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, customizable models to help you protect your time, boost your productivity, and work with your brain, lifestyle, and stage of business.  

About the Host

Diann Wingert is a former psychotherapist and serial entrepreneur turned business coach, specializing in helping entrepreneurs with ADHD and other “not-so-neurotypical” brains thrive.

Drawing from both her clinical expertise and personal experience, Diann delivers actionable advice, real-world strategies, and a refreshingly honest perspective on building a business, balancing priorities, and protecting your most precious resources: your time and your creative energy.

Here’s your quick guide to Focus Days, ADHD-style:

The Single Focus Scheduling Method

Think of this as giving every day its own “job”—Mondays are CEO days (big picture, strategy only!), Tuesdays and Thursdays are for clients, Wednesdays for content creation, and Fridays for building connections.

The magic? You get to deeply immerse in one type of work at a time—no more multitasking burnout.

The Essential Three Model: Create, Connect, Consume

Perfect if you don’t want to lock yourself into a five-day structure. Allocate days based on energy: Create (any kind of output work), Connect (people-focused work like client calls), and Consume (input tasks like learning or admin).

You can spread these across your week however you like—and it totally honors both structure and spontaneity.

The Split-Screen Approach

Not all of us can devote a full day to a single focus. With the Split Screen model, you match tasks with your daily energy: deep work when your brain’s sharpest, creative or relational work when it feels right, and breaks when you need them. It’s about flowing with your energy patterns, not fighting them.

Which one to try?

• Are your days packed with interruptions? Go for the Essential Three.
• Thrive with structure? Try Single Focus Scheduling.
• Need max flexibility or have health/family stuff? Split Screen’s your friend.

Protect your boundaries (and sanity):

Most “emergencies” can actually wait. Create clear expectations and communicate your availability so you’re not always on call—this protects your energy, time, and creative spark.

Embrace experimentation over perfection:

Whether you need more structure or more flexibility, give yourself permission to tweak any system. Growth comes from iteration, not rigid adherence. Try one approach for a few weeks, then adjust as needed.

Not-so-fun fact:

Research shows it can take UP TO 25 MINUTES to fully recover your focus after switching tasks. And with ADHD? Yep, it can take even longer. It’s like trying to cook five different cuisines at once—the results are always a little…messy. 

Mentioned in this episode:

Changes Diann made based on her quarterly review during a CEO Day:

• Zoom Pro to Google Meet_savings: $160
• Loom to Konvey_savings: $71
• Calendly to TidyCal: $91

Links to Diann’s three-part momentum series:

• Starting Strong
• Stopping Smart 
• Shifting Smoothly
• Start, Stop, Shift Toolkit for ADHD Entrepreneurs 

If you tried one of the three Focus Day models shared in this episode, let Diann know!  Leave a comment on Spotify or leave a review on Apple Podcasts

Whether you crave more structure or more flexibility, you’ll leave this episode with permission to tailor your week—and your business—to what actually works for your ADHD-ish brain.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved. 

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 mainstream ADHD narratives.

Drawing on both personal experiences and clinical insights, Gilly and Diann unpack hot-button topics such as the gaps in diagnostic criteria, why women are often diagnosed later in life, and the profound impact of being emotionally sensitive in a world that expects conformity.

Whether you’ve been told you’re “extra,” struggled with impulsivity, or have battled feelings of not belonging, this conversation will offer validation, strategies, and a healthy dose of humor. Grab your headphones—it’s time to celebrate the quirks, strengths, and unique challenges of being a woman with ADHD. 

What you’ll hear in this episode:

Emotional Dysregulation is Fundamental (and Overlooked): While most people associate ADHD with distractibility and impulsivity, Diann and Dr. Kahn remind us that emotional sensitivity and reactivity are just as central—especially for women. Emotional outbursts, rejection sensitivity, and the complexities of self-regulation often remain unaddressed but profoundly impact daily life and professional relationships.

