I quit my day job when I was 35, and never looked back.
I often regret not doing it earlier, but what I’ve discovered since is that that decade-and-a-bit gave me a lot of experience that trips up younger entrepreneurs as they scale.
I thought I’d recap my days in the corporate mines just as a heads up to anyone who wants to make the leap one day.
I got a business degree
When I was at school, I had zero idea of what I wanted to do when I started work. I knew I wasn’t going to be a doctor or an engineer, and a business degree seemed like the best way of exploring options.
I got kind of lucky that the business school I went to had some direct response experts in the marketing department. That mix of technical skills and creativity really appealed to me, and I found which direction to take my first steps in.
I learned three things that really helped when I set out on my own:
Basic accounting – honestly this isn’t much harder than managing a household budget, and you should hire someone else to do the legwork of book-keeping and the skilled work of working out your taxes. A few of days on this and you’ll have an ok grounding.
HR rules – UK businesses in particular screw themsleves up by learning this off LinkedIn and think that US law is UK law. They’re not.
When you have to significantly change someone’s job description, or let someone go, this is where you need to act fast. It’s the one place where you don’t have tim to learn “just in time”.
Contracts – This is so much easier with ChatGPT to give advice, but get a pro involved when you’re talking about money you can’t afford to lose. Just understanding the convoluted language that some lawyers still pride themselves on has saved me a fortune.
Learning that contracts are always negotiable and that it’s a power game is something that came later.
Doing this again, I could fit the useful parts of a 3 year degree into 6 intense months, and doing it today I’d start something on the side at the same time. Back then, you needed a lot of capital or time, now you just need to start experimenting.
There’s so much wasted time in formal education, I really think you need to experience the workplace for a bit to decide what you do and don’t like, and then pick something that builds on that.
There’s just so many different options for you to pick up knowledge and experience these days. Designing your own curriculum for life is something more people should think about.
That’s a rant for another day though.
My first job was in a big multinational
Spending two years learning how a big company thinks and makes decisions was a huge lesson.
I was lucky that my first job started at the tail end of a recession. They hadn’t hired any graduates for years, and I worked directly for the CMO. I got exposure to the C-suite because of the project I was on, and I understood most of what they were discussing in meetings.
It was an educational publishing business, and a lot of people had very academic backgrounds. I managed to leapfrog a lot of these people quite quickly, because I could have useful conversations about things like budgets.
One thing I learned is that there is a massive difference between people spending other people’s money and spending their own. How decisions get made in owner-managed businesses vs. corporates is completely different.
Small businesses are looking for upside. Big businesses want to avoid the downside.
I discovered affiliate marketing.
I made my first pennies on the Amazon affiliate program when I was about 26. It took another couple of years before I discovered affiliate networks and the huge range of offers I could pick from.
By then I was working in agencies and marketing services businesses with some huge names like Sony, Electronic Arts and Phillips.
I can remember looking at Trade Doubler, and thinking it was unbelievable that I could run a campaign for major UK brands without having to pitch for them.
I just had to be able to get a sales result.
Everything I know about building websites and landing pages, growing lists, and making online sales started in this era.
There’s an incredible amount of bullshit written about affiliate marketing. Lots of people talking up their numbers to 10x what they really do, but you can definitely make enough to change your life from worrying about money every month to stashing a bit away.
Here’s a few lessons I learned along the way:
Learn to spot great offers.
I’ve had a few opportunities to promote the exact same product from different retailers. Some of them just price it better, have better delivery, or bundle products up in a more attractive way. Those guys will convert more traffic, get bigger average order values, and because they convert more, they can pay a bigger affiliate commission.
It’s just wins all the way down once you find them.
Sell expensive stuff.
My first sale was a book on Amazon. I think I made about 30p.
My biggest sale was when a county council replaced all the computers in their office using one of our affiliate links. 6-figures in one transaction and we took 7%.
My most valuable sale was some high-end email marketing software that pays out over the whole lifetime of the customer. £1k a month in commissions and they were with me for 7 years.
Sell what you know.
Don’t just sell stuff to make a buck. Sell things you believe in.
That email software is something I still use, the affiliate commissions now cover more than my bill every month. I know it inside out, and the reason I can sell something that costs three times as much as its nearest competitor is because I know how to use it to replace an enterprise system that costs five times as much again.
Find things you use every day and teach people how to use them better.
It could be an air fryer, Excel, a jump rope, a chainsaw, a car. Find things that you know how to use better than the average person.
I married the right woman.
Have you ever seen “My Big Fat Greek Wedding”?
That’s what my extended family looks like, but Italian.
My family is the stiff English ones. Parents with gold clocks for long service.
Hers is the loud mediterranean one. Parents who ran family businesses because nobody would give them a job when they first arrived in the UK.
Starting businesses is in their blood. It turns out it was in mine too.
Without that different attitude – that starting your own thing is normal – I don’t thinkI’d have made the jump when I did.
If you’re surrounded by people with corporate jobs, they tend to talk you out of making the big jump. I honestly think most of it is because it challenges their own identity.
My parents were like that, and then my dad got made redundant.
Then I got made redundant.
I realised that when the chips are down, there is no loyalty in business. I went on a furious mission to learn everything I could about running my own business.
It was kind of funny. Management had me tagged as some kind of rising star because I had interests in what was going on above my level. They couldn’t see me building my escape tunnel in the background.
On the side, I was building websites and email systems for people in the evenings. Then I was blogging and sharing advice on forums. All the money I made was split between plowing it back into the business and building an escape fund.
Know when to make the leap.
I’d started building email projects for a small London agency. They were very old school. Still lots of print advertising and brochures, but they’d made good money over the years and had cash.
I was having one of those “How’s business going?” conversations with the owner, when he asked if I’d be interested in selling the business.
I looked up from my cheap laptop. Stared around the kitchen and wondered what business he was talking about.
I knew I didn’t have anything ready to sell just yet, but this was the moment. I was as good as any other small digital marketing business, I had a client who needed me long-term, and I’d almost matched my day job income.
Know if it’s for you.
Going all in on your own business is terrifying. A lot of people do it thinking they’ll be able to do what they want all day long, but the reality is, someone’s always paying you. That’s either one employer, a small group of clients, or a big group of customers.
You still have to keep them happy.
And once you make the leap, you have to do all the other stuff as well. HR, Finance, Sales, Marketing, all of it.
Some of the best employees I ever had were freelancers who just wanted to get back to doing what they did best. Designing all day long or writing code all day long. They were really appreciative that somebody else took on all those other tasks for them.
You can make a very good living with a stable job that doesn’t cut into your evenings, and a fun, profitable hobby.
One of the reasons my agencies did okay is because I was hell-bent on avoiding hiring people for as long as possible.
My mantra of “eliminate, delegate, automate” was built into the business from day one.
The other reason is I keep experimenting.
My side hustle became a full-time career, but I still have little projects I run on the side. Most of these don’t make much money, if any, but they build rare skills that I can sell to the right business.
I hope you found something interesting in here that convinces you to either quit yor day job, or to stay there. Honestly I don’t care which, I just want you to recognise which is the right one for you and be happy with it.
