Celebrate episode 300 of ADHD-ish with a bold, unfiltered conversation on entrepreneurship with ADHD. Expect real struggles, honest wisdom, and powerful takeaways. Listen now if you want truth over hype and growth that actually sticks.

If you're an entrepreneur with ADHD, chances are you've lost count of the nights you've stared at your computer, debating whether to add "just one more thing" to a project that's already good. Understanding how ADHD strengths and struggles make you stronger is essential for breaking this cycle. In this episode, ADHD entrepreneur coach Diann Wingert dives into a rarely discussed pattern: never knowing when you've done enough. This chronic uncertainty leads to overdelivering, overworking, and an endless hunt for "safe" territory—a direct path to ADHD burnout. The urge to keep working isn't about ambition; it's about an internal meter that doesn't know where to stop. Diann presents the "Enough Already" framework—five steps to recalibrate your inner meter and prevent ADHD burnout. Redefining "enough" isn't about lowering standards—it's about staying in the game long enough for your excellence to compound. As ADHD entrepreneur coach Diann Wingert says, "Exhaustion isn't strategy—sustainability is." Every hour you over-polish is energy stolen from future growth.

Dr. Dante coined the term "neurobaddies" on TikTok to rebrand neurodivergent women as beautifully unique and admirably strong. He insists that traits like honesty, hyperfocus, and authentic passion make neurodivergent women exceptional—not just in relationships, but in communication and leadership. But years of negative feedback create internalized doubts. For ADHD women, emotional sensitivity is a hallmark—we experience intense emotions, react sharply to rejection, and struggle with regulation. We rarely do things by halves: "I refer to it as being full ass or no ass." This relentless drive fuels entrepreneurial success but also creates vulnerability. Narcissists are drawn to our empathy, honesty, and willingness to overlook red flags. Hyperfocus and the tendency to self-blame make us especially susceptible. Healing demands reclaiming the neurodivergent narrative, not waiting for permission from neurotypicals. The neurodivergent edge isn't just about surviving challenges—it's about reshaping the conversation and building businesses where different truly means better.

At this time of year, it's hard to miss the avalanche of content urging us to plan, journal, set goals, and envision our dream year ahead. Vision boards, 90-day planners, accountability workshops—everywhere you look, someone has a new system. But for ADHD brains, all that noise leads to guilt, overwhelm, and a nagging sense of inadequacy. Here's the truth: those frameworks were created for brains that operate consistently. ADHD brains operate on peaks and valleys of interest and energy. Forcing yourself to fit that mold won't make you more productive—it just makes you feel like shit. Try something radically different: create three simple lists reflecting on Energy, Money, and Time. What gave you energy versus what drained you? What actually made you money versus what you thought should be profitable? When are you truly at your best? Then comes the bold move: subtraction. Let go of draining clients, offers you despise, and projects you never started. This anti planning approach isn't a typical plan—it's an advantage.

If your brain is a non-stop idea generator but you struggle to choose which ideas to pursue or actually finish what you start, you're not alone. ADHD entrepreneurs tend to be natural polymaths—individuals with both breadth and depth of expertise across many areas. The challenge isn't the ideas themselves; it's transforming brilliant concepts into real-world impact. Guest Sarah shares her Capture-Connect-Structure-Iterate-Express-Reflect framework for wrestling with creative chaos, using AI tools like ChatGPT and Claude as digital thought partners. One of the most powerful secrets? Radical self-acceptance and boundary-setting. Instead of trying to fix ADHD traits, lean hard into your passions and hyperfocus, offloading tasks you're not naturally equipped for. As Diann says: "If I'm too much, go find less." Stop shaming yourself for your energy, creativity, and wild ideas. Build frameworks, protect your bandwidth, and your brilliant ideas will finally get their moment in the world.

Entrepreneurship is often painted as the ultimate destination for creative, rebellious ADHD minds. But this "one-size-fits-all" message is damaging and misleading. Entrepreneurial traits don't guarantee entrepreneurial success—and pushing everyone with ADHD into this mold leaves many feeling burnt out or broken. Enter intrapreneurship: bringing entrepreneurial energy inside existing organizations. The innovators who developed Gmail at Google or invented the Post-It Note at 3M weren't CEOs—they were employees with infrastructure, resources, and support. Intrapreneurial roles let you channel creativity, solve problems, and create impact without sacrificing the stability and structure that helps many ADHD brains actually thrive. There's no shame in prioritizing stability or thriving within the right organization. You're not settling—you're being strategic and intentional about creating conditions where you can thrive. That's what neurodiversity in business should really look like.

On episode #292 of the ADHD-ish Podcast, Diann Wingert sits down with Cat Orsini to explore a radically different approach to lead generation—one rooted in neurodiversity, authenticity, and relationship-first thinking. Drawing from her lived experience with ADHD, autism, and trauma, Cat challenges the idea that automation has to feel cold or transactional. Instead, she shows how thoughtful systems can support follow-up, reduce executive-function strain, and free up energy for genuine human connection. By mapping interactions, leaning into pattern recognition, and practicing radical self-acceptance, Cat demonstrates how entrepreneurs can stop chasing leads and start attracting aligned opportunities. Her approach proves that when customer relationship marketing is built to fit neurodivergent brains, it becomes not just easier—but far more effective.