Misdiagnosis & Misunderstanding Persist: Many women spend years feeling misunderstood, misdiagnosed with anxiety, depression, or even personality disorders, before discovering ADHD’s unique presentation in females. Trauma from chronic misunderstanding—whether “big T” or “little t”—leaves lasting scars on self-esteem and career confidence.

Diversity of Thought = Business Advantage: The strengths that come with ADHD—creativity, expansive curiosity, resilience in the face of rejection—aren’t just “superpowers” for individuals. As Dr. Kahn eloquently puts it, teams excel when they have true diversity of thought. Those who think differently spark innovation and challenge the status quo.

“You can’t have strengths without also having weaknesses, especially when the strengths are extreme.” – Gilly Kahn, PhD

Gilly Kahn, PhD, is a clinical psychologist, ADHD advocate, researcher, and author in private practice in Atlanta, GA, USA.   Before pursuing a master's in experimental psychology and a doctorate in clinical psychology, Gilly studied creative writing, a passion since childhood, and regularly publishes articles on Psychology Today and ADDitude Magazine. Gilly and Diann are both members of the Committed Partners of FindTheADHDGirls.org, an advocacy group for ensuring that future generations of girls with ADHD are not overlooked.  

Find Gilly Kahn, PhD, online:

Website: https://www.drgillykahn.com/

Book:  Allow Me to Interrupt: A Psychologist Reveals the Emotional Truth Behind Women’s ADHD by Gilly Kahn, PhD. 

Instagram  and LinkedIn 

ADHD experts mentioned during the episode:

William Dodson

Russell Barkley

Want to know more about ADHD in girls and women?  #FindTheADHDGirls.org

Don’t forget to subscribe/follow the podcast, and leave a review so more ADHD-ish business owners can find THE podcast full of real talk and real solutions for neurodiverse business brains.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved. 

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 as the insightful host of ADHD-ish.

With both lived experience and deep professional expertise in ADHD, Diann guides neurodivergent entrepreneurs toward greater self-awareness, creativity, and sustainable success— with her signature blend of no-nonsense advice, compassionate understanding, and a dash of sass.

WHAT TO LISTEN FOR:

Ghosting = Brain Spiral Town.

Most of us with ADHD are natural connectors, really tuned in to people’s emotions and needs (sometimes to a fault!). So when a prospect suddenly ghosts, our brain doesn’t just let it go. We cycle through: Did I misread everything? Did I say something wrong? Should I follow up? The open mental tabs never close!

Why Does It Hit So Hard? 

It’s about more than lost potential business — it chips away at our confidence and identity. Thanks, rejection sensitivity! Our brains crave closure, and ghosting feels like an unsolvable mystery that burns a hole in our mental inbox.

3 Practical Ways to Prevent & Recover:

1.Set Clear Expectations on the Call:

Instead of ending with vague “I’ll send info and we’ll go from there,” clearly address what comes next. Give the prospect space to say if they need to think or consult someone else. Your brain will thank you later.

2.Summary Follow-Up Email:

After the call, send a recap: “Here’s what I heard you need, and how I’d help.” It’s not just professionalism — it helps you remember details if the anxiety spiral hits.

3.One Professional Follow-Up (Then Let Go):

Send a single, polite check-in. Example:

“Hi X, just following up on the proposal. Totally understand if timing isn’t right. Let me know if you have questions!”

Then, mentally… close that tab. Their silence is about their stuff, not your value.

Bonus Brain Hack: 

If you catch yourself spiraling, say out loud, “My brain is trying to solve an unsolvable puzzle.” Set a 15-minute timer to ruminate if you must, then move your body — walk, jump, play with the dog, whatever. Shifting gears really does help!

Real Talk: 

Ghosting is not a judgment of your worth or skill. Often it’s got nothing to do with you. Life happens. Budgets cut. Crises pop up. Sometimes people just freeze on big decisions.

Focus on what you can control: being a pro, building your pipeline (more prospects = less sting), and separating your self-worth from any one client’s decision. And, always redirect energy into new opportunities — don’t dwell on what’s done.

