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/