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 this conversation is exactly that: an honest check-in.If you’ve been feeling like you’re in a season of transition, rebuilding, or simply trying to figure things out as you go, this one is for you. 🤍🎙️Stay Caught Up With Me and the Podcast:Follow @by.whill on InstagramFollow @will2winpodcast on Instagram

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 legible, even when our lived experience is still evolving in ways that can’t always be explained.But queerness is not a single aesthetic or performance. It is expansive, personal, and often nonlinear. The pressure to be visibly “understood” can quietly pull us away from authenticity, replacing presence with performance.True freedom isn’t always about being fully seen, it’s about being allowed to exist without translation. Without explanation. Without having to turn identity into something digestible.Because you don’t owe anyone a polished version of who you are. Only honesty, even while you’re still becoming.Stay Caught Up With Me and the Podcast:Follow @by.whill on InstagramFollow @will2winpodcast on Instagram

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, even when it’s actually just familiarity.Attachment is rooted in fear,fear of loss, silence, and abandonment. Love is rooted in presence. But when you’re used to inconsistency, stability can feel unfamiliar, even uncomfortable. This is why intensity often gets mistaken for chemistry, when it’s really just emotional activation.Rewiring this pattern isn’t about finding different people first, it’s about changing how you respond. Learning not to chase clarity from confusion, not to confuse anxiety with intuition, and not to mistake emotional distance for something you need to fix.Because real connection doesn’t leave you in constant emotional survival mode. And anything that requires you to abandon yourself in order to hold onto it isn’t love, it’s attachment asking to be healed.Stay Caught Up With Me and the Podcast:Follow @by.whill on InstagramFollow @will2winpodcast on Instagram

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 what I’m calling a survival identity; the version of you built to get through something, not necessarily to express your full truth. The challenge is that this version doesn’t always retire when life changes. It can quietly continue shaping how you love, work, and see yourself.But there’s a shift that happens when you start noticing the difference between survival and authenticity. You begin to realize you’ve outgrown certain patterns, even if they once served you. And instead of resisting that, you start paying attention to what actually feels aligned now.An identity audit is really just that moment of awareness. Asking what parts of you were built out of fear or necessity, and what parts feel true when everything else falls away.Because you are not fixed. You are evolving.And at some point, growth becomes less about becoming someone newand more about choosing who you are on purpose.Stay Caught Up With Me and the Podcast:Follow @by.whill on InstagramFollow @will2winpodcast on Instagram

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. But despite all of that access, many people still feel emotionally disconnected, unseen, and isolated in ways that are becoming increasingly difficult to ignore.I talk about the shift that happens in adulthood when friendships become harder to maintain, relationships naturally evolve, and connection no longer exists through shared environments the way it once did. Growing older often means navigating distance, changing priorities, different schedules, and realizing that some relationships fade not because of conflict, but simply because life keeps moving.I also reflect on how technology has changed the depth of human connection. Sometimes we confuse digital proximity with genuine intimacy. Seeing someone online is not the same as truly knowing how they’re doing. Reacting to content is not the same as feeling emotionally connected. And over time, those small substitutions can quietly deepen feelings of loneliness without us fully realizing it.But more importantly, this episode is about rebuilding connection intentionally. Because community no longer happens automatically for most people — it has to be created. Real connection now requires effort, vulnerability, consistency, and the willingness to reach out even when it feels uncomfortable.Because loneliness doesn’t always mean you’re failing socially.Sometimes it simply means you’re living in a world where connection has changed.And maybe healing startswhen we stop waiting for connection to happen naturally…and start building it intentionally instead.Stay Caught Up With Me and the Podcast:Follow @by.whill on InstagramFollow @will2winpodcast on Instagram

