ADHD-ish™
ADHD-ish™ is a podcast for entrepreneurs with ADHD who struggle to run their businesses using conventional advice. The host, Diann Wingert, an ADHD business strategist and coach, explores topics such as business growth, delegation, decision-making, executive function, and burnout prevention. Each episode offers practical strategies, honest conversations, and personal stories to help business owners build systems that work with their unique brains. The show aims to help listeners reduce cognitive load, avoid burnout, and achieve sustainable success without trying to think or work like everyone else.
Episodes
Your Overthinking ADHD Brain Is the Best Thing About Your Brand
Kristina Flynn has had a psychiatrist since she was twelve, collected diagnoses like frequent flyer miles (anxiety, depression, OCD, bulimia, and more), and still didn't get an ADHD diagnosis until her thirties, after her daughter's birth blew up every workaround she'd been quietly running for two decades.Now she runs Story EQ, where she helps people find the story underneath their work. Everybo
Stop Confusing Options for Opportunities: A Practical Guide to Decision Making for ADHD Entrepreneurs
Ever find yourself saying yes to a new collaboration, tool, or project—then months later wondering how you got there? If you run a business (especially with an ADHD-ish™ brain), you’re not alone.In this episode, I break down why our brains confuse options for opportunities, how dopamine clouds our judgment at the moment of the ask, and share a practical “screen door” filter to make better decisio
A Skeptic's View of Using an AI Coach
Traditional business coaching falls short when late-night decision-making spirals hit, leaving many ADHD entrepreneurs feeling isolated and tired of generic productivity advice. As a stubbornly self-sufficient business owner, your urgent questions, pivot ideas, and friction points rarely line up with a pre-scheduled coaching call.In this episode, Diann Wingert shares how her digital clone, Di AI,
Out of Sight, Out of Mind: How ADHD Object Permanence Leaks Money From Your Business
Welcome back to ADHD-ish! For many ADHD entrepreneurs, "out of sight, out of mind" is a daily reality, whether that means active client projects, strategic goals, or vital admin tasks. When working memory struggles to keep priorities front and center, simple operational gaps quickly turn into overwhelming friction, trapping business owners in cycles of panic work and unnecessary stress.In this ep
Eliminating Friction & Fatigue as an ADHD Solopreneur: A Client Success Story with Kathryn Bird
Standard productivity frameworks and hustle culture often sell a rigid, neatly divided version of work-life balance that rarely works for high-achieving neurodivergent brains. When you try to force hyperfocus into conventional schedules, attempting to balance intense professional drive with personal well-being frequently leads to emotional exhaustion and severe ADHD burnout in entrepreneurs.To bre
What Procrastination, Resistance & Avoidance Are Trying to Tell You About Your Business
If you are a business owner with ADHD trapped in procrastination, resistance, and avoidance, stop fighting your nervous system. Standard productivity tips fail because running a business with ADHD requires a different approach. In this episode of the ADHD-ish™ Podcast, Diann Wingert reframes procrastination as essential diagnostic data signaling operational bottlenecks.Using the ADHD-ish™ Method,
No Diagnosis? No Problem! Embracing Neurodivergence Without Labels with Dr. Naketa Ren Thigpen
If you suspect you have an ADHD-ish brain but lack a formal diagnosis, you might hesitate to step into neurodivergent leadership. Driven entrepreneurs often struggle with imposter syndrome without an official label. In this episode of the ADHD-ish™ Podcast, Diann Wingert and Dr. Naketa Ren Thigpen discuss embracing your neurodivergence without clinical validation.Running a business with ADHD requi
The Recurring Revenue Trap: The Hidden Cost of "Stable" Income for Business Owners with ADHD
If you are a business owner with ADHD, mainstream advice says business growth requires recurring revenue. However, predictable retainers often cause burnout for neurodivergent entrepreneurs who thrive on novelty. In this episode of the ADHD-ish™ Podcast, Diann Wingert exposes the "recurring revenue trap" and the mismatch between traditional models and an ADHD brain.Instead of forcing rigid operati
You're a F*cking Wizard: Why Your Business Needs a Game Master, Not a Guru, with Paul Pape
Traditional business blueprints fail visionary ADHD entrepreneurs who think non-linearly. If you struggle with rigid strategies, this episode explores why standard methods fall short for neurodivergent minds. Diann Wingert and creative coach Paul Pape discuss using gamification and play to turn overwhelming operations into high-impact quests.Discover how a tailored ADHD business strategy unlocks y
