A conversation with Jill James, contributor to The Wisdom Collection

For fifteen years, international bestselling author and business consultant Jill James chased the same elusive promise: finding a business environment that would appreciate who she was and what she believed in. From investment banking to personal financial management to technology startups, she kept hitting the same wall.

“Each place I thought, okay, well there’s more space in this next place for me and what I think and how I want to do it,” Jill recalls. “And in each place, I found that there was this strict limit of shareholder value or the board says we have to do this, or this is just the way things are. Suck it up, buttercup.”

The Breakthrough Moment

Everything changed when Jill started her own business and began working with entrepreneurs who shared a common refrain: “I don’t want to do it that way.” This simple statement became the foundation of her approach—and the core message of her chapter in The Wisdom Collection.

“You don’t have to separate who you are and what you believe in when you walk into owning a business,” Jill explains. “Who you are in your day-to-day life and what you stand for, when carried over into how you design and operate a business, makes it a better business for you and makes you more successful.”

This isn’t just feel-good philosophy—it’s practical business strategy. Jill James discovered that entrepreneurs who build businesses aligned with their values don’t just survive; they thrive. More importantly, they stick with entrepreneurship instead of burning out and returning to corporate jobs.

Why This Message Matters Now

In an era where many people feel they’ve lost agency in their lives, Jill James’s approach offers something powerful: the ability to create meaningful change through work while earning a healthy living.

“I find fewer people that feel like they have agency in their lives,” she observes. “There is a wave of things that happen to them, and if they don’t jump on and ride that wave, there is no other option. But the ocean is large, there are many waves.”

For entrepreneurs moving from small to larger businesses, this message is especially crucial. Complexity can pull founders away from their core values, leading them to “do stuff without really understanding why you’re doing it.”

The Co-Creation Approach

Jill’s work centers on what she calls “co-creation”—working with entrepreneurs not to plug their ideas into someone else’s formula, but to ask fundamental questions: “What do you want this to be? What are the things that are available to you if that’s how you want it to be?”

This process requires ongoing vigilance. Even successful entrepreneurs can slip into conventional patterns when surrounded by people “doing it the conventional way.” Jill regularly reminds clients of their original intentions: “No, you said you didn’t want to have to work every Saturday. You said you wanted to have vacation with your family.”

Beyond the One-Size-Fits-All Model

Jill’s message challenges the prevailing startup narrative that success requires following a predetermined path toward venture funding and eventual exit. Instead, she champions the “many ways to be successful in a smaller-sized business” that create good jobs, serve communities, and provide fulfilling work—all while generating healthy profits.

“There are so many business owners that are small to mid-size that have very healthy companies that have never taken a dime from an investor,” she notes. “They are truly CEOs of these businesses. And there is a way to do that.”

The Wisdom Collection, featuring Jill James’s insights on values-driven entrepreneurship alongside other transformative perspectives, is now available from Summit Press Publishers.