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 mornings, expensive candles, wellness content, and curated peace. But I wanted to explore whether some versions of the “soft life” are actually attainable for everyone, or if certain forms of softness are deeply tied to privilege, financial access, support systems, and visibility online.I also talk about the difference between true peace and emotional avoidance. Sometimes what we call “protecting our peace” is actually disengagement, isolation, conflict avoidance, or refusing to confront the harder realities of growth, responsibility, and healing. Rest is necessary. Ease is beautiful. But escapism can disguise itself as self-care if we aren’t honest with ourselves.I reflect on what a sustainable life really looks like — not a perfectly aesthetic one, but a life that feels emotionally manageable, grounded, intentional, and human. A life where softness is not about avoiding discomfort entirely, but creating enough stability within yourself to move through life without constantly being in survival mode.Because maybe the goal isn’t to build a life that looks soft online.Maybe the goal is to build a life that actually feels safe to live in.Stay Caught Up With Me and the Podcast:Follow @by.whill on InstagramFollow @will2winpodcast on Instagram

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 us, and multiply our sense of self. Some connections leave you inspired, regulated, and grounded. Others leave your nervous system in debt.I also unpack the concept of emotional ROI — the return we receive from the energy we pour into others — and why so many of us stay emotionally overdrawn trying to maintain relationships that no longer feel reciprocal, safe, or aligned.We often think boundaries are selfish, dramatic, or emotionally cold. But sometimes boundaries are simply financial decisions for your nervous system. You cannot continuously spend emotional energy in places that never replenish you and expect to remain whole.Not every connection is expensive in obvious ways.Some people cost your clarity.Some cost your confidence.Some cost your peace.And healing sometimes begins by auditing where your energy has been going all along.Stay Caught Up With Me and the Podcast:Follow @by.whill on InstagramFollow @will2winpodcast on Instagram

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, spiral, overreact, laugh too hard, cry unexpectedly, or feel everything at once. That doesn’t make you broken — it makes you real.This episode is your reminder that a temporary moment does not define your character. You’re allowed to feel it, release it, and move forward. Sometimes the healthiest thing you can do is let yourself be messy for a minute… then reset.Feel it.Laugh at it.Move on.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 and emotionally destabilizing dynamic, what it felt like to lose connection with myself, and how silence sometimes becomes a necessary form of protection. I also discuss navigating emotionally complex experiences in spaces where vulnerability didn’t always feel understood, and the loneliness that can come with processing difficult seasons internally.I also unpack performative healing culture — when therapy language becomes aesthetic instead of embodied work — and why true healing is often quiet, messy, nonlinear, and deeply personal. Some lessons need privacy before they need an audience.You do not owe the world your wounds in real time.Clarity takes space.And healing is not a brand.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 highlight reel will always distort your perspective. The truth is, most lives are not linear. People pivot, restart, rebuild, and reinvent themselves at every age.This episode is a reminder that growth rarely happens on schedule. Detours are not failure. Delays are not proof that you missed your chance. Sometimes the path that looks slower is the one building the strongest foundation.Your timeline is your own.Reinvention is normal.And your life is not late.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 is still happening. I also share the very humbling (and slightly chaotic) tumble I took at the bar because sometimes life will remind you to stay grounded in the most unexpected ways.This episode is honest, lighthearted, and rooted in the reminder that growth doesn’t always look polished. Sometimes it looks like reflection. Sometimes it looks like resilience. And sometimes… it looks like falling down and laughing anyway.You’re allowed to grow.You’re allowed to restart.You’re allowed to laugh on the way there.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 showing up fully as yourself, this conversation is for you.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 willingness to let go of the identity that no longer aligns with where you’re going. If you’ve been feeling stuck between who you were and who you’re becoming, this episode will help you understand that discomfort isn’t failure—it’s transformation. Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 still support who I’m becoming?Because growth doesn’t always look dramatic.Sometimes it looks like discomfort in spaces that once felt like home.Sometimes it sounds like your inner voice getting louder… asking for more alignment.This episode is for anyone feeling disconnected, misaligned, or quietly ready for change—but unsure where to begin.Because a life audit isn’t about tearing everything apart.It’s about making sure your life still reflects who you truly are.And sometimes, the most powerful thing you can do…is give yourself permission to evolve.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 been feeling disconnected, creatively blocked, or unsure of your next step, this is your permission to pause—not quit.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 growth happens in seasons where the path isn’t clear, the answers haven’t arrived yet, and the next step requires faith rather than proof.Trusting the unknown isn’t about passivity or blind optimism. It’s about learning to stay grounded while things are still unfolding, listening to intuition when logic runs out, and choosing courage even when outcomes aren’t guaranteed.If you’re in a liminal season, between who you were and who you’re becoming, this episode is a reminder that uncertainty doesn’t mean you’re lost. It often means you’re expanding.You don’t need the full map.You need self-trust.And sometimes, the unknown is where alignment begins.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 delayed gratification isn’t about deprivation; it’s about discipline, emotional maturity, and long-term alignment.If you’ve been feeling stuck, impulsive, or frustrated by slow progress, this episode offers a grounded reframe, reminding you that what’s built slowly often lasts the longest.Growth doesn’t rush.Confidence compounds.And sometimes, waiting is the win.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 updatesWhat I’m saying no more to in 2026What I’m intentionally welcoming in this yearRedefining success, growth, and self-worthMoving into the new year with clarity instead of pressureIf you’re looking to reset for the new year, feel more grounded, or need permission to move at your own pace, this episode is for you.New year. Same heart. Stronger boundaries.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 InstagramFollow @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 about showing up, learning, and moving forward with intention.Thanks for being here this year. See you next year!xoxo, Will Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 perfect timing. I’m sharing strategies to identify realistic goals, cultivate consistency, and shift your mindset so that when the new year hits, you’re already ahead. Grab your planner, take a deep breath, and let’s get started on building the life you want—right now.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 your limits with confidence, and how to create a season that actually feels good to you. Pour something warm, take a breath, and let’s walk through this together.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

