Skip to main content

Jay Clouse Wants You to Be Your Own Boss

Today, Jay Clouse devotes most of his professional life to helping other people with their professional lives. He encourages any who wants to do so to take the plunge into self-employment, whether as a freelance writer, a musician, a business consultant, or whatever else makes use of a person’s skills and passions — keeps them out of the traditional workforce.

Why? Because Clouse genuinely believes that the “solopreneur” approach to work is a fine approach, and one never better suited to the times than today. And no, we’re not talking about gig life; we’re talking about a career, just one without a bunch of bosses to whom you have to answer.

Jay Clouse
Kyle Asperger/Studio 301

The only huge, glaring, terrifying problem? That means you’re your own boss. And your own HR team. And your own direct report. So yeah, you might want a bit of help getting started.

Recommended Videos

Enter Clouse, who arrived at his current position via a career in the startup space. Startups were, as he puts it, “alluring and just in vogue in the 2000s.” They were, at the time, the antidote to working in a more traditional corporate setting. He started a ticketing company (think StubHub), which he built up and then burned out on and sold. Next, he took a job at a venture-backed startup in the healthcare field, and “after about a year,” he says, “I finally realized I really didn’t like having a boss. So I decided to go back out on my own and have been essentially freelancing ever since.”

In the early days of Clouse’s second go at being his own boss, he assumed he would be serving primarily as a consultant for startups, but instead found “lots of individual professionals — creatives — coming to me looking for help getting their businesses going. So many of them were super talented, were so good at creating projects, at creating work for their clients, but they just had no idea how to run a business. They weren’t comfortable with the ins and outs, with finance, with organization.”

Jay Clouse
Kyle Asperger/Studio 301

Clouse worked with multiple clients from all walks of life, helping them create business plans and models for themselves. With the hours put in to set up a genuine framework on which the logistics, organization, communication, operations, and, of course, the budgeting of a solo operation can stand secure, the freelancer was then free to focus on the work, be it journalism, editing shows or audio programs, writing software, making music, consulting, public speaking, and so on.

Related Reading

Clouse found himself streamlining the way he helped teach “really talented people who did great work make a living doing it. And that’s really been the through-line here.” This led Jay to create the Freelancing School, a program that let him reach a larger group of people than his one-on-one work, connecting with individuals who might not have the grounding in the nitty-gritty of business operations how to be their own business without running it into the ground.

He sums up the goal informing all of his work as: “Helping creative people become sustainable and thriving business owners.”

Jay Clouse
Kyle Asperger/Studio 301

Clearly, he had hit on something with appeal even beyond his own clients and trainees. Clouse next went on to start a podcast, Creative Elements, in which successful (often wildly successful) creative individuals discuss not their work — their art, writing, or music, e.g. — but instead about how they built up and maintain their personal brands as a business. Every Tuesday, episodes drop featuring people like Seth Godin and Ash Ambirge addressing topics you’ve likely never heard them cover even if you know their work well.

So, how can you take the plunge yourself and make working for yourself work? First, you need to know what skills you (genuinely) bring to the table, then how to bring them to the table.

“Having valuable, diverse skills that are in demand is critical, and so is building a name for yourself as someone who has those skills,” Clouse explains. “And then get comfortable with money — with budget and financing, the more boring stuff that comes with freelancing. Because when you know your budget, you know what you can spend as you build up: paying for leads, a site, marketing yourself. If you can get comfortable with that finance stuff and not outsource it, if you see it as part of the job, you’re going to be so much better off.”

As for the types of careers that best lend themselves to freelancing, Clouse wants you to think beyond being a writer, consultant, or another prototypical freelance job. “The more your skills can be used digitally, the more effective you can be freelancing. If you’re really good with different software programs, like from the Adobe suite, even Microsoft programs [like Excel], or with production, like audio for a podcast — if you have those technical skills, those can be monetized because most people frankly don’t have those [skills].”

Jay Clouse
Kyle Asperger/Studio 301

Once you know what you can do and what want to do (and you have gotten comfortable with money) Clouse urges people to make sure they position themselves properly for the best chance at success. “Think about how to offer your services online; how you’ll differentiate and reach the right clients online,” he says. “Think about how you’re going to build your own network and pipelines of people who will want to work with you. And the best way to do that is a lot of outreach, and effort to build real relationships, both online and offline. And come up with a way to make it really easy to explain what you do in a way that people will remember it. Then rinse and repeat that over and over and over again, and soon some of those people will be hiring you themselves, or recommending you to people in their network.”

So, should you take the plunge and go freelance? Yes, if you want to.

“If you’re drawn to it, I think you should go for it,” says Clouse. “It’s not for the faint of heart, it can be a lot of work, but the story of job security we grew upon and were sold on is a total myth. If you can do it on your own you’ll be more secure, not less.”

Steven John
Steven John is a writer and journalist living just outside New York City, by way of 12 years in Los Angeles, by way of…
Jeremy Allen White was born to run in the first trailer for Springsteen: Deliver Me From Nowhere
The movie follows Springsteen as he makes his album 'Nebraska.'
Jeremy Allen White in Deliver Me From Nowhere

Music biopics are all the rage these days, and Bruce Springsteen is the latest icon to get the treatment. The first trailer for Springsteen: Deliver Me From Nowhere sees The Bear star inhabiting the role of The Boss. The film is based on Warren's Zane's book of the same name, which focuses on the period when he was making his 1982 album Nebraska.

The film is directed by Scott Cooper, who also directed Jeff Bridges in Crazy Heart. In the trailer, we see White embodying Springsteen as he sings "Born to Run," and we also get a lengthy monologue from Jeremy Strong's Jon Landau as he explains why Springsteen feels the need to make this album.

Read more
Tony Soprano vs. Walter White: Who is the ultimate antihero?
TV's biggest heavyweights duke it out for the antihero crown
Breaking bad season 4 screen shot

Sports fans often debate between two heavyweight legends. For basketball, it's LeBron James and Michael Jordan. Switching to tennis, you have Roger Federer fans and Rafael Nadal diehards. Debates like these are ingrained in the culture of athletics, but TV fans have their own version of this sparring match.

Tony Soprano from The Sopranos and Walter White from Breaking Bad are the two characters who still send shockwaves through every drama in the 21st century. These men were the perfect mix of good and evil. They navigated family life and the criminal underworld with cunning intelligence and ruthless risk-taking. Every show with morally gray characters at the center owes its storyboard to Walter and Tony, but which character deserves the antihero crown? This is Tony Soprano vs. Walter White for all the marbles.
Who was the more complex character?

Read more
Learn how to smoke a pipe the proper way with our guide for beginners
Let us show you the classy way to smoke a pipe
Packing a pipe

Pipe smoking is the most aesthetically distinguished way to enjoy tobacco, but you lose the classy effect if you don’t know how to smoke a pipe properly. Smoking a pipe has become a lost art, and these days, most people who engage in pipe smoking do so to achieve a sense of nostalgia. Perhaps your grandfather enjoyed a puff now and again paired with a good stiff whiskey, or maybe your goal is to emulate a pipe-smoking artist.

I know that I enjoy a good puff on a pipe now and then, and knowing the right way to enjoy a pipe has made the experience much more pleasurable for for me. Whatever the case, if you intend to take up the time-honored tradition of unwinding with a pipe like me, you should learn how to smoke a pipe the right way. And smoking a pipe is very different than smoking a cigar (except you shouldn't be inhaling either).

Read more