Thriving in the Messy Middle

Amy Wilkins
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The Messy Middle Isn't a Detour. It's Your Pathway to Thriving! This podcast is for women leaders who are holding it all together, but know deep down, there's more. Hosted by leadership coach and former media executive Amy Wilkins, this is your weekly exhale and power-up. It's for the ambitious, big-hearted leaders navigating change, craving clarity, and ready to rise—even when it's messy. Thriving isn't about perfection. It's about alignment over achievement, peace over proving, and growth that feels good. Tune in every Wednesday for candid conversations and mindset shifts to help you lead with purpose, alignment, and, most importantly, to thrive.

  1. 2d ago

    How Storytelling Transforms Your Personal and Professional Life

    In this episode of Thriving in the Messy Middle, host Amy P. Wilkins talks with strategic storytelling expert Laura Nespoli to explore the powerful role of narrative in both personal and professional contexts. The conversation delves into Laura's career transformation, highlighting how her personal experiences informed her professional journey and led to the creation of her debut book, "Threads of Me and You." Listeners gain insights into Laura's conceptualization of story as a tool for growth and meaning-making, learning valuable lessons on resilience and self-discovery. Laura shares her insights on navigating life's inevitable transitions, shedding light on her journey through pivotal life moments that prompted deep introspection and change. By understanding the power of storyline, Laura explains how we can redefine our self-worth and use storytelling as a framework for personal transformation. This episode is rich with themes of curiosity, resilience, and the courage to embrace the messy parts of life, offering listeners practical tools to rethink their own narratives and grow through challenges. Key Takeaways Storytelling is more than a business tool; it's a way to process personal growth, find inner resilience, and redefine narratives. Transformation doesn't always require drastic changes; it often starts with internal shifts in mindset and perspective. Following the "thread" of curiosity can unveil purposeful pathways, even in seemingly directionless times. Frequent reflection on past experiences and lessons can bolster confidence and mitigate future challenges. The messy middle of life offers potent opportunities for introspection, helping us to find clarity and refine our purpose. Laura Nespoli Quotes You have to be able to do this for yourself, or you're never going to get anywhere. Our lives are ruled by narratives… a lot of times these are limiting beliefs. I always say when I'm feeling uncomfortable, this is a gift. Ultimately, the biggest realization in all of it was I am accountable for the life that I want, and I can't rely on anybody else. The story arc is so important because it frames marketing products and innovations around real human experience. I never felt like I was a protagonist in my own life. I lived in service to other people.  Truly, it's your mind, and you have the ability to manage your mind.  I always say I follow the thread guide as I move through information. About Laura Nespoli Laura Nespoli is a strategic storytelling advisor whose clients have included Google, Salesforce, and JPMorgan, and the founders and women professionals who are building the next chapter of their careers. As founder of Meshin Movement and creator of the Story For Growth app, she believes story isn't just a business tool; it's how we make meaning, drive change, and find ourselves. Her debut book, Threads of Me and You, is where that belief gets personal: a memoir paired with strategic frameworks to help you own your story from the inside out. Laura Nespoli LinkedIn Profile Laura's website: Meshin Movement Laura's Book: Threads of Me and You