The ADHD Expert's Trap: Performing Your Value Instead of Owning It: A Client Success Story with Jabari Allen
Leaving corporate life promises freedom, yet many ADHD entrepreneurs recreate burnout through scope creep and people-pleasing. If you overwork to prove your value, setting clear business boundaries is essential for your strategy and well-being. In this client spotlight, Diann Wingert and tech consultant Jabari Allen discuss shifting from performing value to owning authority.Discover how an aligned
"Somebody Stole My Sh*t!" : Copycats, Counterfeiters, and How to Protect What You've Built, with Dani Donovan
From her unexpected rise as an ADHD comic creator to pouring over 3,000 hours into designing The Anti-Planner, a "productivity spell book," Dani Donovan is a force of nature.In this lively interview, Dani shares her unfiltered journey of building a tool for people tired of feeling like failures, dealing with the emotional roller coaster of intellectual property theft, and navigating impostors sel
Time Blindness is a Pricing Problem, not Just a Productivity Problem
Traditionally seen as a productivity flaw, time blindness is revealed here as a money problem, quietly undermining pricing, profits, and self-worth for solopreneurs with ADHD.This episode explores why common fixes like timers and time blocking miss the deeper issue, and instead, offers practical ways to design around the unique ADHD brain.Listeners can expect actionable tools—like range pricing,
You Want to Be a Published Author, but You Have ADHD, with Meg Casebolt
Ever wondered how someone with a full plate—a thriving business, a family, a neurodiverse household, AND a stack of published books—still finds time to sleep?Or better yet… how they use their ADHD to power all of it? If you’ve ever felt overwhelmed by your own creativity or wondered if you’re “too much,” you’re going to love this interview with returning guest and my SEO consultant, Meg Casebolt.
How Successful ADHD Entrepreneurs Trigger Hyperfocus on Demand
Welcome back to ADHD-ish™, where we're kicking off a five-episode series reframing the most talked-about ADHD traits as tools for entrepreneurial success, starting with hyperfocus.Forget the myth that hyperfocus is a rare, unpredictable gift. ADHD-ish™ host, Diann Wingert, reveals that the most successful ADHD entrepreneurs create the conditions for hyperfocus rather than hoping it just shows up.H
Myths About Virtual Assistants That Prevent ADHD Entrepreneurs From Getting The Help They Need, with Avigail Schondorf
ADHD fundamentally impacts executive function—the mental skills for planning, prioritizing, delegating, and following through. So, when an entrepreneur hires a VA and is expected to onboard, direct, and give detailed instructions, they’re faced with a mismatch: the very skills they struggle with are those they now must use to instruct their assistant.Traditional VAs, trained to “do what they’re to
Four Ways High Functioning ADHD Entrepreneurs Put Their Mental Health at Risk
You’ve scrolled past Mental Health Awareness Month posts thinking, “That doesn’t apply to me.” Your business looks fine. On the surface, YOU look fine. But what if the very skills driving your success are quietly putting your mental health at risk? The ADHD-ish ™ Podcast tackles the conversations mainstream mental health awareness misses—especially for high-functioning ADHD entrepreneurs.For thos
Hire the Hurricane Chasers: Why The Best Team You'll Ever Build Looks Nothing Like You've Been Taught, with Ian Wilson
Welcome back to ADHD-ish! In this episode, my guest Ian Wilson, a creative agency owner of over 16 years, is what I call a natural-born entrepreneur.From hustling for his first job at age eleven to building a unique partnership with his neurodivergent business partner Eric, Ian sheds light on why traditional approaches to team building rarely work for people whose brains are wired a bit differentl
When Your ADHD Brain Hits Empty: Decision Fatigue, Emotional Labor & Ego Depletion
Ever found yourself unable to make the simplest decision or making impulsive choices you later regret at the end of a long day? You're not lazy—you're depleted. Understanding ADHD strengths and struggles means recognizing that our executive function ADHD capacity is finite—and knowing how to manage it strategically.This episode of ADHD-ish dives into the science and lived reality of ego depletion—
How Celebrating Tiny Wins with ADHD Boosts Motivation & Beats Burnout, with Risa Williams
Too often, those of us with ADHD (and, honestly, just about anyone striving for success) fall into the “check the box and move on” mentality, downplaying our achievements and racing toward the next goal. Sound familiar?In this episode, host Diann Wingert and returning guest Risa Williams, LMFT, challenge listeners to radically rethink what counts as a win. What if making a sandwich, sending a toug
Stimulant Medication for Entrepreneurs with ADHD: What Difference Does it Make?
