Should You Start a Business as a Side-Hustle?

For a short period of time in late 2016, I was obsessed with the song “Hold Me Down” by Halsey. It is a ballad (of sorts) for artists who must face daily inhibitions in order to create art. Halsey likens her creative process to a relationship with the devil, to whom she feels as if she’s sold her soul just to manifest her work.

side-hustle rewire pbsHalsey’s creative process was very different from mine at the time. It still is. She is a pop star and I am a writer, stylist and small business owner. At the same time “Hold Me Down” was featured prominently in my Spotify rotation, I was an aspiring entrepreneur and “marketing and communications manager” for a small, family-run design company.

My career trajectory post-college graduation was a little unconventional. During my senior year of journalism school, I co-founded a magazine called The Riveter. I felt passionately about working outside of the journalism industry in order to devote all of my creative energy, and as much free time as possible, to developing my business. In cobbling together a series of odd jobs, however, I found that I still couldn’t devote enough time to the magazine. I began to flirt with the idea of working full-time in an industry that was tangential to my ultimate goal of being a full-time writer and editor, ideally for my own publication. That landed me in my marketing gig.

On a certain level, I related to my boss at that company—she was passionate about her business, and she wanted it to grow. At the time I accepted the job, I thought I would be able to learn from her in this capacity while also impacting her business. She knew about The Riveter, and I marketed myself to her as a self-starter with an entrepreneurial attitude. While I was ready to acquire such luxuries as paid-time off and company-subsidized health insurance, I was not ready to give up on my business or my ultimate career goals.

Hybrid entrepreneurship on the rise

In an article published in the Academy of Management Journal, “Should I Quit My Day Job? A Hybrid Path to Entrepreneurship,” “hybrid entrepreneurship” is identified as “the process of initiating a business while simultaneously remaining employed for wages.” This approach allows entrepreneurs to reduce the risk associated with launching their entrepreneurial endeavor by reducing or eliminating opportunity cost. It is a career path increasing in popularity, according to the U.S. Bureau of Labor Statistics, which states that, “in 2011, roughly 10 percent of self-employed workers were also employed by existing firms.”

entrepreneurship side-hustle start a business rewire pbsBut, if you’re trying to get your own business off the ground, what’s the best kind of day job to have? After only six months with the family-run design company, I left to work within the retail sector of a large corporation. Since making the switch from working for another startup to a big corporation, I’ve had a lot of entrepreneurial growth. The structure of a corporate workday—definitive start and end times, required breaks and an expectation for decency and respect—provided me with more time and energy to take The Riveter to the next level.

Maggie Happe, 26, worked for the same company I did. I was her immediate predecessor in the marketing role. During her tenure, she launched her own business, Happe Media, to do social media and digital marketing campaigns for small to mid-size businesses.

A year after launching, she quit her full-time role, but stayed on as a contractor, “with the understanding that they were looking for someone else (to replace me) during that time… However, they didn’t actually hire anyone until about one year later when I quit flat out.”

“Though I was clear about my time commitment up front, there was a lot of psychological angst that occurred while I was trying to manage both, even though I was fulfilling all of my commitments to the full-time job,” she said.

Communication smooths the transition

Whether you should work for a corporation or another startup (or just for yourself) as you launch your new business depends on your personal finance situation, as well as the culture of the company you’d be working for.

Michael Carter, 26, co-founded Colorado-based biotechnology research and development firm Sporitas in 2014. At the time, he was also employed full time as a sales executive for Zillow Group, an online real-estate marketplace.

After six months as Zillow, Carter quit to focus on Sporitas exclusively.

“I wanted to ensure that Zillow was aware of what I was working on at Sporitas,” Carter said. “I slowly began to hint at my startup over the course of a few months while working at Zillow. My coworkers and management were very supportive of my external endeavors. During my last few months at Zillow I was very transparent about the rate that Sporitas was growing and mentioned that I may have to leave Zillow Group soon.”

entrepreneurship side-hustle start a business rewire pbsWhen Carter put in his two-weeks at Zillow, the company was supportive, and the transition “was smooth,” Carter said.

“I would… recommend that it’s better for someone in the process of starting their own business to work for a larger corporate structure,” he said. “As someone who has worked for both small businesses and corporations, I find it apparent that corporations have a much more defined role for employees. This allows the employees to have clear expectations for what they will be doing on a day-to-day and month-to-month basis.”

Starting slowly reduces risk

Theresa Berens launched Boss Dotty Paper Co. this spring in advance of the National Stationery Show. She continues to work full-time as an in-house graphic designer for a nonprofit organization.

She said her full-time employer and coworkers are supportive of her entrepreneurial endeavors. She has talked about her business with coworkers, and several of them have stopped by events where Berens was selling her Boss Dotty products.

“Unless you’re some type of heiress, working a full-time job when you’re starting your own thing is a necessity,” she said. “It’s definitely not easy to basically work two full-time jobs, and you’re going to sacrifice a lot in all aspects of your life to make it work. But I think there are benefits to working full time and starting a business, too…

“My whole life isn’t riding on the success or failure of Boss Dotty or my illustration work, and I’m happy about that. It allows me to be selective, and to take risks that I don’t think I’d take if I were worried about being able to pay rent.”

Find out what a small business expert says about knowing when to quit your day job.

Kaylen Ralph

Kaylen Ralph is the co-founder, editorial development director and brand director of The Riveter Magazine, a longform women’s lifestyle magazine in print and online. She works as a personal stylist for Anthropologie. Follow her on Instagram @kaylenralph for books and fashion. You can also find her on Twitter at @kaylenralph.

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