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 InstagramFollow @will2winpodcast 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 (and not so much), plus the new ways I’m choosing to elevate my well-being, protect my peace, and redefine what success looks like right now.Stay Caught Up With Me and the Podcast: Follow @issawillhill on Instagram Follow @will2winpodcast on Instagram

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 connection and purpose.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

Fear is something we all share, but how we face it shapes who we become. In this episode, I’m opening up about my own fears—both personal and societal—and the ways I’ve learned to navigate them as a queer person of color in today’s world. From daily anxieties to systemic challenges, we’ll explore what it means to own our fear, reclaim our power, and keep showing up with courage, compassion, and purpose. Stay Caught Up With Me and the Podcast: Follow @issawillhill on Instagram Follow @will2winpodcast on Instagram

Mysticism isn’t about robes, candles, or crystal balls—it’s about connection, reflection, and learning to trust the unseen parts of ourselves. In this episode, I’m taking you through spiritual experiences that shifted how I see the world, from honoring Hestia at Betula’s Botanica to diving into Tarot readings over tea. Together, we’ll explore how simple rituals and mindful moments can help us feel more grounded, intentional, and at peace in our daily lives.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

We all carry monsters inside us—the insecurities, fears, and doubts that creep into our relationships and self-talk when we least expect it. In this episode, I open up about the ways these monsters have shown up in my own life, how they’ve tested trust, and what it looks like to face them with honesty and compassion.Together, we’ll unpack where these struggles come from, explore tools like mindfulness, journaling, and boundary-setting, and talk about what it means to communicate openly when your inner monsters try to sabotage connection. I’ll also share how therapy and other resources can help when the weight feels too heavy to carry alone.This is an honest, practical guide for anyone who’s tired of pretending their monsters don’t exist and is ready to meet them with courage, awareness, and self-love.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on InstagramShare your reflections on this episode—what “monster” are you facing right now?

