When to Turn Your Side Hustle into a Business, and When it Should Stay a Hobby

When to Turn Your Side Hustle into a Business, and When it Should Stay a Hobby

How To Transition Your Hobby Into A Hustle Without Killing It: A One-on-One Interview with Ben Hawes

I went into my conversation with Ben prepared to hate his business. This is how he changed my mind.

Ben Hawes is an entrepreneur in New York City with a long history of building businesses. He started by creating a web show in high school to entertain viewers online, then posting music videos on YouTube, followed by opening his first Etsy shop in college selling wallets made out of poker cards. Ben has always enjoyed marketing himself to the public and using social media to make his initiatives known. Once he entered the workforce, he continued his side hustle hobby, building out his own photo booth business for corporate parties after his day job. Throughout his entire life, Ben has wanted to bring his creative and passionate ideas to the world.

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Currently, Ben is coaching and consulting side hustlers on how to turn their passions into successful businesses by strategizing and partnering with them when they may need extra support and guidance. Whether you are 24 and wanting to start your own Etsy shop or you are 40+ looking for help on how to use Instagram to get your name out there, Ben will work with you to make those dreams become reality. 

Okay, I may have been dramatic when I said that I went in hating his business, but in actuality, I came into our conversation pretty skeptical about turning hobbies and things we do for fun into businesses and modes of making money. I spoke about this topic in great length in my recent podcast episode with The 20/20 Perspective Podcast: I have come from a childhood of overachievement, and that mindset has turned anything I want to do for the pure joy of it into something I must do for the resume. Once I got to college, the idea of doing anything that wouldn’t propel me toward a future career did not feel worthy of my time, so I forgot my hobbies to prioritize jobs and academic pursuits. I am just now slowly trying to incorporate hobbies back into my life, so when I heard that Ben’s current venture is to help people turn those hobbies into jobs, I wanted to hear more about his perspective on monetizing passion and how people can remain excited about their hobbies while pursuing them professionally. 

Ben totally understood where I was coming from. 

In two simple, yet vital, steps, Ben answered my critical question: When should you pursue a business career through your hobby or passion, and when are you better off keeping these passions as personal joys to fall back on?


His main tip, which seems painfully obvious to me now, but totally changed my mind on people who want to build successful businesses from their side hobbies: You have to want to. 

I don’t just mean enjoying something outside of work and wanting to make money from that talent. I’m talking about an inner, uncontrollable, exciting passion that bursts inside of you whenever you think about making this hobby your full-time gig. I’m talking about a talent that you think about more than anything else in the world, including your day job. If you don’t have that excitement bubbling up every time you talk to someone about what you do for fun, then it might be better to stay as something you do part-time. 

Ben said that when he started his photo booth business, he loved the gigs so much that it became a part of his identity. He wanted to be known for his ability to bring life to the party through his photos, rather than his 9-5. That is the kind of passion I’m talking about: the identity-encompassing kind. 

Ben’s current clients exemplify these special passions. He coaches an aspiring motivational speaker and writer in building her personal brand of inspiration. He helps run many Etsy shops filled with beautiful crafts and handmade artifacts that his clients put love and passionate energy into. Another client plans yoga retreats and has turned their love for yoga into a business to help others find their peace. And my personal favorite, an at-home-bakery, where his client bakes their delicious treats to share with the world.

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Hearing about his examples completely shifted how I have been looking at hobbies-turned-side-hustles-turned-businesses. Yes, I love to sing, cook meals with my friends, go out to eat, and read novels, but I don’t see my hobbies as my identity and I don’t think about them enough to have this inner desire to monetize them. And that’s okay! Part of Ben’s consulting services is offering 20-minute free consultations. In those 20 minutes, Ben can recognize whether or not his potential client is all in or if their heart is not completely invested in making their hobbies into a monetized gig. Ben works with people who have the uncontrollable passion and I am hella impressed by those people who have the tenacity to go after it.

Once you have established your bursting excitement and desire to want to take your side hustle to the next step, Ben shared the need to commit to focusing on improving your work while remaining balanced in your very-blurred work/life separation

Controlling your improvement in your uncontrollable passion can be really tough, Ben says. That’s one of the reasons he is making a career out of coaching side hustlers in dealing with constructive criticism. If you really want to make your hobby your full-time career in the future, you need to get comfortable with asking people to give you feedback and advice on your work. 

While this may seem daunting - after all, it doesn’t seem too fun to get constructive criticism on the thing you care most about in the world - these pieces of feedback and evidence will give you the confidence to believe that your service or product is good enough to share with the world and that people will pay money for it. You want to provide value for others, especially since this hobby has provided so much value to you. The focus on embracing feedback is key, Ben said, in order to receive the honest feedback without being afraid of what people will say. Your confidence will grow exponentially and you will get better at selling yourself. 

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The other side of the coin is to intentionally incorporate balance into your side-hustling pursuits. Your hobby can feel quite personal, and therefore you might want to work on the tasks at hand during every second of the day. I’m thinking about my own supervisor, Dan, who talks a lot about his work-life balance and the struggles of being an entrepreneur who also wants a personal life. Ben insists on balance as vital to avoiding burnout. If you don’t want to lose the pure love that you feel toward your hobby, you must set boundaries so you can focus on the other parts of your life that are just as important: your relationships, family, and fueling yourself as a physical person. 

Ben made me feel proud to have hobbies, but did not make me feel bad for lacking the entrepreneurial passion that his clients inhabit. If anything, at 21 years old, I haven’t seen enough of the world yet to develop a hobby that I hold so dear to my heart that could also help or impact others. Ben said that the older you get, the more ideas you will have. It’s hard to know what you can provide to people when you are so young.


So, whether I end up finding that passion that needs to be shared with everyone or I keep my hobbies to myself, I know that Ben will be there to help me figure out what to do next. Not everyone is made for the side-hustling life, but I have learned from Ben that there is no right way to have hobbies or build businesses. It is all extremely personal and everyone deserves to feel empowered in their career decisions. 

I do not hate Ben’s business. In fact, I think his work provides that empowerment to those who decide that their side-hustle is ready to become their ~main~ hustle.

There are MANY ways you can connect with Ben if you would like to seek out his services! Follow him on Instagram @hustlewithben, find him on his website, benjaminhawes.com, and book a consultation with him using this link

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