What a 66-year-old trans woman taught us about real courage in business
We weren't prepared for this one.
This week's conversation with Bobbi left us sitting in silence, touched, moved, inspired, for a good few minutes after we stopped recording. You know that feeling when something shifts inside you and you know you’re better for it? That's what this episode does.
Bobbi is 66, a transformational speaker and coach, and one of the most genuinely courageous humans I've had the privilege of speaking with. After decades of living in a man's body and conforming to everyone else's expectations, she made a choice that terrifies most of us: she chose truth over safety. She chose to transition her gender and body to a woman.
And what she's built from that place? It's extraordinary.
Here's what we took from it:
You can't outwork misalignment. Bobbi didn't find freedom by hustling harder or perfecting her strategy. She found it by paying attention to what felt alive inside her. When your actions flow from alignment rather than obligation, everything changes. Energy returns. Decisions get easier. Work stops feeling like you're dragging a boulder uphill.
Ask yourself this: Where am I working against myself instead of with myself?
Most of who you think you are wasn't your idea. For years, Bobbi believed she was introverted, limited, meant to stay quiet. She never questioned those labels until they started suffocating her. How many of us are building businesses around identities we inherited rather than chose?
Worth considering: If no one else's expectations mattered, who would you allow yourself to be?
People trust truth, not polish. When Bobbi stopped hiding, her confidence didn't vanish, it deepened. Her presence became unshakeable. Her message, clear. We're so afraid that showing our whole selves will cost us credibility. Usually, it does the opposite.
The entrepreneurs who move people aren't the ones with the perfect story.
They're the ones brave enough to tell their real story.
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About Bobbi
Bobbi is a keynote speaker and transformational coach who supports people and teams to release conditioned beliefs and to live aligned with who they truly are, not who they were told to be.
🎧 This conversation will stay with you. Listen to the full episode wherever you get your podcasts, or watch it here on YoTube.
We'd love to know what lands for you.
Until next week, founders! Remember, entrepreneurship isn't about having all the answers - it's about backing yourself when the answers aren't clear yet.
If you, like us, love to lean in and keep growing, we'd love to see you at our next free masterclass on Thought-Leadership & Personal Branding.
Vicki Abraham and Laura Ann Bell
Resilient Entrepreneurs Podcast | RE: Women Founders Circle