At the age of 22, I took a big leap.
Despite having a politics degree from the University of Manchester, I decided NOT to follow a conventional career and life path and, instead, go with what my heart was telling me to do.
On the 19th March this year, I turned 46. Although this isn’t a significant birthday, it got me thinking.
Was I right to make the bold decision to follow my dreams?
Might my life have been better if I didn’t and, instead, stuck to the path that was laid out before me?
To answer these questions, I reimagined my life (with a little help from Chat GPT) as if I had chosen not to follow my dreams and, instead, pursued a more conventional path. I then ranked the two paths according to four criteria – wealth, health, relationships, happiness – to determine which option would have been better.
Of course, for you to get anything out of this thought experiment (which, essentially, answers the question – is it worth following your dreams?), I’m going to have to be brutally honest. I can’t shy away from my failings.
My hope in taking such an unflinching stance is that you’ll finish this article with something of benefit.
Afterall, haven’t we all, at various points in our lives, dreamed of abandoning convention and doing exactly what we want?
Haven’t you been inspired by an idea and fantasised about following it through to the end, wondering where you might end up?
Below is my lived answer to what happens when you follow that calling.
Before I can assess the two different paths, I need to tell you how my life ended up after I decided to follow my dreams aged 22.
The year after that I trained as a tennis coach and have worked in this field ever since (running my own business and working as a Head Coach since 2011).
The year after that, I completed my training as a hypnotherapist and have been doing these two jobs simultaneously. However, neither tennis coaching nor hypnotherapy was my ultimate dream.
Ever since I was 22, I’ve aspired to become a bestselling self-help author.
It took me until 27 to take action on that dream. At 31, I self-published my first book. Aged 38, I got a book deal for my second book and, as of writing this blog post, I have 4 books available to buy and am 200 copies short of 10,000 book sales.
Am I satisfied with these achievements?
Yes and no. While I can recognise the impact I’ve had (coaching children to play national level tennis, assisting numerous clients to free themselves from lifelong issues and giving thousands of people inspiration and hope with my words), I can also see that I’ve fallen short of my mark.
I didn’t set out to sell 10,000 books. I set out to sell 1 million. The mission is not complete.
But what would have happened if I didn’t follow my dreams?
What would have occurred if, having left university, I used my degree to get a graduate job and pursued that path?
I honestly don’t know what career I would have chosen had I followed this path. However, both my parents were lawyers so, for arguments sake, let’s say I followed them into this profession.
At this point I turned to Chat GPT.
I asked it to make a projection for an intelligent but demotivated new lawyer who did a 2-year law conversion course in 2003 and then went on to have a career in London. Where would they have ended up in 2026, aged 46?
My lack of motivation would have ruled me out from ever making partner in a major firm and earning the big bucks. However, according to Chat GPT, I’d have still gone on to have a respectable career.
Right now, I’d be a senior in-house lawyer making around £130,000 per year.
So, with that in mind, let’s compare this alternate reality, with my actual, real life in 2026, using the aforementioned four categories to determine which Joe came out on top (Conventional Joe or Rebel Joe).
This one is a no brainer.
At present, and despite having three income streams, I make an average amount of money (and what would be considered low for a graduate).
My problem is that the income stream I’m most passionate about – writing – makes me the least amount of money and takes up almost as much time as my hypnotherapy and tennis coaching businesses combined.
As a senior lawyer, I’d be on a good salary and could likely afford to live in a home valued at somewhere close to £1 million. I’d be taking multiple holidays a year and, if I was sensible with my money, would have zero financial concerns.
Making this kind of money from writing is far harder than I anticipated.
My naïve assumption that I just needed to write an excellent book and that it’d sell itself has been shattered. I can’t find words to express how difficult it is to get yourself noticed on Amazon or the internet.
Winner: Conventional Joe
I dread to think what shape I’d be in right now had I followed a conventional path and become a lawyer. I’m sure I’d look 10 years older than I do and have nowhere near the level of fitness and energy.
Chat GPT estimates that the early years would have been the worst. My career at a law firm would have seen me working 60 hour weeks and regularly having to be on call to meet deadlines. I wouldn’t have had time for exercise (not if I’d wanted a social life) and it’s likely I’d have aged a lot in this period.
While the move to becoming an in-house lawyer somewhere into my 30s would have seen me working less hours, I’d still be following the 9 to 5 lifestyle and structure.
This would take its toll. I currently exercise 5 times a week (tennis, weights, running and a little bit of boxing) and have done so for well over 20 years. I sleep well, eat a relatively healthy diet and feel great.
A big part of the reason I’m able to do this is because I set my own schedule. I’ll gladly shift or cancel clients or writing sessions so I can fit in a game of tennis or a trip to the gym.
I can only do this because I chose to follow my dreams. Making this decision means deciding how to prioritise your life and not allowing a company to do it for you.
Winner: Rebel Joe
This is the most difficult category to rank.
I think if I followed a conventional path I’d have spent a lot less time on my own. However, I’d question the quality of the friendships and relationships I’d have built as someone living their life in a totally inauthentic way.
One thing that would have been better about following the conventional path is likely having two children, aged around 10 and 8, by now. But even then, I wonder what kind of father I would have been.
Of course, I’d love and provide for my kids but could I mentor them? Could I honestly say anything else to them other than “just follow the crowd” and not look like a total hypocrite in their eyes?
The great news is that me and my partner are expecting our first child in July. I know for a fact I’ll be a better father having been true to myself throughout my life. However, that authenticity has come at the cost of loneliness and rejection.
Winner: Tie
I think when you follow your dreams, as compared with the conventional path through life, the highs are way higher but the lows are more devastating.
You’re truly alive.
I can’t explain the joy I feel when I receive a book review like the one below or successfully help a client with an issue that’s been affecting them for years. I’m living my life purpose.

Compared to that, I imagine my life as a lawyer would have been pretty flat. Sure, I would have enjoyed having a family but I don’t think I’d have gained much satisfaction from my work. I’d have been living and working in a system I didn’t believe in and I think that’d have drained me.
In contrast to this, I’m proud of the choices I’ve made in my actual life.
Sure, I wish following my dreams hadn’t been so damn hard and I do have regrets about what I’ve missed out on, but I can feel happiness in the smallest of things (a sunset, a song, waking up and reading in bed for 10 minutes).
I doubt I’d have that ability if I’d followed a conventional path. I’d be too stressed, rushed off my feet and concerned about all the small things we’re told to care about but don’t really matter.
Winner: Rebel Joe
I hope you’ve found my breakdown useful. I’m a huge advocate for following your dreams and this might make me biased.
Bear that in mind when forming your conclusions about which path is right for you.
For me, following my dreams was not the inspirational ascent some self-help books told me it would be.
It was grittier, tougher and uglier than I’d ever imagined but the intrinsic rewards just about make it worthwhile.
If you want to discover a passion you can make a living from and overcome the fears that are holding you back, check out my free course 30 Days to Escape The System. Click here to get the course right now! (You’ll find the tips on developing belief and self-confidence fascinating!)