I Don’t Know Where This Conversation Is Going to Go…

Ever wondered what it really takes to conquer self-doubt, switch careers, or start a business from scratch—especially when you have no clue what you’re doing? In this episode, I sit down with Emmy Award-winning former TV news anchor turned on-camera coach, Kerry Barrett, to unpack the winding road from the newsroom to entrepreneurship.We both open up about the messy side of pursuing new dreams: overcoming fear of public speaking, dealing with imposter syndrome, learning on the fly, and making peace with failure. You’ll hear how Kerry pivoted her business multiple times, faced a steep learning curve, and discovered the power of relentless self-improvement.Whether you’re thinking about your own career leap, struggling with self-confidence, or just craving an authentic peek behind the scenes of working for yourself, I think you’ll find our conversation insightful. Plus, we share some practical wisdom on the importance of building a support network, testing your ideas, and (finally) not letting other people’s opinions define your story.Tune in for an empowering conversation loaded with real talk, lots of laughs, and actionable takeaways for anyone on the journey of reinventing themselves.Links mentioned in the show:Kerry’s LinkedIn Profile: www.linkedin.com/in/kerrybarrett/Check out Kerry’s YouTube Channel: www.youtube.com/@IAmKerryBarrettKerry’s Website: www.kerrybarrett.comMichael’s Website: MichaelPiperno.com

In this episode, I caught up with Tami Wong, and we had a wonderful conversation that touched on a variety of themes, including vulnerability, resilience, and personal growth.Tami is the founder of Hair Loss Pride and author of the children’s book "Hair Pride." In our conversation, she shared her personal journey of living with alopecia since her teens, detailing the struggles she faced with confidence, shame, and self-acceptance, as well as the turning points that led her to become an advocate for women experiencing hair loss. We also talked about Tami's transition from a corporate career in biotech and healthcare to launching her own business—one that offers not only coaching, wig consultations, and support groups, but also a powerful online community where women can share their stories and feel less alone. The conversation covers the significance of breaking silences around topics often considered taboo, including estrangement, anxiety, and grief. We delved into the challenges and rewards of entrepreneurship, the importance of representation in beauty and fashion, and the ripple effects created when people are brave enough to step forward and speak openly about their experiences.It's a great conversation about the transformative power of connection, sharing personal struggles, and embracing your story. Links Mentioned:Tami’s website: therealtamiwong.comHair Loss Pride on Instagram: www.instagram.com/hairlossprideShedding the Shame Podcast: therealtamiwong.com/podcast

In this episode, I sit down with Erin Davis to dive into a candid and wide-ranging conversation about connection, inclusion, and embracing change—both in and outside of the workplace. From stories about childhood belonging (or lack thereof) to how we make people feel in our everyday interactions, this episode explores how our lived experiences shape the way we form relationships and communicate across differences.You’ll hear Erin share her journey from being a hockey skeptic to lacing up her own skates, and how trying something new on the ice turned into powerful lessons about leadership, teamwork, and building truly inclusive spaces. Michael and Erin also share honest reflections about networking, communication challenges among generations, and how recalibrating our beliefs can be healthier than relentlessly pushing forward.Tune in for practical insights, a few good laughs, and a reminder that we all just want to feel included.Links Mentioned:Erin’s website: www.erindavisco.caFollow Erin on LinkedIn: www.linkedin.com/in/erin-davis-co/Unapologetic (Erin’s Podcast): www.erindavisco.ca/unapologetic-podcast

In this episode of I Don’t Know Where This Conversation Is Going to Go, I sit down with my friend and colleague Greg Ippolito — someone I’ve known for so many years that our conversations tend to zig, zag, loop back, and somehow land exactly where they’re supposed to.We talk about a lot — connection, marketing, music, creativity — but it all comes back to one simple truth: people. How we show up for each other. How we communicate. How we build trust. And how, despite all the digital noise we navigate every day, the most meaningful moments still happen one human at a time.Greg and I riff on where marketing is headed. We also get into why genuine, personal connection matters more than ever — not as a tactic, but as a way of being.Some of my favorite parts of our conversation are about music. We swap stories about rediscovering it during the pandemic, the strange comfort of gathering around a piano, and the science behind why certain songs make us feel seen, understood, or simply less alone. We even wander into the nostalgia of vinyl. You'll see.We also talk business. The messy blend of sales and marketing. The power of referrals. The magic that happens when you experiment with content instead of overthinking it. And the humble, often invisible ways people help shape our lives without us realizing it until years later.It’s a thoughtful conversation, and it’s a reminder that connection — real connection — is still at the heart of good work and a good life.Takeaways:Real connection always beats slick, surface-level marketing.Revisiting old passions (like music) can bring people closer.Creativity thrives when you’re willing to experiment and not take yourself too seriously.Many of the moments that shape us don’t look significant until we look back.Links Mentioned:IMA: ima314.comMichael Piperno: michaelpiperno.com