  2. Jul 22

    Build Resilience Through Emotional Regulation to Become a Better Leader

    Are you a woman leader navigating an uncertain career path? Join host Amy Wilkins on Thriving in the Messy Middle with her guest Alanna Fincke, a seasoned expert in resilience and organizational behavior. Amy invites Alanna to share her experiences of transitioning from magazine journalism to becoming a subject matter expert in resilience. They delve into Alanna's unique journey, discussing how early shifts in the internet landscape required her to rethink her career strategy from the onset. The episode offers profound insights into bridging the gap between professional roles and personal passion, especially amid today's constant change in the work environment. Alanna emphasizes the importance of resilience as a learnable set of skills vital for thriving amidst uncertainty. She shares strategic methods like visualization and positive affirmations, unveiling her struggle with impostor syndrome and the significance of emotional regulation in leadership. Moreover, Alanna's personal narrative of overcoming breast cancer provides a roadmap for navigating personal and professional challenges. This conversation highlights how leaders can model better stress management, create healthier, more resilient work environments, and find purpose in daily work to maintain personal well-being. Key Takeaways Resilience as a Skill: Resilience isn't just about bouncing back but about advancing and thriving. It involves a set of teachable skills like emotion regulation and visualization. Career Transitions: Navigating career changes, such as Alanna's shift from magazine journalism into resilience expertise, underscores the importance of aligning professional paths with personal values. Avoiding Manager Burnout: A significant pattern amongst leaders is burnout. Strategies for managing stress and modeling self-care can prevent the 'manager crash.' Purpose and Meaning: Purpose doesn't have to be overwhelming; it can be as simple as recognizing the benefits of one's current job or valuing team interactions. Post-Traumatic Growth: Challenges can spur significant personal and professional growth, as evidenced by Alanna's experience with cancer and resilience-building. Alanna Fincke Quotes Resilience is not just about pushing through with grit. It's a set of skills that support us in thriving and moving forward. Step into your power by silencing those inner critic voices and practicing visualization. The core of resilience lies in emotion regulation, helping us manage stress effectively amid constant change. Purpose doesn't have to be monumental. Small connections to meaning can make a significant impact in challenging times. You sometimes have to break down to break through; that's where real growth happens. And whatever the practices that work for you that keep you in that confidence zone, it is a practice. It's not a one-and-done. About Alanna Fincke Alanna Fincke is a senior behavioral-health and workplace-wellbeing executive with 10+ years leading content and services that drive measurable engagement and outcomes at enterprise scale. An innovative, creative, and commercially minded partner, she collaborates across functions to drive growth. As Executive Director of Content & Learning at meQuilibrium, she developed and led the enterprise content engine, translating CBT and performance psychology into digital journeys, live learning, and blended synchronous programs. She developed role-specific products for managers and teams—including manager skills and resources, team-based challenges, and live sessions—to build psychological safety, focus, emotional intelligence, change readiness, and more. She also integrated AI into in-product content (personalized member content, chatbot, product navigator) and into the content development process to speed production and improve the member experience. Her team's innovation doubled monthly sessions, doubled engagement rate, and lifted average in-product time to ~7 minutes. A board-certified coach, frequent speaker, and executive trainer, she not only designs high-impact interventions—she delivers them as a trusted customer partner, as well. Alanna is also a subject matter expert in resilience, performance, and mental health. She is a thought leader in the field of workplace performance.  Alanna Fincke LinkedIn Profile

