.
Happiness and fulfilment lie elsewhere – community, family, self-expression, being of service to others… oh, and hard work.
But I’ll stop there.
I have no idea what I’m talking about, anyway.
CASE STUDY: Blueprint Of A $10m Online Education Business:
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