Advice on Turning Money-Making Hobbies Into Careers

I asked people with money-making hobbies what advice they have for people considering whether to keep their hobby as pure pleasure or as an income-producing career or business. Not surprisingly, they had very different things to say about their experiences and their advice varied. That’s because there isn’t one path that is true of everyone, but individual circumstances and decisions. See what resonates with you.

cut-cable-todayIn March of 2016, I quit my teaching job and started CutCableToday as a passion project to teach people how to cut ties with cable companies. Little did I know it would take off like wildfire. I was able to quit teaching last summer and go full-time with the blog. Do I enjoy it? You bet. I work hard, but my schedule is more flexible than ever. I’m able to employ other freelancers now and focus on outreach as I build my expertise in the cord cutting field.
Chris Brantner, Founder, CutCableToday.com

Gray and AssociatesI teach wedding and event planning certification to students. To own your own business, you have to be able to do bookkeeping, sales, marketing, networking, and management. For a lot of people looking to turn those hobbies into careers, those are tasks that are intimidating. So, then the question becomes, “Do I want this enough to push myself outside of my comfort zone to pursue it as a business?”
Shaun Gray, Owner, Gray & Associates Events

fitpackingMy hobby was backpacking so I started a company that organizes backpacking adventure vacations to get fit and alter body composition. Although the business is over 10 years old now, it’s still a continual struggle to make ends meet. Fortunately, backpacking is my passion so even though the business isn’t lucrative, I live an incredible quality of life.
Steve Silberberg, Founder, FitPacking

CheekdIf you want to turn your hobby into a business, don’t give up. I left my architecture career and founded Cheekd, a mobile dating app. My business needed investors so I appeared on ABC’s Shark Tank. I’d never been more nervous in my entire life. When I proclaimed I was going to change the population with my online dating business, Mark Cuban rolled his eyes, called me delusional and immediately snapped, “I’m out.” Kevin O’Leary demanded that I quit my “hobby'”and shoot my business—my passion– like a rabid dog. All five investors declined to work with me. But 48 hours after the broadcast, Cheekd’s website received a record-breaking 100K unique visitors and 50 interested investors contacted me. Since the Shark Tank aired in February of 2015, we’ve raised five times the amount I’d sought on the show and I’ve gotten a CTO on board who’s helped facilitate and finance the new face and technology behind our upgraded app. The newly launched dating app allows users to solve missed connections with a new Bluetooth technology that was not available when the patented Cheekd idea was launched in 2010. I’m thankful I didn’t take the Sharks’ advice to quit and move on.
Lori Cheek, Founder and CEO, Cheekd

honest-marijuanaI decided to turn my landscaping career and my passion for green living, all-natural marijuana cultivation, and holistic pain relief into a full-time career. After seven years of exploring under the Colorado Medical Marijuana Program, I wanted to deliver the knowledge I had gained from personal experience to the marketplace. I grew in a small facility focused on pesticide-free, organic methods, which I believe is the only option for connoisseur quality. You must do something that you truly care about and love, so it isn’t just a means to make money. Another thing I recommend all business owners to do is constantly recognize what you are good at and what you need to learn. Don’t be a jack of all trades and a master of none. While having a broad range of skill sets is vital, I think it’s more important to focus specifically on what makes you valuable to the team. This helps clarify roles, delineate work streams, and increase overall productivity by allowing yourself and your team to focus on their individual strengths to achieve team goals.
Anthony Franciosi, Founder, Honest Marijuana Company

zeus-lawsuit-fundingFrom an early age, I knew I wanted to become a lawyer and I had a high interest in the field of torts and personal injury. My hobby was to read all the personal injury cases that I could get my hands on, and I would write down what I learned from every case. Today I work as a case evaluation expert at our firm. When a case comes in, I will review it and based on my past experience, I can usually tell if it is a viable case. I enjoy this job and cannot imagine doing anything else. Don’t wait for the perfect time to do what you enjoy. It will never feel like the perfect time; every day, there is an excuse why today is not the right day to do it. My suggestion is to do it today, even though it does not feel like the perfect time.
Jesse Harrison, Lawyer, Zeus Legal Funding LLC

