Summary

In this engaging conversation, Indra K and Megumi explore the complexities of navigating the messy middle of careers, personal growth, and entrepreneurship. Megumi shares her journey from Tokyo to Kansas City, her career pivots from marketing to acting, and ultimately to creating a community-focused wine events company. The discussion highlights the importance of creating supportive spaces for women, the art of gathering, and the lessons learned through trial and error in both personal and professional realms.

Takeaways

• Megumi's journey reflects the importance of embracing change.
• Creating spaces for women fosters community and support.
• Wine events can be a platform for empowerment and connection.
• Understanding what you don't want is as crucial as knowing what you want.
• Entrepreneurship often comes with unexpected challenges and surprises.
• The importance of intentionality in event planning and execution.
• Curiosity and playfulness enhance the experience of learning about wine.
• Networking in a supportive environment can lead to personal growth.
• Self-discovery is a continuous journey, especially in entrepreneurship.
• Building a community can provide validation and encouragement.

Useful Links

• Megumi on Instagram: https://www.instagram.com/megumicalver/
• Megumi's Newsletter: https://merobebe.beehiiv.com/
• Indra Klavins on LinkedIn: https://www.linkedin.com/in/indrak/
• The Messy Middle Matters Merch http://messymiddlemerch.com
• Feedback for The Messy Middle Matters: http://messymiddlematters.com/feedback

Keywords

career pivots, entrepreneurship, women empowerment, wine events, personal growth, community building, marketing, acting, self-discovery, networking

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.

Useful Links

• The Messy Middle Matters Merch: messymiddlemerch.com
• The Messy Middle Matters Glossary: messymiddlematters.com/glossary
• Feedback for The Messy Middle Matters: messymiddlematters.com/feedback
• Amanda Jane Lee on LinkedIn: https://www.linkedin.com/in/amandajanelee/
• Indra Klavins on LinkedIn: https://www.linkedin.com/in/indrak/

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.

Takeaways

• AI can help identify personal strengths and preferences.
• Mind mapping software is a useful tool in self-discovery.
• Asking the right questions is crucial for self-exploration.
• AI can generate questions to guide personal discovery.
• Understanding green flags is important in career choices.
• Self-discovery can be enhanced through technology.
• AI can streamline the process of finding suitable roles.
• Personalized guidance can lead to better career decisions.
• The role of AI in career exploration is growing.
• Embracing technology can aid in personal development.

Useful Links

• The Messy Middle Matters Merch: messymiddlemerch.com
• The Messy Middle Matters Glossary: messymiddlematters.com/glossary
• Feedback for The Messy Middle Matters: messymiddlematters.com/feedback
• Amanda Jane Lee on LinkedIn: https://www.linkedin.com/in/amandajanelee/
• Indra Klavins on LinkedIn: https://www.linkedin.com/in/indrak/

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.

Takeaways

• Transitioning to leadership is a significant emotional and practical shift.
• New managers often feel isolated from their previous peer relationships.
• Organizations frequently lack adequate support for new leaders.
• Effective communication is crucial for setting expectations and managing teams.
• Feedback should be a two-way street, involving both giving and receiving.
• Self-discovery is essential for understanding one's leadership style.
• Coaching can provide valuable external perspectives for new leaders.
• Understanding company leadership styles is vital for alignment.
• New managers should focus on fundamental skills before reshaping their identity.
• The landscape of leadership is evolving towards a more empathetic approach.

Useful Links

• Laura on LinkedIn: https://www.linkedin.com/in/the-manager-coach/
• Laura on Instagram: https://www.instagram.com/the_manager_coach/
• Laura’s website: https://www.lauralilliecoaching.com/
• Laura’s resources for new managers: https://www.lauralilliecoaching.com/managers-resources
• The Messy Middle Matters Merch: messymiddlemerch.com
• The Messy Middle Matters Glossary: messymiddlematters.com/glossary
• Feedback for The Messy Middle Matters: messymiddlematters.com/feedback
• Indra Klavins on LinkedIn: https://www.linkedin.com/in/indrak/

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.

Takeaways

• The job market is unpredictable, leading to frequent career changes.
• Identity can shift significantly when changing roles or companies.
• Experiential design and community engagement can be fulfilling career paths.
• Humility is essential when starting anew in a different field.
• Community support plays a crucial role during transitions.
• Vulnerability can lead to deeper connections and support.
• Redefining one's identity is a journey that requires self-reflection.
• Embracing change can lead to personal growth and new opportunities.
• It's important to align actions with personal values.
• Every small impact can create ripples in the community.

Useful Links

• The Messy Middle Matters Merch: messymiddlemerch.com
• The Messy Middle Matters Glossary: messymiddlematters.com/glossary
• Feedback for The Messy Middle Matters: messymiddlematters.com/feedback
• Mikki on LinkedIn: https://www.linkedin.com/in/micaelahoffman/
• Indra Klavins on LinkedIn: https://www.linkedin.com/in/indrak/

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.

Takeaways

• Co-creation can often feel like a delegation of responsibilities.
• Leaders should come prepared to collaborate, not just delegate.
• Providing structure is essential for effective collaboration.
• Blank slates can lead to confusion and misalignment.
• People often don't know what they want until they see it.
• Documenting past experiences can help avoid future pitfalls.
• Understanding your bandwidth is crucial before taking on new tasks.
• Negotiating expectations can lead to better outcomes.
• The concept of 'what's in it for me' is important for all parties.
• OKRs should not be a bottom-up process without clear guidance.

Useful Links

• The Messy Middle Matters Merch: messymiddlemerch.com
• The Messy Middle Matters Glossary: messymiddlematters.com/glossary
• Feedback for The Messy Middle Matters: messymiddlematters.com/feedback
• Amanda Jane Lee on LinkedIn: https://www.linkedin.com/in/amandajanelee/
• Indra Klavins on LinkedIn: https://www.linkedin.com/in/indrak/

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.

Useful Links:

• Derek on LinkedIn: https://www.linkedin.com/in/derekkastner/
• Indra on LinkedIn: https://www.linkedin.com/in/indrak/
• The Messy Middle Matters Merch: messymiddlemerch.com
• The Messy Middle Matters Glossary: messymiddlematters.com/glossary
• Feedback for The Messy Middle Matters: messymiddlematters.com/feedback

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.

Listen for:

• How to turn a downturn into a creative turning point
• The value of lifelong learning and fearless experimentation
• Why “nothing is ever wasted” — even the hard parts
• How staying true to your craft helps you weather change

Useful Links:

• The Messy Middle Matters Merch: messymiddlemerch.com
• The Messy Middle Matters Glossary: messymiddlematters.com/glossary
• Feedback for The Messy Middle Matters: messymiddlematters.com/feedback
• Nancy’s Website: https://www.realnancykrulik.com/
• Monsters Aren’t Real???: https://www.youtube.com/@MonstersArentRealCartoon
• Indra Klavins on LinkedIn: https://www.linkedin.com/in/indrak/