The Messy Middle Matters
Organizations are always sending signals. Some are obvious. Most are subtle.
The Messy Middle Matters® is where we explore the hidden dynamics shaping how organizations actually work—from invisible work and decision-making to leadership, change, and the patterns that emerge when people build together.
Through the podcast, her writing, and public speaking, Indra Klavins helps leaders, operators, and builders make sense of what they're already seeing but may not yet have words for.
Whether you're listening to the podcast, reading an essay, or exploring a keynote, the goal is the same: to help you see your organization differently.
Because once you begin noticing these patterns, it's hard to unsee them.
themessymiddlematters.com | @themessymiddlematters

The Messy Middle Matters® podcast shines a much-needed spotlight on what it really takes to work in, survive in, and even thrive in the messy middle of work.
This is the space where real work gets done but rarely celebrated: the glue work, the emotional labor, the quiet tradeoffs, and the subversive strategies that keep everything moving forward.
Episodes

Mar 25, 2026
Mar 25, 2026
13 min
Indra reflects on her podcast journey over the past year, sharing successes, challenges, and personal growth. She discusses the evolution of her podcast, technological hurdles, and how the experience has transformed her confidence and voice.
Takeaways
Consistency in content creation builds confidence.
Technological hurdles are significant but manageable.
Reflecting on progress reveals areas of growth and improvement.
Feedback from listeners is vital for motivation and direction.
More from Indra and The Messy Middle Matters
Indra on LinkedIn: https://www.linkedin.com/in/indrak/
Indra’s Blog: https://peopleprocessthings.substack.com
The Messy Middle Matters on Instagram: https://www.instagram.com/themessymiddlematters/
Feedback for The Messy Middle Matters: https://messymiddlematters.com/feedback
The Messy Middle Matters Merch https://messymiddlemerch.com
Podbean Podcast Hosting - https://www.podbean.com/messymiddle
Keywords
podcast journey, personal growth, technology challenges, self-confidence, retrospective, podcasting tips
Chapters
00:00 Reflecting on Season One
03:09 What Went Well: Celebrating Successes
06:04 Challenges Faced: Technology and Consistency
09:06 Personal Growth: Finding Confidence Through Podcasting
11:55 Looking Ahead: Future of the Podcast
12:40 Outro + Post-roll - Like and Subscribe

Mar 18, 2026
Mar 18, 2026
32 min
In this episode, Indra and Ana Fabiano explore the intricate journey of Ana's career in the wine industry, her deep connection to the Rioja region, and the launch of her new venture, Rioja Holistic Home. They discuss the importance of passion, authenticity, and building trust with craftspeople, especially in a traditionally male-dominated industry. The conversation highlights the shift towards sustainability and intentional living, emphasizing the value of community and patience in navigating the 'messy middle' of personal and professional growth.
Takeaways
Let your passion guide you in your career.
Authenticity is crucial in building connections.
Rioja represents more than just wine; it's a cultural experience.
Building trust with craftspeople requires respect and dedication.
The wine industry is becoming more inclusive of women.
Intentional living can enhance well-being and connection.
Sustainability is a growing focus in consumer choices.
The messy middle is a vital part of any journey.
Patience is essential when navigating challenges.
Community support is key to success in business.
More from Ana Fabiano
Rioja Holistic Home on Instagram: https://www.instagram.com/riojaholistichome/
Ana’s Book: https://www.anafabiano.com/riojabook
Ana’s Website: https://www.anafabiano.com/
Ana’s on Instagram: https://www.instagram.com/anafabianorioja
Ana Fabiano on LinkedIn: https://www.linkedin.com/in/anafabiano/
More from Indra and The Messy Middle Matters
Indra on LinkedIn: https://www.linkedin.com/in/indrak/
Indra’s Blog: https://peopleprocessthings.substack.com
The Messy Middle Matters on Instagram: https://www.instagram.com/themessymiddlematters/
Feedback for The Messy Middle Matters: https://messymiddlematters.com/feedback
The Messy Middle Matters Merch https://messymiddlemerch.com
Keywords
career paths, authenticity, Rioja, wine industry, craftspeople, sustainability, holistic living, intentionality, women in business, personal growth

