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Traditional multi-page business plans often cause overwhelm and execution paralysis for neurodivergent entrepreneurs. In this episode of ADHD-ish, host Diann Wingert breaks down how to construct a lean, flexible strategy that aligns with an ADHD brain rather than working against it.
Discover how simplifying core goals, focusing on high-impact actions, and building adaptable systems support consistent revenue growth. If you are a visionary entrepreneur seeking tailored ADHD business coaching to turn ideas into structured, profitable outcomes, this actionable episode provides a clear path forward.
EPISODE HIGHLIGHTS & TIMESTAMPS:
01:15 - Rethinking Traditional Planning for ADHD Entrepreneurs
05:40 - Core Frameworks of an ADHD Friendly Business Plan
10:15 - Streamlining ADHD Business Operations for Focus
15:30 - Managing Cognitive Load and Decision Making
19:50 - Sustainable Growth and Systems for ADHD Founders
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 Hidden Costs of ‘Winging It’:
Introducing the ADHD-Friendly Minimal Business Plan Framework:
Making Your Business Plan Visual & Flexible:
Get it Done (Without Overwhelm) with The Sprint Method
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
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.
Sustaining a successful company with ADHD requires leaving behind cookie-cutter advice that ignores neurodivergent trait dynamics. In this episode of ADHD-ish, host Diann Wingert breaks down how to structure operations around natural energy cycles rather than rigid corporate standards.
Gain insight into how aligning client offers, daily workflows, and boundary frameworks creates lasting profitability without burnout. If you are a visionary founder seeking targeted ADHD business coaching to build an enterprise that honors your unique brain, this episode offers clear, practical steps.
EPISODE HIGHLIGHTS & TIMESTAMPS:
01:15 - When Your Business Refuses to Focus
06:30 - Spotting Patterns in ADHD Business Operations
12:10 - Adapting Workflows to ADHD Executive Function
18:45 - Managing Cognitive Load Across Multiple Projects
24:20 - Establishing Decision-Making Systems for ADHD Founders
30:00 - Overcoming Entrepreneur Accountability Fatigue
36:15 - Aligning Daily Operations with ADHD Self-Trust
42:30 - Building Sustainable Systems for Long-Term Growth
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:
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.
High-stakes entrepreneurship frequently heightens emotional reactivity, leading to stress, fatigue, and erratic decision-making. In this episode of ADHD-ish, host Diann Wingert breaks down how nervous system arousal directly impacts leadership and business execution.
Gain practical tools to stabilize focus, protect emotional bandwidth, and process intense stress during demanding business cycles. If you are a founder looking for targeted ADHD business coaching to restore equilibrium and lead with confidence, this conversation delivers essential guidance.
EPISODE HIGHLIGHTS & TIMESTAMPS:
01:15 - Passion Paradox and ADHD Entrepreneur Dysregulation
05:30 - Identifying Early Signs of Business Overwhelm
09:45 - Managing Cognitive Load in High-Drive States
13:20 - Emotional Regulation for ADHD Business Operations
16:50 - Sustainable Growth and Long-Term Business Stability
Here are 5 keys you’ll pick up from this episode:
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
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.
ADHD entrepreneurs often struggle with anxiety, self-doubt, and overthinking. In this episode, Mikey Schumacher shares how embracing imperfections and insecurities became a powerful business strategy and storytelling tool.
You’ll learn how ADHD business coaching, executive function support, and community can help small business owners reframe setbacks, improve productivity, and scale a business with ADHD. This conversation resonates with pain points like burnout prevention, delegation, and decision-making—offering practical solutions for sustainable growth and authentic leadership.
EPISODE HIGHLIGHTS & TIMESTAMPS:
00:00 - Introduction to ADHD Entrepreneurship and Founder Growth
05:15 - Failing Forward and Overcoming Business Setbacks
12:30 - The Comfort of Plush Toys for Adults
19:45 - Building Community for ADHD Creators
27:10 - Embracing Creative Chaos and Overcoming Overthinking
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
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.
Constantly bouncing between high-level strategy and administrative micro-tasks costs neurodivergent entrepreneurs hours of focus every day. In this episode of ADHD-ish, host Diann Wingert details why task switching triggers cognitive inertia and executive fatigue.
Access actionable methods to batch operations, create smoother workflow transitions, and protect creative momentum. If you are an entrepreneur seeking tailored ADHD business coaching to optimize daily routines without feeling constrained, this episode provides a realistic structure for deep work.
EPISODE HIGHLIGHTS & TIMESTAMPS:
01:15 - Navigating Task Transitions in ADHD Business Operations
07:30 - Preserving Focus and Reducing Cognitive Friction
13:45 - Workflow Hacks for Managing Executive Dysfunction
20:10 - Preventing Productivity Crashes in Business Schedules
25:40 - Designing Sustainable Routine Shifts for ADHD Entrepreneurs
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!
Hyperfocus can feel like a double-edged sword for neurodivergent founders, driving intense productivity while risking burnout and neglected operations. In this episode of ADHD-ish, host Diann Wingert breaks down how to channel deep focus states without derailing long-term goals.
Access actionable methods to set intentional boundaries around intense work blocks, protect energy, and maintain operational momentum. If you are an entrepreneur seeking tailored ADHD business coaching to turn intense focus into sustainable results, this conversation provides a practical roadmap.
EPISODE HIGHLIGHTS & TIMESTAMPS:
01:15 - Breaking Free from Perfectionist Tweaking Loops
08:30 - Overcoming Rejection Sensitivity in Launch Phases
15:45 - Using the Completion Compass for Project Offramps
23:10 - Neutralizing Endless Research in Business Operations
30:25 - Sustainable Delivery and Ending the Improvement Vortex
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.
Stuck between endless planning and impulsive launches? In this episode of the ADHD-ish podcast, host Diann Wingert breaks down the starting paradox facing every business owner with ADHD. When execution friction stalls progress, relying on perfect motivation or willpower leads straight to burnout and incomplete projects.
Learn how to navigate task avoidance and execution hurdles using actionable ADHD business strategy tools like the Messy Start Method. For every ADHD entrepreneur seeking sustainable neurodivergent leadership, this episode provides simple systems to build momentum and achieve consistent business growth without overthinking.
EPISODE HIGHLIGHTS & TIMESTAMPS:
00:00 - Starting Strong with ADHD
08:30 - The Real Fear: Sustainability
15:45 - Five-Minute Blind Spot Check
23:00 - Built-In Course Correction Systems
27:15 - Sustainable Momentum Through Imperfect Action
Episode Overview — What to Expect:
The Two ADHD Starting Problems:
Why Both Approaches Set Us Up For Failure:
The Real Root: Sustainability Fear
The Messy Start Method:
The Five-Minute Blind Spot Check:
Mood-Independent Starting Systems:
Built-in Course Correction:
🎙️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 music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.
Ever find yourself overcommitting to client requests or spiraling over a colleague's tone in Slack? In this episode of the ADHD-ish podcast, host Diann Wingert and guest Dave Greenwood discuss how people-pleasing and rejection sensitivity directly fuel overworking and chronic burnout for every ambitious business owner with ADHD.
Together, they unpack Adlerian psychology and practical tools like the separation of tasks to set clear boundaries, navigate rejection sensitivity, and foster authentic neurodivergent leadership. Discover how tailored ADHD business coaching principles help protect your energy and build a resilient, sustainable business.
EPISODE HIGHLIGHTS & TIMESTAMPS:
00:00 - ADHD Rejection Sensitivity and People Pleasing
05:00 - Why Rejection Feels So Overwhelming
10:30 - Can Adults with ADHD Really Change?
15:30 - Breaking Free from Old Patterns
20:00 - Fixed Mindset, Excuses, and ADHD Burnout
25:00 - Taking Responsibility Without Self-Blame
30:00 - Why ADHD Challenges Are Often Relational
40:00 - Self-Acceptance, Boundaries, and Living Present
Top 3 takeaways for anyone navigating work or life with ADHD (or just being human):
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:
Mentioned in this episode:
© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.
When something feels fundamentally unjust, it doesn't just annoy you—it can completely derail your day and lock up your decision-making. For business owners with ADHD, that intense wiring is justice sensitivity.
This episode explores why unfairness hits so hard and how to channel that righteous energy into authentic leadership. Discover how to stop justice-driven burnout in its tracks and turn an exhausting emotional burden into your greatest competitive edge for scaling with integrity.
