How to turn a hobby into a career, without regrets

Not every entrepreneur wants to build a multimillion-dollar company. Some just want to live the dream of transforming a hobby into a career.

It's an idea that sounds great in theory: Take something you love to do in your spare time and make it your sole business focus. And for some it works out swimmingly—it may even finally convince a spouse that there was a method to the madness behind all those bills piling up over the years for what seemed like a frivolous basement activity. For others, making the move from hobby to Hobby Inc. can prove to be a hasty decision and major life regret.

So think twice before betting that your hobby will be your dream job. You might lose both the hobby and your livelihood if it's a transition not thoroughly thought through.

Arthur Lucas, owner of Charleston, South Carolina-based Freehouse Brewery, said he has no regrets about making the jump from home brewer to professional.

"It's more a vocation," said the former management consultant, who also has a law degree. "I don't really feel like it's a job. It's an overexpanded, all-encompassing hobby now. Everything has challenges—and I prefer these challenges. I'm allowed to do my own thing, even if it's hard, as opposed to being what someone else is looking for. That takes a huge weight off my shoulders."

Turning a passion project into a career is not without its hurdles. Many people find that the day-to-day realities of running a business are a little more difficult than they imagined.

Jay Adan, co-owner of Greenfield Games, experienced that after his business had been open for a short while.

Adan left a career in public relations to open Greenfield, which is now the largest game store in Western Massachusetts, with two partners—Seth Lustig and Dave Fifield—who had previously run a smaller game store. (All three had met and worked together at the video game company Cyberlore.) When Fifield left to focus on a career in the video game space, it proved challenging.

"It was a critical time," said Adan. "None of us had ever run a retail store before. There really wasn't a full-time business person."

Adan and his partner brought on Joe Minton, a former business associate of theirs from Cyberlore who had experience running a company. He successfully identified where things were going wrong with Greenfield Games—and the team was able to correct them.

"There's always stuff to learn," Adan said. "Passion can only take you so far. I know a lot about games and how they work, but that doesn't translate into how you run a successful business."

The dangers of making the jump from hobbyist to someone who makes a career of that hobby aren't just on the economic side.

"When your dreams become reality, they are no longer your dreams," said Hugh MacLeod, author of "Ignore Everybody: And 39 Other Keys to Creativity."

"When its a hobby, you're doing it for yourself, on your own time. But when you're doing it for a job, it doesn't feel like that," MacLeod said. "What happens is, your hobby, all of a sudden, is a source of major anxiety because you still have bills to pay."

The activities that used to be a source of stress relief can become anxiety-inducers themselves. That can force people to find other hobbies, which might cause their interest in the original field to wander, MacLeod said.

Adan acknowledges that his game-playing time has been limited lately, but he's making an effort to correct that.

Lucas said he is yet to experience a downturn in his own private brewing. "I still like to do small batches and throw out a 5-gallon batch now and then to remember how simple beer really is," he said. (The benefit of those small batches? They can also give him ideas to try on a larger scale at Freehouse.)

Adan and Lucas said their decision came after weighing their satisfaction with existing jobs against the potential problems of one based on their hobby.

"I was going in a very different direction," Lucas said, "achieving the things I was setting out to do. But at the end of the day, I always thought I wanted to run my own business—and with the field I was in, it felt like there wasn't any way to do so."

Adan said PR was something he did to promote something he loved, but PR itself wasn't interesting to him. "When someone [would] hand me a widget and say, 'I need you to write a release about this now,' I had to force myself to become enthusiastic. ... And that was sucking my soul. Now, even on the worst day at the store, I'm still working at a place that's surrounded by cool games. So how bad can it possibly be?"

—By Chris Morris, special to CNBC.com