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. 3d ago

    The Rising Leader: Learning to Lead in a New Role

    In this episode of Thriving in the Messy Middle, host Amy Wilkins delves into the nuanced challenges of being in a Rising Leader phase, a pivotal transition phase often marked by self-doubt and expanding responsibilities. As part of her Messy Middle Archetype™ series, Amy invites listeners to reflect on their current roles and whether they truly feel ownership or are still catching up to their new responsibilities. Throughout the episode, Amy explores inherent challenges faced by those stepping into higher visibility roles, particularly the internal conflict between perceived competence and actual capability. Using personal anecdotes from her career, she paints a vivid picture of her own experiences and missteps. The episode highlights the importance of trusting and leveraging team dynamics rather than carrying the burden alone. This insightful discussion targets emerging leaders seeking to ground themselves amidst unfamiliarity while emphasizing that confidence is often a product of stepping into new roles rather than a prerequisite. Key Takeaways Embrace the discomfort that comes with stepping into a larger role; it signifies a "Rising Leader" season that is ripe with growth opportunities. Competence in leadership roles often develops through experience; confidence follows action, not the other way around. Attempting to shoulder all the responsibility may hinder not only personal growth but also the growth of your team. Balance the expectations set by the new role with trusting your team to rise with you. Utilize support systems like mentors or coaches to ease the transition into more visible positions. Quotes You've already proven yourself. You've delivered and earned the trust. That's what led you here. What if confidence isn't what comes first? What if stepping into the role is what builds it? Messy seasons are signals that growth is coming. Trusting the people around you to rise with you instead of carrying it alone. It was unnerving how stepping up into this new position suddenly had me questioning my every move. Here's a question I want to leave you with. What if confidence isn't what comes first? What if stepping into the role is what builds it? Mentioned in this Episode Messy Middle Archetype Assessment™ Visit ChooseAwe.com for more resources and information about Amy P Wilkins and her coaching work.

  2. Oct 21

    The Dreamer: When It's Time to Pull Toward New Possibilities

    In this episode of Thriving in the Messy Middle, Amy Wilkins tackles the complexities of the Dreamer archetype, a recurring theme for those feeling the pull toward new possibilities while maintaining existing responsibilities. Amy opens the discussion by asking listeners to reflect on their own hesitations to pursue dreams due to the weight of current obligations. This thought-provoking conversation explores the tension between responsibly staying the course and yearning for something more aligned with one's true self. Listeners will gain insight into the nuances of the Dreamer season, learning that "someday" thinking can keep dreams perpetually out of reach. Amy sheds light on how to recognize these signs and invites listeners to reevaluate how their dream might coexist with other important life commitments. Encouraging a brave first step, Amy shares strategies for beginning the exploration of new paths before full clarity arrives. By addressing common fears and external influences, this episode empowers the Dreamer within us all to take action in pursuit of a more fulfilling path. Key Takeaways Acknowledge and explore the persistent pull towards something new. Understand the barriers of "someday" thinking and how it prevents progress. Recognize that pursuing your dream doesn't have to be at the expense of existing responsibilities. Learn to involve mentors and supportive individuals early in the process of exploring new possibilities. Embrace the idea that the messy middle signals upcoming growth and evolution. Quotes The pull didn't go away. It just got more persistent. There was something else calling me. What if your dream doesn't have to compete with everyone else's needs? I was doing well, being responsible, staying the course, and for a while that felt like enough. But underneath, something started to shift. Answering that call wouldn't take anything away from what I had built. But ignoring it started to feel like I was holding myself back. You're doing good work and have made thoughtful choices. And from the outside, your path makes sense. Someday, when the stars align, you'll give yourself permission to pursue that dream. But for now, you keep going. Your dream can surface its own doubts about what it would mean to move in a different direction. The vision feels real, but the next step doesn't. So you stay where you are. Messy seasons are signals that growth is coming. Mentioned in this Episode Messy Middle Archetype Assessment™ Visit ChooseAwe.com for more resources and information about Amy P Wilkins and her coaching work.

