This as-told-to essay is based on a conversation with Ben Hawes, a comedy musician and side hustle coach based in New York City. It has been edited for length and clarity.
I moved to New York when I was 22, and I was really in pursuit of security. My parents had steady jobs throughout their whole careers, and they were able to retire comfortably — I saw what their jobs had done for them, and I really wanted to climb the corporate ladder, too, so I joined ClassPass, which was a big, growing company at the time.
I was making a name for myself there when, five years later, in 2020, the pandemic happened. The CFO said we were recession-proof, but we certainly were not pandemic-proof. When all the gyms closed, the company had to let go of a lot of people — I was one of them.
I spent 10 months unemployed.
During that time, one of the things I did to keep myself busy was build a job-hunting network that grew to about 250 people. It was a Slack channel and a blog, and it was a nice way for people to connect. But then I actually developed a merch store for it, and that’s what became most successful about it.
Shortly after that, I started my photo booth side hustle, called Rent My Booth. I’d go to events, and essentially just make people smile and have fun at parties with my booth, with fun backgrounds and props, and my camera.
It wasn’t enough to get by on its own at that point, so I started another corporate job. I was there for three years, and when I got laid off again in January 2024, it was the catalyst I needed to finally accept the fact that I just need to do my own stuff and be on my own, making my living from my own endeavors.
Now, I have a few small businesses to diversify my income streams.
I still do my photo booths, and I tour performing musical comedy in New York, Los Angeles, and San Francisco. I’m scaling my business up, but I make enough to pay my bills. With just 10 photo booth events a month, I can replace my corporate salary, which takes about 60 hours of work at the events, plus an hour or two a day to promote the business and do administrative things.
My friends started noticing that I was always busy with some new project. I’m a doer, and a lot of creative people get in their head about how to get started, whether that’s launching a new website, starting a podcast, or opening a business of their own. It was a friend who actually suggested that I start teaching people how I do it.
So I started coaching
I wrote a book on Amazon called “How to Start” about finding and starting a side hustle. I started meeting with people on a weekly basis who would have an idea, and I would basically help them bring it to life.
What I do is not really business coaching, because I don’t think that what I’m necessarily going to be the best at is training you over two years to make your business successful, but what I am really good at is helping you bring an idea to life. It’s more like creative launch consulting, so if someone wanted to start a Shopify store or an Etsy store, start a podcast, or start something else for their business or even just something for themselves, I’m someone who can really help get you going.
That often takes the form of creative services and content production, because I find that what a lot of people really need are the technical skills of making a website, or editing a podcast, and things like that. But I’m also there to be a cheerleader and help you get out of your own way.
I coach people one-on-one, but I realized one of the interesting things about side hustle coaching is that someone who needs an extra $300 a month probably shouldn’t be paying a coach $1,000 a month. So, to make it more accessible, I make it about content creation, and I do some workshops that people can pay $10 or $20 to attend.
When I talk to a new client for side hustle coaching, I start by telling them that it requires optimism and an ability to rise above the highs and the lows. To go full-time with your endeavors is not a one-month thing; it’s not something you do quickly. You build over time. And I stress to them that I’m working every day. I don’t really have weekends, every day I’m doing something for the sale of a photo booth or building a website or some kind of creative endeavor.
The other big thing is that you have to be authentic. If you think of the fundamentals of business, they’re all about relationships and customer service, and it has to be genuine. It has to be something you care about deeply and that you will be OK with spending 18 hours a day on.
If you’re trying to put out something that doesn’t feel authentic or feels half-assed, double-check with yourself that you’re proud of it. And if you yourself are proud of it, you will be more likely to be successful as an entrepreneur, because in order to thrive at a side hustle, you have to talk about it all the time and promote yourself constantly.
Don’t fall for some online guide that tells you that you can make $10,000 a month in three simple steps; it takes real work to rely on yourself full-time. But you’ve got to choose your challenge. It’s hard to work for yourself, but it’s hard to work for someone else, too. So decide which one you’d rather do, be bold, and go for it.