EPISODE HIGHLIGHTS & TIMESTAMPS:
00:00 - Navigating Operational Complexities as an Entrepreneur
05:15 - Overcoming Decision Fatigue and Cognitive Bottlenecks
11:30 - Establishing Delegation Frameworks and Team Accountability
17:45 - Preventing Burnout Through Strategic Pacing and Workflows
23:10 - Claiming Your Authority as an Empowered CEO
Here’s what you’ll learn in this episode:
What Justice Sensitivity Actually Is:
We bust the myth that it’s just being “too emotional”—it’s a real, measurable trait, and science backs that up!
Why It’s SO Common in ADHD Brains:
Discover why our brains are wired to spot (and feel) unfairness at lightning speed, and what emotional dysregulation has to do with it.
The Double-Edged Sword in Business:
Justice sensitivity can help you build a business with true integrity—but (yup, there’s a but), it can also lead to exhausting decision paralysis and burnout if you’re not careful.
The 3-Part Framework to Make it Work For You (Not Against You):
Audit your outrage, channel your fire, and protect your resources—so you can transform that righteous energy into business gold without burning out.
Action Steps for Real Impact:
From “name it to tame it” to boundary-setting and finding your values-driven tribe, I spell out concrete ways to work with your justice compass, not against it.
Fun Fact from this episode:
ADHD justice sensitivity can turn you into the “canary in the coal mine” for spotting unfairness—but just like a smoke detector, you don’t want it blaring 24/7! Learn how to schedule your “outrage hours” so you can still get sh*t done.
Thanks for listening, for caring, and for being a good human. Take care of your sensitive heart, and let’s keep building sustainable businesses that actually stand for something.
Ready to Take Aligned Action?
If you want to make a difference for girls with ADHD (seriously, they lag behind boys by decades in getting identified and treated), check out Find the ADHD Girls—an amazing organization I’m proud to be a part of. Click this link to find out more.
© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.
For creative solopreneurs with neurodivergent brains, forcing rigid corporate schedules often stifles inspiration and leads to chronic friction. In this episode of ADHD-ish, host Diann Wingert examines how to build flexible operations that support spontaneous creative focus.
Implement practical frameworks to design fluid routines, protect mental energy, and maintain project momentum across high and low-energy periods. If you are an entrepreneur looking for targeted ADHD business coaching to align creative freedom with sustainable profitability, this conversation delivers essential guidance.
EPISODE HIGHLIGHTS & TIMESTAMPS:
01:15 - Creative Flow and ADHD Business Operations
07:45 - Unlocking Intuitive Systems for Solopreneurs
14:20 - Balancing Structure and Spontaneity in Business
21:50 - Overcoming Creative Friction and Decision Fatigue
28:10 - Sustainable Growth Models for Creative Entrepreneurs
Highlights of this episode:
The Magic of Collaborative Branding:
Jess reveals why the best branding isn’t transactional—it's about deep collaboration that reveals what makes you (and your business) truly unique.
Owning Your Brain—Labels or Not:
We talk candidly about labels like ADHD, anxiety, and depression, and why the label itself might not matter as much as learning to work with your “big beautiful brain” (as Jess calls hers)
Making Space for Joy, Mess, and Rest:
Ultimately, the episode is a reminder not to confuse hustle with success, or routine with progress. The goal is to create a life and a brand that reflects your truest self, even when that looks different from the mainstream. Jess and I both agree: eat the cake, savor the little moments, and let your business be as unique as the brain behind it.
Jess’s superpower: Jess’s approach to branding involves making her clients step into their metaphorical red stilettos— pushing them out of their comfort zone so they can find their x-factor. In her words, “I don’t want small talk. Show me your fucking soul.”
Want to connect with Jess? Here’s how:
Brand Transformations Private Podcast - Instagram - Website
Mentioned in this episode:
Julia Cameron’s The Artist’s Way
Want to hear how Jess helped me rebrand my podcast and business? ADHD-ish episode # 226 - The Transformational Power of Rebranding with Jess Malli Mercier
Thinking about working with me? I have many more Client Success Stories you can check out for inspiration!
Click here to explore
© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.
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