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. 17h ago

    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

  2. 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

  3. 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

  4. 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.

  5. 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

  6. 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

  7. May 20

    Balancing Motherhood, Marketing, and Professional Success in a Changing World

    In this episode of Thriving in the Messy Middle, host Amy P Wilkins engages in a vibrant conversation with Michele Fino, a strategist renowned for her ability to bridge the realms of marketing and entertainment. Michele sheds light on her unique journey transitioning from corporate roles to running her own consultancy where she helps brands, nonprofits, and tech companies convey their stories through innovative content strategies. Michele's experience as a seasoned storyteller and consultant provides a window into the blend of creativity, leadership, and adaptability needed to succeed. Key topics include navigating the intersection of motherhood and career, the revolution in professional environments brought about by AI, and the importance of authenticity and making meaningful connections. With a particular focus on work-life balance, personal growth, and professional development, Michele offers practical advice for thriving during chaotic times and how meaningful storytelling can drive change and engage audiences. Through this episode, Amy creates a thoughtful space to explore pivotal moments and the challenges of the "messy middle" that women leaders often navigate. Key Takeaways Balancing Roles: Michelle shares the intricate balance between being a mom and a marketing leader, illustrating the unique challenges and strategies in managing diverse responsibilities. Career Transitions: Her leap from structured employment to establishing a consultancy highlights adaptability and creativity—keys to mastering the transition from employee to entrepreneur. Navigating AI: The episode delves into how AI is transforming marketing, offering insights into leveraging technology while mitigating associated workforce challenges. Storytelling & Strategy: Michelle emphasizes the power of storytelling in marketing, illustrating how purpose-driven strategies can bring brands to life. Valuable Networking: Personal connections and remembered details about others can significantly enrich professional relationships and open doors to new opportunities. Michele Fino Quotes I like working for myself and helping as many companies as I possibly can. The definition of insanity is doing the same thing and expecting different results. Get out there and meet people. Remember something about them. The value of a firm handshake, eye contact, and a smile. You don't get that from staying in a cube all day for nine hours. It's important to know what you're good at and what you're not good at. Mentioned in this Episode Beth Comstock  About Michele Fino Michele Fino is the principal of her own minority owned, woman-run Branded Entertainment strategy consultancy.  She is a Creative & Connected Strategic StorySeller. She helps brands, non-profits, production companies, media companies, tech companies, and networks with their content strategy and their StorySelling.  She speaks at major conferences, runs thoughtful roundtables at events, & jumps in for creative ideations at agencies & brands. She believes that great storytelling can elicit behavior change. . . but people have to see it first.  She is an idea generator that also plans, makes the right connections & writes deal terms for branded content, distribution, and marketing.   She lives on the UES of NYC, has three kids, and owns a lot of gym shoes, but does not belong to an actual gym. Michele Fino Website Michele Fino LinkedIn Profile

  8. May 13

    The Hidden Grief Behind Career Transitions and New Beginnings

    In this Messy Middle Moment, host Amy P Wilkins shares a deeply personal journey through professional challenges. With a history as a leadership coach and former media executive, Amy unravels a story many women encounter: a dramatic career transition that shook her confidence. The episode sheds light on the toll of toxic work environments and the slow erosion of self-belief, culminating in a profound session with an industrial psychologist. The conversation evokes a reflection on the values of resilience, validation, and self-awareness in overcoming professional setbacks and finding one's true path. The narrative continues with Amy's strategic career pivot, choosing a seemingly smaller role that prioritized her mental well-being and self-healing. This decision defies conventional wisdom but highlights the importance of safety and groundedness in rebuilding confidence. Amy eloquently articulates the necessity of grieving career losses and how processing these emotions is crucial to thriving in new opportunities. Her insights cater to women leaders facing transitions, encouraging them to pause, reflect, and embrace the winding road to leadership. Through compelling storytelling and actionable advice, the episode resonates with those navigating their messy middle while striving for growth and authenticity. Key Takeaways Toxic work environments can significantly undermine self-worth and confidence, often without immediate realization. Validation from external observers can act as a catalyst for self-reflection and change. Embracing career transitions, even if they seem like a step back, can offer a crucial space for healing and personal growth. Grieving the loss of a professional identity or role is essential, even when the departure was beneficial. Leadership is a winding path, demanding pauses and reflection to truly thrive in uncertain times. Quotes Thriving isn't about having it all figured out. It's about learning how to grow, lead, and move forward, even when things feel messy. You've just described a morally bankrupt organization. You need to ask yourself why you're still here. Whenever something ends, even something that needed to end, there is still a loss. Not a straight line forward, but moments where something ends, and you're asked to pause, process, and begin again. You rebuild it by honoring what was. Thriving in the Messy Middle Podcast Mentioned In This Episode A Redirection: The Truth About the Right Path for You, with featured guest Adrienne Valencia Garcia, a lawyer and transformational career coach.

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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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