Most business advice assumes you're wired like everyone else. What if you're not?

In this episode, we sit down with Diann Wingert—former therapist, business coach, and host of the ADHD-ish podcast—to talk about what it really means to build a business that works with your brain, not against it.

We unpack the myths around ADHD, how to radically accept your own wiring, and what happens when you finally stop trying to “fix” yourself and start designing systems that fit you.

Jessica and Meg share their own neurodiverse workarounds (including why their assistants actually manage them), and Diann breaks down how she flipped her brand, rethought her support systems, and uses tools like Claude.ai as external executive function—not a replacement for her brain, but a co-pilot for organizing all the genius.

This one’s for the quirky kids, the not-quite-diagnosed, and anyone who’s ever tried to follow business advice that wasn't designed for their brain.

* Why Diann rebranded her podcast and business to center ADHD-ish, not as a niche but as a reality

* How radical self-acceptance (not self-awareness) is the real first step to change

* The business systems that work because they’re nontraditional (like letting your assistant be the boss)

* Why “It depends” is the real ADHD business motto

* How tools like Claude and Notion help organize brilliance without replacing your voice

* Why standard business advice falls apart when your brain doesn't fit the mold

* What Diann learned from neurodivergent-friendly spaces (hello, marching band at a conference) and how to bring that into your own business model

* The role of AI in organizing, not empathizing—and why therapy still needs a human touch

“Human beings, by and large, are damaged through relationships, abuse, neglect, trauma. Most of the things that bring people to a therapist happened as a result of some failure of human nature. And so the whole transformation of therapy is that it is using the professional use of self. We are harmed by humans. We are healed by humans. It’s one of the most intimate and powerful ways of working. And I loved it.” - Diann

About Our Guest

ADHD-ish Podcast

Mastering Your Entrepreneurial ADHD

Diann Wingert’s LinkedIn Newsletter

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Connect with Meg and Jessica

Meg Casebolt

Jessica Lackey

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