If you’re ready to get found everywhere online, check out Meg Casebolt’s “Findable Everywhere” 5-Day challenge — Sept 15th - 19th.  It could be the redirect your brain and business need! Meg is the SEO expert who saved my bacon after my social media accounts disappeared, and this is your chance to work with her for under $100! 

Click here to register

Don’t forget:

You. Are. Not. Alone.

And you’re honestly better at this than you think. ❤️

Stay tuned for more empowering conversations and practical tools for thriving in business with ADHD—right here on ADHD-ish!  Be sure to follow/subscribe so you don’t miss a thing! 

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved. 

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 Software” in the field of automation.  In this fast-paced episode, Will and I unpack the challenges of scaling a business and how AI, automation, and what Will calls “top-tier human talent” are the elegant solution you may be looking for.  

If you’ve struggled with overcomplicated, clunky systems that slow you down and failed to find team members who match your drive, creativity, and commitment, this candid conversation is packed with practical strategies that move the needle and boost your bottom line.  

Will Christensen (he/him) is a systems thinker and automation expert who helps entrepreneurs take back their time and scale their business.  Will is the founder of The Entrepreneur’s Apprentice and host of Automation Hunter. He specializes in building teams and tech stacks that let visionary minds focus on what they do best.

Will is also a champion of the “Automate, Delegate, Eliminate” approach and has a brilliant strategy for hiring “entrepreneurial apprentices” who help founders scale without burning out.  Will’s revolutionary“15-1-1-5” framework, which he developed to manage his own executive functioning challenges, is an ADHD-friendly alternative to traditional time management strategies. 

Episode Highlights

• You Don’t Need a Clone—You Need Your Opposite: Will reveals that hiring someone just like you might double your chaos, not your output. The real solution? Find an apprentice or two who complements your weaknesses and excels where you struggle. Sometimes, your best partner is someone with a different brain!
• Automate, Delegate, Eliminate—In That Order: Learning to let go is harder than it looks, so start with identifying what can be automated (especially now that AI makes it easier than ever). Save your executive functioning and cognitive energy for the big, creative stuff rather than routine busywork.
• Equity and Ownership Breed Commitment: Want your team to “own” their work? Will recommends offering phantom equity to empower top-tier talent to act as “mini-CEOs.” This transforms their sense of responsibility and buy-in, leading to loyalty and drive you can’t just hire for.

• Automation Hunter YouTube Channel
• Entrepreneur’s Apprentice
• Kolbe Assessment  
• RemoteWork.com 
• Books referenced:
• The E-Myth by Michael Gerber
• The One Thing by Gary Keller & Jay Papasan
• Buy Back Your Time by Dan Martell
• The 6 Types of Working Genius by Patrick Lencioni
• Never Split the Difference by Chris Voss

Want to Find Out More?

Will is offering a FREE 15-minute call for ADHD-ish listeners to jumpstart your “Automate, Delegate, Eliminate” journey. And if he doesn’t blow your mind, he’ll give you a $50 Amazon gift card. (Spoiler: it never happens!)

Book your call now, for listeners of ADHD-ish only: EntrepreneursApprentice.com/adhd-ish/

Don’t forget to subscribe/follow the podcast, and leave a review so more ADHD-ish business owners can find THE podcast full of real talk and real solutions for neurodiverse business brains.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved. 

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-world frameworks for sorting out which ideas deserve your effort and which ones are just quick idea flings.

ABOUT THE HOST

Diann Wingert (she/her) is a former psychotherapist turned ADHD entrepreneur coach and business strategist, as well as the insightful host of ADHD-ish. With both lived experience and deep professional expertise in ADHD, Diann guides neurodivergent entrepreneurs toward greater self-awareness, creativity, and sustainable success— with her signature blend of no-nonsense advice, compassionate understanding, and a dash of sass.

