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 Instagram

Follow @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 Instagram

Follow @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 updates

What I’m saying no more to in 2026

What I’m intentionally welcoming in this year

Redefining success, growth, and self-worth

Moving into the new year with clarity instead of pressure

If 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 Instagram

Follow @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 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 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 Instagram

Follow @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 Instagram

Follow @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 Instagram

Follow @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 Instagram

Follow @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 Instagram

Follow @will2winpodcast on Instagram