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ADHD-ish

Diann Wingert
ADHD-ish
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  • Starting Strong: The Momentum Series Guide to Getting Things Done
    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 researchCannonball starting: Diving in impulsively without enough prepWhy Both Approaches Set Us Up For Failure:Perfectionism and over-planning create pressure and stall actionImpulsivity leads to chaos, burnout, and stopping problemsThe Real Root: Sustainability FearWhy 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 unstuckHow to combine just-enough planning with tiny, immediate actionThe Five-Minute Blind Spot Check:Five quick questions to avoid overthinking or reckless startingMood-Independent Starting Systems:How to set up external cues and “pathetically small” first stepsUsing the two-minute rule for unstoppable momentumBuilt-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 youI 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.©...
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  • 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 universal human feature. They are one of the tools evolution handed us to allow for snap decisions instead of getting overwhelmed by information. But for those of us with ADHD, these shortcuts don’t always get us where we want to go. Sometimes, they spark innovation, but other times, they lead us straight into frustration or failure.Drawing inspiration from Vicki Tan’s book “Ask This Book a Question,” we’ll break down why our ADHD brains are uniquely wired to fall into these “mind traps,” from relentless optimism and the sunk cost fallacy, to judging ourselves and others with double standards. But it’s not all doom and gloom: you’ll find out how understanding these biases can help you harness them as tools, create better decision-making habits, and transform your relationship with your business and your team. Let’s unravel the stories we tell ourselves—and learn how to write better ones.Here’s what you’ll learn in this episode:What cognitive biases are, and which ones our ADHD brains are most prone to The Optimism Bias - why we are grossly unrealistic about how much time and energy things take, and how to calibrate your big dreams.The Fundamental Attribution Error—why we give ourselves grace but judge our team, clients, and competitorsSunk Cost Fallacy— why we can’t let go of things we’ve worked hard at, even when they are doomed to fail My personal hacks for reality checking, perspective shifting, and accountability building, and my four-step “fresh start” framework.Tools to reset your decision-making: decision journals, external accountability, and Post-its that help you keep your eye on those sneaky bias blindspots Spoiler alert: Cognitive biases aren’t a bug; they are a feature. These mental shortcuts are part of the brain’s operating manual. The key isn’t to eliminate them, but to learn how to spot them and flip them into tools for smarter (and kinder) entrepreneurship.🏆 Want to get better at spotting your cognitive biases and make better decisions as a result? I created a free companion handout with the various patterns discussed in this episode, plus my four-step framework for rewiring your biases. Grab your copy right here. Mentioned in this episode:Vicki Tan’s “Ask This Book a Question” Goblin.tools Estimator 🎙️And be sure you're following/ are subscribed to ADHD-ish on your favorite podcast app, so you don’t miss a single episode. © 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.
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  • Lessons in Embracing Neurodiversity from Wicked
    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 —from the hopeful longing of "The Wizard and I" to the defiant liberation of "Defying Gravity"—my goal in this episode is to connect them to the distinct stages of our ADHD journey in learning to embrace our differentness. So, grab your broomstick and let’s go on an adventure to Oz. Episode Highlights:Let's take a trip through four major songs from “Wicked” that map out the ADHD journey to self-acceptance:“The Wizard and I”: The bittersweet hope that someone or something outside of us will finally fix what feels broken.“Popular”: The pressure to fit into neurotypical molds, no matter how unnatural it feels, and why those “helpful tips” so rarely work.“Defying Gravity”: The exhilarating breakthrough of embracing your true self and rejecting systems that were never built for your brain.“For Good”: Honoring everyone who contributed to your journey, finding peace with imperfection, and stepping into deeper self-acceptance.Whether you’re still searching for that magic fix, trying to fit into neurotypical norms, or learning to soar with your own brand of brilliance, this episode is an invitation to recognize the real magic within yourself. Join me as I encourage us all to “keep defying gravity together”—and celebrate just how far we’ve come, thanks to a little help from our friends in Oz.Inspired by this episode? Click this link to share it with a friend. Complete song lyrics for “The Wizard and I”, “Popular,” “Defying Gravity,” and “For Good” can be accessed here for reference. Used with permission by Scribd. All songs from “Wicked” were written by Stephen Schwartz and the clips used in this podcast recording were performed by various artists from The Studio Allstars Used with permission from One Media PublishingDigital distribution label based in Pinewood Studios, UK ©2008 © 2025 ADHD-ish Podcast
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  • Entrepreneurial Strengths & Vulnerabilities with Psychiatrist, Researcher & Serial Entrepreneur
