ADHD-ish

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. 

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 found herself trapped in the endless loop of online business tactics, quick fixes, and shiny promises.Drawing on her upcoming book, Leaving the Casino: Stop Betting on Tactics, and Start Building a Business That Works, Jessica explains why so many of us end up gambling away our sanity (and savings) on the latest tactics, instead of building actual strategies that work for our lives and brains. Get ready for frameworks, real talk about defining your own version of success, and practical advice on bringing more intentionality and enoughness into your business (and life). It’s time to leave the casino behind—and reclaim your agency.Top Takeaways from this Episode:Start with Strategy, Not Tactics: The endless cycle of purchasing the latest digital course or marketing hack often leads to overwhelm, wasted resources, and lost confidence. Sustainable businesses are built on strategy and thoughtful decision-making, not reactive, one-size-fits-all tactics.Ask Yourself the Big Questions: Before chasing the next big thing, get clarity on key fundamentals:What type of business do you really want to run?What stage are you in?What is the right pace and amount for your life and brain?What level of responsibility and commitment matches your reality?What does “enough” look like for you? These questions ground your business in reality instead of fantasy.Don’t Compare Your Solo Journey to the Big Players: The polished marketers often have large teams and structures flattening out the chaos. If you’re a team of one (especially with an ADHD-ish brain), your output and path will—and should—look different.There’s power in slowing down, cutting through the noise, and building a business that fits you—not a casino of empty promises.About Jessica Lackey Jessica Lackey is the founder of Deeper Foundations, a consulting and training firm that helps expertise-based business owners grow and scale sustainable companies rooted in stronger business foundations. She brings a unique blend of corporate expertise and soulful business building, drawing on an MBA from Harvard Business School, a coaching certification from iPEC, and experience at McKinsey & Company and Nike, Inc. Jessica has supported over 200 entrepreneurs through her programs, blending systems thinking, operational rigor, and deep values alignment. She lives in Charlotte, North Carolina, with her husband.Jessica can be reached at https://deeperfoundations.com/Buy the book, or get a free chapter: Leaving the Casino by Jessica LackeyMentioned during this episode:Digital Course Academy - Amy PorterfieldGary V - Gary VaynerchukCodie SanchezRobin Wall Kimmerer’s book, Braiding SweetgrassElizabeth Gilbert’s book Big Magic Want to share this episode with a friend who's still in the entrepreneurial casino? https://bit.ly/episode-blog-290 © 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved. 

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 it. 7 Things You’ll Learn From This Episode:The Real Reason You Get Bored: Learn the neuroscience of ADHD boredom and why your brain craves novelty (hint: it’s about dopamine, not discipline).The “PROOF” Framework:A practical tool to help you decide if it’s time to renew or release your business offers.How To Build Boredom-Proof Systems: Discover strategies to rotate, redesign, and reinvent your business model so you stay engaged long term.Strategic Delegation & Role Redesign: Find out how letting go of the dull stuff (or handing it off!) can reignite your passion—and even grow your business.Permission to Evolve: Why shifting your focus is not failure, but good business and good self-care.Want your entrepreneurial journey to last? Build boredom-proofing in from day one.Alternate focus areas each quarter.Design offers so they evolve or rotate naturally.Proactively plan breaks, new challenges, or learning cycles.And, most importantly, give yourself grace when you need to pivot, change, or retire offers. Evolution isn’t failure; it’s strategic adaptation.Fun Fact from This Episode:Did you know that constraints—NOT unlimited freedom—are actually better for the ADHD brain? Giving yourself playful “rules” can boost creative energy and bring the spark back to your work.Next Steps: Download the FREE cheat sheet and put the PROOF framework to work today. Re-listen to Ep #277_ “The Soulmate Phenomenon: How ADHD Fuels Idea Infatuation In Your Business”  It’s the other side of the same coin! Mentioned in this episode: Episode # 288 “ADHD is Not Just in Your Head: Exploring Embodied Neuroscience” with Dr Miguel Toribio-Mateas About the HostDiann Wingert is a seasoned psychotherapist-turned-business coach who blends neuroscience, entrepreneurial strategy, and real-life ADHD experience. Her specialty? Helping entrepreneurs design businesses around their brains, instead of fighting them. She’s the creator of The Boss Up Breakthrough coaching framework, where she brings actionable wisdom to entrepreneurs with ADHD who want a stand-out, sought-after, profitable business built on their unique brilliance, without burning out.  © 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops  / Outro music by Vladimir /  Bobi Music / All rights reserved.