In this episode of The Messy Middle Matters, Indra Klavins sits down with Rachel Saslaw, product marketing director and founder of NYC’s storytelling community StoryTell, to explore the messy middle of career, purpose, and identity.

Rachel shares her journey of balancing a corporate career with a passion project, protecting her creative space from the pressures of monetization, and navigating societal expectations around hustle culture and “following your passion.” They discuss how work can serve as a fuel for life rather than a constant source of striving, and how intentionality, radical permission to change your mind, and embracing a multifaceted identity can bring clarity, freedom, and fulfillment.

Key Takeaways:

• The messy middle often means balancing meaningful work with personal passions and financial stability.
• Work does not have to be your life’s calling; it can provide fuel for a life you love outside of the office.
• Saying “not for me (right now)” is a valid, intentional approach to career and passion projects.
• Preserving your passion requires setting boundaries and resisting the commodification of personal interests.
• Community and storytelling are powerful tools for empathy, belonging, and nuanced human connection.
• Identity is multi-faceted; your job title does not define your worth or your whole self.
• Experimentation and radical permission to change your mind allow flexibility and clarity in career decisions.

Follow Rachel and StoryTell:

• Rachel Saslaw on LinkedIn: https://www.linkedin.com/in/rachelsaslaw/
• Rachel’s Website: https://rachelsaslaw.com/
• StoryTell on Instagram: https://www.instagram.com/storytellnyc

More on Indra and The Messy Middle Matters

• Feedback for The Messy Middle Matters: http://messymiddlematters.com/feedback
• Indra’s Blog: http://peopleprocessthings.substack.com
• Indra on LinkedIn: https://www.linkedin.com/in/indrak/
• The Messy Middle Matters Merch http://messymiddlemerch.com

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/