Do you have the courage to make the riskier choice if you know it will make you happy?

That’s the question that faced Canadian entrepreneur Carol Leaman when she sold her share of social analytics company PostRank to Google in 2011. The deal came with a cushy, well-paid job if she was willing to stay on–an offer many founders would have accepted with enthusiasm. But declined to take the job and chose to start over instead. Her story illustrates beautifully how putting your own dreams first and refusing to play it safe can make all the difference for those who dare to do it.

Here’s Leaman’s approach:

1. Ask yourself what makes you happy.

PostRank started out as a free web tool that she developed into a powerful social ranking service that Google knew would fill out its analytics offerings. When the search giant acquired PostRank, the job offer to Leaman for staying on was quite enticing. “It would have doubled my annual compensation, plus given me Google stock and options worth a significant amount,” she says.

Why did she say no? “If I were in my 20s, I would have gone to Google,” she says. But now, in her 40s, “I’m of an age when I know what I’m good at and what is going to make me happy, and my sweet spot is growing an early-stage company from a tiny nut to a big tree.” With PostRank already established, she was ready for a new challenge.

2. Be willing to gamble on yourself.

Turning down the Google job took particular courage because just nine months earlier, Leaman and her husband of 18 years had divorced. It was an amicable split, she says. “We recognized that we are different people who have different goals, and one of the key differences is I am a risk taker.”

Leaman proved her willingness to take a risk when it came to dividing up the couple’s assets. Although both were working at the time of the divorce, Leaman’s husband had spent five years as a stay-at-home dad, allowing her to pursue her career. “I was the ambitious one,” she says.

When it came time to divide up assets, they realized both would be much worse off if they simply split it all down the middle. “I didn’t want to leave him feeling unsafe so I made the decision to take it on the chin myself,” she says. “I looked in the mirror one day and realized that I believe in myself. I’ve always been able to figure out a way forward.”

And so she agreed to leave her husband with most of the marital assets, taking only her PostRank salary. When the company was sold, she split the proceeds with him as required by Canadian law. Having turned down the Google job and paid off some debts, that left her with about two years’ worth of money to live on, if she was frugal.

3. Double down.

But Leaman wasn’t prepared to be frugal because she’d already found her next opportunity. In the winter of 2010, a few months before Google acquired PostRank, the founders of a start-up called Axonify contacted Leaman, asking for some general advice. At the time, she says, “It was not a company, it was a piece of code and one customer.”

Leaman saw a lot of potential in the new venture, which provides a platform for three-minute daily employee training on any topic, with gamification to reward learning. When PostRank sold, she began thinking that Axonify could be her next venture.

Axonify’s founders wanted to hire her as CEO, but she wanted to be an owner instead. So she found a business partner to invest along with her and help her run the company, and together they bought the founders out. “Basically, I put every cent I had into buying Axonify,” she says now.

That was a big leap for someone with no job, no income, and monthly child support payments. Four years later, it’s looking like the right choice. “When we took it over, we pitched the old platform on the trash heap because it was poorly architected. We hired developers to rebuild it,” she says. In essence, what she’d paid for was the concept and the company’s relationship with a single big-name client, Pep Boys. “We ended 2012 with $300,000 in revenue and four customers, and we’ll end this year with about 12 million in annual revenue and 100 customers,” she says. Those 100 customers are an impressive group that includes Walmart, Johnson & Johnson, and GE.

4. Remember that the safe thing may not be the right thing.

“Taking the Google job was without question the secure option because I had no safety net,” she says. “And I am 1,000 percent glad I made the choice I did because the new company is going to be massively successful.”

That’s the lesson she wants to pass along to other entrepreneurs. “Life is here to challenge us,” she says. “We all have the capability of meeting challenges if we just believe that we can. I’ve always expected to be successful no matter what life threw at me. I feel like a cork bobbing in the ocean–no matter how big the waves I will always pop back up and eventually hit dry land.”

“If your gut tells you to do something that is causing you a lot of stress, think back to how you got past other challenges and just have faith that you will get past this one as well,” she adds. The safe thing to do isn’t always the right thing to do. “So you have to feel OK and secure within yourself.”