Trust the Boat: Courage, Failure, and the Long View of Leadership
Some leaders follow a map.
Others learn by jumping — and figuring it out midair.
Janis Mitchell has never waited to feel completely ready. A longtime entrepreneur, woman in tech, and talent strategist, she built her career by trusting instinct, embracing failure, and leaning hard into resilience when certainty wasn’t available. Listening to her story feels like sitting across from someone who has lived many chapters — and isn’t interested in sanding down the edges.
For Tiffany Odutoye, this conversation is less about titles and more about truth. Janis offers a rare blend of grit, humor, and hard-earned wisdom — especially for women who feel pressure to have everything figured out before they begin.
A Career Built Without a Straight Line
Janis’ journey into leadership didn’t follow a neat trajectory. She began her career young, navigating sales, law firms, medical sales, and eventually technology — learning each space by doing, not waiting for permission. Living with dyslexia shaped how she approached work: differently, creatively, and unapologetically.
Rather than seeing that difference as a limitation, Janis leaned into it. She found patterns others missed, identified real business problems, and built solutions from lived experience. Over the years, she launched multiple businesses, entered industries she’d never formally trained for, and rebuilt herself more than once.
Failure was not a detour — it was the classroom.
Time Behind the Boat
One of Janis’ most powerful lessons comes through a simple metaphor.
In water skiing, she explains, safety and confidence don’t come from staying upright — they come from leaning back and trusting the boat. But you can only learn that trust by spending more time behind it.
Leadership works the same way.
Without experience — without falling, failing, and navigating rough water — it’s impossible to anticipate challenges or respond with grace. Janis sees this lack of “time behind the boat” as one of the biggest gaps facing young leaders today.
Her message is clear: resilience, work ethic, and confidence can’t be downloaded. They’re built — slowly — through experience.
Standing Strong Without the Emotion
Janis speaks candidly about another leadership shift: learning to remove emotion from decision-making without losing kindness.
Strength, she says, often earns labels — especially for women — but clarity and grace can coexist. Business decisions don’t have to be personal, and feedback isn’t a verdict on self-worth. The ability to separate the two is a skill learned over time — and one she believes women deserve permission to practice.
Advice to Her 25-Year-Old Self
When asked what she would tell her younger self, Janis answers honestly — and without sugarcoating:
“You have to trust the boat, and you only learn that by having more time behind the boat.”
“Don’t do it.”
Spoken with humor and hindsight, her answer reflects both the difficulty and the depth of the road she traveled — and the strength it ultimately built.
Her Superhero / Mentor: Donna James
For Janis, mentor and superhero are one and the same.
She credits Donna James with grounding her, inspiring her, and walking alongside her through decades of growth. Donna’s vision, commitment to community, and ability to lead with both strength and heart continue to shape Janis’ leadership today.
“She keeps me inspired,” Janis shares. “And she keeps me honest.”
Why Janis Mitchell’s Story Matters
Janis’ story is a reminder that leadership is not about perfection — it’s about persistence. It’s built through courage, repetition, and the willingness to trust yourself before the outcome is clear.
Her life proves that you don’t rise by waiting.
You rise by jumping — and learning on the way down.
🎧 Listen + Subscribe to How She Rises to hear this conversation in Janis’ own words.