Back in 2020, I launched my own podcast. Managed to record and publish 85 episodes before deciding to shut it down. I’ve also been a guest on many a podcast, too.
One of the questions podcast hosts love to ask, as well as being one I used to love to answer, was:
“What would you tell your 18-year-old self?”
I would jump at the chance to answer it.
But it’s a completely bullshit question.
Here’s why (and a better question to ask instead).
It’s A Stock Answer To A Stock Question
A podcast host asked me this question and smirked a little as he waited for me to answer.
“I’d tell myself not to get a job, not to work for anyone else”
He started laughing, “I knew you were going to say that”.
And it isn’t the 25-year-old me saying this. It’s the 41, 42, even 43-year-old me saying it.
Also, I was working full-time as a software developer. And I hadn’t had the insight of any other alternative.
I had an answer to the question, one that I thought was a “banger”.
Why do I now think that this question (and my answer) is complete horseshit?
As I write this, I turn 46 in 5 or 6 weeks.
So it’s not as if a decade or two have passed; it’s only a few short years.
I no longer like the question because it has no substance. It’s for entertainment purposes, not any form of education.
And hindsight is also a useless tool.
Both remove all forms of context, failures, and experiences. And lessons learned from your timeline.
Things like:
Hating The Education System
I hated primary/junior school and would spend my time daydreaming. Doing the smallest amount of work I needed to, or could get away with.
Then, I spent the holidays begging my Mum to homeschool me, so I didn’t have to go back into that godforsaken place.
Secondary/high school was even worse. Flitting between different girlfriends, staying out of trouble. Making sure I did enough again to see me through my GCSEs. Unless I liked a subject, then I would be all in.
I counted down the years till I could finally leave.
“College will be different, as long as I’m doing things I enjoy and am good at, it will be better”.
It wasn’t, it was too much like school, but at least I could wear my own clothes.
I spent those last few years looking to the future.
It Will Be Different When I’m Working, At Least I’ll Get Paid
Or so I thought.
I’d worked at McDonald’s during college.
Then, like most people in the late 1990’s. As soon as I turned 18, I looked for an office job. A “career”.
I started working for this big company as the post/stationery “boy. Then, I moved “upwards to work as a Payroll Clerk.
I fucking hated it.
After 5 years, and the fact that I was drinking every night to get through the misery of that job. I left and went to University as a mature student. Getting a BSc in Computing Science, and worked for Rolls-Royce Motor Cars as part of a placement year.
I loved every single minute of those 4 years.
Graduating at the grand old age of 27 and starting work as a software developer, 10 days later. I had a lightbulb moment.
“I know what it is!”
As long as I’m making money doing something I’m good at, enjoy, but also challenge me, that will work.
I was wrong!
Again!
This time it was 3 short years, a house, a mortgage and turning 30 that made me think “Is this what my life has become? Chained to a desk, making a grade A wanker, rich!
I was looking forward yet again.
This time, there was nothing on the horizon, or so I thought.
Then something found me, and it changed everything.
One Book, A World of Possibilities
Living on my own, having the commitment of a mortgage, with little to no money.
Much of my time was spent sitting on the sofa, either playing on my PlayStation or browsing the internet.
There were no “deep dives”, going down “rabbit holes” either. I was searching “How to get rich, quick”.
The timeline and steps that led me to this one book are hazy; all I know was it was 2011.
But I downloaded the book The Four-Hour Workweek onto my Kindle.
And it changed my life.
It pulled back the curtain and the mystery around starting a business.
As well as revealing the possibility of having full autonomy of your life.
Something I never thought possible.
Know Thyself
This is why the 18-year-old self-question doesn’t hold up anymore.
Everything I’ve gone into.
Hating school, work, and feeling trapped by commitments.
It points to one thing.
Freedom.
Having the freedom, well, autonomy, which is more important than freedom. To control your life, well, your time and how you choose to spend it.
So, if I did have a time machine, would I tell my younger self to start a business as soon as I left school?
My younger self would be missing out on that discovery.
He wouldn’t have the context, the understanding. He wouldn’t know himself as he should.
There are Things You Wouldn’t Change
Going to University was huge for me.
I’ve met people who are going to be friends for life. Some were members of my wedding party. Others I don’t see or even speak to for years at a time. Then, when we do meet up, the connection is instant, and that bond is still there.
And I wouldn’t change this for the world.
It had also given me autonomy over my life.
I wasn’t forced to be there. My success was all on me. And I could dictate my life, and I loved it.
Something I didn’t realise until a few years later.
Because Experiences Outweigh Assets
I do have to admit this.
Most of my weekend, from the age of 16, 17 up to the age of 30, I spent “pissed as a fart”.
But I wasn’t sitting alone in a pub or flat, I was out with my friends.
Going on trips, holidays abroad.
I’ve been to China and Thailand twice. Greece more times than I care to remember.
I shared a flat with one of my closet friends in the centre of Manchester and lived the city life.
