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The Peering Podcast

The Peering Podcast

Di: Mike Richardson
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Peers chatting about the demand upon leaders these days, peering into the challenges of collective intelligence and agility to remain future proofed in the face of accelerating disruptive change. With your hosts Mike Richardson and colleagues, we will be peering into how the peer power fuels leaders powered by collective intelligence and wisdom. The Best Way to see the Future is to Peer into it Together.© 2026 Mike Richardson Economia Gestione e leadership Leadership
  • Transforming Midlife Careers Through Portfolio Models and Peer Communities
    Jan 19 2026
    For professional women navigating midlife career transitions, the traditional corporate ladder often presents diminishing returns coupled with increasing ageism and sexism. The problem isn't just external barriers but internal psychological and emotional challenges—fear of change, identity crises tied to titles and salaries, and financial anxieties about stepping away from established careers. This episode presents a powerful solution: reframing midlife as an expansion of choices rather than a decline, and embracing portfolio careers as the pathway to purpose, passion, and profit in what Heidi Hutchison calls the "Third 30"—the final third of life where longevity offers a blank slate for reinvention.Heidi Hutchison, founder of Third 30, shares her personal journey from being unexpectedly let go during a corporate reorganization to building a multifaceted portfolio career that now helps other women navigate similar transitions. The conversation explores how portfolio careers represent not just a fallback option but a strategic choice for greater security, fulfillment, and impact. Unlike traditional employment where one phone call can end a career, portfolio careers offer diversification that creates genuine independence and resilience.The episode introduces the concept of "elegant simplicity"—the idea that true simplicity emerges only after working through complexity, not by avoiding it. This framework becomes essential for women seeking to identify their core values and through-lines that will guide their portfolio career development. Heidi emphasizes that midlife represents a shift in values: from climbing corporate ladders and chasing titles to seeking meaningful contribution, feeling valued, and leaving a lasting impact.Practical strategies emerge throughout the discussion, including building a financial runway while still employed to enable smoother transitions, leveraging peer advisory communities for support and accountability, and doing the deep internal work to identify what truly matters at this life stage. The conversation reveals that portfolio careers aren't just about having multiple income streams but about aligning work with evolving values and creating work structures that support rather than constrain personal growth.Mike Richardson shares his parallel journey from corporate executive to portfolio professional, highlighting the universal nature of these transitions and the importance of community support. Both hosts emphasize that portfolio careers are becoming the new normal—not a question of "if" but "when"—and that starting the exploration process earlier rather than later creates more seamless transitions and better outcomes.HighlightsTransform midlife from perceived decline to an expansion of career choices and personal agencyBuild financial runway while employed to create buffer for portfolio career developmentIdentify evolving core values that shift from title-chasing to impact-driven workLeverage peer communities for safe exploration of vulnerabilities and transition planningDevelop portfolio careers as strategic diversification against corporate instabilityTranslate mindset shifts into actionable roadmaps for career activationRecognize that midlife represents your power years of maximum wisdom and confidenceImportant Concepts and FrameworksThird30 Framework — Heidi Hutchison's model for women navigating midlife career transitions with purpose, passion, and profitElegant Simplicity — The concept that true simplicity emerges only after working through complexity, not by avoiding itPortfolio Career Model — Building multiple professional roles and income streams around a common core passionAgeism in Corporate Environments — External barriers facing experienced professionals in midlife transitionsSexism in Workplace — Additional gender-based challenges women face in career advancementCore Values Assessment — Internal work to identify what truly matters for meaningful career transitionsPeer Advisory Groups — Structured communities for executive support and collective intelligence Tools & Resources MentionedThird30 — Heidi Hutchison's platform helping professional women rediscover purpose and activate their next chapter - https://third30.com/Vistage — Executive coaching and peer advisory organization where both hosts previously worked - https://www.vistage.comCalls to ActionStart exploring portfolio career options while still employed to create a financial runway for smoother transitions.Join peer advisory communities or mastermind groups to gain support and accountability during career transitions.Conduct a core values assessment to identify what truly matters at your current life stage versus earlier career phases.Begin building your portfolio career in parallel with current employment rather than waiting for a forced transition.Connect with Heidi Hutchison through Third Thirty for structured guidance through midlife career transitions.Reframe your ...