  3. Oct 14

    The Restless Achiever: When You're Ready for a New Challenge

    Join Amy Wilkins in this special episode of Thriving in the Messy Middle as she delves into the realities of navigating the Restless Achiever archetype. With her unique insights, Amy extends an invitation to her audience to explore the uncomfortable yet potentially transformative phase in one's career, where ambition meets a desire for growth despite external stability. This episode is part of the Messy Middle Archetype™ series, intended to help listeners identify their current season and understand the nuances of different archetypes. In this episode, Amy reflects on her experience in an executive role, where she felt the pull toward something more despite her success on paper. The "Restless Achiever" archetype is explored as a phase of professional life where one's enthusiasm and drive call for fresh challenges and meaningful growth, even when existing conditions appear favorable. Amy emphasizes recognizing this restlessness not as dissatisfaction but as valuable feedback. The episode serves as a guide to embracing change, encouraging professionals to assess their readiness for new opportunities and to engage with mentors or coaches for perspective and support. With these insights, Amy Wilkins invites listeners to embrace the Restless Achiever within and urges them to explore what's beyond their current challenges. Tune into this episode to find clarity, inspiration, and empowerment in the midst of your own Messy Middle. Don't forget to follow the podcast for more guidance on leading through life's inevitable messiness. Key Takeaways The Restless Achiever period can occur when outward success doesn't align with your desire for deeper growth. Recognizing restlessness is crucial, as it often signals readiness for a new phase, even when nothing seems wrong externally. Ignoring restlessness can lead to frustration, low energy, and diminished drive. Trusted mentors or coaches can provide perspective and help navigate the Messy Middle. Messy seasons are growth opportunities, appearing repeatedly in career and personal life. Quotes When nothing is wrong, it's easy to ignore what's no longer right. Restlessness doesn't just sit there quietly. It starts to leak out as frustration, as low energy, as your own drive slipping. What if restlessness isn't something to suppress? What if it's information? My ambition and drive had outpaced the opportunity in front of me. It's easy to tell yourself to stay, to be grateful, to be responsible, to not disrupt something that's working. Mentioned in this Episode Messy Middle Archetype Assessment™ Visit ChooseAwe.com for more resources and information about Amy P Wilkins and her coaching work.

  4. Oct 7

    The Quietly Burning Out: When Survival Becomes the Only Option

    In this enlightening episode of Thriving in the Messy Middle, host Amy Wilkins delves into the complex subject of burnout, specifically focusing on the archetype of Quietly Burning Out. Amy recalls her personal experiences in high-pressure environments and shares the poignant realities of masking burnout, maintaining external performance, yet internally feeling depleted. This episode is part of the Messy Middle Archetype™ series, which aims to illuminate and provide clarity on various overwhelming career phases, empowering listeners to navigate these challenging periods with awareness and choice. Amy paints a vivid picture of quietly burning out, a state where individuals keep up appearances but internally feel exhausted and unsupported. She explores the dangers of ignoring the subtle signs of burnout, emphasizing the importance of acknowledging one's limits and sharing the burden with someone trustworthy. This episode is rich with practical advice on recognizing the stealthy pathways to burnout, reframing the narrative around professional endurance, and realigning priorities to ensure personal well-being is not compromised during challenging times at work. Key Takeaways Burnout Masked by Performance: Often, burnout doesn't manifest through missed deadlines or errors, making it difficult to detect, both by the individual and those around them. Awareness and Sharing: Recognizing signs of burnout needs honest reflection and open conversations with others, breaking the silence before cracks become more evident. Growth from Discomfort: Messy seasons signal potential growth and present opportunities to develop self-awareness and resilience. The Illusion of Choice: Acknowledging that there is often more agency in managing workload and stress than it may initially seem. Persistent Patterns: Burnout and challenging seasons recur, requiring new strategies and greater self-awareness over time to navigate them effectively. Quotes You're carrying more than your share… holding things together in ways that don't show up on a job description. Quietly burning out doesn't look the way people expect…that's exactly why it goes unnoticed. By the time those cracks show, you've often already pulled back from the very people who might have noticed sooner. What if the goal isn't to push through? What if it's to start noticing the cost before it gets too high? Messy seasons are signals that growth is coming. Mentioned in this Episode Messy Middle Archetype Assessment™ Visit ChooseAwe.com for more resources and information about Amy P Wilkins and her coaching work.