WHAT TO LISTEN FOR:

How the "Soulmate Phenomenon” shows up for entrepreneurs with ADHD

• Romancing the Idea: attraction, infatuation, honeymoon, and reality
• Why falling for new ideas isn't about lack of commitment or follow-through
• How dopamine cravings and novelty-seeking drive this cycle
• Concrete examples: coaching, consulting, and creative service businesses
• Key questions to ask yourself when a new idea lands
• Why the honeymoon phase is creative gold and how to use it intentionally
• Four actionable frameworks for managing new ideas:
• The "dating period" (test ideas before big changes)
• The side project approach (explore without derailing your main business)
• Integration (fold new ideas into what you already do)
• Relationship maintenance (recommit and work through boredom and obstacles) 
• How to distinguish between ideas worth a long-term run vs. a temporary high

TIMESTAMPS 

• 00:00 — Getting Obsessed: The Soul Mate Phenomenon Hits Hard
• (Falling for the idea, dopamine rollercoaster, full rom-com montage)
• 02:10 — Why This Happens: Dopamine, Novelty, and Hyperfocus
• (Science of ADHD meets daily business life, shiny object syndrome explained)
• 05:15 — Pattern Recognition: Attraction, Infatuation, Honeymoon, Reality
• (Breaking down the idea romance step by step)
• 09:40 — Classic ADHD Business Moves: Case Studies
• (Real-life business examples with coaches, consultants & service providers)
• 14:35 — The Crash: When the Fizz Fades and the Next Idea Calls
• (Losing steam, misreading the end of infatuation, jumping ship too soon)
• 17:50 — Deep Truth: The Real Problem Isn’t Commitment
• (It’s unrealistic expectations, not a lack of grit — and what to do instead)
• 21:40 — The Gold in the Honeymoon Phase: How to Use It
• (Why that first burst of energy is actually your secret weapon)
• 24:20 — Four Frameworks for Working With ADHD, Not Against It:
• The Dating Period
• The Side Project Approach
• The Integration Question
• Relationship Maintenance Plan
• 32:10 — The End Game: Choosing Long-Term Commitment (Or Not)
• (Learning to spot quick dopamine hits versus real growth opportunities, radical self-acceptance)
• 35:10 — Final Pep Talk and How to Get In Touch
• (Reminders, contact info, encouragement, closing thoughts)

SHARE YOUR STORY:

What’s the big “soulmate idea” that got away? Did it deserve a second chance, or was it just a quick dopamine hit? Hit me up by email, send me a DM on LinkedIn or leave a voice message on my website.

SUMMARY

ADHD brains light up for new ideas…and then we feel like changing everything for that rush. Don’t fight the pattern, work with it. Date your ideas. Don’t move in with them at first sight. Keep your current business healthy and figure out what deserves real commitment. That’s how you survive idea infatuation and the “Soulmate Phenomenon” and make your next hyperfocus phase count for something.

Your brain is a brilliant and busy place. Let’s make it your greatest business asset. Stay tuned for more empowering conversations and practical tools for thriving in business with ADHD—right here on ADHD-ish!  Be sure to follow/subscribe so you don’t miss a thing! 

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved. 

What happens when two accomplished psychotherapists discover, well into adulthood, that they have ADHD?

In this thought-provoking episode, host Diann Wingert welcomes Lisa Lackey, a licensed therapist, coach, speaker, and community builder, to candidly explore their parallel journeys of late diagnosis, high achievement, and the transformative power of midlife self-discovery.

Together, they unpack what it means to awaken to neurodivergence after decades of "successful" living, the intersection of menopause and mental health, and the unique journey women take as they move from striving and struggle toward authenticity and fulfillment in their second act.

Guest Bio: Lisa Lackey (she/her)

Lisa Lackey is a licensed psychotherapist, coach, and speaker with decades of experience supporting high-achieving individuals facing addiction, anxiety, depression, and now, navigating the complexities of neurodiversity and midlife transitions. 

After being diagnosed with ADHD later in life, Lisa transformed her approach—creating supportive spaces for women, particularly Black women, to rediscover their authentic selves, reclaim joy, and build community in the second half of life. Lisa is passionate about spiritual growth, legacy work, and helping others write their own rules for fulfillment.

