How to Figure Out What's Next in Midlife

Tiffany Scott sat down with me still healing a set of ribs she broke falling off a skateboard, and she is 51, and she took up skating in the first place because she moved to Austin and could not get to the ocean the way she used to, and she refused to let surfing go without finding something to put in its place. That is who was on the other side of the screen, a woman who picks up a new board in her fifties knowing full well she will be the slowest one in the park.

She spent years as a Creative Director for global brands, Speedo among them, and she built and then sold two women's communities before this one, and somewhere in the middle of all that she worked out that what she actually loves is the curating itself, the making of a room.

You Me She Fest is the biggest version of that, a one day world on a women owned ranch outside Austin, coming September 19, where everything is for women by women. A body positive pool party, self love workshops, a market alley of women owned and non binary owned businesses, immersive art, and a stage for female and non binary artists who have never had one before.

What she kept saying is that she did not build a lineup with women on it, she built a place where women own the stage. And when they come back to her afterward, they use the words safe and seen and celebrated and in sisterhood, which are the exact four words she had written down for herself before any of it existed.

She is a Compassionate Healer

You can watch that archetype move through the whole hour. Year one she held every performer and every market vendor and every woman walking through those gates so completely that she carried a stress headache for two weeks. This year she is six weeks out with no sponsors signed and she is in trust, because she made a promise to herself first, before she made one to anybody else, and then she kept it.

We talked about the North Star underneath all of it, and how hers arrived as a download after she sold that last community and sat in the limbo of COVID for a couple of years with no idea what came next, though she always knew it would be something about women. We talked about turning 50 and the stigma that showed up out of nowhere, and about her mother turning 80 in Australia and a full day of shopping on the Gold Coast that turned out to be love. And we talked about her dog Rio, who is 11, and who has recently developed boundaries.

Come sit with us.

A few moments from the conversation

"I was thinking about my trajectory, snowboarding to surfing to skating, and it actually has nothing to do with age. And it has everything to do with age."

"Before, it was to maintain a body type. Now it's to maintain the strength so I can continue to snowboard, surf and skateboard."

"I'm hopeless at it, which is why I'm so excited. I'm always the last and the longest person to learn something, so I have to really work hard at getting half decent. But the passion actually gets me there."

"I just follow what feels intuitively right. And I guess that's breadcrumbs."

"It's that North Star that keeps you getting up over and over and over again."

"The thing I kept coming back to when I was journaling was, selfishly, what lights me up. What really truly makes my heart full."

"Last year I had so much anxiousness that I had a stress headache for two weeks."

"We're six weeks out and we don't have a sponsor signed. The old me would have been in pure panic stations. And now I'm in a place of trust."

"They said, I felt safe, I felt seen, I felt celebrated, I felt in sisterhood. Those words are my words."

"My 30s were amazing. My 40s sucked."

"She's 11, so we're kind of at the same age, and she has boundaries now, Sora. And I'm like, girl, who are you?"

"You have to do the internal work to hold the space for the vision. As you step into holding sisterhood, all your sisterhood wounds come up."

About Tiffany

After building and selling two women's communities, Tiffany realized something was still missing, spaces where women did not only participate, they owned the stage. So she created You Me She Fest in Austin, a women centered festival where musicians, artists, entrepreneurs, and creators take the spotlight across music, arts, and small business.

After years as a Creative Director for global brands like Speedo, she discovered her love for curating powerful experiences, and You Me She Fest is the biggest expression of that passion, a one day world where women lead, create, and celebrate each other, reminding every woman just how powerful she truly is.

When she is not working on the Fest, you will find her paddleboarding, surfing, traveling, and chilling with her dog, Rio.

Find Tiffany

You Me She Fest: youmeshefest.com

Instagram: @youmeshefest

Facebook: You Me She Fest

About You Me She Fest

You Me She Fest is a one day women's festival founded by Tiffany Scott, held at Rancho Moonrise in Manor, Texas, about twenty five minutes from downtown Austin, and the 2026 festival is Saturday, September 19. Her site calls it the largest annual women only festival in Texas. The day holds live music from female and non binary artists, self love workshops, a body positive pool party, a curated market of women owned businesses, and immersive art, and women can camp or stay overnight at the ranch. Tickets and details are at youmeshefest.com.

Where to go next

If you have ever listened to a woman describe her North Star and felt a small ache because you are not sure you could name yours out loud, the Magic and Medicine Quiz is the doorway. It is free, it takes a few minutes, and it emails you your Devoted Archetype so you have somewhere real to start. soraschilling.com/quiz

And if you are the woman holding a vision that is bigger than the way you are currently running your business, LUSH Business Academy is where I teach you to fold your scattered gifts into one container that holds them. Doors are open. soraschilling.com/lush-business-academy