“From Your Big Break to a Big Mistake: How to Have Resilience and Remain Authentic.” From the instant I read that headline, I was compelled to attend this Rotman School of Management talk, featuring internet veteran Lorna Borenstein. A Toronto native now living in California, Borenstein launched eBay Canada out of her guestroom with a newborn baby on her hip. As her bio says, “after 15 years in high-profile roles at eBay, HP, Yahoo!, and Move, Inc., Lorna challenged long-held beliefs about business culture and wellness, and decided to start her own own company focused on pursuing your best self, Grokker.”

The part about “challenging long-held beliefs about business culture” spoke to me. I think that’s because, since starting Felicity more than five years ago, I’ve challenged these long-held beliefs on a daily basis. And even if I’ve gotten really good at setting my own “off the ladder” definition of career and business success, I had never taken the opportunity to leave the working world entirely behind, to explore what “success” might look like on the outside. Lorna had.

Once Borenstein had made her mark on of some of the world’s best-known brands, she was hired by a large corporation with the task of turning it around, complete with an activist shareholder, and the dysfunctional team she’d inherited. She used a powerful sailing analogy when discussing this period in her career: that as women especially, we are conditioned to tack against the wind. She came to believe that the measure of a woman isn’t how you fare when the wind is at your back, it’s how you deal with it when it’s in your face.

The effort left her overwhelmed and burned out. A good friend challenged her to think of an alternative she hadn’t considered: quitting.

Said Borenstein, “I had worked so hard at accumulating success as a gateway to joy. But it’s not.” And Borenstein found herself miserable at the thought of pushing forward into the wind any longer.

So she stepped out of the rat race, and resigned.

But if success (as she had traditionally achieved it) wasn’t the gateway to joy, what was?

While “off the ladder,” Borenstein realized that rather than working against the oncoming wind, the path to joy could be found by starting with what authentically ignites your passion, and growing from there.

There are definitely times that I do things because I feel “should,” even if I have to tack against the wind to do so. I think there is a certain amount of tacking against the wind that you need to go through, at times, in life and especially if you live life as an entrepreneur. But Borenstein’s talk impressed upon me the need to pause before I act, to evaluate: am I tacking just because I “should?” Will the struggle be worth it in the end? Or are there ways I can harness the headwinds, sail in the other direction, and succeed in business as my authentic self?

By virtue of having already stepped off the traditional career path to start my own business, I’d already shed some of the prevailing definitions of success, such as titles and corner offices. I’m happy with my office, in a (mostly) quiet corner of my home, and there is a certain badge of pride I wear for being able to define my own title and career path.

I selected the name “Felicity” because it means “to do things with ease.” I was fed up with the convoluted processes of the traditional business world and wanted to build a company that would do things the most efficient way, with the best outcome. Borenstein’s talk was a good wake up call to me as the skipper of the ship that is Felicity, to be on the lookout constantly for ways to sail, both personally and professionally, with the wind at my back.

After sharing this post with her, Lorna had one more piece of inspiring advice: “The more we contrarians speak up and provide alternative pathways to personal fulfillment, the better off the next generation will be.”

Originally published at felicitypr.com