What does it really mean to have an entrepreneurial mindset? Is it about founding startups, hustling 24/7, or quitting your job to “follow your passion”? For John Wightkin—a veteran entrepreneur of 40 years, leadership coach, and co-founder of TakingFlyt—it goes much deeper.
In a recent conversation, John broke it down.
“Let’s start with grit,” John said. “It’s a buzzword these days, but it’s also a roadmap. For me, the entrepreneurial mindset lives inside that four-letter word.”
Let’s explore what each letter of G.R.I.T. means through John’s eyes—and how you can apply it, whether you’re launching a venture, stuck in a job, or just trying to navigate your next big move.
Entrepreneurs take chances. But John isn’t talking about reckless risk. It’s about calculated courage.
“I’ve launched over 50 different ventures,” he says. “Some inside companies, some outside. What helped? I kept taking swings at the bat. You try. You explore. And when one of those swings connects—you go deep.”
That “Go” mentality is crucial in today’s world, where the old model of one job, one company, one ladder is fading fast. John encourages young people to move beyond fear, explore opportunities, and embrace the reality that most careers will evolve and pivot multiple times.
“The world is uncertain,” John added. “Higher ed hasn’t fully caught up, but we can prepare students to move in uncertainty. That’s what I try to instill in my classes.”
Choosing a path is only part of the equation. Sticking with it—especially when it gets hard—is where grit shows up.
“There will be bumps. Highs and lows. People doubting you. But if something lights you up, if it aligns with your strengths, be relentless in the pursuit.”
Resilience is built through exposure to discomfort in safe environments. John shared how TakingFlyt’s Cognitive Play program trains the brain to navigate uncertainty without freezing.
“When your brain is primed for change, that’s neuroplasticity at work. We use improv, neuroscience, and entrepreneurship to simulate uncertainty. That way, when the real world hits—you’re ready.”
Creativity isn’t just for artists and designers. In John’s world, it’s essential for survival and success.
“Be innovative. Be curious. If you can’t get through the front door, find a side window.”
Ingenuity means optimizing what’s in front of you—even within a job you’re not thrilled about. It also means redefining your work based on your strengths and what brings you joy. That’s where flow comes in—a concept from positive psychology that describes the magic moment when your skill meets the right challenge.
“When you find flow, creativity, joy, and innovation spike. If you’re disengaged, it might be because your strengths are capped. You’re not in the flow zone.”
This may be the hardest one, John admits.
“Trust your gut. I used to get goosebumps when something felt right—but I didn’t always listen. I regret not chasing certain opportunities that I knew were right for me.”
Trust doesn’t mean impulsivity. It means being tuned into your instincts and letting your body and mind work together. John emphasizes having the right guardrails—supportive tools, mentors, and data—to make wise but bold decisions.
“Intuition ties it all together. When you feel that tingle, that knowing—chase it. You don’t get unlimited chances.”