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Polywork, Personal Brands, and Jobs of the Future

Have you heard the term “Polywork” before?

From Digiday:

The professional workforce, particularly millennials (aged between 25 and 40 years old) and Gen Z (up to 24 years old), is increasingly rejecting the concept of a full-time job and a single boss in favor of something that’s being dubbed “polywork,” or having multiple jobs at once.

It sounds like an attempt to (re)brand what’s more commonly referred to as “having multiple income streams.”

YouTuber, course creator, and podcaster Dr. Ali Abdaal is my go to example of this in action (in this video, Ali shares 9 passive income ideas and how he makes $27k per week).

Check out this breakdown of Ali’s online income from 2020:

The craziest part?

During this time Ali was also earning a salary as a doctor with England’s National Health Service. Ali has since left his job as a doctor to focus on his online efforts.

I can’t say I blame him.

When you’re already earning well over $1,000,000 / year as a creator, being a junior doctor seems like a distraction.

But Steph Smith‘s situation is a little different…

“Officially” Steph is a Senior Analyst at Trends, a newsletter and online community for entrepreneurs.

Steph also writes for her own website, as well as her 30,000 followers on Twitter, and her ~5,000 newsletter subscribers.

Even more impressive, Steph’s self-published book, Doing Content Right, raked in over $100,000 in sales in under a year, and her new productivity course, Doing Time Right, is close to 500 sales in just a few weeks (currently on sale for $100).

Having a job and a side project is not exactly a new phenomenon.

But it’s not like Steph is a lawyer who happens to teach a few yoga classes or sell cupcakes on the side. The work that Steph does for Trends is very closely related to her own business.

You might even argue that by writing for Trends, Steph is competing with herself (or vice-versa). But then you would miss an important point:

Steph’s role at Trends increases the visibility of her personal projects. And the fact that she has a sizeable audience of her own also benefits Trends.

We’re All Celebrities Now?

It’s a bit like the Hollywood model.

Having an A-list actor will attract bigger audiences to a new movie. And all the money spent on ads and talk show appearances promoting the movie will raise the actor’s profile. Win-win.

It’s this idea of celebrity-creator-as-an-employee that I find particularly fascinating.

Conventional wisdom says that you shouldn’t mention your side project to your boss or prospective employers, in case they’ll see it as a distraction or assume that you’re more likely to jump ship.

But the opposite might soon be true. Here’s Steph on how she landed her job (from an interview with SparkLoop):

Sam [founder of The Hustle and Trends] found me!

I started writing my blog in early 2019 and it quickly took off. Several of my articles went viral. The first one that got really big was You Don’t Need to Quit Your Job to Make and the second was How to Be Great? Just Be Good, Repeatably.

Both of these (and two more of my articles since), went to the top of Hacker News and ended up being read by over 30k people.

By the time the second was making its way around the web, Sam had heard of me. But this time, he reached out and wanted to get me involved with Trends.

If I could give advice to anyone, whether they are actively looking for jobs or not, it would be to openly create things online when people aren’t watching. Anyone can hype themselves up in an interview, but the best way to find great people or access opportunities that you didn’t even know existed is to show what you can do when “no one is watching”.

Jobs of the Future?

Kyle Prinsloo is another a successful creator. He’s taught thousands of students how to become freelance web developers. He has over 46,000 followers on Twitter and over 17,000 newsletter subscribers.

So Kyle knows first hand the hopes, dreams, and fears of someone building an online business — and what it takes to succeed.

All of that makes Kyle a perfect fit for his new role as Head of Marketing for Gumroad, the popular platform for creators selling ebooks, courses, and other digital products.

But why get a job if you’re already doing so well?

Again, increased visibility and access. But also: money.

Freelancers, creators, and entrepreneurs often have irregular income, especially in the beginning. Lots of lean months in between big launches. Having a steady paycheck helps.

Jobs at Gumroad pay $100-125 per hour, but they don’t require too many hours:

Most people are part-time, working on average 22 hours a week. We also have an “anti-overtime” rate: past twenty hours a week, people can continue to work at an hourly rate of 50 percent.

This allows us to have a high hourly rate for the highest leverage work and also allows people to work more per week if they wish.

(Having one client or job that takes 20 hours per week and pays enough for you to live on is ideal, as Niall and I discussed on the Never Normal podcast ep. 7: How to Make Money Online).

Gumroad is not a normal company, as founder Sahil Lavingia explains in No Meetings, No Deadlines, No Full-Time Employees:

Working on Gumroad isn’t a majority of anyone’s identity.
People work at Gumroad as little as they need to sustain the other parts of their lives they prefer to spend their time and energy on: a creative side-hustle, their family, or anything else.

Does this all sound too good to be true?

The Great Exodus

For now, offering so much flexibility gives companies like Gumroad a massive advantage when it comes to attracting talent.

But soon companies may not have any other choice.

The best and brightest workers are demanding more freedom. From the Digiday article above:

Johnston points to the dramatic power shift from boss to talent during the pandemic. “We are seeing the largest shift to entrepreneurs in history,” he said. “Think about what just happened in the world — it was such a collectively intense situation we all went through. I don’t know if there could be a bigger kick in the butt [to inspire people] to do what they want to do. You can become a full-time writer or start a business.”

That desire to live a multifaceted professional life must be understood and supported by employers, as Johnston sees it. “If businesses do not listen to their talent, we will see those companies start to become dinosaurs,” he said.

What about you?

If you’re considering quitting a job, starting something new, or if you have any feedback on these topics, then let me know. I’d love to hear from you.


I write occasional emails (like the one you just read) and posts on this website to share what I’m learning and the stuff wish I knew back when I was getting started.

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