ADHD-ish

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, honest inventory. Just three lists: Energy, Money, Time. Here’s the breakdown:Energy InventoryWhat gave you energy this year? What absolutely drained you—even if it was profitable or “successful”?Which tasks, clients, or projects left you jazzed up… and which made you want to flee the building?Notice the patterns. Pattern recognition tends to be a skill that ADHD brains excel at.Money InventoryWhat actually made you money, versus what you thought should make you money?Which offers did people really buy? Where did revenue flow in from? What’s gathering dust (subscriptions, courses, tech) in your digital library?If most of your money came from one thing, but you spent all your time on everything else—this is info, not failure.Time InventoryWhen did you do your best work? Was it in performance windows that don’t match “normal” business hours?Was your magic at 10 pm in the car, Friday mornings, or after a walk or shower?This is about gathering intelligence, not shaming yourself. Design your days around your actual brain, not someone else’s ideal.Subtraction is StrategyEvery time I let go of what wasn’t working, the good stuff got even better. So maybe your “stop doing” list is more important than any “to-do” list. Eliminate the clients, offers, or systems that drain you, no matter how much they pay. Permission granted to not start that newsletter, podcast, or YouTube channel you’ve been “planning” for two years.Final step:Commit to ONE thing that’s already working and carry it forward. Whether it’s sticking to your creative window or leaning into your night owl energy, just one thing that fits your brain. For me, it’s this podcast. No pressure, no massive goals, no breakthroughs required. 2026 is happening no matter what. Go in knowing what energizes, pays, and fits your unique brain—and that’s your built-in advantage.Mic Drop Moment:“We're great at building these complex offers that we think people want. We spend months perfecting the positioning, creating the fancy framework, building out the whole fricking thing. And then we're genuinely shocked when that simple little thing we threw together in an afternoon is the one that actually makes more money.”About the Host:Diann Wingert (she/her) is a seasoned coach, consultant, and the creator/host of ADHD-ish. Drawing from her many years of experience as a former psychotherapist, business owner, and someone who thinks "outside the box," Diann is known for her straight-talking, no-nonsense approach to the intersection of neurodiversity and business ownership. Enjoyed the...

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 your creative engine. It's about building frameworks that let you honor your ideas without drowning in them.Who This Episode Is ForFounders juggling multiple business ideas or revenue streamsCreatives who struggle with follow-through despite abundant inspirationConsultants and coaches who feel scattered across too many offersAnyone who's been shamed for having "too many interests."Serial entrepreneurs who want to build interconnected businesses without burning outThe Big IdeaHaving an ADHD brain means you're wired for abundant creativity. The challenge isn't generating ideas—it's knowing which ones deserve your energy and how to move them from concept to completion without burning out or abandoning ship halfway through.Sarah's approach: treat your ideas like they matter, but give them structure so they don't hijack your focus.What to Listen For The Reality of Being a Creative PolymathFor many ADHD entrepreneurs, being interested in multiple things isn't a distraction —it's how they’re built. Sarah explains why being a polymath is actually an advantage in today's business landscape, as long as you set boundaries around what gets your attention.The "Catching Butterflies" System: Capture, Connect, Structure, Iterate, Express, ReflectSarah walks through her six-stage process for managing creative output. It starts with capturing every idea without judgment, then moves through connecting related concepts, building structure around the keepers, iterating on them, expressing them in the world, and reflecting on what worked. Simple in concept, powerful in practice.Using AI as Your Digital Thought PartnerBoth Sarah and I use AI tools (ChatGPT, Claude) to externalize our thinking. Instead of letting ideas swirl in our heads, we dump them into our AI assistants to help us organize, connect dots, and build project folders. It's like having a patient colleague who never gets tired of your tangents.The 3D Jenga Model for Interconnected ProjectsRather than treating each business or project as a standalone tower that could topple, Sarah visualizes her work as a 3D Jenga structure. Each piece supports the others. When one idea doesn't work out, the whole thing doesn't collapse—the remaining pieces actually get stronger.Energy Management Over Time ManagementReflection isn't self-indulgence—it's how you build a feedback loop that keeps you moving forward. Regular check-ins about how you feel, what your vision is, and whether your projects still serve that vision help you stay aligned instead of spinning your...

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, innovation, and entrepreneurial spirit into an existing organization—and how this path might be the most strategic decision for many ADHDers.If you’re wrestling with the decision to go solo or stay employed, give this episode a listen. It just might give you permission to build a life—and career—that truly works for your brain.Three key takeaways:Entrepreneurial traits ≠ Entrepreneurial career: You can be creative, visionary, and disruptive without having to start your own business. Don’t fall for the myth that employment is “settling.”Intrapreneurship unlocks impact & stability: Express your entrepreneurial strengths inside an organization. Lead without authority, innovate processes, and treat your role like you own it—while benefiting from structure, resources, and a steady paycheck.Signs that traditional employment isn’t right for you:Not everyone is meant to shine as an intrapreneur. If every manager is a nightmare, structure feels suffocating, or your best ideas die in committee, maybe going solo is your move. But it’s all about matching your brain and real life with the right path—not shame, not hustle-culture FOMO.Workplace roles & cultures where ADHD-ish traits thrive:Look for product development, business strategy, internal consulting, startups, project-based work, or innovation labs. Go where experimenters are rewarded, hierarchies are flatter, and outcomes matter more than bureaucracy.Mic Drop Moment:“Infrastructure isn't the enemy of innovation. Structure, when it's the right structure, is what lets your brain do what it does best without getting derailed by all the shit you hate doing."Action Step:Take 10 mins for honest self-reflection. Where do you really do your best work? What structure supports you? Then, make the choice that serves your life—not LinkedIn optics or anyone else’s expectations.About the Host:Diann Wingert is a seasoned business coach, consultant and speaker. Drawing from her many years of experience as a former psychotherapist, serial business owner, and someone who thinks "outside the box," ADHD-ish host, Diann is known for her straight-talking, no-nonsense approach to the intersection of neurodiversity and the world of work. Enjoyed the Episode?Share your thoughts! Leave a review and let Diann know what resonated, challenged, or inspired you. Your feedback helps ADHD-ish reach more listeners who need to hear these honest conversations. © 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

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 a little tech magic to make life easier and more fun). You’ll hear not just the triumphs, but also the complex, sometimes messy moments of “unmasking” and designing a business that fits your actual brain and values, not someone else’s idea of success.Episode Highlights:Strategic Relationship Marketing vs. AutomationCat breaks down why automation and relationship-building aren’t mutually exclusive—and how smart systems can let neurodivergent business owners focus on authentic, meaningful connections.Attract, Don’t ChaseMove over “hustle culture.” Cat and Diann discuss how building genuine relationships and letting people self-select nurtures business without the creepiness or pressure of hard selling.Neurodivergent Thriving in BusinessHow Cat’s ADHD and autism traits fuel her ability to notice patterns, create unique solutions, and support her clients in efficiently reaching their goals.Automating the Human TouchLearn how emails, follow-ups, and event workflows can be automated, freeing up energy for one-on-one connections with those who are ready for deeper engagement.Ethical Reciprocity & Non-Bro MarketingCat outlines how heart-centered reciprocity builds lasting relationships and why neurotypical tactics often miss the mark for neurodivergent individuals.Meet our Guest: Cat OrsiniCat Orsini has an MBA, is a master-certified coach, an entrepreneur, and co-author of the book "Experts Never Chase." She specializes in relationship marketing, strategic conversations, and building automated systems that allow her—and her clients—to focus on human connection over busywork. Through radical acceptance of her neurodivergence and trauma history, Cat has crafted a career and life that honors her strengths and refuses to squeeze herself into a neurotypical mold.Links & Resources:Connect with Cat on LinkedInLearn more about Cat Orsini and her workThe Book Cat Co-Authored - Experts Never ChaseKnow someone who identifies with ADHD + Autism (officially diagnosed or not…)? Think this episode would inspire them? Here is the link to share it with them, in the most comfy way possible: https://bit.ly/episode-blog-292 © 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! 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 business model, specifically how her notion of collaboration revealed a lack of boundaries, which led to burnout. Their coaching journey took an unexpected turn as Steph was faced with redefining her work, grappling with exhaustion, and eventually reshaping her business to prioritize authenticity, personal connection, and family in the wake of a heartbreaking loss.Together, they explore the challenges of managing emotional labor, the reality of ADHD-driven blind spots, and the courage it takes to rethink your path when everything changes. If you've ever felt caught between ambition and overwhelm or questioned how your neurodivergence shapes your entrepreneurial journey, this episode is for you. Here are 3 key takeaways from this conversation:Scaling “as-is” can scale your problems, not just your profits: Before trying to grow, pause to check if your foundation—relationships, workload, boundaries—truly supports the life you want.Give yourself permission to redefine success: It’s not all-or-nothing. You can reshape business relationships and paths to fit changing needs, values, and energy levels.Clarity fuels action: The sooner you move from overthinking to taking action (even messy, uncertain steps), the faster you learn, adapt, and build the business—and life—that truly work for you.Mic Drop Moment: "You don't have to be the glue holding all of this together. If you enjoy working with them, work with them, and if you don't, don't."Connect with Steph Cottrell: Website: https://www.blueelephantcreative.comLinkedIn: https://www.linkedin.com/in/bluelecreative/How Steph discovered me: ADDItude Magazine webinar: “How to Build a Business That Works for Your ADHD Brain” Want to hear more Client Success Stories? Click here for the custom playlist Is it time to redefine your success as a business owner with ADHD? I have two openings for one-on-one coaching engagements, starting in January. The first step is scheduling a free consultation where we talk about your goals and see if we are a good fit. Click here to book yours now. And, don’t forget to leave a comment on Spotify (I personally respond to every one) or leave a review so more ADHD-ish business owners can find THE podcast full of real talk and real solutions for neurodiverse business brains.© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.