You’ve probably heard that medications like Ritalin, Adderall, or Vyvanse simply "fix" your attention. But what if I told you that most of what you think you know about how these meds work is actually wrong—or at least seriously incomplete? Understanding why neurodiversity is good for business starts with accurate information about how our brains actually function—including the real science behind
ADHD & The Lifetime Legacy of Bullying with Brooke Schnittman
In this vulnerable and eye-opening conversation, ADHD-ish host Diann Wingert sits down with fellow ADHD coach, Brooke Schnittman, to explore the lasting impact of bullying for those of us with ADHD, drawing from her own lived experience and groundbreaking research.One of the most surprising insights? While bullying trends downward in the general population as we age, it barely drops for those with
Introducing Di AI, My ADHD Business Coach Digital Clone
Welcome to ADHD-ish, where we explore the strengths and struggles of being an entrepreneur with an ADHD brain. In this episode, host Diann Wingert introduces a groundbreaking new resource – Di AI, her ADHD business coach digital clone, created to be accessible 24/7 for those moments when you need support most, not just during scheduled calls. Di AI isn’t a replacement for human coaching, but an e
Three Ways to Pivot in Business to Avoid Burning Out or Burning It All Down, with Megan Eckman
If you’ve ever felt weighed down by burnout or the urge to abandon it all and start fresh, you’re not alone.In this lively conversation, serial entrepreneur Megan Eckman shares her delightfully candid journey of starting, scaling, hibernating, and moving on from multiple businesses, offering honest lessons you won’t find in most business books.We talk about Megan’s recent ADHD diagnosis, the three
The True Cost of a Delayed ADHD Diagnosis in Women
In collaboration with other independent podcasters during the global Podcasthon charity event, ADHD-ish host Diann Wingert is opening up about the real costs women face when their ADHD goes undiagnosed for far too long—especially those running their own businesses.From emotional tolls and damage to self-worth, to identity crises and financial setbacks, Diann unpacks how the ADHD diagnostic criteri
Is Cognitive Ergonomics the Missing Link to ADHD Motivation? with Jeff Copper
Welcome to another episode of ADHD-ish! In today’s conversation, Diann Wingert, host and therapist-turned-business strategist, sits down with longtime ADHD coach and thought leader Jeff Copper to explore his groundbreaking new approach: “Cognitive Ergonomics from the Inside Out.”Together, they dive into the roots of executive function challenges, drawing on insights from Dr. Russell Barkley, and d
Which Company Culture is Your ADHD Brain Building?
If you’re an entrepreneur or founder who feels like you have to work twice as hard just to keep your business from spiraling, you’re not alone—and your company’s chaos might not just be “part of the job.”Most founders don’t realize their business “vibe” is a mirror of their brain. ADHD traits like chasing dopamine, avoiding conflict, or struggling with structure aren’t just personality quirks– the
Using Joy to Fuel Productivity for Neurospicy Entrepreneurs with Alexis Hope
Joy isn’t a luxury, it’s a strategy: As ADHD-ish host, Diann Wingert, and today’s guest, Dr. Alexis Hope, agree—joy needs to be intentionally built into our routines and workspaces.Rather than waiting for motivation, seek and design pockets of joy to unlock creativity and productivity. Social connection is powerful dopamine:For Alexis Hope, sharing small wins, positive feedback, and a sense of com
The ADHD Follow-Up Problem: Why You Forget Commitments and How to Fix It
If you have ADHD, you may find yourself constantly playing catch-up on commitments—forgetting promises made in a flurry of good intentions.Promises made in the car, at a networking lunch, in a Zoom chat, or even running into someone at Target, all exist in separate universes—voice memos, post-its, texts—but rarely make it into your actual task system.This isn’t just about a single “dropped ball.”
3 Hard Truths, 0 Fucks Given, 0 Apologies: Lessons Learned from Podcasting My Way to 300 Episodes
Welcome to a milestone episode of ADHD-ish! In episode 300, host Diann Wingert invites listeners into a raw, unfiltered conversation about the realities of entrepreneurship with ADHD.Rather than a feel-good celebration, this episode delivers the hard truths that other neurodivergent entrepreneurs need to hear—no sugar-coating, no apologies, just authentic wisdom earned through real-world experienc
ADHD and Working Memory Challenges: The Business Problem Nobody's Talking About
While everyone talks about ADHD and time blindness, ADHD-ish host Diann Wingert spotlights the real bottleneck: working memory.She unpacks what working memory is (and how it's not just short-term memory), why ADHD brains often struggle to keep pace in business, and why brain games probably won't fix the problem.But it’s not all doom and gloom—Diann shares honest strategies that actually work, from
Adding Novelty in Your Business with Pop-Up Offers with Erin Ollila
Welcome back to ADHD-ish! In this episode, host Diann Wingert sits down with marketing strategist, copywriting expert, and podcaster Erin Ollila.This convo is all about pop-up offers—and how adding a dose of novelty can transform your business. Inspired by her own ADHD-driven creativity, Erin shares the thought process behind developing two unique, time-limited offers just before a major launch.Wh
"Enough Already": Breaking the ADHD Habit of Overcompensating in Your Business
No one launches their own business in search of exhaustion. But for so many of us with ADHD-ish tendencies, overworking, over-delivering, and over-researching often become our default—especially when our own sense of “enough” is broken or never got calibrated in the first place.This episode goes deeper than productivity advice; it’s about safety, self-worth, and learning what sustainability truly
The Neurodivergent Edge: Redefining Strength in Relationships & Business, with Dante Assad Williams
Welcome to another episode of ADHD-ish!Today, host Diann Wingert is joined by psychologist and viral TikTok creator Dr. Dante for a raw, insightful look at the "Neurodivergent Edge"—how ADHD traits transform not just personal relationships but entrepreneurial success.In this conversation, Dr. Dante shares the story behind his celebrated term "neuro baddies," celebrating the honesty, intensity, and
The ADHD Brain's Year-End Inventory (That Has Nothing to Do With Goals)
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, hone
Chasing Butterflies: Managing ADHD Idea Overwhelm as a Serial Entrepreneur, with Sarah Dowd
What This Episode Is AboutIf 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
Why Entrepreneurial ADHD Traits Don’t Always Mean You Should Start a Business
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, inno
Attract, Don't Chase: Relationship Marketing & ADHD with Cat Orsini
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
Redefining Success After Loss: An ADHD-Informed Approach to Grief & Burnout: a Client Success Story Episode with Steph Cotrell
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 busi
The Big Questions Every Business Owner Needs to Ask, with Jessica Lackey
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
Boredom-Proofing Your Business: When to Renew or Release What's Lost Its Shine
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
ADHD is Not Just In Your Head: Exploring Embodied Neuroscience with Miguel Toribio-Mateas
If you have spent years trying to 'hack' your dopamine with planners and external fixes, you are missing a vital piece of the puzzle. ADHD is far more than a brain-based disorder; it is a full-body experience connected to your nervous system, gut health, and daily rhythms.Diann Wingert sits down with clinical neuroscientist Dr. Miguel Toribio-Mateas to explore embodied neuroscience. Discover how s
Reactive to Regulated: Managing Emotions as a Business Owner with ADHD
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 r
Daily Habits That Make Your ADHD Worse with ADD Crusher, Alan P. Brown
Many adults unknowingly make their ADHD symptoms harder to manage through everyday habits that drain focus and executive function. From dopamine-driven sugar cravings to revenge bedtime procrastination and screen overload, small daily routines can sabotage your brain's natural ability to regulate focus, mood, and productivity.In this episode of the ADHD-ish™ podcast, Diann Wingert sits down with A
When Less is More: The Case for a Single Offer in Your Business
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 tr
Neurodiversity, Intersectionality & Authenticity with Ron Sosa
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
What is an ADHD Business Coach?
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
Developing Confidence as a Business Owner: a Client Success Story with CherylAnn Crego
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 Che
Find Your Flow: Three Focus Day Models for ADHD Brains
Every time you switch between calls, emails, and content creation, your brain loses momentum to context switching. For an ADHD entrepreneur or small business owner with ADHD, rigid time management systems often lead to task paralysis, overwhelm, and multitasking burnout. Protecting your energy requires a system built for neurodivergent focus.In this episode, Diann Wingert shares three tailored "Fo
Feeling Chronically Misunderstood as a Woman with ADHD with Gilly Kahn
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 bu
When A Prospect Ghosts You (and Your ADHD Brain Won't Let It Go)
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 HOSTDiann Wingert (she/her) is a former psychotherapist turned ADHD entrepreneur coach
How to Clone Yourself as an ADHD Entrepreneur with Automation, AI & Apprentices, with Will Christensen
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 ca
The Soulmate Phenomenon: How ADHD Fuels Idea Infatuation in Your Business
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 h
When High Ability Meets ADHD: Delayed Diagnosis and Midlife Transformation with Lisa Lackey
What happens when high ability and late-diagnosed ADHD intersect in midlife? In this episode, Diann Wingert sits down with licensed psychotherapist Lisa Lackey to explore the unique journey of a high-achieving business owner with ADHD receiving a diagnosis later in life. High intelligence often masks executive function struggles for decades until life transitions like menopause make traditional co
The ADHD-friendly Business Plan You'll Actually Use
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 r
When Your Business Has ADHD, Too with Diane Mayor
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.
