Willing & Winning

Willing & Winning

Download on the App Store

Willing & Winning episodes

  • Queer People & Wellness: How to Maintain Mental Health Amidst Juggling Mulitple Roles

    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 Instagram

    Follow @will2winpodcast on Instagram


    34 min
  • Pride 365: Why Queerness Deserves to Be Celebrated Every Day, Not Just in June

    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 Instagram

    Follow @will2winpodcast on Instagram

    22 min
  • Queer and Confident: How to Build Self-Worth in a Culture That’s Always Telling Us We’re Not Enough

    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 Instagram

    Follow @will2winpodcast on Instagram

    24 min
  • Fast v Slow Fashion: The Shift We Need to be Talking About

    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 Instagram

    Follow @will2winpodcast on Instagram

    43 min
  • The Power of Saying No: Setting Boundaries in Business and Life

    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 Instagram

    Follow @will2winpodcast on Instagram

    41 min
  • Love Yourself First: Building the Relationship That Shapes All Others

    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 Instagram

    Follow @will2winpodcast on Instagram

    44 min
  • Wiser, Queerer, and Still Winning: Aging in a Culture That Worships Youth

    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 Instagram

    Follow @will2winpodcast on Instagram

    34 min
  • My Gay Life in 2025

    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 Instagram

    Follow @will2winpodcast on Instagram

    16 min
  • I’m Building a Business to Help Save the Planet

    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

    11 min

About Willing & Winning

From the publisher's feed

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…