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Second Acts: Jennifer Olsen

The Coach

By Rob Smith October 18, 2024

A woman with long brown hair sits on a chair outdoors, wearing autumn essentials: a black cardigan over a patterned blouse, smiling at the camera. Green foliage is in the background, embracing autumn's charm.
Photo courtesy of Jennifer Olson

This article originally appeared in the September/October 2024 issue of Seattle magazine.

Our Second Acts feature is proof that it’s never too late to find success in entirely new ventures. These stories celebrate individuals who discovered purpose and fulfillment in the later chapters of life.

For many, turning 50 is a tipping point, a time to reflect on mortality, health issues, retirement concerns, and youth slipping away. For Jennifer Olsen, it meant a new career.

Olsen, who recently hit the midcentury mark, launched Jennifer Olsen Coaching last February, and earned an executive coaching certificate from Harvard Business School shortly thereafter. She previously worked in biotech, and founded HR consultancy Resourceful. Four years ago, she sold the company to HR consulting firm OneDigital, where she became principal of the Northwest practice.

Olsen admits to some serious soul searching on her birthday last year, but — unlike many who fear starting over — she took the plunge, figuring it was now or never. She wanted more time to take care of her parents, who have health issues, and be more present for her son, who is entering his senior year in high school.

“I’ve got a drum kit behind me, but I wasn’t able to really practice in the way that I wanted. I had been a big runner, but wasn’t doing that anymore. There were just other aspects of myself that I felt I was denying and losing.”

“Was I living the life that I wanted to be living? Why was I waiting to start the next journey? I get a lot of joy from watching people become more who they are.”

Most of all, though, she wanted to pursue her longtime passion of owning her own executive coaching business. She became a certified executive coach in 2016, but her work at OneDigital — where she was focused mainly on sales and operations — took her further away from doing work she loved.

“Was I living the life that I wanted to be living? Why was I waiting to start the next journey?” she recalls. “I get a lot of joy from watching people become more who they are.”

There were tradeoffs. Her income is significantly less. She enrolled in the Hudson Institute For Coaching in Santa Barbara, Calif., an in-person program that “took a significant amount of time.” And while business has been steady, mostly because of referrals, the executive coaching field is crowded and competitive, but growing. Allied Market Research estimates that the online coaching market is $6.2 billion, and will reach $11.7 billion in the next eight years.

Jennifer Olsen Coaching offers personalized executive and small-team coaching for leaders across a wide range of fields. She says her clients so far are generally navigating a time of transition, a new team, or an organizational change. Some are contemplating “big decisions” such as changing jobs, starting a business, or selling a company. She also offers customized workshops for teams.

She adds that she “absolutely loves” the work.

“I told myself that this is the year to play with ideas,” she says, adding that she’s creating new workshops and trying different approaches. “It’s ended up being a lot of fun. I’m kind of getting to use some creativity that I didn’t get to in the past. What drives me is to really help people.”

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