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The Best Way to Be Your Own Boss: Selling Advice on How to Be Your Own Boss

Three years ago, Dana Sitar ditched college life at the University of Wisconsin-Madison for the romanticism of what she called the “starving writer’s life.” Lacking any writing credentials or credits, she thought dropping out and going solo would be better than changing academic course.

She began  blogging “about how to be a writer without any writing experience” in an effort to connect with like-minded writers on unconventional paths. She penned some columns for SF Weekly’s arts and entertainment blog and self-published a short story collection (which sold fewer than 100 copies)—in all, a few clips, but not nearly enough e-book sales to garner attention from agents or publishers.

Despite her lack of mainstream writing “success,” in 2013, she published an e-book called A Writer’s Bucketlist, full of tips for those looking to get started in any sort of writing. Readers who found her work through her guest posts on higher-profile writing blogs flocked to her site for inspiration on “the writer’s life,” particularly making money writing online.

“Because the book and blog speak to an array of writing paths, we’re able to meet writers where they are and start conversations about what they’re interested in learning,” Sitar says. She took a few odd side jobs along the way, but focused most of her energy and financial hopes on the promotion of her guides and “coaching” services. She charges $145 an hour for consults on e-book writing, personal branding, and blogging, not unlike current going rates for many online teletherapy and life coaching services. Sitar, now 28, has in turn managed to make a career not from writing, but instead in teaching others how to craft independent writing careers.

Sitar is part of a wave of lifestyle entrepreneurs, or “solopreneurs,” who seek the lifestyle and independence we so often hear workers—particularly millennials—long for. As Jonathan Rauch described in a 2012 National Journal article, solopreneurs are self-employed individuals who create “microconglomerates” out of multitasking: “These one-person start-ups believe that if you succeed in branding yourself and building a portfolio of multiple online businesses, you will enjoy not only more freedom than a traditional job can provide but also more security,” he writes. Some estimates suggest more than 20 percent of millennials are self-employed, and 35 percent have a business on the side of a full-time job.

The solopreneur trend isn’t new; it’s an extension of the growth of Internet self-publishers that started over a decade ago. More than just a solopreneur, Sitar also epitomizes a larger shift in self-employment: Instead of making money on what they set out to do—in Sitar’s case, writing—the entrepreneurs make their livelihood by guiding wannabe free agents to do the very things they've done (or, in some cases, only set out to do). A meta cottage-industry has popped up to capitalize on aspiring independent workers and creatives. When looking at the new “industry” as a whole, we see a new stream of people who are eager to gain a following—and make a buck—online, who are willing to pay for a magic formula, and who are desperate for guidance from anyone who purports to have done so, regardless of their individual financial circumstances and successes.

But when you read between the tweets and look at bottom lines and time sheets, it’s hard to imagine that this freelance economy, or the “new world of work,” will bring any more freedom or success—personal or financial—than the corporate, nine-to-five one.

Washington, D.C.-based lifestyle entrepreneur Alexis Grant, now 33, founded Socialexis, a social media and content marketing business, after a career as a journalist. She first built an online audience writing about her six months of solo travel in Africa, and taking on social media consulting clients on the side of her day job. Today, her guides, e-books, and courses are a key part of her multifaceted business that began as a lifestyle entrepreneurship venture (she now has ten other employees working on a part-time, contract basis). Her success, and the way Socialexis grew its wings, is a testament to the market demand for a make-money-on-your-own-and-online elixir.

Only about 5 to 10 percent of Grant’s total income comes from this part of her business, including sales of guides with titles like “Turn Your Side Hustle Into a Full Time Job,” “How To Take a Career Break to Travel,” and “How to Create a Freakin’ Fabulous Social Media Strategy.” The success of her first e-book, “How To Start a Part-Time Social Media business,” in 2011 (at $24 a pop), helped her blog gain even more traction. By then, it had evolved from a travel blog to one about the evolution of her business and the future of the working world. But the success of that e-book, and this advice-focused aspect of her business, pushed her toward making the side business a full-time one. That year, Grant left her job as a careers reporter at U.S. News & World Report to focus on the business full-time.

