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: diann@diannwingertcoaching.com
• 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 /

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

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...

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.

Did this episode inspire you?

Thank you for listening to ADHD-ish! Subscribe & leave a review if this conversation brought you comfort, courage, or just a smile.

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

If you’re a solopreneur, consultant, creative, or independent professional, you know there’s more to running a business than hustling between deadlines and client meetings. The real challenge? Moving reliably and efficiently between your various roles, priorities, and ideas, especially if you relate to the “ADHD-ish” brain.

In this final episode of the three-part Momentum Series, the focus is on the overlooked but critical skill of shifting smoothly. I share practical strategies, frameworks, and rituals to help you master transitions—whether between clients, projects, or shifting from creative to administrative tasks—in a way that reduces friction and avoids brain drain.

Of course, no system’s perfect. Illness, emergencies, or just a bad day will derail even the best intentions, so I’ll also share my three-step strategy for re-entry that totally sidesteps the usual overwhelm.

What You’ll Learn in This Episode:

The Cost of Context Switching

Switching between tasks and roles eats up your energy and time, especially with ADHD. Listen for why transitions feel SO exhausting and what’s really happening in your brain.

The Transition Bridge System

Trade your mental cliff-jumping for supportive “bridges.” Learn how building small systems makes every future switch easier and less energy-draining.

Breadcrumbs You Won’t Want to Sweep Up

From one-sentence task summaries to two-minute project recaps, discover the magic of leaving yourself notes (not novels) that make picking up where you left off a breeze—and why voice memos count too!

Micro and Macro Rituals for Seamless Shifts

Reset your brain with quick mini-rituals, and get step-by-step on bigger resets when shifting between wildly different projects or after a disruption (hello, post-vacation slump).

Quick Tip from the Episode: Back-to-back client meetings on Zoom? Simply saying your client’s name out loud before opening the meeting room can help your brain switch gears and avoid those “oops, wrong person” moments.

Ready to go from learning to implementing?

Click here to download your free “Start Stop Shift Toolkit” for all the strategies shared in the three-episode momentum series, including listener challenges with getting started, knowing when to stop, and dealing with competing priorities, juggling projects, and getting interrupted, solved!

Don’t know Diann Wingert?

ADHD coach, former psychotherapist, and business strategist for neurodivergent entrepreneurs. Diann combines her professional expertise with lived ADHD experience to offer practical strategies for entrepreneurs whose brains work a little differently. Through her podcast and coaching, she’s passionate about helping others embrace their unique strengths and build sustainable businesses while avoiding boredom and burnout.

Loved this episode?

Share it with your entrepreneurial friend—the one who’s always saying, “Wait, what was I doing again?” Here’s a link to make it easy.

© 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! I’m your host, Diann Wingert, and today we’re diving into the “Stopping Smart” episode—a must-listen for any ADHD entrepreneur who’s ever struggled with getting projects across the finish line.

If you’ve ever found yourself in the dreaded “improvement vortex”—tweaking, reworking, and researching just a little bit more instead of actually finishing, publishing or launching—this episode is for you.

We’ll explore the three major ways we get stuck when it’s time to stop: perfectionist tweaking, fear of rejection, and getting lost in endless research.

Discover why “good enough” is often more than enough, and learn practical strategies—including my Completion Compass—for diagnosing your type of project stuck-ness and moving forward.

Whether you avoid launching because you’re terrified of what people will think, or you endlessly tweak in hopes of creating the perfect product, today’s episode will give you permission—and a clear plan—to stop digging and start delivering.

Stick around as we reframe launching as a learning experience, talk about managing rejection sensitivity, and give you real-world solutions for finishing what you start.

Here’s what you’ll learn from this episode:

The Real Reason We Don’t Finish - three sneaky forms of “stuck” - perfectionist tweaking, fear-driven stalling, and getting lost in the research rabbit hole. Yep, she names names.

The Exit Strategies That REALLY Work You’ll learn how to diagnose your type of stuck and use my “Completion Compass” to escape the improvement vortex for good.

How to Write Your Own ‘Good Enough’ Rules (Before You Start Anything!) Set smart, clear criteria BEFORE you begin your next big project to keep perfectionism at bay.

Emergency Protocols for When You Hit That Mid-Project Panic Practical, step-by-step advice—including my golden rule for ADHD entrepreneurs: you’re not allowed to learn anything new until you put what you already know into action.

Real-World Smart Stopping Tips for Every Biz Project Whether it’s a course, website, community, or service—I’m serving up examples of what “smart stopping” actually looks like so you can stop tweaking and start shipping.

Fun Fact!

I recorded an episode after a botched launch—and guess what? It’s one of the most downloaded shows ever.

Turns out, real talk and imperfection win every time! So, stop fearing messy launches. Your people seriously want your honest journey.

🎙️Mic Drop Moment:

"Put it out into the world when your main point is clear and actionable, even if there are three more things you could add. There always will be. Your audience will tell you what they want to know more about, I promise."

Help me help you

I am creating a FREE starting-stopping-switching gears toolkit. Click here to complete an anonymous 30-second survey on your STOPPING PROBLEMS to let me know what you need most.

Don’t know Diann Wingert?

ADHD coach, former psychotherapist, and business strategist for neurodivergent entrepreneurs. Diann combines her professional expertise and lived ADHD experience to offer practical strategies for entrepreneurs whose brains work a little differently.

Through her podcast and coaching, she’s passionate about helping others embrace their unique strengths and build sustainable businesses.

