Full-time side hustles

There's a special satisfaction that comes with doing hard things of your own choosing.

In 2018, I moved to Hong Kong with two obligations: Teach English to local toddlers and write my blog. 

The first one stemmed from necessity, the second was self-imposed. I wanted to find a way to make a living as a writer, but I lacked experience. I had to start off earning a living so that I could write. 

The teaching job was demanding. Ten hours a day I stood before a class of rowdy three-year-olds who would bite and cry and pee their pants. I stepped in countless classroom puddles that no one ever fessed up to.

During breaks I dealt with authoritarian administrators whose limited English and sidelong glares made me think they were conspiring toward my letter of resignation. To this day I haven’t done anything more mentally draining.

Nonetheless I treated my blog like a second job. Not because I was clever or learned to do so in a self-help book, but I figured the only way to become the best writer I could be was by writing as much as possible. That turned out to be a smart approach. 

I sat down to write at the same time every evening, clocking in and out as if someone were paying me to. Publishing essays while exhausted from the day made me better and my writing sharper. The universe took note and after six months my blog earned me a job with a local newspaper. 

Working for free had freed me to work. I was 22 years old — and someone was officially paying me to write!

There’s a special satisfaction that comes with doing hard things on your own volition. Like doing a workout you hate. The work feels more meaningful, and you get better faster compared to doing what someone else forces upon you. 

Here’s a quote I’ve always liked. “I only write when inspiration strikes, but fortunately it strikes at nine every morning.” It’s commonly attributed to William Faulkner, but other names get floated too. Point is, people do their best work when they take it seriously — when you treat it like a job, as if it mattered. 

I realize it’s cliche to become an evangelist for a routine or path that worked for you. Recruiting others to get on board with something you found useful is a natural next step. But I’ve seen others follow the calculus I’m describing with similar success. The best writers I know keep a schedule. Most write multiple days a week. There is no dawdling or procrastination. They get a lot done. 

Meanwhile, I’ve also met reporters who tell me they have been working on a book for five years but it still isn’t ready for edits or another set of eyes. 

These are not the type of people who treat their writing like a job. Like opportunity, inspiration comes to those who show up. Otherwise it’s like waiting for Godot. 

The only way to turn a side project into your main pursuit is by giving the latter the same priority as the former. For crafts like writing, programming, or painting, if you do the thing long enough for free, you will inevitably get good at it. That should be exciting to anyone who wants a creative career. Creativity comes down to practice, after all. 

The simplest way to do this is of course by making a plan and sticking to it. The more specific, the stickier. “I will write everyday” is not as strong as “I will write at my desk with a black coffee at noon on Tuesdays and Thursdays for 30 minutes each time.” Less is more when consistency is the goal. 

Among people I know who already write for a living, only a handful are interested in turning their day job into an independent pursuit. I’m betting on the ones who regularly write outside of business hours. They don’t always have an end result in mind, but they do show up and create on a consistent basis. 

A consistent detail about this group: They are not the ones talking about writer’s block.

Now, I’ve been writing every day since I was in college. Most people who know me know that. One under-the-hood detail is that much of what I write never gets published. I have to exorcize the sludge to get to what’s decent. 

A fraction of that material sees the light and receives good feedback. An even smaller share of that stuff reaches virality. 

It’s interesting when that happens because, for whatever reason, your work is suddenly getting a lot of attention. It feels good for a brief moment but when you zoom out, it matters very little. Going viral is an impossible target. I always appreciated the idea of building a body of work. People may discover you through one internet home-run, but if there’s no library to back it up, there is slim chance of staying power. 

Think about Hawk Tuah girl (ask Google if you haven’t heard of her). Overnight, she became the most famous person on the internet. I’ve since seen reports that she’s getting her own reality show as a result of her one witty quip. 

To be clear, I wish her the best. Though I do wonder how long the internet will stay interested in her. She had no substantive body of work before becoming a meme. 

Let’s get back to the plot. Treating my writing like a job got me a job as a writer. Taking it seriously — building a schedule that evolved into a habit — led to increasingly interesting projects.

There is no scenario I’ve seen that gets worse after putting in more effort. 

The more serious you take your work, the more the right people will notice. Financial upside is always welcome, but to me the most rewarding component of doing great work is the opportunity to do more of it.