ADHD-ish™

Diann Wingert | ADHD Business Strategist & Coach
  • 5.0 (99)
  • Entrepreneurship
  • Updated Weekly

Running a business with ADHD isn't hard because you're distracted. It's hard because most business advice wasn't built for your brain. Many entrepreneurs with ADHD try to solve business challenges with more productivity hacks, stricter routines, or systems they can never quite sustain. Others keep chasing new ideas, opportunities, and strategies, hoping the next one will finally make everything click. The result? More cognitive load, more unfinished projects, more decision fatigue, and often more burnout. ADHD-ish™ is the podcast about ADHD business strategy for business owners with ADHD who want to grow a successful company without forcing themselves to think, work, or lead like everyone else. Each episode explores the real-world challenges of running a business with ADHD, including ADHD business growth, delegation and accountability, decision-making, executive function in business, burnout prevention, leadership, and building business systems that actually work for your brain. You'll hear practical strategies, honest conversations, personal stories, and expert insights designed to help you make better decisions, follow through on what matters most, and create sustainable success. I'm Diann Wingert. As a business coach, former psychotherapist, serial entrepreneur, and the creator of ADHD-ish™, I've spent years helping entrepreneurs and business owners with ADHD stop fighting their brains and start building businesses that work with them. Whether you're an ADHD entrepreneur, an ADHD small business owner, or a founder trying to scale a business while managing the realities of ADHD, this show will help you lead more effectively, grow more intentionally, and build a business that's designed for the way you think.

  1. 17h ago

    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. Everybody tells you to stop overthinking. Kristina Flynn built a company on it. ‍We talk about why doing your own branding is a fool's errand (spoiler: your brain isn't primed for reality, it's primed for your perception of reality). We talk about the Mensa-level geniuses who sit across from her and say "I'm not that interesting." ‍We talk about the specific, weirdly universal terror of what your old colleagues will think. And we talk about AI — not as a voice replicator, but as something that can understand your context if you feed it properly. ‍Fair warning: if you're sitting on an abandoned rebrand, three different mission statements you don't believe, and a nagging sense that you should be further along by now — you're going to feel a little called out. Stay with us anyway. ‍ WHAT’S INSIDE: ‍● Why Your Old Story Isn’t the Whole Story: How narrative identity, negativity bias, and corporate conditioning have shaped the way you show up ‍ ● The 4 Stories Framework (Stealable Worksheet): Start mapping your old story, bridge story, and how to shift from “it’s about me” to “it’s about them” ● Radical Self-Acceptance Checklist: 5 mindset shifts to finally move past shame, imposter feelings, and waiting for permission ‍ ● Overthinking as an Asset: Quick exercises to turn rumination into action, content, and connection (instead of procrastination) ‍ ● Your First Move Blueprint: Micro-steps to start building story-driven content — without oversharing or burnout FUN FACTS Kristina and Diann are both pretty sweary and swear by the research that concludes swearing is a sign of intelligence. You decide! ‍Kristina & Diann met through Coach Vox - the platform where they both built their digital clones. If you haven’t signed up for Di AI yet - what are you waiting for? Here is the link to sign up for free. ABOUT KRISTINA Kristina (with a 'k') Flynn is an Overthinking High-Achiever (OHA) helping other OHAs turn their wild careers and stories into personal brands that feel like them and make sh*tons of money. ‍For 18+ years and across 11 roles in 8 industries, she's built brands for NBA All-Stars, Olympians, venture capitalists, Youtubers, founders, and executives. The through-line across all of it: wildly capable people who are great at seeing other people's value, but can't see their own. In 2023, she built StoryEQ™ to close the gap. ‍ LINKS & RESOURCES ‍Kristina’s: ‍ WebsiteStory EQ Framework PDF LinkedIn ‍ The episode with Evan Sargent on branding ‍ 20 Feet From Stardom (2013) — the backup singer documentary I mentioned Brené Brown Simon Sinek ‍ ‍ YOUR ADHD-ish™ HOST ‍Diann Wingert is a former therapist turned coach, speaker, and consultant who blends her expertise in entrepreneurship and neurodiversity to help others thrive. ‍Host of the top-rated ADHD-ish™ podcast and creator of The ADHD-ish™ Method, Diann works with ADHD-ish™ business owners who are ready to create stand-out, sought-after, profitable businesses based on their unique brilliance. ‍ WORK WITH ME If this conversation hit a nerve — if you've been hiding behind your credentials and waiting to be discovered on the strength of good work alone — that's a strategy problem, not a character flaw. Let's fix the strategy problem together — schedule your call here. ADHD-ish is hosted by Diann Wingert. If you got something out of this one, the single most useful thing you can do is send it to one person who needs it. Second most useful: leave a review. © 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