  5. Sep 30

    The Juggler: Putting Something Down is Essential for Growth

    In this episode of Thriving in the Messy Middle, host Amy Wilkins delves into the concept of the 'Juggler' archetype. Designed to help listeners navigate the complexity of juggling multiple roles and responsibilities, Amy offers valuable insights into how to recognize when one is in a Juggler season. She shares personal experiences of balancing a demanding career and motherhood, highlighting the importance of prioritizing crucial tasks over treating everything as equally important.  In the heart of this compelling episode, Amy explains that thriving isn't about simply having everything under control but choosing what truly deserves your energy. The discussion focuses on helping individuals identify the real importance of their various commitments, distinguishing between what's critical and what can be postponed. Listeners are reminded that feeling overwhelmed is a signal of growth and an opportunity to embrace a more purposeful path. By exploring the Juggler archetype, Amy aims to bring clarity and encourage listeners to lead with greater awareness and self-trust. Amy encourages seeking guidance from mentors or coaches to gain clarity and emphasizes the significance of embracing and learning from life's messy seasons for continuous growth. Key Takeaways The Juggler archetype centers around balancing numerous important roles, often leading to a feeling of being overwhelmed. Prioritization is crucial; not everything on your plate carries the same weight or urgency. Recognize when you're reacting rather than leading your time and energy, a common pitfall in a Juggler season. Dropping the ball is more common when there hasn't been a conscious choice in prioritization. Growth often comes from recognizing messy seasons as valuable signals for change and self-reflection. Quotes When everything feels important, you aren't actually prioritizing anything. What if the goal isn't to juggle better but to start putting something down on purpose. Messy seasons are signals that growth is coming. When we try to do too many things at once, we actually slow down our progress. Eventually, you drop a dish. And not on purpose, not because you chose to set it down. What if the goal isn't to juggle better? What if the goal is to start putting something down on purpose? Mentioned in this Episode Messy Middle Archetype Assessment™ Visit ChooseAwe.com for more resources and information about Amy P Wilkins and her coaching work. About Amy P Wilkins, The Messy Middle Coach Amy P Wilkins is a leadership coach, former media executive, and the founder of Choose Awe—a coaching practice devoted to helping women leaders navigate transitions with clarity, courage, and self-trust. After decades in senior leadership roles, Amy now empowers women to lead with purpose and thrive through the "messy middle" seasons of life and leadership. Schedule an Exploration Call HERE Take the Messy Middle Archetype Assessment™ HERE Read The Messy Middle Blog HERE Subscribe to Magic in the Messy Middle Newsletter HERE

