IConnect with Gwen at www.everydayeffectiveness.com

Uncovering Blind Spots in Successful Businesses

A Journey Through Systems Thinking: From Programming to Business Wisdom

This conversation between Karen Spies and Gwen Bortner reveals an unconventional career spanning four decades and 47 industries, showing how systems thinking helps entrepreneurs build sustainable, fulfilling businesses.

Gwen went to college in 1984 to become a math teacher but took a required programming class that changed everything. The teacher recognized her extraordinary talent. He revealed he’d been an original IBM hacker and told her, “You have more natural gifts than I’ve seen.”

At 19, she started working professionally, with General Mills as her first client. As a young woman in a male-dominated field, she faced skepticism but quickly proved herself capable.

As a freelance programmer in the early PC era, Gwen created databases for businesses before Oracle existed. This took her deep into countless industries—from cereal manufacturing to her favorite: the largest international supplier of bull semen, a hundred-million-dollar business run from a tiny farm town with 30 employees.

Working across these industries revealed her superpower: systems thinking. She could instantly see how disparate points connected. What seemed obvious to her wasn’t obvious to others—but she didn’t realize this was special until colleagues pointed it out.

After running an IT department that grew from 1 to 150 people in 18 months, the company’s IPO was cancelled due to 9/11. After cutting two-thirds of her department (including herself), Gwen became a professional knitting instructor—her “first second wind.”

Gwen now works with women entrepreneurs from early-stage to eight-figure businesses. She sees a common pattern: women who appear successful but privately wonder how long they can maintain their pace before something breaks.

Many were straight-A students who think there’s a “right answer” and work toward what they think success should be rather than what they actually want. They’re exhausted, doing all the right things, but not feeling successful.

Gwen’s core value is “context matters.” She helps clients get clear on what success means to them—not society’s definition, not what it was five years ago, not what it should be in five years. This requires considering spouses, children, aging parents, obligations, and where the business actually is.

She shared a powerful example: a woman who worked constantly to reach a success level that would give her more time with her kids. But by the time she achieved it, her kids were grown and barely spoke to her because she’d never been present—working even when she showed up to soccer games.

“You may have given up all the time with the kids because by the time you actually get there, the kids aren’t home,” Gwen explained. “Maybe you don’t have the $5 million job now, but in six years when your youngest is out of high school, you’re still going to have plenty of time. But they’re not going to go through high school again.”

When someone once called her an “out of the box thinker,” she laughed. “I’m not an out of the box thinker. I just know what’s in everybody’s box.” With 47 industries worth of experience, she can pull solutions from unexpected places.

You can find her at everydayeffectiveness.com for a 30-minute clarity call, or listen to her podcast to hear how she thinks—because it’s definitely not what you typically hear.

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