All My Side Hustles

And what they taught me

At one time, side hustles were unusual. Now it seems like everybody and their shadow has one. Maybe I’m basing my opinion on an unrepresentative sample; writers on Medium. Writers are creative, and creatives are more likely to have side hustles (a business is as much a creation as an article, a piece of art, or a musical composition).

Everybody seems to be writing about side hustles. Mostly they talk about success. I think that creates unrealistic expectations. There are more failures than there are successes, and unless you know that, the first setback could take all the wind out of your sails and consign you to the ‘could have beens.’

In this article I’ll tell you about the side hustles I’ve had over the years and what they’ve taught me.

Job satisfaction

With a couple of exceptions, the only ‘job satisfaction’ I’ve ever experienced has come from side hustles. Nowadays, you don’t need a lack of job satisfaction to spur you on. Developed economies are in freefall, so unless you’re in the top 1%, protected from paying taxes by self-serving and avaricious governments, you need an extra income, and you need a safety net.

Side hustles will either fail, supplement what you get from your job, replace what you get from your job, or make you rich. Most people only want to write about those last two.

So far, none of my side hustles have made me rich. But they have taught me a few things that will help me do better next time. There’s always a next time.

A history of hustling

Rock and Roll. When I was fifteen I picked up a guitar, and it took me about twenty seconds to get hooked. By my early twenties I was pretty good, so I put up some home printed fliers advertising ‘rock, blues and metal guitar lessons’ in London’s Denmark Street. It didn’t take long for the phone to start ringing. I’d advertised at £20/hour, but after delivering my first lesson, I was told that price was not acceptable! The student’s father had been a photographer in the music business and he knew a bit about music. He told me I should charge more and paid me £30. In a single hour, I’d increased my fee by 50%.

Over the next six months, I built up to having ten students and making £300 every weekend just for doing what I love. As I took on more students, I developed a syllabus which could be recycled again and again. Work that had initially required hours of preparation became a ready-made series of lessons that I could use over and over again. After about a year, I felt I had no more to teach the students. I’d been a great teacher, without a doubt, all of their playing improved markedly. But I failed to get more students and let the business fizzle out.

Keep the tips. After graduating from university I got a job teaching English in Poland. When I returned to the UK I was offered a job in the reception at my doctor’s surgery, to tide me over until I found a ‘proper job’. Within a week I’d progressed to the position of medical secretary. As I could get all of necessary work done in a couple of days a week, I joined an employment agency to get work at other surgeries. That lasted a couple of weeks until one of the staff there told me I wouldn’t be paid because I hadn’t submitted the time sheet. I knew I had and I told him so. He asked me who the hell I thought I was, I told him to fuck himself. The end result was that I told the surgery manager if he wanted my services, he’d have to employ me directly. He agreed. I got a lot of referrals, and everything went quite well.

Fast forward a year or so and I was working with a minor surgeon and general practitioner who provided male circumcision services. He was making an absolute killing. I set about finding surgeons, finding a suitable premises and getting some insurance. At the same time I was handing out cards at local places of worship (all Abrahamic religions traditionally ordain male circumcision). Within six months I held my first clinic. It was on a Sunday afternoon. I left with a over £1000 in profit. Still in my twenties and averaging at least £1000 a week, I stopped working at the doctors surgeries. Less than two years later I was left without surgeons and without a business.

Your money or your life. After the circumcision clinic, the best money I made per hour was selling life insurance. I loved finishing work then heading out on appointments in the evening. Especially when I realised that even at the lower commission levels I was making about £100 per hour, if I was in the right market. The right market however was homeowners. At that stage in my life I didn’t know any homeowners. In the wrong market, I quickly hit a dead end.

Spread betting. I was introduced to spread betting by an ex Solomon brothers and Rothschild investment banker. It took £5000 and a lot of balls to get started, but once things were rolling it was fantastic. I lost my nerve in the 2008 financial crisis and never got back into the game, but it was the best game I’ve ever been in. I remember making £16,000 in the first couple of hours of trading one morning. Some of that money paid for an engagement ring.

Writing. The same guy who introduced me to spread betting also introduced me to Medium. I started writing on the platform in August 2020, and for the first 18 months made next to nothing. Then out of the blue, I had an article that got thousands for views. That was followed by another. Last month, I made $241 dollars on Medium. Considering each one of those articles took less than an hour to write, that’s not bad going. And they’re still making money now.

Lessons learned

All of the side hustles I’ve had have taught me something. From my foray into music tuition, I learned the danger of resting on my laurels. There are three obvious things I could have done to keep the students coming in: Kept advertising! Asked students to refer me to their friends, and a offered first lesson for free. Whatever side hustle you have, you must keep bringing in the clientele. If you don’t, your star will fall very quickly. That first guitar lesson also taught me not to be afraid to charge high prices. People actually believe that higher prices must be indicative of a better product. But be warned, if you charge for diamonds and deliver coal you won’t last long.

The circumcision business taught me the danger of not having enough staff. I organised the premises, I did the back office work, I arranged insurance, I did the advertising and brought in the clientele, but without the surgeons I was helpless. The first surgeon wanted the business for himself, offering to pay me a salary. There was no way that was happening. The second surgeon had two sons in the Iraqi army and decided to return to Iraq. I was stranded. I could have protected myself by continuously advertising for new surgeons, offering to call them up as soon as a position became available. That way I would have had an ‘expanding business’ rather than one that crashed and burned.

My biggest professional regret is not sticking to the life insurance business. Some of the ones who stuck at it are millionaires now. The guy who introduced me to the business makes over half a million a year. If you have a way into something really good, even if you have years without success, stick at it if it’s not costing you anything. Perseverance can work miracles.

With spread betting, I made double-digit returns several months of the each year. Until you’ve experienced watching your money grow like that, you can’t understand how great it is. Anything that can make compound interest work for you is worth having.

Creativity is a fabulous skill if you can monetize it. The only way you're going to monetize your writing is by getting it in front of people. Thank God I love to write, because if I’d only been in the game for money, there’s no way I would have stuck it out. Right now I have articles that make me around ten dollars a day. Over time I could have many articles that make me that much, or more.

Writing takes time to start making money in my experience. That’s fine, take time, keep writing. If you want to create, create. Keep putting your work out there. Do not give up. You never know, you might have the next international best seller in your head, or even better, on your laptop. But unless you put it out there, nobody will ever know.