  2. Aug 11

    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 decisions going forward. ‍Dopamine is a talent scout, not a bookkeeper: That rush of excitement we feel with something new? It’s all about anticipation—not reality. The cost and maintenance of a new yes don’t hit until much later. The trick is to slow the yes. ‍Clever ways options pretend to be opportunities: ‍The Flattering Ask: feeling chosen and visible can feel like opportunity, but might be just an option that doesn’t fit your goals. ‍The Closing Door: artificial urgency and manufactured scarcity prey on impulsive decision-making. ‍The Adjacent Idea: our shiny new ideas often show up exactly when important work becomes tedious, tempting entrepreneurs to jump ship. ‍ Why is this so hard for ADHD brains?‍Because dopamine is LOUD and it fires at anticipation, not the actual result. That new offer or collab invitation? It’s pure possibility—no fatigue, no disappointment, no downside at first. The evaluation part comes much later, usually after you’re already committed. Story Time ‍Diann once bought a high ticket course to “launch a high-ticket course,” and not only never opened it, but kept paying a monthly subscription for three (!) years (ADHD dopamine at work, folks—don’t feel bad, you’re not alone! 😂 ‍Try this: The 4-Question "Screen Door" Filter ‍Before you say yes, ask yourself: 1. What existing goal does this serve?2. What does it leverage that I’ve already built?‍3. What are the terms of this commitment?‍4. Does it survive 72 hours? Nothing new gets a same-day yes. That 72-hour pause is where the real magic happens (and where many “opportunities” evaporate). ‍Start here: *Make an idea parking lot for every new ask or idea.*‍Practice the pause: “Let me check a couple things and get back to you.”‍*After 72 hours, run the 4-question test. Some asks will quietly disappear. Others will become real, intentional decisions. Give it a try and notice how different your “yes” feels and the discomfort of waiting. That’s data. ‍ Mantra for the week: Every yes is not a purchase—it’s a subscription. Read the terms before you sign. ‍ But what about all the past decisions you’ve made that have made your business messy and chaotic? ‍I’ve got you! Click here to read the companion blog post “How to Know When Your Business is Too Complicated: A Right-Sizing Guide for ADHD Entrepreneurs.” ‍ ‍ Your ADHD-ish ™ host ‍Diann Wingert, MSW is the insightful host of ADHD-ish™, where she helps entrepreneurs and professionals navigate the challenges of running a business with an ADHD brain. ‍Known for her practical wisdom, Diann regularly explores topics like decision-making, teaching her audience how to filter choices more effectively. ‍Through her relatable storytelling and expertise, Diann shares lessons gained from serial business ownership, a 20 year career as a psychotherapist and a lifetime with ADHD. ‍ Want deeper support untangling your yeses and rebuilding your decision-making? Schedule a free consultation to explore 1:1 ADHD entrepreneur coaching with ADHD business strategist and coach, serial business owner, and former licensed psychotherapist, Diann Wingert, MSW. ‍ New to ADHD-ish™? Subscribe/Follow ADHD-ish on Apple or Spotify for more ADHD-informed business strategy, inspiring guest expert interviews and client success stories. ‍ © 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

