Will Hill
Willing & Winning
Welcome to the Willing + Winning podcast, come join me- Will Hill, your host, digital bestie, mentor, etc., etc.,, . I've created space within my digital platform to allow us to connect beyond the highlight reels + share what’s helping me grow through life so that together we can all win!
Be sure to visit the podcast's website and support the creator: podcasters.spotify.com
Author
Will Hill
Category
Podcast website
Latest episode
Oct 14, 2026
Where to listen?
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Episodes
This Is Your Sign to Start The Thing You've Always Wanted to Do 14.10.2026 15:16
Sometimes, the thing you’ve always wanted to do is the very thing you keep putting off. In this episode of Willing & Winning , I’m sharing a personal announcement that feels a little surreal to say out loud: I’m writing a book. Without giving too much away, I wanted to take a moment to share this new chapter of my creative journey, what it means to finally pursue something I’ve been passiona...
Back on the Mic: A Little Life Update, A Lot to Catch Up On 07.10.2026 50:28
Sometimes life gets busy, the technology decides to stop cooperating, and suddenly it’s been a couple of weeks since you’ve sat down behind the mic. In this episode of Willing & Winning , I’m finally back and catching you up on what’s been going on lately. After navigating some unexpected tech issues, coming out of summer, and settling into September, I felt like it was time to just sit down,...
My Summer of Reflection: Grief, Growth & Figuring Out My Next Chapter 19.08.2026 34:49
Summer has a funny way of slowing you down enough to actually hear yourself think. In this episode of Willing & Winning, I’m catching you up on what’s been going on in my life lately — from entering my full-on Nantucket Era with Elin Hilderbrand books, to growing as an entrepreneur, continuing to navigate grief, and taking a step back to reflect on what I want the next chapter of my life to look l...
Healing Isn’t Linear (And That’s the Point) 12.08.2026 30:26
In this episode of Willing & Winning, I’m talking about something I’ve been experiencing in a very real way lately: the reality that healing doesn’t move in a straight line. I’ve recently said goodbye to my cat, Cosmic. Losing Cosmic, my cat and a deeply loved part of my life, has brought me face-to-face with a kind of grief that I’m still learning how to move through. And one of the hardest parts...
You’re Not Behind, You’re Distracted: Escaping Comparison & Finding Your Own Timeline 05.08.2026 14:51
In this episode of Willing & Winning, I’m exploring the feeling of being “behind” and how often that belief has less to do with where we actually are—and more to do with where our attention is being pulled. The idea of falling behind has become one of the most common ways we measure ourselves. Behind in our careers. Behind in relationships. Behind in success. Behind in becoming the person we thoug...
The Validation Trap: Breaking Free From External Validation & Self-Doubt 29.07.2026 37:27
In this episode of Willing & Winning, I’m exploring the difference between wanting to be seen and needing to be approved—and how easily our sense of self can become tied to the reactions of others. Validation is a natural human desire. We want to feel understood. We want to know that our work, our choices, and our existence matter. But there is a point where seeking connection can quietly become d...
Rebuilding, Finding Joy & The Secret Lives of Mormon Wives 15.07.2026 18:09
This week is less of a structured conversation and more of a catch-up. I'm sharing where life has honestly been lately, what I'm learning as I navigate this season, and why I'm choosing to embrace exactly where I am instead of pretending to have everything figured out. Sometimes growth looks less like a breakthrough and more like giving yourself permission to start again. And because not everythin...
Life Currently 24.06.2026 21:11
Life has been life-ing lately, so I thought it was time for a proper catch-up. In this episode, I’m sharing a real-time look at what’s currently unfolding in my life—from career shifts and creative projects to the challenges, lessons, and moments of uncertainty that have been shaping this season. Sometimes we’re so focused on what’s next that we forget to acknowledge where we are right now, and th...
The Performance of Identity 17.06.2026 26:28
In this episode of Willing & Winning, I’m looking at the tension between visibility and authenticity, especially within queer identity, and what happens when being seen starts to turn into being performed. In a world that constantly asks us to define, explain, and package ourselves, identity can shift from something lived into something curated. Online especially, we learn how to make ourselves le...
Attachment Isn’t Love 10.06.2026 19:28
In this episode of Willing & Winning, I’m exploring the difference between attachment and love, and how often emotional dependency gets mistaken for connection. We don’t always miss people for who they are. We miss the emotional patterns they created: the intensity, the unpredictability, the highs and lows that keep the nervous system activated. Over time, that cycle can start to feel like love, e...
The Identity Audit: Who You Became vs. Who You Actually Are 03.06.2026 22:00
In this episode of Willing & Winning, I’m exploring the space between who we are and who we had to become. Most of us don’t grow into identity in a clean or intentional way. We adapt. We survive. We learn what keeps us safe, accepted, and moving forward. Over time, those survival patterns can start to feel like personality, even when they were originally just responses to circumstance. This is wha...
The Loneliness Era: Why We Feel More Disconnected Than Ever 27.05.2026 31:03
In this episode of Willing & Winning, I’m exploring something that so many people are quietly experiencing but rarely talking about openly: loneliness in modern life. We are living in a time where we can reach anyone instantly. We can see people’s lives in real time, stay updated through social media, react to stories, send quick messages, and remain digitally connected at all hours of the day. Bu...