Episode Highlights – What You’ll Learn

• Why ADHD is often missed in high-achieving women, and how self-awareness—and even reading the “right” book—can be a game changer.
• How hyper-competence, overachievement, and the ability to "make it work" can hide ADHD symptoms for decades.
• Understanding how hormonal changes bring ADHD and identity struggles front and center for so many women in midlife.
• Lisa’s concept of the “second knowing”-  waking up in midlife, letting go of societal shoulds, and connecting to your true purpose and inner wisdom.
• How women—especially women of color—can build new definitions of success, heal generational burdens, and lift each other up.

Connect with Lisa Lackey

• Website: Inside Out Recovery
• LinkedIn: Lisa Lackey on LinkedIn

Mentioned by our guest:

Driven to Distraction by Ned Hallowell, MD - the book Lisa read in 2 hours & recognized her own ADHD 

Bell Hooks - Black author, best known for her work on race, feminism & social class 

Sankofa - a word in the Twi language of Ghana, meaning “to retrieve” 

If something in this episode struck a chord, share it with a friend,  leave us a review, or drop a comment on Spotify about your own late diagnosis and mid life awakening. 

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved. 

If you've ever felt overwhelmed, boxed in, or just plain bored by traditional business plans as a small business owner with ADHD, this episode is for you! 

Host Diann Wingert is here to reimagine business planning in a way that's actually ADHD-friendly—lean, flexible, visual, and, most importantly, useful. 

Whether you’re new to entrepreneurship or tired of winging it and hitting hidden roadblocks, Diann guides you through a business planning approach that celebrates how the ADHD brain works best.

Get ready to create a plan you'll actually want to use!

Episode highlights: 

The Big Lie:

Your ADHD brain thinks planning cramps your style—but done right, the opposite is true. Planning can be the external structure that fuels freedom, creativity, and calm in your business.

The trick? Ignore the boring templates and create a plan tailored to how your brain truly operates.

Why Traditional Business Plans Don't Work for ADHD Brains:

• The pitfalls of rigid, lengthy plans and how they trigger resistance and procrastination.
• Why our tendency to wing it isn’t always as productive (or painless) as it feels.

The Hidden Costs of ‘Winging It’:

• Missed opportunities
• Wasted energy
• Unfinished projects.

Introducing the ADHD-Friendly Minimal Business Plan Framework:

• Four simple pillars (instead of 40 pages)
• North Star: Your “why,” distilled for everyday decisions.
• Revenue Reality Check: Getting real with three simple numbers.
• Zone of Genius: Maximizing what energizes you and minimizing the rest.
• Next Three Moves: Concrete, short-term steps—no five-year forecasts here!

Making Your Business Plan Visual & Flexible:

• Why a one-page, visual dashboard beats a document you’ll never open again.
• Tools and formats—Trello, Canva, voice-to-text, and more—that play to ADHD strengths.

Get it Done (Without Overwhelm) with The Sprint Method

• 25 minutes a day, one pillar at a time, over four days.
• Walk away when the timer rings—even mid-sentence.
• No giant blocks of time, no perfectionism, no overwhelm.

Homework:

Take 25 minutes this week and pick ONE pillar to focus on—whichever feels easiest or most fun. (Money anxiety? Start with your North Star instead!)

Next week, another pillar. Within a month, you’ve got an ADHD-friendly business plan that you will actually use! 

Share your ADHD-friendly  business plan with Diann 

• Email: [email protected] 
• LinkedIn: https://www.linkedin.com/in/diannwingertcoaching/
• SpeakPipe voice messaging: https://www.speakpipe.com/AskDiannAnything

About the Host:

Diann Wingert (she/her) is a former psychotherapist turned business strategist with a passion for supporting neurodivergent entrepreneurs.

With real-world experience as both a clinician and a business owner—and her signature no-BS, motivational style—Diann specializes in helping business owners find strategies and systems to balance their passion and purpose, with profit, and avoid burnout in the process. 

Be sure to subscribe/follow so you don’t miss future episodes full of practical, ADHD-friendly business advice!

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved. 

