Willing & Winning

Willing & Winning

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Willing & Winning episodes

  • Honoring Our Ancestors: Finding Ways to Love the Lost Daily

    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 Instagram

    Follow @will2winpodcast on Instagram

    23 min
  • Owning Our Fears: What Scares Me and How I Deal With Fear

    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

    13 min
  • Embracing Mysticism & Exploring the Spiritual Realms

    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 Instagram

    Follow @will2winpodcast on Instagram

    24 min
  • Dealing with the Monsters Inside Us: Navigating Mental Health

    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 Instagram



    Follow @will2winpodcast on Instagram



    Share your reflections on this episode—what “monster” are you facing right now?

    25 min
  • The Scary Truths of Entrepreneurship

    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 Instagram



    Follow @will2winpodcast on Instagram



    Share your own “scary truths” of entrepreneurship, tag the podcast, and join the conversation

    31 min
  • Stop Chasing How Life Should Be: Learning to Master Acceptance and Embrace Reality

    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 Instagram

    Follow @will2winpodcast on Instagram

    40 min
  • Taking Control of Change: Using Feng Shui to Reclaim Your Energy and Flow

    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 Instagram

    Follow @will2winpodcast on Instagram

    23 min
  • Life Lately

    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 Instagram

    Follow @will2winpodcast on Instagram

    25 min
  • You Don't Need to Major in Business to Build a Successful One: How to Build a Business from the Ground Up in the Modern Day

    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 Instagram

    Follow @will2winpodcast on Instagram

    36 min
  • From the Closet to the Boardroom: How Coming Out & Embracing Your Authentic Self Can Emower Your Career Journey

    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 Instagram

    Follow @will2winpodcast on Instagram




    27 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…