ADHD-ish

As we wrap up 2025, it seems like everywhere you look, it's all about reflection journals, vision boards, 90-day planners, and goal-setting frameworks.

If you're feeling absolutely nothing (or, let's be real, maybe a little guilty it's not working for you), I’m right there with you.

So, instead of one more system to make you feel “less than,” I’m serving something totally different—a simple, honest inventory. Just three lists: En...

What This Episode Is About

If your brain generates ideas faster than you can execute them, this conversation will make you feel seen. Sarah runs five businesses and has developed a systematic approach to managing what I call the "burden of creativity"—that relentless flow of inspiration that can fuel or derail you, depending on how you work with it.

This isn't about picking one lane or shutting down your creative engine. It's about b...

Is it possible to have a brain wired for entrepreneurship, but actually thrive best within traditional employment?

This insightful episode flips the script on the common narrative in both the ADHD and business worlds: that entrepreneurial traits automatically mean you should start your own business. 

Instead, host Diann Wingert explores the concept of intrapreneurship—bringing creativity, innovation, and entrepreneurial spirit ...

Diagnosed recently with both ADHD and autism,  Cat Orsini’s candid storytelling takes us on a journey from feeling like an outsider to building a thriving business based on authentic relationships, automation with heart, and radical self-acceptance. 

In this interview, Cat reveals her unique approach to business—one that centers curiosity, genuine connection, and meeting people where they are (with a little tech magic to m...

Welcome back to ADHD-ish! In this episode, host Diann Wingert sits down with her client Steph Cotrell for a candid and relatable discussion about what it really means to build—and rebuild—a business when you have ADHD traits and life throws you curveballs. 

Originally hired to help Steph Cotrell grow and scale her successful business, Diann quickly uncovered some uncomfortable truths about her business model, specifically how h...

In this episode, I’m sitting down with my good friend, business strategist, consultant and author, Jessica Lackey, for a candid conversation about what it really takes to build a sustainable business—especially when you have an ADHD-ish brain. 

Jessica shares her journey from Harvard, McKinsey, and Nike to the wild world of entrepreneurship, revealing how even with such impressive credentials, she found herself trapped in the e...

Ever launched a program, course, or membership that once set your heart on fire, only to find yourself completely over it just as it starts running like a well-oiled machine? If you’re an entrepreneur with ADHD, this scenario is all too familiar. 

In this straight-talking solo episode, Diann Wingert unpacks why boredom hits hardest when your business finally starts working—and what to do about it. 

7 Things You’ll Learn Fro...

If you’ve ever felt overwhelmed by advice to “hack your dopamine,” or wondered why traditional approaches feel incomplete, this interview with Dr. Miguel Toribio-Mateas, “The Creative Scientist,” delivers refreshing insights and compassionate tools for thriving as a neurodivergent human. 

ADHDers often spend years trying to “fix” themselves from the outside in—through medication, planners, routines, and hacks—only to discover t...

Ever had one of those days where your emotions run the meeting, instead of you? You’re not alone—and this week’s episode is all about giving you the tools to handle those moments with skill (and way less shame).

In this episode,  we are getting real about the very real challenges ADHD business owners face when emotions take the wheel.  No HR department, no middle manager… and nowhere to run when your brain decides to get u...

For this last episode of ADHD-ish during ADHD Awareness Month,  host Diann Wingert welcomes Alan P. Brown, acclaimed ADHD coach and creator of the ADD Crusher program, for a candid and practical conversation about the everyday habits that make ADHD more challenging. 

Focusing on making ADHD easier to manage (and avoiding the traps we so often fall into), Diann and Alan break down what really sabotages our brains and share ...

For years, conventional business advice encouraged solopreneurs—especially coaches and consultants—to create an “offer suite”: a series of programs at different price points to capture and serve more clients.  

At first glance, more offers seem to promise more income and greater accessibility. But each new program isn’t just something else to sell—it’s a whole new decision tree to keep track of, pitch, deliver, and market....

Welcome to another episode of ADHD-ish! In this thought-provoking conversation, host Diann Wingert is joined by neurodivergent leadership coach Ron Sosa for an in-depth conversation on neurodiversity, intersectionality, and authenticity. 

Together, they explore the complex ways our overlapping identities, including neurodivergence, sexuality, race, and disability, shape how we experience the world and present ourselves to other...

There’s never been more buzz about ADHD and entrepreneurship. Awareness is growing, and that’s a victory worth celebrating.

More business owners are recognizing that an ADHD brain brings both game-changing opportunities and unique challenges—ones that generic business advice just can't touch.

But where there is growth, there is also noise, and the ADHD business coaching scene is becoming a bit of a “Wild, Wild West.”

No licensing bo...

Today’s guest, CherylAnn Crego, joins me on the ADHD-ish podcast for a Client Success Story episode.  She first heard me speak on a webinar for ADDitude Magazine called “How to Build a Business That Works With Your ADHD Brain” and decided to reach out a short time later.  In this episode, CherylAnn and I share the outcomes from our six-month coaching engagement. 

Here are three key lessons from CherylAnn’s story for a...

Ever feel like your workweeks slide into chaos, no matter how many productivity hacks you try? If you have ADHD—or just a brain that refuses to follow “traditional” time management—you’re not alone.

This week on ADHD-ish, Diann Wingert breaks down the problem of context switching for ADHD entrepreneurs and introduces the concept of “focus days” with three different models to choose from.

Get ready to discover practical, customizabl...

Welcome back to ADHD-ish! In this episode, host Diann Wingert sits down with Dr. Gilly Kahn, author of the recently published Allow Me to Interrupt: A Psychologist Reveals the Emotional Truth Behind Women’s ADHD.  Together, Gilly and Diann tackle often overlooked elements of ADHD, like emotional dysregulation and rejection sensitivity, shining a light on the daily realities that many women face but rarely see reflected in main...

Ever had a discovery call or free consultation that felt so right — only to be met with complete and utter silence afterward? No reply. No “thanks, but no thanks.” Just… crickets. And if your ADHD brain is anything like mine, that silence turns the situation into a 3D crime scene you just have to solve.

ABOUT THE HOST

Diann Wingert (she/her) is a former psychotherapist turned ADHD entrepreneur coach and business strategist, as well a...

In July 2020, I wrote a blog post titled “I Want to Clone Myself” and I’ve fantasized about cloning as the solution to growing my business many times since then. I bet you have too.  Being an entrepreneur means wearing many hats, especially in the early years, and most of those hats are unflattering and don’t fit well. 

Enter serial entrepreneur and fellow ADHD-er, Will Christensen, who has been called “The Tony Stark of S...

You know that wild rush when a new idea lands in your lap and suddenly you’re reinventing your entire business model? You’re not self-sabotaging - that’s your ADHD doing exactly what it’s supposed to do—chasing novelty and that sweet dopamine hit. 

In this episode, I expose the pattern of idea infatuation, break down what I call  “The Soulmate Phenomenon” for solopreneurs with ADHD, and hand you a set of scrappy, real-worl...