Mar 11, 2026
Mar 11, 2026
36 min
In this episode of Messy Middle Matters, Indra and Kat delve into the complexities of Imposter Syndrome, exploring its roots, manifestations, and the societal conditioning that often exacerbates it, particularly for women. They discuss practical tools and strategies for reframing negative self-perceptions, the importance of coaching and mentorship, and the need for authentic role models. The conversation emphasizes the significance of finding support and resources to navigate the challenges of self-doubt and encourages listeners to embrace their true selves.
Key Takeaways
Imposter Syndrome is often more prevalent among women due to societal conditioning.
The concept of 'secret memos' illustrates how people feel out of place in social settings.
Reframing negative thoughts is crucial in overcoming Imposter Syndrome.
Writing down negative beliefs can help in assessing their truth.
Coaching provides an objective perspective that can aid in personal growth.
Client preferences can impact self-perception and work satisfaction.
Women often have fewer role models in leadership roles, making it harder to find relatable guidance.
Authenticity is vital in overcoming Imposter Syndrome and finding one's voice.
Support systems, whether human or virtual, are essential for personal development.
Taking small steps and finding resources can help in managing self-doubt.
Resources
Clifton Strengths Finder: https://www.gallup.com/cliftonstrengths/en/home.aspx
Debbie Millman's Design Matters Podcast: https://designmattersmedia.com/
Frances Frei & Anne Morris's Fixable Podcast: https://anneandfrances.com/fixable
Carla Harris - Pearls of Wisdom: https://www.carlaspearls.com/
Brene Brown - The Power of Vulnerability: https://brenebrown.com/
Find Kat
Kat on LinkedIn: https://www.linkedin.com/in/katlogan/
Kat’s Website: https://www.illuminatedcoach.com/
Kat on Instagram: https://www.instagram.com/katlogan01
More from Indra and The Messy Middle Matters
Indra on LinkedIn: https://www.linkedin.com/in/indrak/
Indra’s Blog: https://peopleprocessthings.substack.com
The Messy Middle Matters on Instagram: https://www.instagram.com/themessymiddlematters/
Feedback for The Messy Middle Matters: https://messymiddlematters.com/feedback
The Messy Middle Matters Merch https://messymiddlemerch.com
Keywords
Imposter Syndrome, Coaching, Mentorship, Women in Leadership, Self-Perception, Overcoming Doubt, Personal Growth, Authenticity, Social Conditioning, Professional Development
Chapters
00:00 Understanding Imposter Syndrome
03:02 The Secret Memos and Social Conditioning
06:12 Reframing Imposter Syndrome
08:52 Tools and Practices for Overcoming Imposter Syndrome
11:46 The Role of Coaching and Mentorship
14:49 Navigating Client Expectations and Self-Perception
17:58 The Importance of Role Models
21:19 Raw to Roar: Embracing Authenticity
23:41 Finding Support and Resources
26:52 Final Thoughts and Encouragement

