Here's the one question a serial entrepreneur recommends asking yourself to determine your next career move

Jesse Krieger, 33, has made a lifestyle out of entrepreneurship.

In fact, "Lifestyle Entrepreneur: Live Your Dreams, Ignite Your Passions and Run Your Business from Anywhere in the World," is the title of his best-selling book, which explains how people can create income streams that fund the lifestyle they want to live.

For Krieger, that's a semi-nomadic journey stopping for months at a time in destinations such as China, Sweden, Mexico, Hawaii, and Las Vegas as he builds an online business that he says is on track to earn at least $350,000 in 2015.

He's toured the US as part of a band, founded a string of five businesses throughout his 20s, spent summers learning to speak Mandarin, and written a book that became a bestseller in South Asia before it ever made it to the US. But the one thing he's never had, he says, is "a normal job."

Instead, he's made a living from teaching other people how to make theirs through publishing, author training, and business coaching.

Krieger advises people who wish to overhaul their careers and earnings to ask themselves a single question:

"Normally if I'm talking to client, or even deciding what I want to do, I ask what I call 'the million dollar question': If I wrote a check for a million dollars right now to alleviate your financial concerns, what do you do next? What would you love to be doing if all those other things would be taken care of?"

"Once I'm clear on the lifestyle I want to lead for the foreseeable future, I let that be a driver," he continues, "whether it's exploring something that captures my interest like spending two summers studying Mandarin in Asia, or combining and blurring the line between personal interest and things that generate an income and provide travel opportunities. Somewhere in there, there's a sweet spot that really embodies what it is to be a lifestyle entrepreneur."