The Passion Paradox: When Drive Becomes Dysregulation for Entrepreneurs with ADHD
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
Celebrating Our Imperfections as a Business Strategy with Mikey Schumacher
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
Shifting Smoothly with ADHD: Stop Task Switching Stress – ADHD Tips That Actually Work
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
Stopping Smart with ADHD: Break Free from ADHD Hyperfocus & Perfectionism – Simple Strategies
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 laun
Starting Strong with ADHD: Overcoming Procrastination & Task Avoidance to Get the Ball Rolling
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 ADH
How to Stop People Pleasing and Manage ADHD Rejection Sensitivity at Work with Dave Greenwood
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
ADHD & Justice Sensitivity: From Overwhelm to Advantage in Business
Do you ever feel like you’re walking around with your emotional skin turned inside out whenever you spot unfairness? This week’s podcast episode is for you! I’m Diann Wingert, your neurodivergent navigator, and in this episode, we are unpacking the lesser-known ADHD traits of justice sensitivity—what it really is, why it matters, and how it could become your business’s hidden strength instea
Finding Your Flow as a Creative Solopreneur: A Client Success Story Episode with Jess Malli Mercier
If you’re a multipassionate ADHD-ish creative who tends to be much better at starting a project than finishing it, wonders if it’s really possible to stand out in a crowded market, and struggles to figure out how to make a living from art and make a difference in the world, this Client Success Story episode will resonate with you, big time. My guest today is one of my favorite people, Jess Malli
Mind Traps & Thought Loops: Identifying Cognitive Bias in the ADHD Brain
If you’ve ever invested time or money into a “sure thing” that fizzled, or found yourself insisting, “this time I’ll stick to my schedule!” (despite plenty of evidence to the contrary), you’re not alone. We are talking about cognitive biases, those sneaky mental shortcuts that shape our decisions, our stories, and, often, our downfalls.Cognitive biases aren’t unique to ADHD brains; they’re a unive
When Ambition Overtakes Performance: A Guide for ND Founders
Learning to align our drive and ambition with our genuine capacity tends to be one of those lessons that ADHD entrepreneurs learn the hard way - through cycles of shame, regret, and burnout. But what if there is a better way, like listening to this conversation between two seasoned ADHD coaches? Meredith and I have both struggled with our own untamed ambition and learned that not all id
Wicked Wisdom: Real Talk on Neurodiversity & Self Acceptance
I decided to do something special for this episode, because this week is our 5th podcast anniversary (and it's also Mental Health Awareness Month.) One of the most challenging things about being neurodivergent is learning to accept ourselves in a world where being different often marks you as an outsider. Using my obsession with Wicked and exploring four of Stephen Schwartz’s iconic songs&n
The Psychiatrist’s Take on Vulnerabilities in ADHD Entrepreneurship
Ever wondered why the idea of working for someone else just never quite fit, or why chaos seems to call your name (and you answer with gusto)? If you’re an entrepreneur who’s found yourself drawn to the thrill of building your own path—and maybe even stumbled more than a few times along the way—you are going to love this week’s guest interview. I recently sat down with Dr. Michael A. Freeman,
Shiny New Object Syndrome? Here’s How to Stop It From Sabotaging Your Success
Our edge as entrepreneurs comes from spotting trends and launching fresh ideas. The problem? Most of us have a graveyard of half-baked projects, forgotten launches, half-written newsletters, and more orphaned tech tools than we care to admit. Let’s face it: innovation is our ADHD advantage, but execution moves the needle. Shiny Object Syndrome is not a quirky personality trait; our ADHD
Staying Strategically Solo as a Neurodivergent Entrepreneur
If your head is spinning with marketing messages from high-profile coaches insisting you need a team, a course, a 6 or 7 figure business, when what you really want is flexibility and the freedom to do something you love on your own terms, this episode is your permission slip to have a simple, sustainable solo business. My returning guest, Maggie Patterson, joins me to chat about the significance o
Beyond People Pleasing: Unlearning the Default Yes