  3. Jul 15

    Disruption Creates Choice: How to Rally Around New Possibilities

    In this introspective episode of Thriving in the Messy Middle, host Amy P Wilkins reconnects with her former coach, Terry Yoffe, to explore the concept of navigating life's "messy middle" moments. Amy shares how Terry's coaching transformed her approach to personal challenges during a pivotal time in her life. With warmth and wisdom, Terry shares her rich tapestry of experiences, from overcoming early career setbacks to successfully transitioning into a thriving coaching career later in life. Together, they dissect what it means to grow through adversity and how embracing the messiness of life leads to authentic self-discovery and growth. Tapping into the wealth of wisdom from Terry's extensive career, the conversation transcends mere discussions of professional achievements to delve into personal growth. Key themes include recognizing the narratives that limit personal advancement and the power of choice in transcending these self-imposed barriers. Terry offers guidance on how to harness past learning experiences to navigate present-day uncertainties. The interaction underscores the importance of seeing transitions as opportunities for personal development rather than challenges. This episode is a testament to the resilience required to move through challenging seasons and emerge thriving. Key Takeaways Recognizing Patterns: Understanding past messy middle moments can empower individuals to navigate current challenges with more awareness and choice. Empowerment Through Story: Identifying and questioning the narratives we build can unlock personal growth and halt limiting self-beliefs. Power of Choice: Realize that everyone has the choice to either stay stagnant or use challenging times as a catalyst for personal development. Continuous Learning: Embrace new skills and learning opportunities as tools for thriving amid industry disruptions. Seeking Support: Building a trusting relationship with a mentor or coach can provide the necessary guidance and safety to explore personal narratives and instigate change. Terry Yoffe Quotes The choice is to grow from it and to move forward or to move backward, so to speak, or to stay stuck. If you can change your narrative from I'm suffering to, oh, what a great opportunity I have to work on me and to figure out what tools I need. What you're experiencing has nothing to do with you. They are limiting beliefs and assumptions that you made up at a very early age. Mentioned in this Episode Book: Who Moved My Cheese? The book provides insights into adapting to change. About Terry Yoffe Terry Yoffe is a 4X Certified International Business and Communications Coach with more than 20 years of coaching experience and decades of success in both corporate and entrepreneurial roles. With over 60 years of wisdom, business acumen, and lived experience, Terry has built her career on resilience,  persistence, and courage.  She knows firsthand what it means to step into challenges, confront failure, and emerge stronger – growth and reinvention have been the foundation of her journey. As a trusted coach, Terry has guided hundreds of clients to overcome self-limiting beliefs, embrace reinvention, and develop the mindset that drives success.  Her work spans corporate leaders, entrepreneurs, and individuals navigating life transitions – including those ready to challenge ageism, pivot careers, and create impact in their next chapter. At 83, Terry embodies her philosophy: you are never too old or too late to transform your mindset, live with purpose, and achieve both personal fulfillment and professional success. She takes pride in the meaningful relationships she builds with her clients, helping them cut through the stories that they tell themselves, step out of their comfort zones, and discover their own inner strength & power. Terry Yoffe LinkedIn Profile Terry's website: Try Coaching

  4. Jun 24

    Design Your Future with the Big Life Blueprint

    In this episode of Thriving in the Messy Middle, host Amy P Wilkins delves into the power of celebrating achievements and shifting perspectives with the Big Life Blueprint, a life design tool focused on clarity, growth, and impact. Amy emphasizes the importance of acknowledging what has been accomplished as a foundation for future aspirations. Her philosophy champions moving away from a deficiency mindset and focusing instead on one's current capabilities and accomplishments. Throughout the episode, Amy highlights the significance of shifting perspectives from mere goal acquisition to cultivating experiences, impact, and meaning across all areas of life. This mindset shift underpins the Big Life Blueprint, which begins with a "Celebration Audit" that encourages individuals to look at their lives as a whole rather than at siloed achievements. Additionally, Amy discusses the process of writing a letter from one's future self, exploring personal growth, and choosing how to support oneself in times of stress. This holistic approach ensures that personal development extends beyond professional benchmarks and fosters a rich, purposeful existence. Explore how identifying your true priorities, writing letters from your future self, and recognizing personal patterns can help shape a meaningful future. Connect with Amy for more insights into thriving in transitional periods. Key Takeaways The Big Life Blueprint is not a simple goal-setting or productivity tool but a comprehensive life-design process focusing on meaningful growth and possibility. Acknowledging past achievements is crucial for building a strong foundation for future aspirations, steering away from a mindset of lack and deficiency. The practice of writing a letter from your future self helps translate abstract visions into tangible and achievable goals, emphasizing experience over acquisitions. Amy stresses the need to explore who we need to be to achieve goals, rather than merely listing tasks, to foster true personal transformation. By understanding our patterns and support mechanisms, we can anticipate and navigate life's challenges, maintaining momentum toward our envisioned futures. Quotes The future we create is heavily influenced by the lens we use to see the present. Celebration isn't the destination. It's the launch pad. Looking back isn't about staying there. Goals don't create futures. People do. The Big Life Blueprint isn't about fixing yourself. It's about seeing clearly and creating from possibility. How you show up shapes what becomes possible. Everything is connected, which means if we're going to create a meaningful future, we need to look at the whole picture. The messy middle has a way of shrinking our field of vision. Celebration isn't about pretending everything is wonderful. It is about accurately reflecting your achievements, both big and small. Meaningful futures aren't built in one category. They're built across the full landscape of our lives. The Big Life Blueprint isn't just about creating what comes next. It's about discovering what matters enough to make sure it does. Mentioned in this Episode Take the Messy Middle Archetype Assessment™ Amy P Wilkins LinkedIn Profile

