76. Climb Cringe Mountain | 5 Mindset Shifts Getting Me Through the Second Half of 2026

We're a little more than halfway through the year, and if 2026 hasn't looked the way you thought it would either — you're in the right place. This episode is my honest mid-year check-in: bookings and money haven't been flowing the way they have in past years, but connection, community, and confidence have been some of the richest I've experienced. Both things are true at the same time, and I think that's worth saying out loud.

I'm sharing the five things I've had to remind myself of to keep moving through the back half of the year — from holding onto possibility even in a slow season, to "climbing cringe mountain," to why I'm more afraid of staying where I am than of where I'm headed. I also get into the decision to go to grad school, the identity tug-of-war that came with it, and why zooming in to a day-by-day focus has been the thing that's kept me grounded through all of this year's curveballs.

If your year has felt like a series of pivots instead of the plan you had in January, this one's for you.

In This Episode:

An honest mid-year update on bookings, money, and where things actually stand
Why a slow season and a rich season can coexist
Point 1: Hang onto possibility, always
Point 2: Keep climbing cringe mountain
Point 3: Be more afraid of staying where you are than of where you're headed
The decision to go to grad school, and the identity tug-of-war that came with it
Point 4: You're always going to wish you started earlier — so start now
Point 5: Adopting a day-by-day focus when the big picture feels like too much
My word of the year: "go big, baby"

RESOURCES:

My mindset coach, Amy Austin

✨Connect with Maddie✨

Explore Maddie’s Website | @messywithmaddie

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