Ever felt like your business is just as “ADHD-ish” as you are? This week on the ADHD-ish Podcast, I dove into an eye-opening conversation with Diane Mayor about how ADHD traits show up in our business, for better or worse.  

Diane Mayor is a business-model strategist who deeply understands that revenue is a dopamine number, but profit is a reality number and that you can’t scale what you can’t see.  Diane has the kind of ADHD that makes systems and structure make sense, but she also knows that if it’s not fun,  it’s not going to happen, so she makes sure that it is.

If your business model looks sparkly on the front end, but is duct-taped together behind the scenes,  don’t even think about scaling before taking the lessons in this episode to heart.  Here’s what to listen for:

• Dopamine Is a Double-Edged Sword
• ADHD brains seek stimulation, which fuels creativity and enthusiasm—but the excessive pursuit of new ideas can lead to chaos. The trick? Channel that energy into a structured “idea parking lot”—capture your sparks, but choose your focus.
• Systems Don’t Kill Creativity—They Enable It
• Many of us with ADHD bristle at the word “structure,” but minimum viable systems (even something as simple as a checklist instead of a 10-page SOP) create the freedom to play, innovate, and keep the momentum going.
• Rejection Sensitivity & Executive Dysfunction Are Sneaky Saboteurs
• Uncomfortable truth: your business can’t scale if you get hijacked by every emotional reaction or caught up in decision paralysis. Building in “pause and process” moments—and asking for help where your brain’s not wired to excel—protects both you and your team from ADHD inertia.

You can absolutely harness ADHD as a strength in your business, but not if you ignore what makes your brain unique. The goal isn’t to “fix” anything, but to build a business that works with your neurodivergence in mind.

About Diane Mayor 

After a successful career in corporate finance, Diane transitioned to becoming a business model architect and systems aficionado, after discovering both her ADHD and her passion for untangling business chaos. She helps entrepreneurs create sustainable, scalable businesses built around their unique neurodivergence—not despite it.

Website  - LinkedIn -  The 5- Minute Strategist Podcast  - Strategic Business Diagnostic

Mentioned in this episode:

Marshall Goldsmith’s book “What Got You Here, Wont’ Get You There.”

Next Steps:

“You can’t scale what you can’t see.”  If this tagline lands, you might be ready for Diane Mayor’s Business Blueprint, a laser-focused strategic business diagnostic for telling you exactly what to keep and what to toss before you scale.  Click this link to book yours now.  

Not quite sure whether you want to scale? Click this link for a custom playlist of past ADHD-ish episodes to help you figure out which business model is right for you.

Thank you for listening to ADHD-ish! Subscribe & leave a review if this conversation helped you see your strengths and struggles in a whole new way. 

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved. 

It’s 2 AM, and you’re lying in bed, reliving every word of an email you sent hours earlier, your mind spinning worst-case scenarios that could ruin your business.

If this sounds familiar, you’re not alone—especially if you have ADHD. Entrepreneurial life magnifies our emotional intensity, for better and for worse, and in this episode, I’m getting real about a topic most business circles avoid: the double-edged sword of emotional intensity for entrepreneurs with ADHD.

Running a business and being an entrepreneur with ADHD comes with a unique set of challenges, based on the fact that our emotional intensity can be both a business advantage and a potential hazard at the same time. 

We are talking about the fine line between passion and emotional dysregulation. Emotional dysregulation is not “being too sensitive” or being overly dramatic; it’s brain mechanics.

The same executive function deficits that scramble our to-do lists also juggle our emotional responses, often treating every emotion as urgent.

If you wonder why advice like “just breathe” doesn’t work for us the way it does for neurotypicals,  this is why.  

Here are 5 keys you’ll pick up from this episode:

1. What Emotional Dysregulation Is: Learn why it’s way more than just “being sensitive”—it’s a real neurological challenge for ADHD brains.
2. Solopreneurship’s Perfect Storm: Discover how running a business solo can amplify emotional ups and downs, thanks to isolation and rejection sensitivity.
3. How Emotional Intensity Can Hijack Business Decisions: Find out how unchecked emotions can affect your pricing, negotiations, and every tough conversation.
4. Spotting the Difference Between Passion and Dysregulation: Learn concrete ways to tell if your drive is fueling your business or putting it at risk of burning down.
5. Practical Tools to Build Emotional Resilience: Get real-life strategies for pause protocols, circuit breakers, sleep/nutrition hacks, boundaries, and even the right kind of professional support.