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    47 min
  • Launching Your Portfolio Career: From Corporate Exit to Sustainable Success
    Jan 13 2026
    This inaugural episode of Portfolio Conversations marks the launch of a dedicated series within the Peering Podcast, focused exclusively on the rising trend of portfolio careers. Hosts Mike Richardson and Zed Vakil, with a combined 40 years of experience in portfolio work, introduce listeners to the realities of transitioning from traditional corporate roles to building sustainable, multi-faceted professional lives.The episode begins by defining what constitutes a portfolio career—a professional model where individuals build a collection of diverse income streams and activities such as consulting, coaching, board positions, facilitation, and mentoring. Both hosts share their personal journeys: Mike's 25-year portfolio career began after leaving a corporate aerospace role post-9/11, while Zed transitioned following the 2008 financial crisis after decades in corporate, venture capital, and consulting roles. Their meeting through The Portfolio Collective (TPC) community highlights the growing ecosystem supporting portfolio professionals.A central theme emerges: the transition from corporate to portfolio work represents more than just a career change—it's a fundamental identity shift. Mike describes the stark reality of going from "somebody" in a corporate role to "nobody" in the independent market overnight. This underscores the importance of psychological preparation and the need to rebuild professional identity from the ground up. The hosts emphasize that portfolio success requires deliberate planning, not just luck or corporate credentials carrying over.The conversation reveals critical success factors for portfolio professionals, including the necessity of aligning work with passionate purpose, developing clear value propositions that solve real problems (not just offering solutions seeking problems), and understanding one's marketplace deeply. Zed identifies two common archetypes among transitioning professionals: those who approach the shift with humility and systematic learning, and those who mistakenly believe their former corporate status will automatically translate to portfolio success.Community emerges as a vital component for overcoming the loneliness and complexity of portfolio work. The hosts discuss their creation of Portfolio Peer Forums—structured monthly virtual gatherings that provide ongoing support, collective intelligence, and accountability beyond superficial networking. This addresses what they identify as a significant gap in the support ecosystem for portfolio professionals.Looking forward, Mike and Zed announce their collaborative book project, "A to Z Road Atlas of Portfolio Career Success," aimed at creating a comprehensive reference resource for navigating portfolio careers. They also hint at developing AI-enabled tools to help professionals align their work with their core purpose more efficiently. The episode concludes by reframing the concept from "portfolio career" to "portfolio life," emphasizing how this approach integrates professional fulfillment with personal freedom, health, family considerations, and financial planning into a cohesive whole.HighlightsTransitioning from corporate to portfolio requires rebuilding professional identity from scratch, not carrying over former statusAligning work with passionate purpose is essential for sustainable portfolio success, not optionalPortfolio professionals must shift from being solutions looking for problems to solving real market needsCommunity support through peer forums addresses the loneliness and complexity of independent workSuccessful portfolio careers demand systematic planning and humility, not just relying on past credentialsThe portfolio model integrates professional work with personal life priorities for greater fulfillmentAI tools can accelerate self-discovery and alignment processes for portfolio professionalsImportant Concepts and FrameworksPortfolio Career vs Portfolio Life — The shift from viewing independent work as just a career to integrating it holistically with personal priorities, health, family, and financial planningPassionate Purpose Alignment — The critical process of ensuring portfolio activities align with core motivations and values for sustainable engagementValue Proposition Development — Creating clear offerings that address specific market problems rather than generic solutionsPeer Advisory Forums — Structured group meetings that provide ongoing support, accountability, and collective intelligence for portfolio professionalsIdentity Transition Framework — The psychological shift required when moving from corporate roles to independent portfolio workA to Z Roadmap Methodology — Systematic approach to navigating the complete journey of portfolio career developmentTools & Resources MentionedThe Portfolio Collective (TPC) — Global community for portfolio professionals with freemium membershipLink: https://portfolio-collective.com/REF (Renaissance Executive Forums) — ...
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    50 min
  • Navigating the AI Era: Why Technology Leaders Need Peer Forums Now More Than Ever
    Dec 22 2025
    Technology leaders face unprecedented challenges in the AI era, caught between rapid technological advancement and the human complexities of organizational change. This episode explores why peer forums have become mission-critical for technology executives who must navigate getting a "seat at the table," managing AI implementation risks, and balancing technical expertise with leadership development.The conversation reveals that technology leaders often struggle with being seen as strategic partners rather than "technology plumbers" within their organizations. With AI democratizing powerful tools, non-technical leaders are making technology decisions without understanding security, compliance, and change management implications. This creates both opportunity and risk—technology leaders can elevate their strategic importance but must also protect their organizations from costly mistakes.Scott Krawitz introduces the concept of "conscious AI"—a two-pronged approach that combines humanistic technology leadership with personal consciousness development. The first side focuses on implementing AI responsibly through change management and communication strategies that elevate existing teams rather than simply cutting headcount. The second side emphasizes developing conscious leadership skills that AI cannot replicate, including emotional intelligence, strategic thinking, and ethical decision-making.Peer forums provide the unique environment where technology leaders can process these complex challenges through three key components: educational sessions with expert speakers, roundtable discussions for sharing and self-assessment, and case processing where members bring their most pressing issues for collective problem-solving. This 2% monthly time investment helps technology leaders navigate the other 98% of their work with greater confidence, courage, and strategic clarity.HighlightsTechnology leaders must shift from being seen as "necessary evils" to strategic differentiators who can drive revenue and customer retentionEmployees are technology customers whose satisfaction directly impacts retention and organizational performanceAI implementation requires balancing democratization with security, compliance, and change management considerationsPeer forums provide the only space where technology leaders can be fully transparent about business and personal challengesConscious leadership development is becoming the human edge that AI cannot replicate in organizational contextsImportant Concepts and FrameworksConscious AI — A two-sided framework combining humanistic technology implementation with personal consciousness developmentLink: Conscious AI: Capabilities and the Future AheadPeer Forum Methodology — Structured approach combining education, roundtable sharing, and case processing for executive developmentLink: Peer Advisory Groups for Executives & CEOs | VistageAI Implementation Framework — Responsible approach balancing innovation with security and change managementLink: AI Implementation Framework for Success: CIO's 6-Step GuideTechnology Leadership Development — Systematic approach to developing both technical and human leadership capabilitiesLink: Five Emerging Technologies In Leadership DevelopmentTools & Resources MentionedREF (Renaissance Executive Forums) — Peer advisory organization providing structured forum experiences for executivesCenter for Creative Leadership — Nonprofit organization specializing in executive coaching and leadership development BHMS — Electronic medical record platform specifically designed for residential addiction treatment centersCalls to ActionAssess whether your technology leaders have a true peer forum experience where they can be fully transparent about challengesImplement opening meditations or mindfulness practices in team meetings to develop conscious leadership skillsCreate structured opportunities for technology leaders to share AI implementation experiences and lessons learnedEvaluate how your organization views technology leadership—as strategic partners or tactical implementersDevelop communication strategies that position AI as a tool for elevating human potential rather than replacing itKey Quotes"Technology can be a revenue stream, it can help with customer retention" — Scott Krawitz"Employees are technology customers as well" — Scott Krawitz"AI is a massive disruptive opportunity" — Scott Krawitz"What are you doing to grow in significance?" — Scott Krawitz"The human edge will always be our conscious selves" — Scott KrawitzChapters00:00 — Introduction to Technology Leadership Challenges in the AI Era 01:15 — Scott Krawitz's Journey: From Commodore 64 to Conscious Leadership 06:27 — The Power of Peer Forums for Technology Executives 09:13 — Getting the Technology Seat at the Executive Table 15:23 — Employees as Technology Customers: The Retention Imperative 20:45 — AI Implementation Risks: Security, Compliance ...
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    42 min
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