HeyJaredWilling & Winning
Welcome to the Willing + Winning podcast, come join me- Will Hill, your host, digital bestie, mentor, etc., etc.,,.
- Indexed episodes, last 90 days
- 5
- Latest publication
- Aug 19, 2026
- Audience
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- Earliest in this view
- Jul 15, 2026
Latest episodes
My Summer of Reflection: Grief, Growth & Figuring Out My Next Chapter (opens the original)
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Summer has a funny way of slowing you down enough to actually hear yourself think. In this episode of Willing & Winning, I’m catching you up on what’s been going on in my life lately — from entering my full-on Nantucket Era with Elin Hilderbrand books, to growing as an entrepreneur, continuing to navigate grief, and taking a step back to reflect on what I want the next chapter of my life to look like. Because lately, I’ve been realizing that I don’t actually have all the answers. Honestly, I don
Healing Isn’t Linear (And That’s the Point) (opens the original)
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In this episode of Willing & Winning, I’m talking about something I’ve been experiencing in a very real way lately: the reality that healing doesn’t move in a straight line. I’ve recently said goodbye to my cat, Cosmic. Losing Cosmic, my cat and a deeply loved part of my life, has brought me face-to-face with a kind of grief that I’m still learning how to move through. And one of the hardest parts of grief—and healing in general—is realizing that you can have a day where you feel grounded, prese
You’re Not Behind, You’re Distracted: Escaping Comparison & Finding Your Own Timeline (opens the original)
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In this episode of Willing & Winning, I’m exploring the feeling of being “behind” and how often that belief has less to do with where we actually are—and more to do with where our attention is being pulled. The idea of falling behind has become one of the most common ways we measure ourselves. Behind in our careers. Behind in relationships. Behind in success. Behind in becoming the person we thought we would already be. But that feeling is often built on comparison rather than clarity. We look a
The Validation Trap: Breaking Free From External Validation & Self-Doubt (opens the original)
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In this episode of Willing & Winning, I’m exploring the difference between wanting to be seen and needing to be approved—and how easily our sense of self can become tied to the reactions of others. Validation is a natural human desire. We want to feel understood. We want to know that our work, our choices, and our existence matter. But there is a point where seeking connection can quietly become dependence, where external recognition begins to replace internal trust. In a world built around meas
Rebuilding, Finding Joy & The Secret Lives of Mormon Wives (opens the original)
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This week is less of a structured conversation and more of a catch-up. I'm sharing where life has honestly been lately, what I'm learning as I navigate this season, and why I'm choosing to embrace exactly where I am instead of pretending to have everything figured out. Sometimes growth looks less like a breakthrough and more like giving yourself permission to start again. And because not everything has to be so serious… we're also talking about my newest reality TV obsession: The Secret Lives of
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