Willing & Winning

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...

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 pu...

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...

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 mindfu...

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 a...

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 mo...

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 sp...

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...

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-...

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 findin...

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 essen...

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...

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, cultiva...

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 th...

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 takeaway...

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 relatio...

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...

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: Follo...

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 Instagram Follow @will2winpodcast on Instagram