Mar 4, 2026
Mar 4, 2026
34 min
In this conversation, Kat Logan joins Indra to explore the complexities of agency life, discussing the challenges and rewards of working in a dynamic environment. They delve into the impact of client culture, the revolving door of talent, and the importance of building community and support within agencies. The discussion highlights the nuances of navigating agency culture, managing uncertainty, and adapting to different styles while emphasizing the need for connection and collaboration among colleagues. The episode concludes with a teaser for the next topic on imposter syndrome.
Key Topics
Agency culture and personality influence
Impact of client and company culture
Revolving door of talent and team dynamics
Adapting to agency structure and leadership styles
Supporting each other in agency environments
Managing uncertainty and career stability
Networking and community building within agencies
Impacts of industry crises on agency work
Find Kat:
Kat on LinkedIn: https://www.linkedin.com/in/katlogan/
Kat’s Website: https://www.illuminatedcoach.com/
Kat on Instagram: https://www.instagram.com/katlogan01
More from Indra and The Messy Middle Matters
Indra on LinkedIn: https://www.linkedin.com/in/indrak/
Indra’s Blog: https://peopleprocessthings.substack.com
The Messy Middle Matters on Instagram: https://www.instagram.com/themessymiddlematters/
Feedback for The Messy Middle Matters: https://messymiddlematters.com/feedback
The Messy Middle Matters Merch https://messymiddlemerch.com
Keywords
agency life, career development, networking, agency culture, leadership, adaptability, agency challenges, agency success, agency community, imposter syndrome

Feb 25, 2026
Feb 25, 2026
27 min
In a world full of noise, expectations, and competing identities, how do we hear our inner voice? In this episode of The Messy Middle Matters, Indra sits down with Jameelah Calhoun, founder of Unpopular Decisions, to explore the courage it takes to choose alignment over conformity. Together, they unpack the difference between fear and intuition, regret versus consequences, and why comfort isn’t always safety. They also discuss the realities of responsibility, intersectionality, and privilege — and why listening to your inner voice doesn’t have to mean reckless abandon. Sometimes it’s about small acts of reclamation, play, and returning home to yourself.
Takeaways
Your intuition is often immediate: yes, no, hell yes, hell no. Fear rationalizes. It builds a courtroom case.
What feels comfortable may slowly misalign you.
Growth often begins when comfort stops feeling safe.
Play reconnects us to identities we shed to “fit in.”
Not everyone has the same latitude to take bold risks.
You don’t know the identities, risks, or responsibilities someone carries.
Choosing alignment publicly can give others permission to do the same.
Sometimes what looks like instability is actually a return to self.
Follow Jameelah:
Jameelah on LinkedIn: https://www.linkedin.com/in/jameelah-calhoun/
Unpopular Decisions Website: https://www.unpopulardecisions.com/
Jameelah on Instagram: https://www.instagram.com/unpopulardecisionspod/
More from Indra and The Messy Middle Matters
Indra on LinkedIn: https://www.linkedin.com/in/indrak/
Indra’s Blog: https://peopleprocessthings.substack.com
The Messy Middle Matters on Instagram: https://www.instagram.com/themessymiddlematters/
Feedback for The Messy Middle Matters: https://messymiddlematters.com/feedback
The Messy Middle Matters Merch https://messymiddlemerch.com

Feb 18, 2026
Feb 18, 2026
38 min
Growth isn’t just about what we’re building, it’s also about what we’re letting go.
In this episode, Indra and Stephanie examine the hidden grief that can accompany promotions, career pivots, restructures, and identity shifts. They talk about grieving what you thought would be, survivor’s guilt in the workplace, and why ignoring emotions doesn’t make them disappear. This conversation offers language, perspective, and practical tools for moving through change without bypassing yourself, or your team.
Takeaways
Grief can show up in unexpected ways, even during positive changes.
The 'goo stage' represents the messy transformation process.
Letting go of past identities is crucial for growth.
Community plays a significant role in our emotional well-being.
Grief is not just about loss; it can be about change and transition.
Acknowledging grief in the workplace is essential for a healthy culture.
Emotions are energy in motion; they need to be allowed to flow.
Grief is not linear; it can resurface at any time.
Building a supportive community can help navigate grief.
Compassion for oneself is key during times of transition.
Follow Stephanie:
Stephanie on LinkedIn: https://www.linkedin.com/in/stephaniesimpsoncoaching/
Stephanie’s Website: https://www.stephanie-simpson.com/
Stephanie on Instagram: https://www.instagram.com/stephaniesimpsoncoaching/
More from Indra and The Messy Middle Matters
Indra on LinkedIn: https://www.linkedin.com/in/indrak/
Indra’s Blog: https://peopleprocessthings.substack.com
The Messy Middle Matters on Instagram: https://www.instagram.com/themessymiddlematters/
Feedback for The Messy Middle Matters: https://messymiddlematters.com/feedback
The Messy Middle Matters Merch https://messymiddlemerch.com
Keywords
grief, change, transformation, identity, workplace culture, emotional intelligence, goo stage, community, leadership, burnout

