How to have (and explain) a career with multiple paths

When I did the Career Cruising tests in tenth grade, I always got the impression I had to pick one career and stick with it. Of course, I don’t remember much about the results I got—those tests sucked anyway!—and I definitely don’t remember them telling me that I could add a hyphen, or a slash, and Frankenstein the careers up.

As it turns out, I could! My parents always told me I was a generalist, explaining I’d have to work hard to specialize, which was exceptionally true for their generation. But these days, being a generalist has its perks. It’s the role of the multi-hyphenate. The slash career. The polymath. The talent stack. The multi-path career. The gig economy. Whatever you want to call it, it’s here.

How to describe a multi-hyphenate career

Since I never really wanted to have a conventional “mono-path” career, that’s not what I did. Unfortunately, I also tried, earnestly, to explain this to whomever I was talking to. When someone asked me politely, “So, what do you do?” early in my career, I’d try to smooth an earnest explanation over:

“I work a day job in communications at Xtreme Labs, I was also interviewing recording artists, and freelance copywriting for other tech companies, and writing for publications. I didn’t make any of these things my full-time job.”

But to most people who listened to me, it probably sounded more like this:

“I work at blah blah blah Xtreme Labs, blah blah blah Ryan Lewis, blah blah blah tech companies, and blah blah blah blah. Blah blah blah meaningless jargon.”

I was technically a tech communications-interviewer-copywriter-writer, but that sounded even sillier than it reads. Eventually, I smartened up and just said:

“Most of my time, I’m working at a company that makes apps—Xtreme Labs—and I’m doing some other projects outside of that.”

Sometimes we talked about the projects, but most of the time the conversation moved on—what they did, what I enjoyed writing about, why I only wore black t-shirts, etc.

How to plan a multi-hyphenate career

When interviewers asked Donald Glover how he was juggling his careers as a screenwriter-actor-comedian-recording artist, I remember hearing him reply—it’s all one thing. Even after hours of research, I can’t find a source for it. But, the strength of the quote made it too good for me not to mention.

I’ve been slowly figuring out my thing, too. At some points, it can feel confusing. I would call it writing, but there are other words for it too: editing, communications, world-building, marketing, promotion. At the end of the day, it’s creating good stories and telling them.

Confusion, of course, extends beyond just my craft, but into the business. For example, there’s this narrative that the gig economy is a bad thing—it takes away conventional stability, benefits, and such away from workers. That’s true for many workers in many areas of the gig economy—like labor protection for food and delivery workers. We certainly need more regulation there.

For the purposes of this article, working two or three different jobs out of necessity is very different from what I’m calling a multi-hyphenate or slash career, perhaps just as different as starting a conventional convenience store is to a funded tech startup. But a multi-hyphenate does, in this article, usually work with multiple organizations.

As for these multi-hyphenate careers, like angel investors, and fractional leaders and consultants—or even freelance writers, artists, and graphic designers—the possibilities are much more open. Those people actually may have chosen to work in the so-called gig economy, because they have more freedom and similar pay. Or maybe they make even more money from working on a project basis. Naval Ravikant says, “Rich people get paid by the project and pay by the hour.”

You need to learn very different skills

If you want to thrive as a multi-hyphenate, you’ll need to find ways of bundling your skills together. The more unconventional the combination, the more of a multi-hyphenate you’ll be seen as. By extension, that means you’ll also need to get good at learning new skills. For example, the “entrepreneur” is a classic example of the multi-hyphenate. The role may involve a ton of different skills, but as Glover describes, it really is all one thing. From Applied Divinity Studies:

“A small business owner who manages their own books, handles sales, and manufactures their product is not considered a polymath, no matter how distinct those fields might be. Computational social scientists are not considered polymaths, neither is an OnlyFans creator who single-handedly runs everything from marketing to modeling, nor a translator who has to master ancient Greek, dive deeply into historical context, and also be a great poet in their own right…

Learning these skills will probably benefit your career. Just understand that no one has ever been hailed as a polymath because they’re good at both communication and management. They’re just considered basically competent at their job.”

For example, in my early years, I was known as a freelance writer. Then, a staff writer for Lifehacker, as well as a content marketer. Even a publicist, to some. Then a one-person agency. Then an editor at Shopify Plus and QuickBooks. And currently, thanks to my unique skill sets and experiences, I’ve focused my editorial studio on technical communications. That may change in 18 months, or maybe even sooner, but that’s what we’re focused on for now.

One of the distinct services my editorial studio Wonder Shuttle offers is collaborative writing. Our team combines our technical expertise with interviewing skills with skills in writing and editing, to support experts who don’t have the skill of writing. This sounds simple enough—until you notice the number of freelance writers who don’t like asking questions or answering them, who don’t know and aren’t interested in technology, and who are actually skilled at the crafts of writing and editing. (My team usually hires self-employed trained journalists.) For good measure, we also offer organic promotion into our service, something that sets us apart from enough technical writers.

Again, this isn’t a permanent business position. If you’re reading this in 2023, the Wonder Shuttle website will, hopefully, be onto something new. Few things in this world are permanent; even Shopify needs to go through a storytelling and execution pivot (from ecommerce to entrepreneurship).

I would actually say my skills aren’t that different—I’m not a lumberjack-data scientist-DJ. But because they all rely on working with words (e.g., writing, editing, language) or getting attention (e.g., organic marketing, media relations, working with and building audiences), I can quickly zoom in and out of specific disciplines and make new combinations based on what I see people finding useful.

There’s so much more I’ve been meaning to write about the topic of a multi-hyphenate career in the gig economy. These days, I write at this blog and at Medium. I authored a book and am working on a revised version. I advise companies on their engineering communications. If I were up to it, I’d call myself a blogger-author-editor-advisor-consultant. But it sounds confusing (and silly!), so I just call myself an author or an advisor, depending on who’s asking.

Hopefully, you get an idea of what it’s like working as a multi-hyphenate, or a slash-career. It’s incredibly rewarding and fulfilling. But it’s also completely different from a conventional career path. That learning is part of living an interesting life—it’s not easy, and that’s the point!
If you’re interested in building out your multi-hyphenate career, you need to check out Marci Alboher’s One Person-Multiple Careers: A Guide to Slash Careers, which I recommended in my Best of Books newsletter.

Herbert Lui is the author of Creative Doing, a book of 50 prompts that unblock creativity for your work, hobby, or next career. He writes a newsletter that shares three great books every month. He is the editorial director at WorkOS and Wonder Shuttle.

This article originally appeared on Herbert Lui’s blog and is reprinted with permission.