My Summer of Reflection: Grief, Growth & Figuring Out My Next Chapter episode artwork

EPISODE · Aug 19, 2026 · 34 MIN

My Summer of Reflection: Grief, Growth & Figuring Out My Next Chapter

from Willing & Winning · host Will Hill

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’t even have most of them. But for the first time in a while, I’m giving myself permission to ask the questions anyway.What do I want the rest of this year to look like? What am I building toward? Who am I becoming? What do I want my life, my work, my relationships, and this next chapter to feel like?I don’t know yet. And maybe that’s okay.Sometimes growth isn’t about having the perfect five-year plan or experiencing some huge breakthrough. Sometimes it’s simply creating enough space to slow down, look at where you’ve been, acknowledge where you are, and start getting curious about where you want to go next.So consider this episode a little summer life update, a little reflection, and a very honest conversation about what it feels like to be somewhere in between chapters — still healing, still growing, still building, and still figuring it all out.And maybe that’s the point.Stay Caught Up With Me and the Podcast:Follow @by.whill on InstagramFollow @will2winpodcast on Instagram

Episode metadata supplied by the publisher feed · Published Aug 19, 2026

Embed this episode

Ready to play

My Summer of Reflection: Grief, Growth & Figuring Out My Next Chapter

0:00 34:49

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

No similar podcasts found.

Frequently Asked Questions

How long is this episode of Willing & Winning?

This episode is 34 minutes long.

When was this Willing & Winning episode published?

This episode was published on August 19, 2026.

Can I download this Willing & Winning episode?

Yes. Use the download control on the episode player to save the publisher-provided media file.
URL copied to clipboard!