Cheating on your day job

It’s entirely within the spirit of this blog that I’m cheating by stealing the title from this excellent post by my former colleague Vikki Cheng. In it, she gives the advice that instead of quitting our days jobs we should instead cheat on them.

It’s what the young folks these days would call a “side hustle”: following something you’re passionate about while still turning up at the factory day after day to make widgets or whatever it is Mr Fatbucks pays you to do.

As the nature of work changes, and the idea of a “job for life” becomes a distant memory, having something on the side is about more than fulfilment; it’s also career insurance for the day when you decide to chuck your current job – or it decides to chuck you.

I struck this myself early on in my working life. The RNZAF squadron I was on had an oversupply of copilots, which meant that each of them wasn’t getting to fly all that often. (I was lucky enough to be a captain by that stage so was getting plenty of air time.) One of my copilot mates was very keen to become an airline pilot, but didn’t have the flying hours needed to get a job. His solution: get a gig flying freight around the country at night. It worked – he built his hours, got a job and is now flying very big aeroplanes for a very big airline. (He hardly ever fell asleep during the day, either… which is probably for the best.)

Of course, checking out from work to then work nights and weekend on something else isn’t everyone’s cup of tea. But if it is, here are some tips to get you started.

Be disciplined. It’s called a side hustle, not a side shuffle

Declaring yourself to be, say, a novelist on the side is the easy bit. As English comedian Peter Cook replied when a man he met at a party said he was writing a novel, “Neither am I”. The trick to making your side hustle rock is to be as disciplined as you are in your day job. (You are disciplined in your day job, right?) Sticking with the author thing, some of the best-known writers work to tight self-imposed schedules, rather than waiting for the muse to strike. Steven King set a target of six pages per day. Ernest Hemingway wrote every morning from 6am; Haruki Murakami makes him look like a slouch by starting at 4. Early morning work is a common thread with novelists – which should make fitting a daily burst of side hustle in before your day job a cinch.

Secret squirrel or open otter?

Many employers will see a side hustle as a sign that you’re an interesting and creative person (while actually it’s a sign you hate their dumb job and can’t wait to leave mwahahaha). Others might take it as a sign that you’re not 100% committed to widget making. Whether to fess up that you’re working on something on the side is a line call then. Legally, though, we recommend you …

Check the fine print 

Depending on your chosen side hustle, your current employment contract might have a thing or two to say about it. This is more likely if your day job is similar to your night-time one. Not many banks would grizzle that one of their accountants was spending weekends selling her watercolour paintings, but starting a small business accountancy gig might not make the boss quite so happy.

Find kindred spirits

Slaving away at the kitchen table before the kids are awake can be a lonely life. So it’s important to connect with other people on the same journey. These days, Facebook is bulging with groups made up of everything from semi-professional dressmakers to budding blockchain entrepreneurs. Joining one can be a great way to share ideas and ease that loneliness… just don’t fall into the trap of Facebooking away your hustling time.

Be like Google

Google has long realised that just doing the same thing every day isn’t good for productivity or creativity. So every Googler theoretically gets 20 per cent of their time to spend on work projects that interest them – often leading to useful developments such as, you know, Gmail. Critics of the policy point out that most Googlers don’t have time to do it, and those that do, do it after already-long hours, leading to its nickname “the 120% policy.” Still, if you’re a business owner or leader and want to bring some of that side hustle energy in house, it could be worth a crack.

Run the numbers

Chucking in your day job and deciding to make your side hustle your sole source of income could be (a) the best thing you ever did or (b) your worst decision since spending all your birthday money on a Vanilla Ice T shirt. Like any big calls, the more information you have to work with the better. So, make sure you keep records of not just the money you make from your side hustle, but the time and money you spend on it. The longer your records go back, the better you’ll be placed to make a smart decision when the time comes.