  6. Sep 23

    Reclaiming Your Day: Why 20 Minutes is the New Hour

    In this engaging episode, Amy Wilkins hosts the esteemed Fran Hauser to discuss her transformative journey and her insights on balancing professional life with personal aspirations. The conversation kicks off with nostalgic reflections on their initial meeting and the impactful community ties formed through She Runs It, previously known as the Advertising Women of New York. Hauser dives into her career transitions, especially highlighting her messy yet rewarding shift from corporate America to becoming a successful entrepreneur and author. Continuing with an exploration of Fran's newly launched book, "20 Minutes is the New Hour," the episode unpacks the challenges of managing time effectively and the strategies for moving from a corporate role to a multifaceted career. Hauser emphasizes the importance of understanding different aspects of time, distinguishing between Kronos and Kairos, and shares practical advice for achieving a flow state to enhance productivity. Her "Four P's" framework, Perfectionism, People Pleasing, Procrastination, and Padding, offers listeners actionable insights into overcoming common time management pitfalls and creating more space for creativity and restorative activities. Discover how to harness your natural work rhythms for better productivity and personal well-being. Key Takeaways Fran Hauser discusses the importance of building a supportive network to navigate career transitions successfully. Fran introduces the concepts of Kronos and Kairos, illustrating different perceptions of time management and productivity. The "Four P's" framework addresses harmful patterns that can affect our relationship with time: Perfectionism, People Pleasing, Procrastination, and Padding. Emphasizing the need for spaciousness in our schedules, Fran advises routinely reviewing and optimizing our calendars to align with personal and professional priorities. The episode underscores the potential for growth during "messy" transitions, stressing that these periods often lead to significant personal and professional development. Fran Hauser Notable Quotes Any big transition… is going to be messy. 20 minutes is the new hour. And it's a metaphor for how we spend our time. I really want everyone to know they probably have more control and agency over time than they think. I really want to encourage everyone to challenge accepted timelines. It's important to have open space on your calendar. Mentioned in this Episode She Runs It About Fran Hauser Fran Hauser is a leading career expert and longtime champion of women in the workplace. A former Fortune 500 executive and President of Digital at Time Inc., she has spent the past decade as an author, speaker, investor, and mentor, helping women thrive professionally. She has invested in more than 40 female-founded companies and spoken at more than 200 organizations, including Meta, Google, Unilever, BlackRock, NPR, Mastercard, and The Conference for Women, reaching communities of women at every stage of their careers.  She is also the founder of Bedford Books in Bedford, New York, and the acclaimed author of The Myth of the Nice Girl. Her forthcoming book, Twenty Minutes Is the New Hour, was published by Penguin Random House/Crown Currency in September 2026. Fran's LinkedIn Profile Fran's Website "Regardless of where you are in your career, TWENTY MINUTES IS THE NEW HOUR is the time management guide you need to reclaim your time and get ahead. Everyone—Gen Z, millennial, Gen X, and boomer alike—will find something useful in these pages." Lindsey Pollak, New York Times bestselling author of Becoming the Boss and The Remix "In TWENTY MINUTES IS THE NEW HOUR, Fran Hauser offers a liberating reframing of time in a culture that equates busyness with worth. With clarity and compassion, she reveals how perfectionism and people-pleasing pull us away from what truly matters and how to reclaim our time for the people and work that both add value and make us feel valued, so our days reflect meaningful work, deep relationships, and a life aligned with what matters most." Jennifer B. Wallace, New York Times bestselling author of Mattering and Never Enough

  7. Sep 16

    Take the Risk: How Career Reinvention Creates New Opportunities

    In this engaging episode, host Amy Wilkins interviews Beth Mach, a distinguished leader with three decades of experience in media marketing. Beth shares her transformational journey from leading prestigious roles in the corporate world to co-founding Spacely, a groundbreaking media marketplace. The conversation takes listeners through Beth's numerous career highlights, exploring themes of personal growth, resilience, and leadership. Through personal stories and professional anecdotes, Beth reveals how embracing challenges, taking risks, and betting on oneself can ignite new opportunities and drive sustained success. As Beth reflects on her experiences, she discusses key transitional phases, including her move from Detroit to New York and later, her decision to step into an intense global role. These experiences are characterized by personal challenges but ultimately reveal her capacity to thrive under pressure. The episode provides valuable insights into how Beth has fostered an inclusive and honest team culture at Spacely, encouraging transparency, respect, and open communication among co-founders. For those at a crossroads in their career, Beth's pioneering spirit and practical advice serve as a guiding light. Key Takeaways Visionary Leadership: Beth Mach underscores the importance of embracing vulnerability and direct communication in leadership, especially during times of organizational disruption. Personal Growth: Relocating to New York and accepting a demanding global role helped Beth strengthen her resilience, highlighting the value of stepping outside one's comfort zone. Breaking Stereotypes: Beth defied norms by pursuing roles that offered growth rather than opting for lateral moves, further exemplified by her transition to co-founding Spacely. Entrepreneurial Spirit: Despite not seeing herself as entrepreneurial initially, Beth's story demonstrates that innate qualities and a supportive network can propel entrepreneurial success. Decision-Making Tool: Beth developed the IHAP tool, emphasizing self-reliance and personal values when making pivotal career decisions. Beth Mach Quotes Kindness leads. Direct and respectful communication is critical. Nothing is forever. So it's actually okay to try these new things because you can always change your course. There's not one moment of regret and not one moment that I wouldn't be proud to talk about. I had to rise above some of those moments and say, you've got this. It was okay to show emotion. It was okay not to be a robot. It's actually okay to try these new things because you can always change your course. You have to trust yourself, your gut, and what you know about yourself and what you want to do next. Mentioned in this Episode IHAP Tool: Discover Beth's decision-making tool, IHAP (Intelligence, Happiness, Amplification, and Prosperity) About Beth Mach, COO & Co-Founder of Spacely Beth Mach is a seasoned business leader with extensive experience in marketing, media, and technology. She is currently a Co-founder and Chief Operating Officer of Spacely, where she spearheads operations and marketing for a marketplace revolutionizing offline media buying and selling. Beth has a proven track record of driving growth and innovation and brings over 25 years of experience driving business-building media and communications solutions for Fortune 500 brands across a range of categories including Financial Services, Retail, Consumer Package Goods, Technology, Entertainment, Quick Service Restaurants, and Automotive, with leading marketers such as American Express, LVMH, Procter & Gamble, Goldman Sachs, Nokia, Keurig Dr. Pepper, Applebee's, Jaguar Land Rover, Ford, Stellantis, and General Motors. She has previously held leadership roles at global media and advertising agencies, including more recently the Chief Consumer and Communications Officer for TrueCar, President of Dentsu X/Luxe, and Chief Digital Officer at Initiative. Beth is an Executive in Residence for The Room and actively contributes to several established and start-up boards, including Compliant, Brandstory Architech, and Influential; she is also an accomplished public speaker, mentor, investor, active volunteer, and advocate for women and diversity in the workplace. Beth holds a B.A. from Walsh College and is pursuing a Certificate of Management Excellence through Harvard Business School.Beth Mach LinkedIn Profile Beth's Website TEDx Talks/TEDxDetroit: The Power of Choice