Would the stock answer of “don’t work for someone else” have allowed me to do all this?
Of course it could, but there’s ZERO guarantee that it would have.
So, again, if I had a time machine, and I could sacrifice all these amazing experiences for me to have my own business at 18. Would I take the trade?
I reckon the me of 5 years ago would have been on the fence.
Me of today?
No, I wouldn’t swap them in a heartbeat.
Because my friends mean more to me than that.
And I might never have met my wife.
Something I’m not willing to trade.
It’s Better To Start A Business In Your 40’s
According to the Harvard Business Review. The average age of a successful startup founder is 45.
Average UK entrepreneur age: 42.
Success rate by age: A 50-year-old is twice as likely to build a successful company as a 30-year-old.
We get bombarded with stories about people like Bill Gates and Mark Zuckerberg. Only younger people can start and grow a business.
Now, for tech unicorns, that might be true.
But both Gates and The Zuck lived in the right place at the right time, working on the right thing.
The entire Universe aligned for them.
But for the rest of us, that wouldn’t be the case.
Also, what the fuck did I know at 18?
Future me comes back and tells me not to get a job and start a business.
First, if I told my parents what had happened. They would have thrown me in the loony bin straight away.
Second, no chance would my parents allow me to “doss about” while they feed and water me (and supply me with beer). While I start a business, with no idea, money, or network.
Third, and the most important. If these stats are right. I had a 99% chance of failing.
It’s About The Journey, Your Journey
As I write this. I’ve been running a business full-time for around 8 months. My current business is about 18 months old.
But it isn’t my first business venture.
As I’ve mentioned, the book The Four-Hour Workweek inspired me to start on my own business journey.
That was back in 2011. I was 30/31 years old and had no idea where to start or what to do.
There are a lot of people younger than I was, that have started a business. And with AI are crushing it with brand new, first-time founder businesses as we speak.
That’s the problem with the comparison game.
Thinking that telling your 18-year-old self to start one would mean you’d now be one of these success stories.
What a load of bollocks.
I’ve had between 15-20 ideas, projects and actual full-formed businesses.
Some have even made a bit of money. Not to be able to live off, but it was something.
The rest?
They have all crashed and burned.
Knowledge Is Power
For my journey, the 15 years that it’s taken me to realise the dream of running a business full-time. Well, it’s what I needed to go through.
To bash through the lack of confidence, the low self-worth, and the zero belief.
That trying and failing has been the most valuable thing I could have done.
Not to go back in time and rob my younger self of the life that I’m grateful for.
That’s my journey, the reason I’m here right now, at my standing desk, in the office in my house I share with my wife of 9 years. Writing this article.
These 15 years of grinding while still working full-time and living life have been worth it.
A journey I needed to go on.
It turns out that entrepreneurship is the ultimate personal development framework.
You’ll Arrive At Your Destination (Taking Longer Than You Want)
Are you wondering if my business is crushing it, almost 9 months into going full-time?
Well, the only reason I went full-time is that I got made redundant from my Senior Developer job.
That if I hadn’t, I could still be working for them, complaining about it. Still proclaiming that I have this dream to work for myself.
Thanks to them, I am living that dream.
To go back to your question, I’m surviving, money is tighter than I’d like, but we are still living a good life.
And my thoughts are now turning to not surviving, but thriving. Figuring out how I can grow the business.
Is there a question that can help me do this?
What Is A Better Question To Ask
You might have noticed a theme running through my early life. That I was always looking forward.
But the question is about going backwards. And to the same age, no matter how old you are now.
Going back to that podcast where I answered the question.
If an 18-year-old is listening to me, and they are at a crossroads, my answer might have been educational for them. But I’m guessing the odds of the right person hearing it were slim.
For the rest of us, it’s entertainment.
How do we flip it so the question can educate and help anyone? A question that they can ask themselves at any waypoint in their journey?
As you might have guessed, I hate the corporate world.
The “where do you see yourself in 5 years, even 10 years with us” question makes my piss boil.
I used to have to bite my tongue, but what I wanted to say was. “If I’m still here in 5 years, I’m going to torch the fucking place to the ground”.
But I like the future pacing if it. We need to narrow the timeline.
Here’s the question we need to ask ourselves.
“What do I need to ask future me, who is 18 months older, so that I start working towards what I want?”
Now, that’s a fucking banger of a question if I do say so myself.
Why?
Well, it removes all hindsight from the equation.
There’s no quick stock answer you can give.
It also keeps everything you’ve gone through in context.
And I love the timeline. 18 months is short enough to make real changes. But not too far out that you can excuse away reaching a goal (or at least start working towards it).
Finally, and most difficult, it forces you to stop and think about what you want.
Do you even know what that is?
It might be to stop something or cut something out of your life.
It could be to start that business or go on that trip. Move cities, sell your home and live off-grid.
To take that scary step to make a change in your life.
The possibilities are endless.
And that’s a far more thought-provoking question.
Thanks for reading.