  3. Aug 4

    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, serves as a 24/7 thought partner to streamline your ADHD business strategy and lighten your daily cognitive load. Discover how on-demand support improves ADHD decision making, strengthens entrepreneur accountability, and optimizes ADHD business operations all without losing the essential human connection. Chapters: 00:00 — Introduction: AI Tools for the ADHD Entrepreneur 03:15 — Testing Digital Coaching and ADHD Decision Making 08:40 — Business Systems for ADHD Entrepreneurs 14:20 — Managing Cognitive Load in Business and Tech 19:50 — AI vs Human Entrepreneur Accountability 25:10 — ADHD Productivity for Entrepreneurs: Evaluating AI 31:05 — ADHD Executive Function in Business and Values 35:00 — Roadmap for Business Owners with ADHD The episode explores: How Elizabeth structured the experiment (including the infamous decision matrix and her “wildly unrealistic expectations”)Surprising (sometimes maddening) moments where AI reflected “stupid common sense” she’d never consideredWhat ghosting an AI tool taught her about the difference between digital and human accountabilityThe unexpected role of values alignment and motivation for us “rebels”Cautionary tales about outsourcing too much trust—or too much of ourselves—to technologyWhy critical thinking and intentionality are the only way these tools ever work for ADHD-ish brains Elizabeth and I share both the wins and the “facepalm” moments, plus an actionable tip sheet for anyone skeptical (or hopeful) about using AI for habit-building and organization. Her pro tip: Judge the tool by the quality of questions it asks you Don’t Miss: Elizabeth’s three-question framework (adapted from Naturalistic Decision-Making) for deciding when and how to engage with AI tools—so you never cede too much power to an algorithm If you’re tired of empty promises from productivity apps—or want a peek at what a scientifically-minded ADHD brain learns from kicking the tires on new tech—this episode is for you. Fun Fact Elizabeth shared a story about her 15-year-old niece who, when asked where they should go for dinner, responded: “I don’t know. Let me ask Chat.” The future is here and apparently it’s hungry for chatbot input Your turn! Make it practical: Use Di AI to help implement a tactic you picked up from the podcast, track specific goals, and follow up on progress. Know your “why”: Consider the reason you are looking for accountability and fit AI into your schedule where you need a champion (hello, bookkeeping!) If you haven’t signed up for Di AI yet - what are you waiting for? Here is the link to sign up for free. Grab Elizabeth’s Tip Sheet for making the most of Di AI (or any AI app) About today’s guest: Elizabeth Meyers is an informatics professor, consultant, and owner of Deep Dive Strategies, where she advises early-stage startups and small companies on strategy and product design. Driven by a fascination with how humans navigate complex environments, Elizabeth specializes in Naturalistic Decision Making (NDM), studying how experts make high-stakes choices in real-world settings. As an entrepreneur who respects both human expertise and technology, she blends her deep background in technology and information science to explore how experts interact with AI. Mentioned in this episode: Conditions for intuitive expertise: a failure to disagree. Kahneman D, Klein G. Am Psychol. 2009 Sep;64(6):515-26. doi: 10.1037/a0016755. PMID: 19739881.Naturalistic Decision Making Conference Michael Webb PresentationAdam Mastroianni - “Bag of Words” post on SubstackDALL- E AI image generator Ep #281: Find Your Flow: 3 Focus Days Models for ADHD Brains Ep #212: Get More Done: How to Focus with ADHD & Take Real ActionThe Four Tendencies - Elizabeth is a Rebel. What are YOU? Identifying Your Core Values - self assessment Jodie Cook, Founder of Coach Vox Your ADHD-ish™ host, Diann Wingert Diann Wingert is a former therapist turned coach, speaker, and consultant who blends her expertise in entrepreneurship and neurodiversity to help others thrive. Host of the top-rated ADHD-ish™ podcast and creator of The ADHD-ish™ Method, Diann works with ADHD-ish™ business owners who are ready to create stand-out, sought-after, profitable businesses based on their unique brilliance. Loved this episode? Leave a review and tell us why! © 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