sneakertubI am a sneaker enthusiast and collector so I decided to start a sneaker subscription box. I am into the second month of my business and it’s very successful. Doing this and making a living, I could not ask for more. My advice for people considering making a hobby into a business is to just do it. The reason I am succeeding is that I didn’t think too much and evaluate the pros and cons. I had an idea. I put 300% effort into it and just did it.
Kamaj Silva, Founder and CEO, Sneakertub

scrubzBack in 2006, I felt I had no time for myself. It showed in many ways, including my skin. I finally bought my first body scrub and I was hooked. But I seemed to find something wrong with each batch, so I headed to the kitchen and started making my own. I never dreamed what I was making for my own personal use would become a business that I love every day of my life. I started selling on eBay and at home parties. Then I convinced the owner of a chain of hair salons to carry my line. We will be celebrating our 10th anniversary in June of 2016. Since I opened a brick and mortar store, I am still not making what I want to make, but I am employing two other people and we grow every year. I enjoy everything about it, even the mistakes, because those mean I am learning and growing.
Roberta Perry, Founder, Scrubzbody

project-soulmateI work for a high-end matchmaking firm founded by Lori Zaslow and Jenn Zucher. We love helping people find love…it never feels boring or like something we are obligated to do. Every day is different and exciting because the jobs we’ve created for ourselves stemmed from something we love to do. Our advice for others wondering about turning their hobby into a career/business is to make sure you know enough about the industry and that you have something new to contribute. If you are just going to flood the market, you’ll have a hard time getting business and it won’t be as enjoyable to start a business. If you are bringing something new to the table and are confident that your product or service can be great and innovative, then believe in yourself!
Samantha Cohen, Business Executive Director, Project Soulmate

circuit-earringsWhen you turn your hobby into a career/business and you are in full-blown start up mode, you make substantial investments at the expense of living your desired lifestyle. The financial pressures impact the amount of creative freedom, but it is enjoyable to take up the challenge of streamlining and prioritizing growth. I had no idea I was capable of working 100 hour work weeks until I jumped into this. But it’s true what they say, “When you love what you do, you’ll never work a day in your life.”

My advice to others is that you shouldn’t be romantic about your product. Make sure that people like it and you’re selling some before you go all-in. Be cautious about investing in intellectual property protection. Having a patent doesn’t earn revenue, and you might have a new and improved design by the time your patent is granted. Finally, be aware that Kickstarter is not free money. You have to work hard for those pledges and lay the ground work for your campaign months in advance. While it is a great marketing tool, I am unsure if I would have done better financially had I worked that hard on other parts of my business.
Drew Johnson, Founder, TechWears.com

sam-mcintireI’m in the process of turning a hobby blog of mine, Deskbright, into a full-service online learning platform dedicated to helping people learn software like Excel and thrive at work. So far, it has generated a significant amount of revenue for me and it is well on-track to becoming my full-time job. I’m excited at the explosive growth we’ve seen thus far and eager to make the transition to full-time.

My advice for others is to, “Just do it.” The hardest part to making a living doing what you love is just taking the leap and getting started. Consider working nights and weekends to monetize your hobby while you work another job during the day. Or, if you have enough money saved up, make the leap and transition fully into a new career. Starting a business is incredibly exciting, and you’re going to love it once you convince yourself to make the jump.
Sam McIntire, Founder, Deskbright

brambleberry-soapI took my side hustle of soapmaking and quit my job as a correctional officer to make it into a full time business. Now I make soap for a living. Turning my hobby into a business has not diminished my love of soapmaking one single bit. I crave the creative outlet and the making. I love when I get to make soap. Yes, the stress of making money and running a business is a lot, but it is worth it.

My advice for starting a business out of your hobby? Don’t quit your day job. Push, push, push towards your big goal on the weekends and in the evenings. Turn the TV off, say no to nights on the town and work your dream job on the side until you’re certain it’s something you want to do.
Anne-Marie Faiola, Founder, Bramble Berry


It If you are considering whether you should try to make a living from your hobby, here are some of my favorite resources:

How to Turn Your Hobby Into a Business

5 Tips to Turn Your Hobby into Your Job

4 Questions to Ask Before Turning Your Hobby Into a Career


Do you need help deciding whether to turn your hobby into a career or business or coaching to make it happen? We offer coaching services to assist you.

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