  5. Jun 17

    Escaping Toxic Productivity: How to Design a More Intentional Life

    In this episode of Thriving in the Messy Middle, host Amy P Wilkins converses with Jean Batthany, a groundbreaking thinker in regenerative creativity. Jean shares her journey from corporate success to personal challenges, including the loss of a job and a family member, which prompted a life-changing pause. Jean shares her exceptional journey from being a Chief Creative Officer to embarking on a path of introspection and growth. Jean's story is a beacon for anyone grappling with the challenges of constant productivity pressures. Tune in to discover how pausing isn't a moment of inefficiency but a critical element in nurturing creativity and fostering effective leadership. Listen in as Jean reveals the transformative power of taking deliberate pauses to harness creativity and restore well-being. Key Takeaways The Art of Pause: Taking intentional pauses can restore creativity and foster productivity rather than deplete it. Shifting Paradigms: Toxic productivity and constant hustle are not sustainable; regenerative creativity offers a fulfilling alternative. Impact of Life Events: Transformative personal experiences can provoke profound career and lifestyle shifts. Micro Pauses: Incorporating small, consistent pauses throughout the day helps reduce stress and improve cognitive function. Systemic Change: Creating cultures of safety and collaboration is vital for unleashing human creativity and potential. Jean Batthany Quotes Pause isn't just a woo-woo personal indulgence. It's a proven way to reduce chronic stress and perform actually better. Are we creating cultures where ideas and people can truly thrive? When you take a step back, you notice what wasn't working and pave the pathway to regenerative creativity. We're human beings, not human doings. The world and the industry need creativity and human ingenuity more than ever. That's our superpower: return to human. It sounds so cliché, but you cannot pour from an empty cup. You cannot take care of others when you're at a deficit. Mentioned in this Episode Jean's LinkedIn post: I'm not going anywhere." Jean's TEDx Talk: The Art of the Pause About Jean Batthany, Founder / Chief Creative Officer, The Art of the Pause Honored as one of Business Insider's 30 Most Creative Women in Advertising, Jean Batthany is ruthlessly committed to creating impact. She is the founder of Art of the Pause and a pioneer of Regenerative Creativity. After 30 years in the business of creativity, Jean has created a new operating system and the conditions for ideas to flow with abundance vs being extracted through fear and scarcity. She has spoken at TEDx, Cannes Lions Festival of Creativity, and NASA JPL. As Walmart's first Chief Creative Officer, she led their evolution from a transactional company to an emotional brand. As VP, Global Creative at Disney, Jean transformed the in- house team into an award-winning integrated agency. She grew up making and leading creative agency side at DDB, Merkley + Partners, M+C Saatchi, BBDO, Saatchi, and is currently a fractional CCO, collaborating with mission-driven brands to win hearts, minds, spirits, and wallets. Jean Batthany LinkedIn Profile Jean's websites: Art of the Pause and Jean Batthany Creative Jean's TEDx Talk

  6. Jun 10

    Behind the Scenes: How Messy Moments Make Strong Leaders

    In this Messy Middle Moment, host Amy P Wilkins delves into the importance of authenticity and transparency as a leader. Amy candidly shares a personal story about a challenging day that serves to highlight the pressures leaders face to appear perfect, and how showing vulnerability can positively impact workplace culture. She reflects on how leaders inadvertently model behaviors that either empower or inhibit their teams. This episode provides a safe space for women leaders to glean insights into effectively navigating life's uncertainties without losing their core identity. Throughout the episode, Amy emphasizes that true leadership is not about maintaining a perfect exterior but about being real and relatable. Amy uses her own experiences to unpack themes of vulnerability, creativity, and the freedom that comes with embracing imperfection. By allowing others to see the "messy" parts of leadership, Amy contends that leaders can foster environments where their teams feel empowered to be innovative and open. This thought-provoking episode connects with listeners who find themselves in the throes of the "messy middle," encouraging them to embrace these moments with confidence and grace. Key Takeaways Authentic leadership involves showing vulnerability and admitting imperfection. Embracing the "messy" parts of life can foster a more creative and open environment within teams. The way leaders present themselves impacts workplace culture, including attitudes toward rest, uncertainty, and accountability. Leadership isn't about having all the answers; it's about creating a safe space for others to contribute and grow. Consistently projecting perfection can hinder honest communication and stifle creativity. Quotes When we let a little bit of the messy show, we give people permission to be human. If we pretend we always have the answer, people learn to hide their uncertainty. What we make visible as leaders matters. Leadership asks for presence. It asks for accountability, but it doesn't ask us to be perfect. Creativity lives in spaces where people feel safe enough to speak, to try, not to have it all figured out.