Feb 11, 2026
Feb 11, 2026
17 min
In this episode, Indra explores the multifaceted role of AI in our lives, emphasizing its potential as a tool for accessibility, communication, and personal growth. She discusses how AI can enhance our work, serve as a thinking partner, and help us engage with broader audiences. Indra also highlights the importance of human agency in shaping the tools we use, advocating for a thoughtful approach to technology that prioritizes clarity and dignity.
Takeaways
AI is not about cheating; it's a reflection of our input.
Using AI can enhance accessibility in communication.
AI can serve as a partner in amplifying our thoughts.
Engaging with AI is crucial for shaping the future.
AI helps distill complex ideas into digestible formats.
The world was not built for everyone; AI can help navigate that.
AI can provide perspectives that enhance our understanding.
It's important to communicate in ways that resonate with diverse audiences.
Tools like AI are essential for scaling our efforts effectively.
Human agency must shape the tools we use, not the other way around.
More from Indra and The Messy Middle Matters
Indra on LinkedIn: https://www.linkedin.com/in/indrak/
Indra’s Blog: https://peopleprocessthings.substack.com
The Messy Middle Matters on Instagram: https://www.instagram.com/themessymiddlematters/
Feedback for The Messy Middle Matters: https://messymiddlematters.com/feedback
The Messy Middle Matters Merch https://messymiddlemerch.com
Keywords
AI, accessibility, communication, human agency, technology, innovation, thinking partner, future of work, systems thinking, digital tools

Feb 4, 2026
Feb 4, 2026
39 min
In this episode, Indra and Stephanie Simpson explore the concept of the 'Goo Stage,' a transformative phase in life where individuals experience discomfort and uncertainty. They discuss the importance of navigating transitions, the role of leaders in supporting their teams during these times, and the significance of creating supportive environments. Stephanie shares insights on how to acknowledge and validate feelings during the Goo Stage, emphasizing the need for community and resources to aid in personal growth. The conversation concludes with invitations for listeners to reflect on their support systems and the importance of being present in the moment.
Takeaways
The Goo Stage represents a transformative phase in life.
Transitions are crucial and should be navigated intentionally.
Leaders play a vital role in supporting their teams during change.
Creating a supportive environment is essential for growth.
Acknowledging and validating feelings is the first step in navigating the Goo Stage.
Community support is crucial during times of transition.
One-size-fits-all solutions are often ineffective.
Personal growth requires discomfort and vulnerability.
Resources and tools should be tailored to individual needs.
Reflection on support systems can enhance personal development.
Follow Stephanie:
Stephanie on LinkedIn: https://www.linkedin.com/in/stephaniesimpsoncoaching/
Stephanie’s Website: https://www.stephanie-simpson.com/
Stephanie on Instagram: https://www.instagram.com/stephaniesimpsoncoaching/
More from Indra and The Messy Middle Matters
Indra on LinkedIn: https://www.linkedin.com/in/indrak/
Indra’s Blog: https://peopleprocessthings.substack.com
The Messy Middle Matters on Instagram: https://www.instagram.com/themessymiddlematters/
Feedback for The Messy Middle Matters: https://messymiddlematters.com/feedback
The Messy Middle Matters Merch https://messymiddlemerch.com
Keywords
Goo Stage, Transition, Change Management, Leadership, Support, Personal Growth, Stress Management, Transformation, Community, Resources

Jan 28, 2026
Jan 28, 2026
29 min
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

Jan 21, 2026
Jan 21, 2026
36 min
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









