Finding the perfect balance between work and life is a challenge.

But it’s one Spencer Rascoff conquered a long time ago.

The Zillow (Z) CEO, who is a father and husband,  landed on Fortune Magazine’s “40 Hottest Rising Business Stars Under 40” list, and has helped launch two successful online companies.

“I have three young kids and a wife who is a successful doctor, so it’s a very busy household,” Rascoff said. “I don’t sleep much.”

Oh and he also left a career on Wall Street to live the entrepreneurial dream.

From Wall Street to Main Street

Rascoff began his Wall Street career as an investment banker at Goldman Sachs (GS) and later moved into private equity, working with TPG Capital.

But he always felt like something was missing.

“I left Wall Street because it was too transactional for my taste,” he said. “In investment banking, you provide advisory services during the heat of a deal. We’d collect a fee and move on, but we never saw how the story ended. It’s like watching a series of fight scenes without ever seeing the full arc of its narrative.”

Rascoff said the biggest reason he decided to leave the Street was to move into a more operational field, something more “in the weeds” that would allow him to build and run the company.

“Buying and selling companies (with TPG Capital) remedied one of my objections with the Street because you get to stick around while you own the company, but it presented another thing I didn’t like: I don’t get excited about the arts and science of financial engineering. Balance sheets are boring. For me, that’s not something I can be passionate about.”

So he moved on to something he could find passion in doing.

It was at TPG that Rascoff co-founded HotWire, a discount travel site. TPG became the incubator and lead investor for the company. Once HotWire was sold to Expedia (EXPE), Rascoff moved with it to run the hotel business of Expedia for a year.

Still, something was missing.

“I  wanted to something more entrepreneurial and Expedia wasn’t moving as quickly of a pace as I was used to,” he said. “I missed the energy of a pure startup.”

In 2005, he left Expedia to start Zillow.

Finding Your Passion

Growing up, Rascoff’s  father was a big influence and role model.

“My dad was a partner at a big accounting firm. I watched him leave his cozy, cushy life of partnership to branch out on his own and start business management in music. He went on to be a successful producer of rock concerts and very successful in his industry. It was formative watching someone leave a safe job to be an entrepreneur.”

His father’s success combined with his mother’s career in real estate turned out to be the recipe for Rascoff’s future.

“I’ve always loved real estate. I went to open houses for fun as a kid, and now I take my kids to open houses for fun. So I love real estate, but I also love creating new things, and at Zillow, we’re creating something new,” he said.

Pulling the trigger to actually leave his comfy lifestyle in the world’s financial capital might have been a difficult decision, but it’s one Rascoff fully committed to, and one he says didn’t involve too much risk to change his mind.

His biggest advice for people looking for a career change is to find a “career mirror,” someone who is able to tell you things about your career you can’t see for yourself.

Rascoff said the three times he took a career leap, his wife was there to aid in the decision-making process. She was able to clearly see he wasn’t happy with his career path, so she suggested a change.

“People overstate the level of risk in their decisions,” he said. “No tragedy would have befallen me (if I left Wall Street). People say, ‘Oh, that’s so risky.’ It is and it isn’t. It’s not like I’m jumping out of an airplane without a parachute.”

But more than being happy in his career, Rascoff said the most important part of life is to be happy with your path and find your passion.

“For me, it took a couple of swings at bat…If I’d kept my head down at Goldman or TPG, I would have been successful with a different life. But I wasn’t passionate about either of those industries,” he said. “(My advice) is to do what you love. Don’t get caught up in the risk associated with those changes. Find something you love and do it.”

Follow Victoria Craig on Twitter @VictoriaCraig.