  4. Jul 28

    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 episode, Diann Wingert explores how ADHD object permanence uniquely impacts business operations and daily execution. You’ll discover practical strategies to build visible business systems for ADHD entrepreneurs, improve ADHD follow through, and protect your mental bandwidth—helping you maintain consistent momentum without adding to your cognitive load in business. Chapters: 00:00 - Options vs Opportunities for the ADHD Entrepreneur 06:15 - Dopamine and ADHD Decision Making in Business 13:30 - Three Disguises that Overload Cognitive Load 20:45 - The Screen Door Filter for Entrepreneur Accountability 27:10 - Sustainable Systems for Business Owners with ADHD Where Are You Leaking Money? ‍ I break it down into three layers: 1. Past Clients: Amazing people who loved working with you, would buy again, and just need a nudge. But if they’re not in your calendar or inbox—they don’t exist to your brain. Your ADHD working memory isn't the problem; your system is. 2. Leads in the ‘Dark Pipeline’: Warm prospects you were this close to converting…now forgotten until you randomly find that old email weeks later (and then feel the shame spiral). ‍This is ADHD Object Permanence in action—out of sight, completely out of mind. 3. Your Own Offers: Courses, workshops, or services you actually could be selling—but forgot you even have. How many revenue streams are invisible because of ADHD Object Permanence? What’s the Fix? Structural Visibility ‍ Don’t go buying a new planner or promising to “try harder.” That’s not a strategy—it’s just more stress. Instead, build software (aka systems!) around your brain’s “hardware” constraints. This is how you turn ADHD strengths and struggles into actionable business strategy. Here’s How: ‍ ● Use a CRM to remember leads for you—don't let your ADHD working memory be your only sales tool! This is structural support for ADHD Object Permanence. ● Block off time every week to review offers, check in on clients, and nudge those dark leads back into the light. Regular visibility beats relying on memory. ● Pre-schedule re-engagement emails for past clients + warm leads. Automation handles what ADHD Object Permanence makes invisible. Where to start: ‍ Don’t overhaul everything at once. Pick one area—past clients, dark leads, or forgotten offers—and add a single piece of visibility this week. ‍ It could be as simple as pulling your last 20 clients into a spreadsheet or writing a list of every product you currently offer. The important part is making invisible opportunities visible again. This is how you leverage ADHD strengths and struggles for revenue growth. Mentioned in this episode: ‍ Laura Schulte - LinkedIn ‍ The Pipeline Compounder Kit email marketing platform (affiliate link) ‍ ‍ Other episodes in the Reframing ADHD Traits as Business Strategy series: ‍ Ep #315: How Successful ADHD Entrepreneurs Trigger Hyperfocus on Demand ‍ Ep #317: Time Blindness is a Pricing Problem, Not Just a Productivity Problem ‍ Ep #321: The Recurring Revenue Trap: The Hidden Cost of Stable Income Ep #323: What Procrastination, Resistance & Avoidance are Trying to Tell You About Your Business ‍ Your ADHD-ish ™ host, Diann Wingert Diann Wingert is a business strategist, coach, serial entrepreneur, former psychotherapist, and passionate thought leader at the intersection of ADHD and entrepreneurship. In addition to hosting the ADHD-ish ™ podcast, Diann is the creator of The ADHD-ish ™ Method, a practicing Buddhist, dog mom, and relentlessly curious human. ‍ Want help to reimagine business with your ADHD traits in mind? Schedule a free consultation to explore 1:1 ADHD entrepreneur coaching with ADHD business strategist and coach, serial business owner, and former licensed psychotherapist, Diann Wingert. For more ADHD-informed business strategies, follow ADHD-ish ™ for the rest of the Reframing Your ADHD Traits as Business Strategies, as well as inspiring guest interviews and real client success stories! Subscribe/Follow ADHD-ish ™ on Apple or Spotify ‍ ‍ © 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