Fun Fact:

Did you know that your ADHD brain processes emotions more like a smoke detector than a thermostat?

If you’re tired of advice like “just breathe” and want strategies that actually work for our 🧠 brains, this episode is for you.

Take a listen, share with a fellow entrepreneur who gets it, and let me know what resonated most for you! Remember: Feeling deeply is one of our ADHD strengths—we just need to use it strategically.

About the Host

Diann Wingert (she/her) is a seasoned business coach, licensed psychotherapist, and serial business owner with decades of experience supporting neurodivergent professionals.

Diann specializes in helping ADHD solopreneurs and small business owners turn their energetic passion into strategic success, blending lived experience with clinical insight for real-world solutions.

Connect with Diann 

• Website: diannwingertcoaching.com
• LinkedIn: https://www.linkedin.com/in/diannwingertcoaching/
• Cognitive Bias Hacks for ADHD Entrepreneurs 

Mentioned in this episode:

Dialectical Behavior Therapy for ADHD and emotional dysregulation 

Cognitive Behavior Therapy  for ADHD and negative thinking patterns 

Share the Love 🚀

If this episode resonated, share it with a fellow entrepreneur navigating their own intensity trap. Feeling deeply is part of our ADHD—learning to use it strategically is where the magic happens.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved. 

In this episode, I sit down with Mikey Schumacher, the 29-year-old creative entrepreneur behind “but cute”—a start-up brand of plush toys designed to celebrate mental health and celebrate our imperfections.

In this episode, Mikey & I discuss his entrepreneurial journey, the healing power of community, and how comfort objects can open up much-needed conversations around anxiety, ADHD, and more.

I came across Mikey & but cute on TikTok, became part of the startup’s Kickstarter campaign, and have been an enthusiastic supporter of his mission, vision, and passion.

Mikey is part of a new generation of founders whose businesses serve a social purpose, while meeting a market need, and in his case, a personal one as well.  

About Mikey Schumacher

Mikey, who lives in Oceanside, California, and is the youngest of six children, is a lifelong entrepreneur with a passion for creating meaningful products.

From lemonade stands and failed T-shirt ventures to a master’s degree in entrepreneurship from USC, Mikey’s story is one of resilience, self-discovery, and turning setbacks into springboards. Now, with the viral success of But Cute, Mikey empowers people of all ages to embrace their quirky, anxious, or imperfect sides—one plush toy at a time.

Here’s what you’ll take away from this episode:

1. Learning by Failing Forward

Mikey shares how every “failed” business (including a Kickstarter flop and one epic T-shirt company bust) was actually just a bootcamp for founder growth.

2. Why Comfort Objects Are Powerful (at ANY Age)

Explore the real science and sentimental magic behind plush toys—and why adults are snatching them up too.

3. Turning Insecurity into Community

Discover how But Cute’s Discord became a safe haven for people to share insecurities and get massive support, no judgment.

4. Practical Advice for Overthinkers

Hear Mikey’s simple but game-changing reminder: “Don’t predict the future. Take one step at a time.” (Diann co-signs HARD.)

5. Creative Chaos is Your Friend

Peek into Mikey’s wild idea process: fusion-creature brainstorming, accidental croissant claws, and the beauty of letting go of perfection.

Mentioned during this episode:

Squishmallows

Labubu

Connect with Mikey & But Cute

• But Cute Website 
• TikTok: @butcutetoys
• But cute club Discord channel 

Join the Conversation!

Are you an adult with an emotional support plushie? Has a comfort item helped your mental health? 

Follow but cute, join their discord community and tag them on social media on posts that focus on embracing imperfections. 

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© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved.