The Messy Middle Matters

Starting a new role can feel overwhelming, even when you know the basics—logging in, getting paid, finding the coffee. In this episode, Indra Klavins and Amanda Jane Lee go beyond standard onboarding advice to explore how to truly set yourself up for success in your first 90 days.

They discuss the importance of asking foundational questions, building your own organizational maps, decoding internal vocabulary, and taking a listening-first approach to understand culture and team dynamics. From strategic one-on-ones to creating your own “maps” of reporting structures and workflows, this episode is full of practical tips for making meaningful first impressions, establishing your brand, and navigating both in-person and remote environments.

Whether you’re joining a hyper-growth startup, a large enterprise, or a cross-functional team, this conversation equips you with tools to orient yourself, gather context, and thrive in the messy middle of a new role.

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In this conversation, Amanda Jane Lee discusses the innovative use of AI in self-discovery and career guidance. She emphasizes how AI can assist individuals in identifying their strengths and preferences through targeted questioning, making the process of career exploration more efficient and personalized.

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This conversation delves into the complexities of transitioning into leadership roles, emphasizing the emotional and practical challenges faced by new managers. Indra K and Laura Lillie Goodridge explore the jarring shift from individual contributor to manager, the importance of self-awareness, and the need for effective communication and feedback. They discuss the lack of support many organizations provide for new leaders and the significance of finding the right coaching and resources to navigate this transition successfully. The dialogue highlights the evolving nature of leadership in today's workplace, advocating for a more empathetic and self-aware approach to management.

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In this conversation, Mikki and Indra explore the complexities of navigating career changes and the profound shifts in identity that accompany them. They discuss the importance of humility, community support, and vulnerability during transitions, emphasizing the need to redefine one's identity and align actions with personal values. The dialogue highlights the significance of small impacts and the ripples they create within communities, encouraging listeners to embrace change and seek connection.

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In this episode, Indra and Amanda discuss the complexities of co-creation in the workplace, particularly when it comes to leadership dynamics and the responsibilities that come with collaboration. They explore the importance of providing structure in collaborative efforts, the pitfalls of starting from a blank slate, and the need for clear expectations and communication. The conversation also touches on the challenges of goal setting, particularly with OKRs, and the significance of documenting contributions to avoid repeating past mistakes. Ultimately, the episode emphasizes the need for both leaders and team members to understand their roles and responsibilities in collaborative projects.

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Chapters

00:00 Navigating Co-Creation in the Workplace

01:47 The Challenges of Role Definition

04:58 The Importance of Structure in Collaboration

07:47 The Value of Providing Context

10:59 Understanding Leadership Dynamics

13:44 Assessing Personal Boundaries and Responsibilities

16:56 Negotiating Expectations and Outcomes

19:51 The Slippery Slope of Helping

22:52 The Pitfalls of Bottom-Up Goal Setting

25:56 Documenting and Learning from Experiences

33:25 Outro

What does it take to build—and protect—culture when your team and community are growing faster than your playbook? In this episode, Indra talks with Derek Kastner, Head of Experience at Fabrik, about what it really means to nurture community and connection in a rapidly scaling organization.

From being one of Fabrik’s first three employees to helping onboard its growing team and shape the member experience, Derek shares candid lessons about balancing perfectionism with presence, co-creating culture with members, and learning to set boundaries while staying deeply human. Together, they explore the tension between structure and spontaneity, the invisible “glue work” that holds communities together, and how transparency, trust, and a little messiness can make something truly special.

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When the world shifts under your feet, what do you do next? In this episode, Indra talks with bestselling children’s author Nancy Krulik about the art of resilience and reinvention. From investigative journalism to over 250 books for kids — and now animation — Nancy’s career is a masterclass in adapting, learning, and staying curious when plans fall apart.

Together, they explore what it takes to recognize when it’s time to pivot, how to turn setbacks into opportunities, and why nothing you learn is ever wasted. Nancy shares hard-earned lessons on staying grounded through industry changes, embracing new tools (including AI), and rediscovering hidden talents along the way.

If you’ve ever been knocked down and wondered how to begin again — this conversation is your reminder that resilience isn’t just about bouncing back; it’s about changing course with purpose.

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Business goals and human behavior don’t always line up — and the friction can stall progress, frustrate teams, and leave leaders scratching their heads. In this episode, we dive into real-world examples where business logic clashes with human tendencies, from time tracking to communication challenges and conflicting incentives. We share strategies for bridging the gap, including clear rationale, collaboration across teams, and open forums to build trust. If you’ve ever wondered why good processes fail despite good intentions, this episode is for you.

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Perfectionism can drive excellence — but it can also stall progress, create stress, and keep teams stuck. In this episode, we explore the “pencils down” metaphor, helping you recognize when good enough is actually brilliant. We discuss the roots and benefits of perfectionism, the pitfalls of over-editing and micromanagement, and how leaders can model healthy standards. Packed with practical strategies for releasing control, encouraging iteration, and knowing when to move on, this episode is a guide for anyone ready to break free from perfectionism without sacrificing quality.

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Thinking about leaving corporate America but not sure what it really takes? In this episode, Indra sits down with Ashley Grace Jefferson to explore the mental, emotional, and practical shifts involved in breaking free from the corporate system.

They unpack the culture and incentives of corporate life, address the fears and stigma around leaving, and discuss the logistical realities—from health insurance to financial planning—that often catch people off guard. Ashley and Indra share personal stories of doubt, courage, and resilience, highlighting the importance of community, support systems, and authentic identity when taking the leap.

Whether you’re dreaming of entrepreneurship, a career pivot, or simply choosing yourself over a paycheck, this conversation offers insight, encouragement, and actionable advice for making the jump and building a life on your own terms.

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Join us and discover how to choose yourself, navigate uncertainty, and redefine what freedom and fulfillment mean in your career.

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