  5. Jul 21

    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 break this cycle, Diann Wingert dismantles the myth of traditional balance to reveal an approach built for neurodivergent momentum. Learn how resetting your operational baseline, reducing cognitive load in business, and enforcing clear boundaries can optimize your ADHD business operations while protecting your energy for sustainable growth with ADHD. Chapters: 00:00 - The Truth About ADHD Executive Function in Business 04:30 - Operational Bottlenecks Facing the ADHD Small Business Owner 09:15 - ADHD Decision Making Under Heavy Working Memory Load 15:40 - Streamlining ADHD Business Operations and Daily Systems 21:10 - Delegation for Entrepreneurs Managing Small Teams 26:35 - Overcoming Executive Dysfunction and ADHD Burnout Prevention 32:00 - Real-World Entrepreneur Accountability Strategies for Growth 36:45 - Sustainable Success Frameworks for the ADHD CEO Here are my top 3 takeaways for anyone feeling stuck in their own “success”: You don’t have a million problems—just a few powerful patterns. Identifying and naming them makes change possible.Your worth is not tied to your to-do list. Planning for realistic work hours, protected downtime, and recovery is the key to sanity and sustainability.You get to define your boundaries. Say no, let go of what drains you, and protect your energy—even when it means “hiding” some of your projects from yourself if deleting them feels too scary. If you find yourself working nonstop, feeling guilty about taking a break, or recreating old corporate patterns in your “dream job,” remember: nothing on your list is more important than your well-being. About today’s guest, Kathryn Bird Kat (she/her) is a former Royal Navy helicopter observer and London airspace air traffic controller turned travel blogger and entrepreneur. After leaving her high-pressure career to travel the world, Kat turned her passion into a thriving business, teaching and inspiring fellow adventurers through her content and memberships. Her journey has been marked by remarkable achievements—and the hidden struggle of managing ADHD, perfectionism, and the pressures of self-employment. Connect with Kat: Website: https://www.wandering-bird.com/ Instagram: @wanderingbird.adventures. YouTube: https://www.youtube.com/@WanderingBird Your ADHD-ish™ host, Diann Wingert Diann Wingert is a former therapist turned coach, speaker, and consultant who blends her expertise in entrepreneurship and neurodiversity to help others thrive. Host of the top-rated ADHD-ish™ podcast and creator of The ADHD-ish™ Method, Diann works with ADHD-ish™ business owners who are ready to create stand-out, sought-after, profitable businesses based on their unique brilliance, while eliminating the extremes of boredom and burnout. Inspired by Kat’s results & want to chat about what success can look like for YOUR business? Book a free consultation and let’s talk! Want to listen to other Client Success Story episodes before booking that consultation appointment? I’ve got you. Here is the playlist. Practical Takeaways Be honest about what’s really on your plate. Track your time and get real with your expectations“Nothing on this list cannot wait.” Borrow Kat’s mantra - perfect for ADHD overachieversRest is productive. Building in recovery weeks and being intentional about your workload makes all the differenceLet go (just a little). Not every idea, offering, or piece of content needs to be perfect or even used Not ready for my six-month, one to one coaching program, but want an ADHD-informed, business savvy coach on demand? My digital clone, Di AI is free in beta.Just click the link and start chatting now! © 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops/ Outro music by Vladimir / Bobi Music / All rights reserved.

  6. Jul 14

    What Procrastination, Resistance & Avoidance Are Trying to Tell You About Your Business

    Feeling stuck in a cycle of procrastination, resistance, and avoidance? If you’re running a business with an ADHD brain, it’s time to stop fighting your nervous system and start listening to it. Understanding ADHD means recognizing that your resistance is data. In this episode of the ADHD-ish™ Podcast, part of the Reframing ADHD Traits as Business Strategy series, I challenge the mainstream productivity tips, and offer a new perspective: Procrastination isn't always the enemy—it's often vital business information. 3 Key Takeaways: Procrastination is a signal, not a personal failing. Your nervous system might be telling you something important about your business, like a task you’ve outgrown or a decision you haven’t fully made. This is how ADHD neurodiversity communicates through resistance.Five “signals” behind resistance: Delegation (tasks you should hand off), Decision (incomplete choices), Sunset (offers you need to let go), Revenue (underpriced work), and Clarity (undefined scope/stakes). Most productivity tips miss these underlying issues entirely.Don’t override, diagnose first. Before pushing through with more discipline, ask “What is this resistance telling me?”—then act on the real issue behind your avoidance. This diagnostic approach honors ADHD neurodiversity. The Reframe: Procrastination is regulatory, NOT motivational. Your nervous system is sending a protective signal, not exposing a character flaw or lack of discipline. For ADHD neurodiversity, this shows up when something is off below the surface—even if you don't consciously know what it is. This is why traditional productivity tips often fail. Next time you find yourself stuck, don’t reach for another productivity hack. Instead, ask: “What is my resistance trying to tell me?” Then act on the message, not just the task. Your business, and your brain, will thank you. This is what working with ADHD neurodiversity—rather than against it—actually looks like. Other episodes in the series: Ep #315: How Successful ADHD Entrepreneurs Trigger Hyperfocus on Demand Ep #317: Time Blindness is a Pricing Problem, Not Just a Productivity Problem Ep #321: The Recurring Revenue Trap: The Hidden Cost of Stable Income Looking for an ADHD-informed business coach that is available on demand? Sign up for my digital clone, Di AI Beta access is still free and available now! Your ADHD-ish ™ host, Diann Wingert Diann Wingert is a business strategist, coach, serial entrepreneur, former psychotherapist, and passionate thought leader at the intersection of ADHD and entrepreneurship. Diann is the creator of The ADHD-ish ™ Method, a practicing Buddhist, dog mom, and relentlessly curious human. Want help to reimagine business with your ADHD traits in mind? Schedule a free consultation to explore 1:1 ADHD entrepreneur coaching with ADHD business strategist and coach, serial business owner, and former licensed psychotherapist, Diann Wingert. For more ADHD-informed business strategies, follow ADHD-ish for the rest of the Reframing Your ADHD Traits as Business Strategies, as well as inspiring guest interviews and real client success stories! Subscribe/Follow ADHD-ish on Apple or Spotify © 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

  7. Jul 7

    No Diagnosis? No Problem! Embracing Neurodivergence Without Labels with Dr. Naketa Ren Thigpen

    Welcome to another episode of ADHD-ish, where we explore the lived realities, hidden challenges, and unique gifts of being neurodivergent in business and life. Today’s episode is an intimate conversation between friends, colleagues, and fellow neurodivergent entrepreneurs. Returning guest, Dr. Naketa Ren Thigpen, is an expert at the intersection of relationships and entrepreneurship, who has made the decision to forgo a formal diagnosis, while fully accepting her ADHD traits. Together, we explore how trauma, workarounds, and unapologetic authenticity shape both personal growth and professional impact. 3 Key Takeaways: Workplace Dynamics Are Deeply Human: So many organizational challenges stem from unresolved personal issues that show up at work. As Naketa says, bringing relational intelligence into organizations is the next frontier for trust, performance, and true inclusion.Diagnosis Isn’t Required for Legitimacy: You don’t need a formal diagnosis to embrace your neurodivergent identity. For some, building effective "workarounds" is enough to thrive—labels can be empowering for some and unnecessary for others, as powerfully shared.Hyperfocus Is a Super Tool—With Boundaries: Our ability to “hear the words and the music”—to focus deeply and be truly present—is a neurodivergent gift. Guarding these focus states with strong boundaries is key to making the most of them, both in business and personal growth. About today’s guest, Dr Naketa Ren Thigpen Dr. Naketa Ren Thigpen is the Architect of Intimacy in Innovation, the world's foremost Balance (and) Relationship Advisor, and Co-Founder and CEO of ThigPro Balance (and) Relationship Management Institute. Embodying her wild & rare nature, she moved beyond traditional therapy into something the industry hadn't seen. Double Board Certified and doctorate-trained in Relationship Dynamics, Dr. Naketa licenses Applied Relational Intelligence Systems to mid-market organizations, certifying their own leaders to reduce turnover, stabilize trust, and accelerate decisions from the inside. Her private advisory, BAR COTERIE, serves a select few bold enough to recalibrate success without regret. Named among 100 Women to Watch in 2026 and honored by the NAACP, she proves one thing: intimacy fuels innovation. Connect with Dr Naketa: Website: https://thigpro.com/LinkedIn: https://www.linkedin.com/in/naketathigpen/Instagram: https://www.instagram.com/asknaketaNaketa’s framework: Applied Relational Intelligence System (ARIS)Substack: https://thigproquo.substack.com/ Your ADHD-ish™ host, Diann Wingert Diann Wingert is a former therapist turned coach, speaker, and consultant who blends her expertise in entrepreneurship and neurodiversity to help others thrive. Host of the top-rated ADHD-ish™ podcast and creator of The ADHD-ish™ Method, Diann works with ADHD-ish™ business owners who are ready to create stand-out, sought-after, profitable businesses based on their unique brilliance. What’s the first step for turning the business you have into the business you want? Take the ADHD-ish™ Business Blindspot quiz Loved this episode? Leave a review and tell us why! © 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

  8. Jun 30

    The Recurring Revenue Trap: The Hidden Cost of "Stable" Income for Business Owners with ADHD

    Welcome back to ADHD-ish! I’m Diann Wingert, and in this episode, we’re addressing a question that many business owners with ADHD hesitate to ask themselves: Do you actually like the work that brings you your most reliable income? Not just the money, but the day-to-day tasks, the routine, and the clients you serve month after month. Understanding neurodiversity means recognizing that what works for neurotypical business owners—predictable recurring revenue models—may actively sabotage your success. Because so many of them hate to admit they don’t, I’m breaking down what I call the “recurring revenue trap”—the idea that true business maturity comes from stacking retainers, running memberships, or launching evergreen offers for that coveted, predictable income. This myth is especially damaging for those of us navigating neurodiversity in business. But what happens when your ADHD brain, which craves novelty, challenge, and variety, clashes with the sameness and repetition these models demand? If you’ve ever found yourself bored, resentful, or white-knuckling through work that “should” feel like a win, the problem isn't you—it's a structural mismatch between how neurodiversity is wired and traditional business models. 3 key takeaways for ADHD business owners: Predictability vs. Novelty: Recurring revenue models (like retainers and memberships) are built for brains that thrive on sameness and routine—not the dopamine-hungry ADHD brain, which craves novelty, challenge, and change. Understanding neurodiversity means designing around these realities, not fighting them.Structural Not Personal: Burning out on reliable income streams isn’t a failure—it’s a sign of structural mismatch. ADHD brains are wired to lose motivation with repetitive, predictable work. This is where value based pricing strategy becomes essential—charging for outcomes and transformation, not time.Design for Your Brain: You DON’T have to quit recurring revenue altogether. Instead, intentionally build novelty into your recurring offers—limited run cohorts, rotating scopes, themed “seasons,” and planned refreshes let you keep both financial stability and creative energy. A flexible retainer model can honor both your needs and your neurodiversity. 6 Dopamine-rich alternatives to boring recurring revenue models: Limited-run cohorts: Short sprints, not never-ending slogsRetainers with rotating scope: New focus each quarter keeps it freshMemberships by season/theme: Built-in breaks & changing contentQuarterly intensives: Ditch the monthly grind; go deep, then restPlanned sunsets: Don’t beat dead offers—set a clear end date!Built-in refreshes: Schedule reinventions before boredom strikes The offer you’re white-knuckling today is NOT the offer that’ll get you to the next level. Try, tweak, or sunset—but make it on YOUR terms. Mentioned during this episode: Episode #238_Creative Sprint Days: One Entrepreneur’s Solution for an ADHD-Friendly Business, with Evan Sargent Other episodes in the series: Ep #315: How Successful ADHD Entrepreneurs Trigger Hyperfocus on Demand Ep #317: Time Blindness is a Pricing Problem, Not Just a Productivity Problem Your ADHD-ish ™ host, Diann Wingert Diann Wingert is a business strategist, coach, serial entrepreneur, former psychotherapist, and passionate thought leader at the intersection of ADHD and entrepreneurship. In addition to hosting the ADHD-ish ™ podcast, Diann is the creator of The ADHD-ish ™ Method, a practicing Buddhist, dog mom, and relentlessly curious human. Want help to reimagine business with your ADHD traits in mind? Schedule a free consultation to explore 1:1 ADHD entrepreneur coaching with ADHD business strategist and coach, serial business owner, and former licensed psychotherapist, Diann Wingert. For more ADHD-informed business strategies, follow ADHD-ish for the rest of the Reframing Your ADHD Traits as Business Strategies, as well as inspiring guest interviews and real client success stories! Subscribe/Follow ADHD-ish on Apple or Spotify © 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

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99 Ratings

About

Running a business with ADHD isn't hard because you're distracted. It's hard because most business advice wasn't built for your brain. Many entrepreneurs with ADHD try to solve business challenges with more productivity hacks, stricter routines, or systems they can never quite sustain. Others keep chasing new ideas, opportunities, and strategies, hoping the next one will finally make everything click. The result? More cognitive load, more unfinished projects, more decision fatigue, and often more burnout. ADHD-ish™ is the podcast about ADHD business strategy for business owners with ADHD who want to grow a successful company without forcing themselves to think, work, or lead like everyone else. Each episode explores the real-world challenges of running a business with ADHD, including ADHD business growth, delegation and accountability, decision-making, executive function in business, burnout prevention, leadership, and building business systems that actually work for your brain. You'll hear practical strategies, honest conversations, personal stories, and expert insights designed to help you make better decisions, follow through on what matters most, and create sustainable success. I'm Diann Wingert. As a business coach, former psychotherapist, serial entrepreneur, and the creator of ADHD-ish™, I've spent years helping entrepreneurs and business owners with ADHD stop fighting their brains and start building businesses that work with them. Whether you're an ADHD entrepreneur, an ADHD small business owner, or a founder trying to scale a business while managing the realities of ADHD, this show will help you lead more effectively, grow more intentionally, and build a business that's designed for the way you think.

Information

  • Creator
    Diann Wingert | ADHD Business Strategist & Coach
  • Years Active
    2020 - 2026
  • Episodes
    300
  • Rating
    Explicit
  • Copyright
    © 2026 ADHD-ish™
  • Show Website
    ADHD-ish™

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