Entrepreneurship isn’t all freedom and glossy highlight reels—it’s messy, unpredictable, and sometimes downright terrifying. In this episode, I pull back the curtain on the parts no one talks about: the comparison traps that steal your confidence, the loneliness that creeps in during long nights, the heartbreak of sacrifices made, and the financial instability that keeps you refreshing your bank app like it’s a horror movie.Through honest stories from my own journey, I share how I’ve learned to navigate these challenges with humor, resilience, and a touch of radical self-compassion. You’ll walk away with practical tools to set healthier boundaries, strengthen your support systems, and embrace the messy middle of building something meaningful. If you’ve ever felt like the entrepreneurial path is scarier than it looks online, this episode is your reminder that you’re not alone—and that growth often hides inside the scary parts.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on InstagramShare your own “scary truths” of entrepreneurship, tag the podcast, and join the conversation

Most of the pain we experience doesn’t come from life itself—it comes from the expectations we carry about how life “should” be. In this episode, I explore how I’ve been working to release these expectations and embrace reality as it is. By cultivating radical acceptance, you’ll learn how to meet yourself, others, and your circumstances with compassion, create emotional clarity, and step into a more grounded, peaceful way of living. Through practical tools, reflective prompts, and mindful practices, this episode guides you to let go of disappointment, release control, and discover freedom in the present moment.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

Life shifts without notice—breakups, moves, career pivots—and suddenly everything feels out of your control. In this episode, I explore how the ancient practice of Feng Shui can help us reclaim our power when life feels chaotic. By shifting the energy in our environment, we can create emotional clarity, peace, and a sense of forward movement. From decluttering old energy to creating intentional spaces that support your next chapter, this episode gives you practical and spiritual tools to navigate change with calm and confidence.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

In this episode, I’m catching up with you and opening my journal to share a raw, unfiltered entry. This isn’t a polished story— this is a moment that reminds us how deeply human we all are. Together, we’ll find meaning in the stillness and remember that loneliness is never the whole story. This is your gentle reminder that you are seen, you are valued, and you are never truly alone.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

You don’t need an MBA to be a CEO. In this episode, I break down the myth that only “qualified” people can build successful businesses—and remind us that curiosity, courage, and consistency are more valuable than any degree.From impostor syndrome to social media as startup capital, I dive deep into the unfiltered truths of modern entrepreneurship. I share personal stories (including my own trial-by-fire lessons), practical tools, and powerful mindset shifts for anyone building something from scratch. Whether you're just dreaming of your first launch or knee-deep in DIY branding, this episode is here to remind you: your unique path is your superpower.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

Coming out isn’t just a personal decision—it can be a game-changer for your professional life. In this episode, I’m sharing how embracing your authentic self in business can open doors, deepen relationships, and fuel long-term success.We’ll explore the challenges queer folks face when navigating the business world, but also the power that comes from showing up fully. From building trust to finding aligned opportunities, I’m diving into how authenticity can transform your work and leadership journey. Whether you’re thinking about coming out or already walking in your truth, this conversation is about unlocking your full potential—on your terms. Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

As queer people, we’re often expected to show up in so many ways—professionally, personally, and within our communities. But what happens when all that showing up starts to wear us down? In this episode, I’m digging into the emotional labor we carry and how we can protect our peace while navigating it all.We’ll talk about therapy, mindfulness, exercise, and the power of community support as essential tools—not luxuries—for queer mental wellness. Whether you’re leading a business, showing up for chosen family, or just trying to stay afloat, this conversation is a reminder that your mental health matters. Let’s get into the strategies that help us not just survive—but thrive.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

Pride has never just been about a month for me—it’s something I live every single day. But every June, I watch as rainbow logos pop up, queer folks get momentary visibility, and then... it all fades by July. In this episode, I’m sharing what it means to me to celebrate queerness year-round—and why it has to be more than a corporate campaign or calendar event.We’ll talk about performative allyship, questioning what it means for a brand to show allyship, and the importance of keeping queer voices front and center every day of the year. Whether you're part of the community or an ally, this conversation is about holding space, staying visible, and remembering that queerness doesn’t pause after Pride Month ends.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

In this episode, I’m talking honestly about something I’ve had to work through myself: what it means to build real self-worth as a queer person in a world that’s constantly telling us we’re not enough. From media narratives to family expectations, the pressure to conform can wear us down—but it doesn't have to define us.I’ll be unpacking how we can begin to rewrite those internal stories, cultivate confidence on our own terms, and start valuing ourselves for who we really are. It’s not always easy, but learning to embrace my queerness as a source of strength—not something to tone down or “fit in”—has changed how I show up in the world.If you’ve ever struggled with feeling “too much” or “not enough,” this one’s for you.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