  8. Sep 9

    What Can We Do With This One Big Beautiful Life?

    Welcome to Season Two of Thriving in the Messy Middle with Amy Wilkins, where embracing uncertainty is not just accepted but essential for growth. This episode dives into the deeply personal and transformative experiences that arise when life feels overwhelming and unmanageable. Amy shares her personal story, reflecting on how she coped during a particularly challenging time. Through candid anecdotes, she explores the psychological patterns many experience when they feel isolated despite surroundings filled with people. As she addresses the "fake it till you make it" mentality, Amy elaborates on the immense impact of self-reliance gone too far and the power of vulnerability in seeking support. In this episode, Amy introduces the theme for Season Two, delving into the concept of the Messy Middle and how it manifests in various forms in our lives. With upcoming conversations and episodes focusing on different messy middle archetypes, Amy invites you to listen for insights into breaking patterns, the importance of support, and moving forward with clarity. Amy emphasizes that thriving doesn't mean having all the answers but rather being open to growth and learning. With a promise of stories from others who've weathered their own messy seasons, Amy sets the stage for an insightful journey through self-discovery and empowerment, all anchored by the idea of asking better questions to navigate life's complexity. Key Takeaways Pattern Recognition: Acknowledge the psychological patterns of isolation that often emerge during life's messy seasons. Vulnerability's Value: Understanding the power of vulnerability in seeking support and not relying solely on self-reliance. Redefining Success: Learn that thriving isn't about having it all figured out but being willing to learn and grow through challenges. Self-Discovery: Use challenge periods as opportunities for self-discovery and personal growth. Practical Guidance: Insightful questions and strategies for navigating uncertainty are essential tools in the messy middle. 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. Sometimes you need someone to remind you that you don't have to have it all figured out today. The messy middle isn't a problem to be solved. It's a part of life, and it's where the growth happens. Sometimes you just need enough clarity to take the next step. When you're in the messy middle, you don't always need another answer. Sometimes you need another human being, someone who can sit beside you and listen, maybe ask a question you haven't thought of, and remind you who you are when you've temporarily forgotten. You are not alone. And needing support doesn't mean you're not strong enough or capable enough to handle this on your own. It just means support helps you move through the season more swiftly. Sometimes you discover that the person you thought you needed to become isn't actually who you even want to be. Mentioned in this Episode Visit ChooseAwe.com for more resources and information about Amy P Wilkins and her coaching work. Listen to all of Season One of Thriving in the Messy Middle on the Choose Awe website.

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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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