The Art of Conversation with Charlotte Jackson

After 4+ years as a community builder at the Chief of Staff Network, David opens up about transitioning to an advisor role. Taylor Harrington interviews him about helping build the membership-based community business mainly through events and content. His role focused on growth and member experience. David shares the emotional complexity of leaving something you're known for and how he is thinking about what is next. If you are a community builder, looking to work in the field, or thinking about a work transition, this episode is for you.

In this episode, you will learn from Charlotte Jackson, Co-founder of the Candid card deck, Substack writer, and transitions coach, about transforming conversations through better questions. Charlotte explains why "What's the dream?" works better than "What do you do?" You will learn her “pebble vs. boulder" approach to asking specific, disarming questions that invite genuine responses rather than rehearsed answers. You will also learn about finding conversational "trailheads" and how intentional questions can deepen relationships and self-understanding. Excited for you to build and grow your Portfolio Career!

Misha Glouberman has turned his passion for bringing people together into a thriving consulting business, helping organizations transform their conferences, retreats, and gatherings into meaningful connection experiences. In this conversation, Misha shares how he evolved from co-creating the popular Toronto lecture series Trampoline Hall to building a full-time career improving corporate events. He reveals his four-step framework for successful events (starting with having a clear goal), explains practical techniques like helping attendees find their conversation partners, and discusses why most event organizers focus on entertainment instead of connection. Misha also opens up about overcoming the common aversion to sales that many community-focused professionals face. If you are looking to have a career in events and community building, this episode is for you! 

What happens when you apply corporate strategic planning to your own life? After 12 years in finance and burning out at a high-growth startup, Michelle "Mimi" Casazza created her own strategic framework to design her dream portfolio career. What started as a two-month sailing gig turned into four years of building multiple revenue streams as a CFO consultant and executive coach. Mimi shares her "Matria Life Chart" approach to transitioning from corporate burnout to purposeful portfolio living. Whether you're stuck in corporate or already building a portfolio career, this episode shows how strategic thinking can help you design a life you actually want to live.

When Kevin Zych left his corporate job three years ago to become a full-time live event illustrator, he had just enough proof of concept from brand sponsorships to believe he could make it work.In this episode, Kevin shares his unconventional path from English major to Zen monk to professional street artist, revealing how he built a creative career around "reportage illustration". He discusses the practical realities of going full-time creative without a plan, why he believes art creates human connection, and how his time as a Zen monastic shaped his philosophy of embracing risk and immediacy in both art and career decisions and much more.

Bart Dziedzic and Max Zucker from MrBeast's strategy team share how they went from investment banking to working at one of the world's biggest YouTube channel and media company. In this episode, you will learn their unconventional networking strategies, how LinkedIn is underrated, and the importance of adding value before asking for anything. You will also learn about community building, the creator economy's anti-establishment culture, and why 1,000 true fans beat 10 million passive followers. If you are looking into working at creator companies or transform their career through authentic relationship building, this episode is for you!

Are you looking to start your own thing? Listen to this episode with Tish Dignam about her journey from corporate to entrepreneurship. Tish emphasizes the importance of adopting a business owner mindset, including marketing, operations, and product development. Tish also highlights her emergent strategy for business growth, using AI tools like ChatGPT for introspection and market segmentation. She also shares her success with TikTok, which has generated significant inbound leads. Tish's business has evolved from brand marketing coaching to clarity coaching, driven by client referrals and her ability to help founders communicate effectively. If you are looking to start your own service-based business, this episode is for you!

In a world that often feels chaotic and uncertain, how do we discover what truly matters? In this Hot Pod event episode, you will hear stories about people have been finding meaning through learning, community, service, and more. Whether you're navigating a major life transition or simply seeking deeper satisfaction, this conversation offers insights and ideas for you to hopefully find more meaning.

Are you looking to make work more enjoyable and meaningful? Listen to this episode with Bree Groff, the author of "Today Was Fun.” In this episode, you will hear Bree share her seven rules for better days. Bree advocates for being a "meets expectations employee and an exceeds expectations human," focusing ambition on relationships and personal fulfillment rather than solely on work success. In addition to some moments of personal stories, this episode concludes with Groff's daily journal prompt: asking "Was today fun?" and identifying one moment of joy, even on difficult days, as a way to actively seek and appreciate the happiness available in everyday life. Excited for you to build and grow your Portfolio Career!

Are you looking into better understand yourself and the world around you? Listen to this new episode Mari Andrew about her new book, "How To Be A Living Thing," which explores lessons from animals. Mari discusses her cat Sunny, who taught her about unconditional love and autonomy. She highlights the sensitivity and emotional intelligence of horses, which mirror human emotions. Mari also reflects on rats, likening them to our societal shadows. She emphasizes the importance of embodiment and intuition, drawing parallels between human and animal behavior. She also touches on the connection between pregnancy and creativity, advocating for a devotion to embodiment. Here we go with Mari!Read Mari's book