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How to turn your side hustle into a full-time job

Know when you have a good idea, get ready to spend a lot of time on your business and see how big your side hustle can grow. Here are 4 key questions to ask yourself.

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Twenty-four million Americans want to work for themselves by 2021, according to FreshBooks’ third annual Self-Employment in America report.

If you’re already your own boss, you probably want to stay that way; FreshBooks reports that 96 percent of self-employed Americans surveyed “have no desire to return to a ‘regular job.’” In fact, the majority of self-employed people in the FreshBooks study have a better work-life balance now that they’ve switched over to freelancing or small business ownership.

But how do you make the switch? A lot of us can figure out how to start a side hustle, but don’t know how to turn the extra $50 or $150 we earn every week into a full-time income.

I reached out to three entrepreneurs, all of whom turned side-hustles into full-time jobs, to learn their secrets:

  • David Jacobson, founder and CEO of live trivia entertainment company TrivWorks™
  • Christine Stevens, one of the top sleep consultants in the U.S. and owner of Sleep Solutions By Christine
  • Makenzi Wood, a content writer who has worked with over 60 agencies and entrepreneurs

Their advice? Know when you have a good idea, get ready to spend a lot of time on your business and see how big your side hustle can grow. Here are 4 key questions to consider when turning a side hustle into a full-time job.

Why pursue a side hustle?

David Jacobsen

David Jacobson

Jacobson: After the recession hit in 2009, I realized there was an urgent need for cash-strapped companies in NYC and beyond to reward hard-working employees. As an event planner and bar trivia host, I knew that trivia was a great way to deliver an effective and affordable solution.

Stevens: My daughter was born while I was still working my full-time job. She was never a baby who slept long stretches at night and I was exhausted for months. Everyone from my parents, to friends, to the other moms at daycare kept telling me it would get better, but it never did. By the time she was 8 months old, she was waking every hour all night and I was barely getting 3 hours of sleep a night. At that point, I would have stood on my head for two weeks if that’s what it took to get my baby to sleep! I worked with another sleep consultant and within three nights, my baby slept 10 straight hours. I was contacted by the creator of the Sleep Sense program, the program I used to help my daughter sleep, to see if I would ever teach about sleep — and I made the decision then and there that I wanted to help other working moms get the sleep they desperately need.

Wood: I was feeling creatively frustrated at my full-time job. I wanted to take on work where I could choose the project and the client.

How do you know if a side hustle has the potential to become a full-time job?

Christine Stevens

Jacobson: I was working full-time at another job, but devoted every spare second I had to establishing and building the new side hustle: Early in the morning, late at night, and all throughout the weekends — not to mention on the subway to/from work! Whenever I had a spare moment! Once I started landing some big-name, big paying Fortune 500 companies as clients, I knew that I could soon replace — and even exceed — my current salary. This was the moment I realized this could be not just a side hustle, but a full-time job.

Stevens: Less than 10 hours a week was all I could devote early on. I worked in the evenings and weekends when I could fit in time. Within the first year of becoming a sleep consultant, I was fully booked and realized I was onto something… that new parents really did need sleep and they were willing to pay to get it!

Wood: At first I just pursued my hustle as a hobby. However, once the money started coming in, I realized I could replace my full-time income with more dedication. I started waking up at 5 a.m. every day to do client work. I dedicated evenings and weekends to my side hustle. It was hard, but it was worth the sacrifice (and lack of sleep). After I put in more hours at my side hustle and saw the money that came in as a result, the financial side made more sense. I was almost able to out-earn my full-time salary at a side hustle where I worked 10 hours a week. I knew scaling would make sense financially and also for my time.

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How long does it take to turn a side hustle into a full-time job?

Makenzi Wood

Jacobson: I focused on establishing credibility: Building a client list, obtaining favorable testimonials and referrals, securing positive media coverage, and establishing partnerships with reputable celebrities and organizations. It took every spare moment I had, and I worked nonstop for over two years before finally being able to make the leap from side hustle to full-time.

Stevens: At first, I gave free presentations about children’s sleep to local mom groups and told anyone who would listen about what I did, including my dentist!  I would talk with moms at the coffee shop while carrying my baby and ask how their baby slept. Or, I would get asked “Does she sleep all night long?” by moms everywhere I went. Once I determined that working moms were my ideal client, I asked previous clients how they found me and started branching out from there to let others know what I did and how I could help them.  It took a tremendous amount of drive to cold-call mom groups to set up presentations; I would also stop into daycare centers to pass out my information, so I would spend a few hours a week traveling around town and to start my blog. It felt overwhelming, but as time has done on, I’ve learned where my ideal clients are and where to pinpoint my marketing efforts. Now, I work about 30 hours a week.

Wood: It took me six months to scale to full-time work, once I started taking my side hustle seriously. I stopped pursuing one-off projects and started looking for long-term contracts. I’m so happy that I built up my client base during this time because I had a readymade business when I quit my job in October of 2018.

What’s a good piece of advice for side hustlers?

Jacobson: Set exceedingly clear yet realistic goals and objectives, be persistent, and believe in yourself!

Stevens: If you’re looking to make the leap from side-hustle to full-time job, be prepared for the time commitment. You’ll have to be very diligent with your time, so you don’t get stuck on one task. Be prepared for the ups and downs that starting any business will have. When you run your own business, the amount of time and effort you put into it will determine how successful you’ll be. If you love your side-hustle more than your full-time job, it might also be time to make the leap.

Wood: I made sure to pay off all of my debts before I became self-employed, and that’s what I recommend for everyone. (And don’t tell me it’s impossible because I paid off $65k of loans and my car!) Starting a new venture is scary enough; don’t do it if you have a ton of bills over your head. Because I’m financially secure, I’m able to take more risks with my business. I don’t have nearly as much worry as the freelancers who jumped off without a plan.

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Nicole Dieker is a full-time freelance writer. Her work regularly appears on Bankrate, Lifehacker, The Write Life and numerous other sites. She is the author of Frugal and the Beast: And Other Financial Fairy Tales. This article is sponsored by Haven Life Insurance Agency. Opinions are her own.

TriWorks is a trademark of TriWorks Inc.

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About Nicole Dieker

Nicole Dieker has been a full-time freelance writer since 2012, with a focus on personal finance and habit formation. In addition to Haven Life, her work regularly appears at Lifehacker, Bankrate,, and Vox. Dieker spent five years as a writer and editor for The Billfold, a personal finance blog where people had honest conversations about money, and is the author of Frugal and the Beast: And Other Financial Fairy Tales.

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Haven Life is a customer centric life insurance agency that’s backed and wholly owned by Massachusetts Mutual Life Insurance Company (MassMutual). We believe navigating decisions about life insurance, your personal finances and overall wellness can be refreshingly simple.

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