Maxanne Caines joins me for a real, funny, and honest look at how she becomes who she is, from a childhood shaped by structure and love to a life built on pivots, service, and joy. We talk dyslexia, confidence, career turns, and what it actually means to sit on the City of Hamilton council and represent residents well.

We get real about her experience with severe dyslexia and ADHD traits, what masking looked like in school, and why self-talk, tools, and grace still matter even when you’re confident. If you’ve ever felt embarrassed by how your brain works, this will land hard and hopefully bring you relief.

We also talk about her academic comeback, from boarding school in Canada to thriving at an HBCU at Oakwood University, then making the tough call to leave the expected pre-law track for international relations. Maxanne shares what life is like living in Brussels, working with the Bermuda government office, and chasing a diplomatic future until COVID changed everything overnight.

From there, we get into entrepreneurship and what it means to build The Pristine Group together with trust, boundaries, and room to learn. And yes, we break down what a City of Hamilton counselor actually does, what governance is versus operations, why legislation matters, and how accountability and transparency are supposed to work in local politics in Bermuda.

If you’re into women’s leadership, learning differences, career pivots, entrepreneurship, or civic engagement, hit play, then subscribe, share this with a friend, and leave a review so more people can find Hustle Her Podcast.

You can’t solve a problem you refuse to name, and Bermuda has been trying to address homelessness without even having a legal definition for it. That’s why I invited Denise Carey, executive director of Home in Bermuda, to sit down with me after watching her take the room by storm at Disrupt HR. What she shares is clear, direct, and deeply human: homelessness isn’t a personality type, it’s an experience, and it can happen through far more pathways than most of us want to admit.

We get into what “homelessness” actually includes using the European Typology of Homelessness and Housing Exclusion: roofless and rough sleeping, emergency shelter, housing insecurity, inadequate housing, hidden homelessness, seniors on fixed incomes, people aging out of systems, domestic violence displacement, people leaving institutions, and working people priced out of rent. Denise explains how Bermuda’s housing pipeline gets bottlenecked when “temporary” shelter turns into decades, and why derelict buildings and vacant properties have to be part of any serious housing strategy.

We also talk about community safety and reentry housing for people leaving incarceration, including the uncomfortable truth that stability creates accountability. Housing, employment, and support reduce recidivism, lower public costs, and make all of us safer because we know where people are and how they’re being supported. Along the way, Denise shares the emotional toll of this work and the belief driving her forward: every person in our community has value, and none of us has the right to give up on them.

Subscribe for more real conversations, share this with someone who needs a new perspective on homelessness in Bermuda, and leave a review if you want more guests like Denise. What part of this conversation challenged your view the most?

What if the bravest thing you can say is, “I became a psychologist to save myself”? That line from Dr. Jana Otterbridge sets the tone for a conversation that moves with heart and precision, from adoption and identity to trauma, triggers, and the radical act of finding a therapist who truly fits. We don’t stay on the surface. We talk about the unnamed questions adoptees carry, the long tail of psychological injury, and how healing starts when we stop calling our wounds a personality and start building new responses with care.

We also zoom out to the systems shaping us. Jana shares how UK training sharpened her voice when leadership curricula erased Black examples, and why representation isn’t a buzzword, it’s a map. We get honest about the multigenerational workplace: Boomers, Gen X, Millennials, and Gen Z colliding over “work ethic” and mental health. Instead of the tired “work-life balance” script, Jana offers a practical capacity framework, adjustable daily “bubbles” that match energy to commitments without guilt. It’s a mindset shift leaders can operationalize and individuals can practice right now.

Threaded through it all is purpose. Jana describes peace as the sign she’s on path, able to teach in a boardroom at noon and mentor on a street corner by dusk. She speaks to her younger self with tenderness, “you’re safe, you’re free”, and imagines a next chapter that includes anonymous giving and wider impact. If you care about mental health, organizational culture, representation, or simply living with more truth and less noise, this one will stay with you.

If this conversation moved you, share it with a friend, subscribe for more honest stories, and leave a review to help others find the show. What capacity are you honoring today?