The Soft Life Myth (Peace, Privilege & the Performance of Escaping Life) 20.05.2026 20:16
In this episode of Willing & Winning, I’m unpacking the internet’s obsession with “soft life” culture and asking a deeper question beneath the aesthetics, luxury routines, and aspirational calm: what does softness actually mean when real life still exists underneath it all? Over the past few years, softness has become a form of digital aspiration — romanticized through skincare, travel, slow morni...
The Energy Economy (Protecting Your Peace Like Currency) 13.05.2026 19:53
In this episode of Willing & Winning, I’m exploring the idea that our emotional and mental energy functions a lot like currency — and whether we realize it or not, we are constantly spending it. The question is: what are we investing in, and what is it actually costing us? I talk about the people, environments, habits, and relationships that quietly drain us versus the ones that expand us, restore...
BONUS EP: 5 Minutes of Feral: Why It’s Okay to Have Unhinged Moments (A Reminder to Be Human) 07.05.2026 4:18
In this bonus episode of Willing & Winning, I’m sharing my personal “5 Minutes of Feral” theory — the idea that sometimes, you just need a moment to be dramatic, emotional, chaotic, or a little unhinged before coming back to yourself. We live in a world that constantly pushes perfection, composure, and having it all together. But the truth is, being human means having moments where you vent, spira...
Healing Without Becoming a Brand (Why Some Growth Should Stay Private) 06.05.2026 16:34
In this episode of Willing & Winning, I’m opening up about a deeply personal chapter and exploring a truth we don’t talk about enough: not all healing needs to be public. In a world where growth is often turned into content, there can be pressure to explain your pain, narrate your progress, and share your transformation before you’ve fully lived through it. I reflect on breaking free from a toxic...
Your Life Is Not Late: Why Timelines Are Fake & Reinvention Is Normal (Stop Feeling Behind) 29.04.2026 11:41
In this episode of Willing & Winning, I’m challenging one of the most damaging beliefs many of us carry — the idea that we’re somehow behind in life. Behind on success, behind on love, behind on career, behind on having it all figured out. I unpack where these invisible timelines come from, how social media intensifies the pressure, and why comparing your real life to someone else’s curated highli...
Life Updates: Career Growth, Hard Truths & Laughing Through the Fall 22.04.2026 21:34
In this episode of Willing & Winning, I’m giving you a real and unfiltered life update. From growth in my career to personal reflections on where I’ve been and where I’m headed, this episode is a check-in on progress, perspective, and becoming. I talk about what it feels like to evolve in real time, navigating change, recognizing growth, and trusting that even when life feels uncertain, movement i...
The Courage to Be Misunderstood: Letting Go of People-Pleasing & Choosing Authenticity 08.04.2026 18:07
Not everyone is going to understand you — and that’s a sign you’re becoming more of who you truly are. In this episode of Willing & Winning, we explore the courage to be misunderstood, how people-pleasing disconnects you from your authentic self, and why choosing authenticity over approval leads to deeper alignment, confidence, and real connection. If you’re ready to stop shrinking and start showi...
Your Next Chapter Requires a Different You (Identity Shift, Personal Growth & Self-Discipline) 01.04.2026 16:57
In this episode of Willing & Winning, I explore the truth about personal growth and why stepping into your next chapter requires becoming a different version of yourself. Everyone wants the next level—the new opportunity, the breakthrough, the transformation. But what often gets overlooked is that new seasons don’t just arrive… they require evolution. They require new habits, new discipline, and a...
The Life Audit: When Your Old Life No Longer Fits (How to Realign, Pivot & Evolve) 25.03.2026 21:50
There comes a moment in life that doesn’t arrive with a breakdown or a big announcement—just a quiet, undeniable truth: The life you built no longer fits who you’ve become. In this episode of Willing & Winning, I’m diving into what I call a life audit—the intentional pause where you take inventory of your relationships, routines, career, and environment to ask one powerful question: Does this stil...
Returning to Yourself: How to Find Your Voice Again After Burnout & Life Transitions 18.03.2026 15:26
Sometimes the hardest place to return to… is yourself. In this episode of Willing & Winning, I explore what it really means to lose and rediscover your voice in a world that constantly demands more—more productivity, more content, more noise. This is a conversation about a quiet truth I’ve experienced myself: life gets loud, and somewhere along the way, we stop hearing ourselves clearly. If you’ve...
Trusting the Unknown (Why Letting Go of Control Builds Inner Peace ) 11.02.2026 21:34
In this episode of Willing & Winning, I explore what it really means to trust the unknown, and why releasing the need for certainty can become one of the most powerful acts of self-trust and emotional growth. We live in a culture obsessed with plans, timelines, and guarantees. We’re taught that clarity must come before movement, and that control equals safety. But the truth is, most meaningful gro...
Why Delayed Gratification Beats Instant Satisfaction 04.02.2026 25:48
In this episode of Willing & Winning, I explore why delayed gratification is more powerful than instant gratification, and how learning to wait, build, and trust the process can completely change your relationship with success, confidence, and self-worth. In a world that rewards quick wins, fast validation, and overnight results, choosing patience can feel uncomfortable,even countercultural. But d...
2026 Ins & Outs: Life Updates, Holiday Reflections & Setting Intentions for the New Year 14.01.2026 33:59
In this episode of Willing & Winning, I’m sharing personal life updates from the holiday season, what the past year taught me, and my official ins and outs for 2026 — from habits and mindsets I’m leaving behind to the energy, boundaries, and goals I’m carrying forward. We talk about: Holiday reflections and real-life updates What I’m saying no more to in 2026 What I’m intentionally welcoming in th...
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