How I escaped my day job, after trying everything.

Working as an employee was always a backup plan.

I wanted to work on my own projects, whether as an artist or an entrepreneur. But it took me half a lifetime to figure out how to achieve the modest freedom I currently enjoy.

I must have tried to break free thirty different ways before finding the solution. I tried working part time - 4 days a week, 3 days a week, 2 days a week, I tried borrowing money to quit my job, I tried using breaks between contracts, mortgaging future tax bills against short-term freedom, abusing stimulants to work every hour of my spare time; anything I could think of to build momentum behind something I owned.

Context-switching is a killer. When I had a well-paid but demanding part time job, all my side-project momentum was destroyed on a weekly basis when I would return to the pressures of my day job. If I had breaks between contracts, the stress of needing to find another would cloud my creative faculties.

I needed to focus full-time on whatever I was building, without being interrupted week-to-week or at some point in the future when money problems could no longer be avoided.

But for years I was trapped by the success of my backup plan. I was making money but I wasn't free.

The Middle Class Trap

Ten years into my "career" I could sustain rent payments on a Shoreditch loft on a 2-day-a-week contract.

Mostly.

Sometimes I'd be taken off-guard by a large bill and have to take on extra work Usually this would mean full time contracts during which I would avoid taking vacations because the price of a day's work was so high. I'd keep going until I burned-out. Then I'd have a forced-hiatus where I wasn't earning anything.

I was in the Middle Class Trap. The more I earned, the more I spent, and if I stopped earning, my lifestyle would drown me. I had credit cards because I knew I could pay them off. I could always take take another contract.

I didn't understand how some people were able to devote their lives to some idea.

Then one day somebody explained it to me.

"It's almost impossible to be an entrepreneur if you have to work for a living."

If you need to work to survive, it's extremely difficult to build a business. I can't deny that many people manage this, but it's easy to be distracted by the occasional, unrepresentative rags-to-riches story, when so many of the most successful entrepreneurs achieved their success by not having to work for a living.

Yes, success doesn't come without a tremendous amount of hard work, talent, and luck, but for the chance for any of those factors to matter, you can't be living paycheck-to-paycheck, or mortgage-payment-to-mortgage-payment.

When I learned about the Middle Class Trap I had a lot of credit card debt and extremely high rent payments - not to mention renting a studio and paying an expensive gym membership.

It should have been obvious why every time I tried to break out, I'd be haemorrhaging money on these debts and bills, so my runway was almost non-existent.

To break free, I realised, I'd need ease back on my expensive lifestyle.

Debt-free by forty

I was in my late thirties so I set myself the goal of cutting my costs and clearing my debts before I was forty. I won't go into the specifics of how I achieved this - I was lucky in many ways - but I had to make sacrifices. Despite my current (modest) freedom I'm still in an austerity mindset several years later.

But it's not that hard really. When you have a lot of money coming in it's tempting to buy "fancy" versions of the things you need, but there's no real difference. I bought a dining table set a few years ago which was made to order in Italy but I could have had something functionally identical for a twentieth of the cost. I used to buy my shirts in Selfridges but TK Maxx (TJ Maxx to Americans) has things that are just as nice for, again, a tenth of the price.

I don't want this to come across as a condescending "poor people should learn to manage their money better" lecture - nobody manages their money better than those with very little. It's more that I personally didn't understand money properly so I used it the same way as when I was poor, substituting cheap versions of things I needed with unnecessarily expensive versions when I should have been using this extra money to buy back my time. Don't get me wrong, I thought that's what I was doing by going part time and taking breaks, but it took me a long time to realise that I couldn't have my cake and eat it too.

The advantages of cutting your costs

Beyond the obvious (longer runway, capital, cashflow) the biggest advantage of being debt-free and having minimal expenses is that now those early sales actually mean something.

A $20 sale is no longer some negligible fraction of my contracting rate, it's a meaningful contribution to my monthly bills.

This is profoundly motivating.

My revenue growth doesn't have to be compared to the interest rates on my credit cards, it's all money I get to use.

My two rules

I'm a hard-line kinda person when it comes to experimenting with my life. You might be able to achieve things in a more flexible way, but here are my rules in case you're a weirdo like me.

RULE #1: No contracting.

Or, more specifically, no selling your time. I know I can sell my time for a lot, but if I do that, the capital value is all kept by my employer and can never grow to my advantage. If my time is worth that much to some app startup, then it must be worth that much invested in my own business.

RULE #2: Don't spend money you don't have.

When I was 13 my dad let me borrow from my "grandad money" to buy an Amiga before I'd saved up enough to pay for it with my paper rounds. This set me up with some very unhealthy spending habits. If I knew I could earn enough money I'd then buy something on a credit card (or otherwise commit to a large purchase) to get it sooner. This backfired when I ended up quitting a job or not getting paid for work I'd done.

So now I wait.

Which sucks because I really want one of those new MacBook Pros.

Such is the price of freedom.