“That was my first indication that there was a huge opportunity there,” she says of that first e-book/guide. In Grant's view, the meta-economic nature of today's lifestyle entrepreneurs isn't problematic, and can remain viable as long as there's transparency. While she puts a premium on transparency, even blogging about her income, many solo entrepreneurs and consultants are not so forthcoming, she says, making the entire “industry” a bit more circumspect.

“There are a lot of people who are preaching but not actually practicing,” she says, alluding to proclaimed business coaches without business degrees, online writing consultants who don't actually write, and lifestyle entrepreneurship ventures supported by a day job income but not disclosed as part of an online presence. “You never have to be an expert to share what you know—that’s what blogging is all about,” she says. “But it’s important for the person looking to hire someone or buy a guide to look into what experience they have.”

Last year, Grant started a new venture, a website called “The Write Life,” a website meant as a resource for writers that includes blog posts on both the craft and business of writing. An entire section is devoted to reviews of online products and resources offered by online publishing consultant-types like Grant; as with many online and blogging communities, there is an unofficial constellation of online presences in the solopreneur publishing world, bloggers who blog about writing and business, orbiting around one another.

Carol Tice is one member of this ecosystem. In 2011, Tice started The Freelance Writers Den, a subscription-based online community with e-courses and podcasts about making a living as a freelance writer and content creator. Before the Writers Den, Tice was a freelance writer, writing for corporate and editorial clients, such as Seattle, Seattle Business, and Entrepreneur magazines. But those have become far less frequent since starting the Writers Den, taking time away from generating the bylines that might have impressed her clients in the first place. “I’m barely still freelancing,” Tice admits.

The “den” now has over 1,200 members. Along with teaching, e-book sales, and her blog, it comprises 90 percent of Tice’s business, which she claims brings in six figures total. The Writer’s Den alone nets about $30,000 with 1,200 members at $25 a pop.

Although the “den” has no shortage of fans in the online publishing world claiming to have benefited from its offerings, Tice has skeptics, too. A recent thread on a Writer’s Digest forum discusses a “scam vibe” from her site: “Weird thing is a lot of her posts seem to repeat other people’s advice,” one commenter said, adding that she seemed to repeat her own advice on her site as well. Many bloggers in this universe also offer “affiliate links” to one another’s blogs and products. Usually, this means a blogger can earn a portion of the profits from another blogger’s digital product if they promote it, thereby enabling glowing, LinkedIn-like testimonials.

But Tice says she enjoys the “teaching” and guiding part of her business, which started as a solopreneurship venture but now includes a staff of nine. She’s become a personal branding dynamo, making sure to note in an e-mail that she has many interview requests and wouldn't have time to chat with The New Republic over the phone.

Several months ago, Dana Sitar admitted publicly that the solopreneur route may not be exactly sustainable—even when someone is an “expert” guide. She recently returned to a part-time gig as a barista so she doesn't have to rely solely on her writing-consulting business to pay the bills.  The constant hustle of blogging, selling guides and e-books, and still scrambling to pay rent each month grew wearisome. Consistent hours and a consistent paycheck, she realized, would bring her a kind of creative freedom to do the work she set out to do in the first place.

But she says there's a kind of shame she felt in making this choice. A second income like this, whether from a full or part-time job, savings or cashed out stock options, can all be a great way to grow a lifestyle business, but copping to having one is taboo in the solopreneur community, she says. If the service provider is herself lacking in resources—whether that's money, or time to practice their craft —a self-employed writer becomes a sort of snake-oil salesperson.

“I’m broke, and paying the bills means being too busy to enjoy the life in the lifestyle business I’ve created,” she wrote in a piece for The Huffington Post.

But for now, Sitar has been able to get back to her original plan, sort of: She’s currently working on a memoir … about writing. That’s about as meta as this line of work gets, but at least she’s honest. She’s still working on her guides, her blog, and more consulting-related tasks, but now she can focus on what matters most to her. She writes, “Making a living writing, I learned the hard and naïve way, has nothing to with creating and everything to do with selling.”