The Messy Middle Matters

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/ 

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. 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/

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. 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/

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. Key Takeaways: Recognize the mental and emotional shifts required to leave corporate life. Prepare for practical realities like benefits, finances, and pricing your work. Build community and support systems to replace what you leave behind. Embrace vulnerability, resilience, and the evolution of your authentic identity. Take the leap even if you don’t feel “ready”—your path will grow with you. Join us and discover how to choose yourself, navigate uncertainty, and redefine what freedom and fulfillment mean in your career.   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  Ashley on LinkedIn: https://www.linkedin.com/in/ashleygracejefferson/  Ashley’s Website: ashleygracejefferson.com/  Ashley’s Newsletter: startup-baddie.beehiiv.com/  Ashley on Threads: https://www.threads.com/@startupbaddie  Indra on LinkedIn: https://www.linkedin.com/in/indrak/  Indra’s Website: peopleprocessthings.com Indra’s Newsletter: peopleprocessthings.substack.com/ Interview with Cindy Gallop (3 addictions): https://youtu.be/eAJu225PcQU?si=5HETDKxb62OmbL1w 

In this episode of The Messy Middle Matters, Indra sits down with  Juleen Mahabeer-Jackson to explore what it really feels like to be at a career crossroads. From packing up her life (and two cats!) to drive across the country, to rethinking what success looks like beyond job titles, Juleen shares her story of stepping outside her comfort zone and learning to trust herself. Together, Indra and Juleen unpack the tension between chasing external validation and building a life that feels authentic, sustainable, and joyful. They also reflect on the pressure of “picking your struggle,” filling your own cup, and how content creation can be both a tool for clarity and a leap of faith in itself. If you’ve ever wondered whether to keep climbing the ladder or carve your own path, this conversation is for you. Useful Links: The Messy Middle Matters Merch: shop.themessymiddlematters.com  The Messy Middle Matters Glossary: messymiddlematters.com/glossary   Feedback for The Messy Middle Matters: messymiddlematters.com/feedback  Juleen Mahabeer-Jackson on LinkedIn: https://www.linkedin.com/in/juleenbean/ Indra Klavins on LinkedIn: https://www.linkedin.com/in/indrak/

Branding yourself isn’t optional anymore—it’s essential. In this episode, Indra sits down with Ashley Grace Jefferson, founder of Startup Baddie and F3 (Founders, Funders & Fractionals), to explore how to stand out, show up authentically, and even rebrand yourself when the time is right. They dive into the signs it’s time to rebrand, the difference between corporate and personal branding, and practical steps for making your brand visible—like social media, websites, and visual identity. Ashley shares her own journey, including the story behind her now-famous “Startup Baddie” identity, and offers actionable tips listeners can use immediately. Beyond the practical, they explore the emotional side of branding: vulnerability, imposter syndrome, handling feedback, and embracing radical acceptance as your brand evolves. Whether you’re an entrepreneur or a professional navigating the modern workplace, this conversation is full of insights to help you feel seen, confident, and ready to take bold steps forward. Key Takeaways: Recognize when it’s time to rebrand and why it matters. Align your brand with your values, personality, and goals. Show up authentically while managing fear and self-doubt. Take concrete steps to make your brand visible and consistent. Embrace the ongoing evolution of your personal or professional identity. Join us, and get ready to stand out, show up, and let your brand grow with you!   Useful Links: The Messy Middle Matters Merch: shop.themessymiddlematters.com  The Messy Middle Matters Glossary: messymiddlematters.com/glossary    Feedback for The Messy Middle Matters: messymiddlematters.com/feedback  Ashley Jefferson on LinkedIn: https://www.linkedin.com/in/ashleygracejefferson/ Indra Klavins on LinkedIn: https://www.linkedin.com/in/indrak/

Your professional identity shapes how others see you, how you show up, and the opportunities that come your way. In this episode, we explore the difference between brand (how you want to be seen) and reputation (how others actually see you), and share practical strategies for defining and communicating your identity at work. We dive into real-world examples, tips for aligning your actions with your intentions, and ways to make your presence consistent across teams, projects, and platforms. Useful Links: The Messy Middle Matters Merch: shop.themessymiddlematters.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 episode of The Messy Middle Matters, Indra is joined by Victor Malena, founder of  Ops on Tap, to explore the subtle but powerful difference between being smart and being prepared. Victor shares a career-shaping story from an early mentor who taught him that success often comes less from being the "smartest person in the room" and more from being the one most ready to engage, ask questions, and adapt. Together, Indra and Victor unpack what preparedness looks like in practice—curiosity, clarity, and creating space for others to contribute—while reflecting on how identity, leadership, and even AI play into the dynamics of modern work. Whether you identify as an operator, a leader, or someone navigating the messy middle of your own career, this conversation offers fresh insight into why preparation isn’t just a safety net—it’s a strategy for thriving. Useful Links: The Messy Middle Matters Merch: shop.themessymiddlematters.com  The Messy Middle Matters Glossary: messymiddlematters.com/glossary    Feedback for The Messy Middle Matters: messymiddlematters.com/feedback  Victor Malena on LinkedIn: https://www.linkedin.com/in/victor-malena/ 

Let’s be honest. Networking often conjures awkward happy hours, forced small talk, and a vague sense that you should be doing more of it. But what if it didn’t have to feel gross? In this episode, Indra and Amanda break down how to keep your network warm, show up authentically, and build meaningful relationships that support your career and your humanity. Whether you’re introverted, overwhelmed, or just not sure where to start, this conversation offers a mix of pep talk and practical tips to make networking feel more like connection and less like a chore. Useful Links: The Messy Middle Matters Merch: shop.themessymiddlematters.com  The Messy Middle Matters Glossary: messymiddlematters.com/glossary   Feedback for The Messy Middle Matters: messymiddlematters.com/feedback  Connect with Amanda Jane Lee on LinkedIn: https://www.linkedin.com/in/amandajanelee/  Connect with Indra on LinkedIn: https://www.linkedin.com/in/indrak/ 

Indra drops into your feed with a short update on what’s ahead for The Messy Middle Matters. The next chapter features new voices and experiences, additional stories from the trenches, and an even deeper examination of the work that is rarely seen, heard, or celebrated. Don’t worry. Amanda will still be joining regularly.

In this episode, Indra and Amanda explore the difference between influence and authority and why mastering influence is essential for most people at work. While authority comes with titles and structure, influence is often how real change happens: through relationships, trust, and timing. They share personal stories of leading without formal power, the subtle art of planting seeds and letting ideas take root, and strategies for shifting mindsets and behavior over time. Whether you’re driving change from the middle or navigating a complex org, this episode offers practical tips for using influence to get things done—without steamrolling anyone in the process. Useful Links: The Messy Middle Matters Merch: shop.themessymiddlematters.com  The Messy Middle Matters Glossary: messymiddlematters.com/glossary   Feedback for The Messy Middle Matters: messymiddlematters.com/feedback

In this episode of The Messy Middle Matters, Indra and Amanda unpack a workplace tension that’s all too familiar: what happens when incentives, outputs, and motivation aren’t aligned. They begin by defining key terms: intrinsic incentives (such as purpose or pride), extrinsic incentives (like pay or praise), and outputs (the tangible results of one's work). Then, they dive into two primary sources of misalignment: Conflicting incentives between teams, crafts, or departments Leadership messages that don’t match real decisions or rewards With real-life examples, they explore the awkward dynamics that arise when your motivation doesn't match the system you're working in. Whether it's security versus speed, innovation versus client demands, or personal growth versus team goals, misalignment can erode culture, trust, and progress. Useful Links: The Messy Middle Matters Merch: shop.themessymiddlematters.com  The Messy Middle Matters Glossary: messymiddlematters.com/glossary   Feedback for The Messy Middle Matters: messymiddlematters.com/feedback 

Belonging to a team can be deeply fulfilling, but what happens when that sense of loyalty starts to conflict with your growth in your craft? In this episode, Indra and Amanda unpack the tension between short-term team alignment and long-term career development. They explore what it means to be loyal to your project team, your department, or your craft, especially in roles like program management, design, and marketing, where craft-specific communities may be smaller or less visible. From navigating conflicting priorities to finding time for your own professional development, they offer insights for both individual contributors and leaders. Expect practical strategies, relatable stories, and a reminder that the messy middle is where real growth happens. Useful Links: The Messy Middle Matters Merch: shop.themessymiddlematters.com  The Messy Middle Matters Glossary: messymiddlematters.com/glossary   Feedback for The Messy Middle Matters: messymiddlematters.com/feedback

Why does everything feel urgent all the time — and what does it cost us? In this episode, Indra and Amanda unpack the toll of poor prioritization on teams, leaders, and organizations.  From the illusion of decision-making to the chaos of shifting priorities, they explore the mental and operational burnout that comes when no one says no. They offer practical tools for creating clarity, setting boundaries, and making prioritization a leadership discipline, not just a labeling exercise.  Whether you're the one setting the priorities or trying to survive them, this episode offers validation and strategies for pushing back on the pressure. Useful Links: The Messy Middle Matters Merch: shop.themessymiddlematters.com  The Messy Middle Matters Glossary: messymiddlematters.com/glossary Feedback for The Messy Middle Matters: messymiddlematters.com/feedback 

What do people mean when they say someone is “too senior”? In this episode, Indra and Amanda unpack the layered, often coded ways the word "senior" is used in hiring and professional contexts.  From recruiter conversations to team dynamics, the term is frequently a stand-in for other qualities—such as executive presence, high salary expectations, and perceived difficulty to manage—that often reveal unspoken biases. They explore the disconnect between titles and actual responsibilities, challenge the euphemistic use of senior, and call for clearer, more honest language in describing skills and roles.  If you’ve ever been told you’re too much or not enough without a clear why, this episode is for you. Useful Links: The Messy Middle Matters Merch: shop.themessymiddlematters.com  The Messy Middle Matters Glossary: messymiddlematters.com/glossary   Feedback for The Messy Middle Matters: messymiddlematters.com/feedback 

What do you do when a talented team member has outgrown what your organization can offer? In this episode of The Messy Middle Matters, Indra and Amanda unpack the rarely discussed topic of supporting team members who are ready to move on, not because they've failed, but because they’ve grown. From recognizing career ceilings to embracing talent mobility, they explore how letting go can be an act of leadership, not loss. You’ll hear practical strategies for navigating these moments with honesty, generosity, and long-term vision, turning exits into alumni relationships and potential into legacy. Useful Links: The Messy Middle Matters Merch: shop.themessymiddlematters.com  The Messy Middle Matters Glossary: http://bit.ly/448qQxm  Feedback for The Messy Middle Matters: http://bit.ly/3ZVuFn7