    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, an acclaimed psychiatrist, professor, and serial entrepreneur whose groundbreaking research uncovers the fascinating relationship between ADHD, bipolar spectrum conditions, and the entrepreneurial drive. In this lively conversation, we get real about what makes entrepreneurs with ADHD different—and what it takes to turn those differences into undeniable strengths instead of exhausting liabilities. Here’s what you’ll hear in this episode:Why do so many entrepreneurs have ADHD tendenciesDr. Freeman breaks down fascinating research on why we’re more likely to go solo in our careers—and why we struggle in traditional workplaces.The double-edged sword of the ADHD entrepreneurial brainWe chat about superpowers and vulnerabilities, with a big emphasis on how to recognize your “zone of genius” (and when to call in backup!).Building your own ADHD-friendly toolkit for sustainable successFrom teams and routines, to handling sleep and “offloading the boring stuff,” we talk actionable strategies (yes, including coaching and medication).The myth vs. reality of the entrepreneurial lifeSpoiler: it isn’t all glamor and “get rich quick”—and Dr. Freeman shares why radical self-awareness and resilience are must-haves.Why fun is non-negotiable for the entrepreneur with ADHDTurns out, fun isn’t just a bonus—it’s the main event for the ADHD brain, and Dr. Freeman explains how to keep your business (and life) playfully sustainable.Make it actionable: Take three minutes to reflect: what feels fun, energizing, or “flow-y” in your own work? What support do you need more of?Feeling inspired to start, pivot, or quit? Get a “personal board of directors” before you make big decisions or take big risks.Get to know Michael Freeman, MD Michael A. Freeman, MD, is a clinical professor at UCSF School of Medicine, a researcher and mentor at the UCSF Entrepreneurship Center, a psychiatrist and executive coach for entrepreneurs, and an integrated behavioral healthcare systems consultant. His current research focuses on the identification of emotional overwhelm with early intervention and support. Dr. Freeman’s thought leadership on entrepreneurship and mental health has been featured in the New York Times, Washington Post, Wall St. Journal, Fortune Magazine, Inc., Entrepreneur, CNN Money, Financial Times, and Bloomberg News.Mentioned in this episode:UC San Francisco, UC Berkeley, Stanford University, the Gallup Organization Connect with Michael A Freeman, MDWebsite - LinkedIn 🎙️ Fun Fact From the...
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  • How Shiny Object Syndrome Sabotages Business 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 brains are hardwired for novelty, so creating consistency takes self-awareness and strategy. Lucky for you, this episode is full of candid stories, neuroscience-backed insights, and actionable advice on how to do just that. Loan me your ear holes for the next 25 minutes for: 🧠The Neuroscience-Based TruthWhy your ADHD brain is forever thirsty for dopamine—and why trying to force yourself to focus just doesn’t work for us.🏃‍➡️The Cost of Chasing NoveltyThe sneaky ways shiny object syndrome drains your revenue and energy (and how to recognize it hiding in your business).📋5 Practical StrategiesIncluding: dopamine scheduling and reframing the “messy middle” to creating shiny object parking lots and setting up accountability that actually works.🎨How to Enlist (Not Resist) Your CuriositySpecific ways to channel your creative bursts into profitable execution, instead of abandoned projects.📇Systems That Make Space for New Ideas (Without Derailing Your Progress)Learn how a “shiny object fund” can keep your creativity alive while protecting your core businessFun Fact from the Episode: ADHD expert William Dodson, MD, coined the expression “interest-based brain” to explain how we operate differently. Here is an article from ADDitude magazine that explains it ( including a one-minute YouTube video with a “House of Cards” style soundtrack). 🏆Ready to start creating more consistent business success—and work with your interest-based brain?To make it extra easy to go from innovation to implementation, I created a free companion handout with all the go-to strategies mentioned in this episode. Grab your copy right here. 🎙️And be sure you're following/ are subscribed to ADHD-ish on your favorite podcast app, because next week, I’m chatting with Dr. Michael Freeman, a leading psychiatrist, entrepreneur, researcher, and consultant. Trust me, you’re not going to want to miss it.© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.
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Sobre ADHD-ish

ADHD-ish is THE podcast for business owners with big ideas and busy brains, whether you have an “official” ADHD diagnosis, or not. We have expanded our focus so regardless of your gender or whether you identify as an entrepreneur, soloist, small business owner, creative, independent professional, freelancer, etc) if you are driven and distracted, color outside the lines and think outside the box, this podcast is for you. People with these traits are far more likely to start a business because we love novelty and autonomy. But, running a business can be lonely and exhausting. Having so many brilliant ideas means dozens of projects you’ve started and offers you’ve brainstormed, but few you’ve actually launched. Choosing what to say "yes" to and what to catch and release is even harder. This is exactly why I created ADHD-ish. Each episode offers practical strategies, personal stories, and expert insights to help you harness your active mind and turn potential distractions into business success. From productivity tools to mindset shifts, you’ll learn how to do business your way by embracing your neurodivergent edge and turning passion and purpose into profit. If you're new here, I’m your host, Diann Wingert, a psychotherapist-turned-business coach and ADHD-ish serial business owner, who struggled for years with cookie-cutter advice meant for “normies” and superficial ADHD hacks that didn’t go the distance. In ADHD-ish, I’m sharing the best of what I’ve learned from running my own businesses and working with clients who are like-minded and like-brained. Note: ADHD-ish does have an explicit rating, not because of an abundance of “F-bombs” but because I embrace creative self-expression for my guests and myself. So, grab those headphones if you have littles around, and don’t forget to hit Follow/Subscribe so you don’t miss a single episode. Oh, and if you love the show, reviews are appreciated and so is sharing ADHD-ish with others!
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