How One Man Took the Leap to Self-Employment

Leaving the financial safety of a comfortable full-time job wasn’t easy, but Todd Henry decided he had to jump.

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At first, Todd Henry’s interest in how people can boost their creativity was a hobby. In 2005, he launched a podcast called “The Accidental Creative,” where he explored strategies for creative professionals under pressure to come up with new ideas all the time. His hobby quickly grew into an online community, e-newsletter, products, and most recently, a book, The Accidental Creative. Today, his full-time speaking and consulting business has replaced his full-time job.

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But that shift didn’t happen overnight, and the Cincinnati-based Henry made sure he found his financial footing before taking that leap. We spoke with Henry about his new book, how he decided to leave the financial safety of his full-time job, and his tips for earning money within creative fields. Excerpts:

How did you first get the idea to start the Accidental Creative?

I studied marketing in school and worked in the music business, and then decided I wanted to be more rooted. I ended up as the creative director of a nonprofit. About four or five years into that, I started looking for conversations online about leading the creative process and how organizations deal with the pressure of having to create every day. I couldn’t find anything, so that’s when I launched my podcast. I didn’t intend to start a business, I just wanted to start a conversation.

How did you juggle that with your full-time job?

I ended up blocking off between 5:30 and 7:30am in the morning. That was my time to work on the business, and then when I came home at night, I hung out with my kids, put them down and then I’d go into my office. For many years I worked four hours a day outside of my normal 50 hours-plus a week job.

How did you turn the podcast and blog into something that could earn money?

As more people started listening to the podcast, it started to get expensive and I was putting in a lot of time, so I started thinking how I could create a business, to cover expenses if nothing else. So I created a membership community where people could pay to get extra content and interact with me personally. That was my first monetization strategy. Then, I started getting invited to speak at companies and conferences, and that pretty quickly revealed itself as the most lucrative business model.

That, combined with “idea generation,” where I help companies generate ideas effectively, whether it’s for a new product or something else. We come in, provide a structure and process, and then whittle down the ideas to the best ones that could be implemented. (See Creativity on Demand)

At what point did you feel ready to leave your full-time job?

I loved what I was doing and was very comfortable. It just got to the point where I felt the boat was leaving the dock and I had one foot in each place, so I decided to jump. It’s better to be in the wrong place than to be wet. My wife and I had a conversation and said, ‘If we’re going to make a mistake, it will be an aggressive mistake. I’d rather regret doing something, than not not doing something.’

Did you wait until you knew you could replace your income?

What I did was look at the trend. Is this on the path to becoming a sustainable business? At this point, maybe I won’t replace my income, but at least I could cover my expenses, and having multiple streams of income is important, too. Those are the two factors: The trend line, and how diverse is the stream of income.

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How did you prepare financially for the end of a steady paycheck?

While I was building the business on the side, I made sure we were putting away most of what I was making on the side and not using it as personal income. We made sure we were liquid enough to endure the dreaded two-year period when most companies bail. We have no debt other than a mortgage, own our cars outright, and have liquid savings so we can endure a storm. I went to people around me and asked if we were crazy to do this and almost everyone, including our financial advisor, said, ‘No, you’re where you need to be to do this.”

How is your life different now?

In many ways, my heart had already moved on, and now my head and hands can go where my heart already was. Now I can go have coffee meetings in the middle of the day, instead of before or after my normal job. Now it’s not a hobby, but the main thing, so it’s intimidating as well.

What’s your advice for other creative professionals who want to launch their own side-business?

Almost everyone that I meet who works for a large company has an idea in them for something they would like to do, if they just had the time or energy. I’m always surprised at how many people are toying with something on the side, especially now that it’s so easy to build a platform for those ideas on the side. The most important thing is to block time out to dedicate to it. It will mean adjusting your schedule and making it a priority in your life. It means you will miss out on some things, like TV shows.

Set milestones and start working towards them. Sitting and wishing is not a path to accomplishment. You have to dedicate time and energy to doing those things if you want to see them happen. It gives you a chance to experience, to see how they pan out, and to place small bets. That is the advantage of doing something on the side.

Twitter: @alphaconsumer