  7. Jun 3

    Embracing Vulnerability: A Journey of Growth, Faith, and Resilience

    In this engaging episode of Thriving in the Messy Middle, host Amy P Wilkins speaks with Kenetta Bailey, a respected marketing leader, about navigating uncertainty and transitions in both professional and personal life. Kenetta shares her journey from thriving as a high-level marketer for renowned brands like Pepsi and Sony to overcoming personal trials. She emphasizes the importance of remaining open to new opportunities and how her career path has been shaped by unexpected yet fortuitous challenges. With experience across diverse industries, Kenetta highlights her adaptability and strategic leadership style that have propelled her success. Amidst the backdrop of career transitions, Kenetta recounts a pivotal messy middle moment involving personal upheaval when her father's health declined. She speaks candidly about stepping away from her professional life to take care of her aging parents, an experience that was both challenging and growth-inducing. Throughout this personal story, Kenetta underscores the significance of prioritizing what truly matters, learning from experiences, and being unapologetically true to oneself. As the conversation evolves, the focus shifts to adapting in dynamic professional landscapes, like adopting AI technologies and navigating organizational changes, and how these instances underscore the necessity of continuous learning and flexibility in the workplace. Discover insights on career agility, the importance of vulnerability, and embracing change with courage and resilience. The conversation touches on leadership, the evolving landscape of AI, and finding balance in life's messy middle moments. Key Takeaways Adaptability in Career Transitions: Kanetta discusses the importance of being adaptable and open to seizing new opportunities while turning challenges into stepping stones for career growth. Prioritizing Personal Responsibilities: The episode delves into Kanetta's decision to take a professional hiatus to care for her parents, illustrating the importance of prioritizing family and well-being. Leading Through Change: Insights into leading teams through organizational shifts, focusing on transparency and the transferability of skills to navigate transitions effectively. Unlearning and Relearning: Emphasis on the necessity to continuously evolve in the face of technological advancements such as AI, highlighting the importance of being proactive and adaptive. Personal and Professional Support Systems: The significance of building a robust network, or a 'personal board of directors,' for guidance in both personal and professional spheres. Kenetta Bailey Quotes I've never been afraid of a challenge. If you challenge me, I'm taking you up on it. We've got to be comfortable being uncomfortable. Taking care of the people who took care of me made me a better and more compassionate leader. You can't take yourself too seriously all the time. You've got to protect your mental health. Be yourself, but always be true to who you are and what's important to you. I love to give people advice if they are seeking it, but I don't mean that my advice is the only way that something could be done. Mentioned in this Episode About Kenetta Bailey Kenetta Bailey is a global marketing, communications, and growth executive with 25+ years of experience building and transforming B2B and B2C brands across advertising, media, consumer packaged goods, and entertainment. Known for driving revenue and building high-performing teams, she has a track record of delivering measurable results, from audience growth and digital innovation to product launches and P&L management, for some of the world's most recognized companies. Most recently, Kenetta served as SVP, Marketing at Clear Channel Outdoor Americas, where she led a high-performing team to create data-driven content, enterprise storytelling, and integrated ad sales and product marketing materials, generating multi-million-dollar revenue growth through a full marketing mix including SEO, paid search, and AI-powered search strategies across the company's 28-market footprint. She transformed and relaunched the company's social and digital presence into lead-generating platforms, co-championed CSR and partnership marketing with national nonprofit organizations, and was selected by the CEO to define and implement the company's Mission, Vision, and Values, then led the cross- functional effort to cascade them through the culture, driving measurable improvements in employee engagement and retention. Prior to Clear Channel, Kenetta held senior marketing leadership roles at CBS Radio, WPP/GroupM, Comcast/TV One, AMC Networks, NBC Universal, and Sony Music, and began her career in consumer packaged goods at PepsiCo and Kraft. Across these roles, she drove brand reinventions, launched new networks, won major global accounts, and delivered double- and triple-digit growth. Today, Kenetta is the Founder of The Marketing Den, a consultancy delivering strategy, AI- powered MarComms, growth marketing, media, and digital services to B2B, B2C, and nonprofit clients. Beyond her executive career, Kenetta has served on the boards of the Alliance for Women in Media, Arts Horizons, New Classrooms, and Planned Parenthood Federation of America, and taught persuasive and crisis communications to MBA students at the Wharton School of the University of Pennsylvania. Kenetta holds a bachelor's and master's degree in journalism from Northwestern University's Medill School and an MBA from the Kellogg School of Management at Northwestern. Kenetta Bailey LinkedIn Profile