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

Welcome to ADHD-ish, the podcast for ambitious entrepreneurs whose brains work a little differently.

I’m your host, Diann Wingert, and today we’re kicking off “The Momentum Series,” a deep-dive into what I like to call the “unholy trinity” of ADHD business struggles: starting, stopping, and switching gears.

Ever find yourself stuck in a never-ending planning phase, or maybe leaping headfirst into a project before you’re actually ready?

You’re not alone—it’s what I call the ADHD starting paradox, and it’s a challenge so many of us face. In this episode, we’ll break down why we get trapped in either over-planning or impulsively diving in, and explore the real fear that’s driving both: “What if I can’t keep this up?”

I’ll introduce you to my messy start method—a practical, low-pressure approach that ditches perfection and procrastination for real results. You’ll learn the 2% + 20% formula for action and discover foolproof systems that don’t depend on your mood.

Plus, I’ll walk you through concrete steps, emergency protocols for when you’re stuck, and real-world examples to get you moving—whether your challenge is launching a course, starting a podcast, or finally reaching out to those dream clients.

By the end of this episode, you’ll have practical strategies to overcome your biggest starting hurdles, and set yourself up for momentum that actually sticks. So if you’re ready to get your ass in gear, let’s jump in!

Episode Overview — What to Expect:

The Two ADHD Starting Problems:

• Analysis paralysis: Getting stuck in endless planning and research
• Cannonball starting: Diving in impulsively without enough prep

Why Both Approaches Set Us Up For Failure:

• Perfectionism and over-planning create pressure and stall action
• Impulsivity leads to chaos, burnout, and stopping problems

The Real Root: Sustainability Fear

• Why ADHD entrepreneurs fear they can’t keep things going—and why this fear is rational (but surmountable!)

The Messy Start Method:

• Diann’s proven “2% + 20%” formula to get unstuck
• How to combine just-enough planning with tiny, immediate action

The Five-Minute Blind Spot Check:

• Five quick questions to avoid overthinking or reckless starting

Mood-Independent Starting Systems:

• How to set up external cues and “pathetically small” first steps
• Using the two-minute rule for unstoppable momentum

Built-in Course Correction:

• How to schedule check-ins and adjust your approach without self-judgment
• Emergency protocols for when you’re frozen or tempted to leap in blindly

🎙️Mic Drop Moment:

"The more you practice starting small and adjusting as you go, the more sustainable, quite literally, everything becomes. Because you're not depending on the perfect conditions, or the perfect mindset, or the perfect motivation. You're depending on real systems that work even when you're tired, distracted, or overwhelmed."

Help me help you

I am creating a FREE Start -Stop-Switch toolkit. Click here to complete an anonymous 30-second survey on your Starting Struggles to let me know what you need most.

Don’t know Diann Wingert?

ADHD coach, former psychotherapist, and business strategist for neurodivergent entrepreneurs. Diann combines her professional expertise and lived ADHD experience to offer practical strategies for entrepreneurs whose brains work a little differently. Through her podcast and coaching, she’s passionate about helping others embrace their unique strengths and build sustainable businesses.

© 2025 ADHD-ish Podcast. Intro...

Welcome back to ADHD-ish! In today's episode, I sit down with my friend, author, writer, and ADHD coach, Dave Greenwood, for another honest, thought-provoking conversation—this time exploring the powerful lessons of The Courage to Be Disliked, a book rooted in the teachings of 19th-century psychotherapist Alfred Adler. While not specifically an ADHD book, Dave shares how this book packs a punch of wisdom, challenging beliefs around people-pleasing and how ADHD rejection sensitivity at work connects to ADHD burnout and our endless need for approval.

We tackle the tricky balance between accepting yourself as you are and believing you can change, as well as the incredible (if not a little controversial) freedom that comes with having the courage to be disliked. If you've ever found yourself spiraling over a colleague's tone in Slack or questioning whether your boss thinks you're incompetent, this conversation about ADHD rejection sensitivity will hit different.

Top 3 takeaways for anyone navigating work or life with ADHD (or just being human):

• You are not responsible for how others feel. Adler’s “separation of tasks” is a game-changer—do your part authentically, but let go of trying to control what others think or feel about you.
• You can change—if you want to. It’s easy to blame your ADHD or circumstances (hello, fixed mindset!), but the real magic starts when you open yourself to possibility, even if change is slow and non-linear.
• All problems are (ultimately) relational. Whether you’re late to a meeting or starting a business, our challenges almost always revolve around other humans. Building healthier boundaries and self-acceptance opens the door to genuine connection—and some serious peace of mind.

Dave Greenwood is a repeat guest and friend of the ADHD-ish podcast, known for his authenticity and sense of humor. He is the host of the Overcoming Distractions podcast and author of two popular books on living with ADHD. Though Dave jokingly calls himself a “welding school flunk-out,” he brings a wealth of lived experience, professional insight, and a pragmatic approach to living well with ADHD, especially for the self-employed

🎙️Mic Drop Moment:

Whether it’s with your boss, your partner, your clients, or even your business software (yes, really), most of our challenges come down to relationships - with others and ourselves. Listen for insights on how “people-pleasing,” unhelpful narratives, and unresolved childhood scars shape our work and our lives.

Next steps:

• Buy The Courage to Be Disliked audiobook
• Listen to the other podcast episodes that complement this one (links below)
• Schedule a consultation to work with Dave Greenwood or Diann Wingert

Mentioned in this episode: