Willing & Winning

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

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...

A holiday bonus episode of Willing & Winning — recorded with a drink in hand and zero expectations. Stay Caught Up With Me and the Podcast: Follow @issawillhill on Instagram Follow @will2winpodcast on Instagram

In the final episode of the year, I’m sharing real-life updates: taking a professional risk by leaving one job before fully settling into the next, leaning into slower holiday moments with my boyfriend, and finding comfort in a very cheugy Pretty Little Liars rewatch. We wrap with a reminder to focus on the good you poured into this year—not just the mistakes. Growth isn’t about perfection; it’s a...

The new year is just around the corner, and it’s easy to fall into the trap of “I’ll start on January 1st.” But what if you could start now—today—and gain momentum before the calendar flips? In this episode, we’re breaking down why waiting for the perfect moment keeps you stuck, how to build small, actionable steps that actually stick, and why progress—no matter how small—is more powerful than per...

The holidays can be magical… but they can also be a lot. In this episode, we’re diving into how to set real, sustainable boundaries during the holiday season—whether you’re juggling social expectations, navigating family dynamics, protecting your peace, or dealing with the quiet moments that bring up loneliness. I’m breaking down how to show up for others without abandoning yourself, how to honor...

I’m sharing all the highlights from my birthday—how I celebrated, the vibes, and the moments that made it feel special. But more importantly, I’m opening up about the biggest lesson I learned this year and how it’s shaping the way I move forward. Grab a drink, kick back, and let’s celebrate growth (and good times) together. Stay Caught Up With Me and the Podcast: Follow @issawillhill on Instagram...

In this week’s episode, I’m catching you up on where life’s been taking me lately—personally, professionally, and everything in between. From confronting the bad habits that keep me stuck, to navigating career growth in corporate spaces while still honoring my entrepreneurial spirit, I’m sharing the lessons, losses, and quiet wins shaping this current chapter. We’ll also get into what I’m loving (...

Our ancestors shape who we are in ways that reach beyond time and memory. In this episode, I’m reflecting on how we can honor those who came before us—through small rituals, quiet remembrance, and moments of gratitude woven into everyday life. From lighting candles to sharing stories, we’ll explore how loving the lost can guide, ground, and inspire us to move through the world with deeper connecti...