  8. May 27

    It's a Fine Line: Not All Discomfort Signals Growth

    In this episode of Thriving in the Messy Middle, hosted by leadership coach Amy P Wilkins, listeners are invited to explore the often-overlooked phases of discomfort and uncertainty in their leadership journeys. Inspired by the conversation with Viktoria Degtar, Amy addresses the inevitable moments in life when things seem messy and unclear, offering insights into how distinguishing among types of discomfort can lead to personal growth. This solo episode stands out as it delves into the nuanced differences between expansive and depleting discomfort, urging listeners to carefully assess their emotions and energy to understand which path they are on. Throughout the discussion, Amy unravels the complex emotions tied to discomfort, a necessary part of growth and change, and the courage it takes to assess whether such discomfort is truly pushing one forward or simply a signal of misalignment. As she reflects on personal experiences, she notes key triggers that helped her discern when to embrace challenges and when to recognize situations that were detrimental to her well-being. This theme resonates heavily with women leaders striving to reconcile personal empowerment with professional growth in unpredictable environments. Join her in understanding how to identify and move through these pivotal moments, leading with awareness and choice. Key Takeaways Understanding Discomfort: Recognize that not all discomfort signals growth; distinguish between expansive and depleting discomfort to navigate life's challenges effectively. Energy as a Signal: Use your energy levels as an indicator: expansive discomfort energizes and motivates, while depleting discomfort drains and disconnects. Reflection and Awareness: Stay reflective and aware in the 'messy middle' to discern the lessons or signals your discomfort may be sending you. Growth vs. Harm: Growth can be uncomfortable, but it's crucial to identify when discomfort is actually harmful rather than constructive. Self-trust: Build self-trust and awareness to make informed decisions that honor your personal and professional well-being. Quotes If you're feeling uncomfortable, you're probably right where you need to be. Not all discomfort is the same…some can feel like expansion, some like depletion. The hardest part isn't being uncomfortable; it's knowing which kind you're in. Expansive discomfort might feel scary, but there's still a sense of possibility. Because this is the messy middle, the part of the journey where things aren't clear where you're in it, but you don't yet know what it's here to teach you. For me, it comes down to energy. Expansive discomfort might feel scary, but there's still a sense of possibility. Mentioned in this Episode Thriving in the Messy Middle E26 The Truth About Leading Through Uncertainty with guest Viktoria Degtar

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The Messy Middle Isn't a Detour. It's Your Pathway to Thriving! This podcast is for women leaders who are holding it all together, but know deep down, there's more. Hosted by leadership coach and former media executive Amy Wilkins, this is your weekly exhale and power-up. It's for the ambitious, big-hearted leaders navigating change, craving clarity, and ready to rise—even when it's messy. Thriving isn't about perfection. It's about alignment over achievement, peace over proving, and growth that feels good. Tune in every Wednesday for candid conversations and mindset shifts to help you lead with purpose, alignment, and, most importantly, to thrive.

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