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.