How often do you find yourself agreeing to something and later regretting it? Yeah, me too. In fact, the majority of adults with ADHD identify as people pleasers, but there’s more to this knee-jerk reflex than meets the eye. This solo episode is packed with actionable tips for unlearning the Default Yes, starting with identifying the role of our unique neurological wiring in this dynami
Creative Sprint Days: One Entrepreneur's Solution for an ADHD-Friendly Business
Trying to figure out what you need to do to make your small business more ADHD-friendly? In today’s episode, I sit down with ambitious outlier, Evan Sargent to discuss how she built a business that allows her to thrive, stand out from the competition and honor her ADHD attributes and gifts. With a background in graphic design and advertising, Evan transitioned from a fast-paced ag
Paying Less ADHD Tax: A Solopreneur's Guide
It’s tax time here in the US, and those of us with ADHD traits are paying extra! Have you heard of the ADHD tax? I’m referring to those invisible costs that affect entrepreneurs and solopreneurs with ADHD, draining not only finances but also well-being and relationships. From late fees and impulse buys to missed deadlines and opportunities, these ADHD-related financial and time-related
Innovative Solutions for ADHD Executive Functioning Challenges
Traditional organization tools rarely account for executive dysfunction. In this episode of the ADHD-ish podcast, host Diann Wingert meets with tech founder Mina Raver to examine how executive functioning challenges impact task management, focus, and daily workflows for every business owner with ADHD.Together, they discuss adaptive technology, tailored ADHD business operations, and brain-based sys
Becoming The Leader Your Business Needs: a Client Success Story with Kirsten Beukes
If you are a neurodivergent business owner, one of the biggest challenges can be leading a team, especially if you lead an all-female team in a female-dominated industry like occupational therapy. Today’s Client Success Story features Kirsten Beukes, who is the owner of an OT group practice in South Africa. Through our work together, Kirsten came to understand how her ADHD affects her business an
Let Them See You: Marketing with Courage for Neurodivergent Business Owners
So many small business owners obsess about how their ADHD struggles make things more challenging, but there is a bigger picture at play. When you identify your ADHD strengths and use them as your competitive advantage, now you are cooking with gas. My friend, Iris Goldfeder is a marketing strategist and owner of Gas Stove Creative. She joins us today to talk about how she le
Inbox Strategies That Work for Your ADHD Brain
Is an overflowing inbox hijacking your daily productivity? In this episode of the ADHD-ish podcast, host Diann Wingert addresses how compulsive email checking triggers dopamine loops, fuels task avoidance, and drains valuable focus for every business owner with ADHD.Streamline your digital workflow using practical ADHD business operations methods, including dedicated email blocks and a simple thre
From Idea to Impact: Start a Revolution with Your Business
Most soloists I know want to make a living on their own terms, but many are also driven by a bigger vision of making a difference, infusing both passion and purpose into their work. Have you ever wondered if you and your business could start a revolution? I sat down with Rochelle Moulton, a brand strategist, author, podcaster, and advocate for soloist consultants doing work that t
From Setback to Comeback: Strategies for Dealing with Disappointment
Does disappointment seem to follow you at every stage of your entrepreneurial journey? In this episode, I’ll be sharing why running your own business can set the stage for letting yourself and others down, especially when ADHD is in the mix. In this episode, I share common triggers for disappointment, from overloading yourself with too many clients to underestimating how long things will take
Pivot Your Way to a Stand-Out Business
Brittany grew up in a family with a history of entrepreneurship. Both grandfather and father were small business owners, but, after witnessing the instability and uncertainty of self-employment firsthand, Brittany shied away from entrepreneurship, at least at first. Over time, and by allowing herself to follow her curiosity and pivoting in response to changing market conditions, Brittan
The ADHD Entrepreneur's Guide to Confident Decision Making
Are impulsive commitments and decision fatigue draining your entrepreneurial energy? In this episode of the ADHD-ish podcast, host Diann Wingert breaks down how dopamine tricking ADHD brains leads to overcommitment, shiny object syndrome, and overwhelm for every business owner with ADHD.Discover how to evaluate incoming offers using the 72-hour decision filter and four strategic questions. Cultiva
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