In this episode, I’m getting honest about something I’ve wrestled with personally: the disconnect between my work in fashion and the values I’m trying to live by. I’ve benefited from fast fashion’s convenience and affordability—but I’ve also started to question what those low prices are really costing us.Together, we’ll discuss what fast fashion is, its impact on people and the planet, and why the slow fashion movement offers a better way to shift fashion culture toward something more ethical and sustainable. This isn’t about having all the answers—it’s about learning, questioning, and figuring it out together.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

Saying “no” isn’t just about rejection—it's about protecting your energy and prioritizing what truly matters. In this episode, I break down the importance of setting boundaries, both in personal and professional life. From fear of rejection to guilt, I address the emotional struggles we face when we don’t enforce our limits. Packed with practical advice, real-life examples, and empowering takeaways, this episode gives you the tools on how to confidently say no without guilt and reclaim your time and energy. Ready to protect your peace? Hit play!Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

Before we can truly love others, we first need to cultivate a healthy, loving relationship with ourselves. In this episode, I explore how self-love is the foundation for all healthy relationships, whether romantic, platonic, or professional. With actionable tips on setting boundaries, practicing self-awareness, and prioritizing self-care, this episode is all about empowering you to build a relationship with yourself that will enhance all your other relationships. It’s time to stop looking for love outside and start giving it to the one person who deserves it most: you.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

In this episode, I dive into the complexities of aging in queer spaces, offering personal reflections and cultural insights. From the pressure to stay "young" in a world obsessed with youth to the surprising gifts that come with getting older, I reframe aging as a powerful, liberating experience. This episode is a heartfelt conversation about embracing the process of growing older, finding freedom in it, and connecting with listeners who feel like they're being left behind. Ready to age with grace and authenticity? Tune in!Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

Living in today’s world I think no matter what background you come from or what community you identify with, we all have shared as well as varied perspectives on the world around us. Today, as a member of two communities that face challenges all around, I’m sharing my thoughts on the world I live in as way to keep the voices of those communities alive! Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

I’m so excited to be bringing you along with me as I’m bootstrapping to build a fashion brand that’s on a mission to save the planet! Sharing the details on today’s episode.Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

Am I still vaping ? YES ! Details on today’s episode! Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

Winter is officially gone and Spring hath sprung! With a new season of life I am choosing to lean in and embrace new hobbies! I’m hoping to inspire you to do the same! Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

Over the last year while I was growing through the breakup I’ve spoken about, here on the podcast. I also was dating someone known as The Stallion ( that relationship has also since dissolved ). When I was at my most single, I admit I was all over the dating apps - Hinge, Bumble, Grindr, yep I was there. Dating is an experience with each partner we choose to date but overall it is just an experience in the journey to finding love. Today, I am sharing my experiences in dating, delivering updates on my current relationship status, and a few of my own personally established dating how-to’s. Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

It is crazy to think how one day we are children and then all of a sudden we aren’t. One day we had 0 responsibilities and then suddenly we had 1,000. Today I am sharing my thoughts on growing up and what I believe it may ( or may not ) mean. Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

When you wake up in the morning, do you feel like you are waking up to a life you created for yourself? A life that makes you excited about waking up each day? This is how we ALL should be feeling when we start each day. In today’s episode, I am sharing tips on how to take action steps towards creating a life you want to be excited about waking up to every day!Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

I previously spoke about my thoughts on money and finances here on the podcast before but my thoughts on the subject have grown since the last time I spoke about it and I no longer just see spending or investing to be just about the $. It also includes spending or investing into our lives because yes, it IS all connected! Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram

Lately in my reflections, something that has been coming up in my mind more frequently is my family. I think about how much we have grown from each other since the last time we were all together and that does in many ways tear at my heartstrings. Today I am sharing thoughts from my reflections on missing my family. Stay Caught Up With Me and the Podcast:Follow @issawillhill on InstagramFollow @will2winpodcast on Instagram