Steph Cottrell’s story is a powerful example of how quickly burnout can creep in for ADHD entrepreneurs—and how transformative it can be to pause, reassess, and redefine success. What began as a plan to scale her thriving marketing and web development business turned into an eye-opening realization about uneven collaborations, hidden labor, and the toll of unclear boundaries. With guidance from an ADHD-informed business strategist coach, Steph confronted the patterns that were draining her energy and rebuilt her business model around clarity, agency, and true fulfillment. When the sudden loss of her father reshaped her priorities, she chose to restructure her work to be flexible and “interruptible,” allowing her to support her family without sacrificing her business. Her journey shows that success isn’t about doing more—it’s about aligning your business with your values, protecting your energy, and giving yourself permission to choose what genuinely feels right.

Small business ownership often feels like gambling—especially for ADHD-ish entrepreneurs navigating endless tactics, programs, and quick fixes. Jessica Lackey’s work highlights a simple truth: strategy starts with clarity, not more courses. These five essential questions—what business you're running, what stage you’re in, the impact you want, the responsibility you’re willing to hold, and what “enough” truly means—cut through noise and bring you back into agency. With intention, structure, and honest self-inquiry, you can build a business that fits your capacity, your brain, and your definition of success.

ADHD entrepreneurs are masters at starting strong and losing steam fast, especially when the initial excitement fades and routine takes over. That drop in stimulation can make even your most successful offer feel heavy, confusing you into thinking it’s the wrong path. In reality, it’s often just dopamine dysregulation—not a business crisis. This episode explores the PROOF framework to help you decide whether to refresh an offer or release it entirely, giving you a clear way to separate shiny-object impulses from strategic decisions. You’ll learn how to build rotation, add variety, use constraints creatively, and delegate the draining parts so your business can stay profitable and engaging for your ADHD brain.

Running a business with ADHD can feel like walking through an emotional minefield—criticism, time pressure, and uncertainty can all hit harder when your brain processes emotions more intensely. But emotional reactivity isn’t weakness—it’s wiring. In this episode, discover the SPACE Framework, a powerful system designed to help ADHD entrepreneurs manage stress, regulate emotions, and recover from dysregulation faster. You’ll learn to spot triggers before they escalate, pause effectively, act with intention, clear the air with accountability, and evolve your systems for resilience. These emotional regulation ADHD tools offer practical coping skills for anxiety and overwhelm, helping you shift from reactive to regulated while staying authentic, professional, and grounded.

The rise of ADHD-focused business coaching has opened new doors for entrepreneurs who think differently—but it’s also created a marketplace full of confusion and false promises. With no regulation or licensing standards, anyone can call themselves an ADHD business coach, leaving neurodivergent entrepreneurs vulnerable to generic strategies disguised as specialized help. A true ADHD business coach understands both the lived experience of ADHD and the mechanics of running a sustainable business that works with your brain, not against it. They’ll teach you how to simplify systems, amplify your natural strengths, and turn traits like hyperfocus and innovation into genuine assets. In this blog, you’ll learn what red flags to avoid, what questions to ask before hiring a coach, and how to recognize the “green lights” that signal real ADHD-aligned support. Because when it comes to your business and your brain, you deserve expertise that’s as unique as you are.

When you’re running three family businesses, balance sounds impossible—especially with an ADHD brain. But for entrepreneur and therapist CherylAnn Crego, what might look like chaos from the outside has become a masterclass in adaptability, creativity, and self-trust. With the guidance of coach Diann Wingert, CherylAnn transformed her ADHD traits—like rapid task-switching and intuitive problem-solving—into genuine superpowers. Through intentional coaching, affirmations, and the courage to let go of what no longer served her, she built a renewed sense of ADHD self-confidence and leadership. Her journey proves that late diagnosis isn’t a setback—it’s a chance to rewrite your narrative, embrace your strengths, and build a business that reflects who you truly are. For ADHD entrepreneurs juggling countless roles, CherylAnn’s story is a reminder that confidence isn’t found in control—it’s found in self-acceptance and the courage to grow through discomfort.

Entrepreneurs with ADHD often walk a fine line between passion that propels their business forward and emotional dysregulation that can derail it. In this insightful piece, Diann Wingert explores how understanding the difference—and building the right emotional scaffolding—can turn intensity into a competitive advantage. From recognizing early warning signs to creating structures that protect your decision-making, she offers actionable strategies for thriving in business without sacrificing mental well-being. By embracing neurodiversity and mastering emotional regulation, you can transform your most intense feelings into sustainable success drivers.

In a world where perfection is often praised, entrepreneur Mikey Schumacher is building a brand that finds power in the opposite. As the creator of But Cute, Mikey designs plush toys that celebrate anxiety, quirks, and emotional complexity—transforming insecurities into symbols of connection. On the ADHD-ish Podcast, he shares how his own struggles with anxiety, failed ventures, and creative detours led him to create a community where vulnerability is the foundation, not the flaw. With designs like the Anxious Moon Bunny and the Grumpy Croissant Crab, Mikey's message is clear: small business ownership doesn’t have to be perfect to be impactful. His journey reminds us that embracing our flaws might just be the most effective strategy for growth, belonging, and sustainable success.

ADHD entrepreneurs face more than just the challenge of starting or finishing tasks—the real energy drain lies in switching between them. In this episode of the ADHD-ish Podcast, Diann Wingert explores the hidden productivity cost of task switching and how it wreaks havoc on momentum, focus, and mental energy. Through relatable stories and practical solutions, she introduces the Transition Bridge System, a method designed to help you move between tasks with more ease and intention. By using simple but powerful tools like breadcrumbs and transition rituals, ADHD minds can finally protect their flow, reduce overwhelm, and rebuild confidence in their workday. If you’ve ever ended your day feeling drained—but unsure why—this is your call to stop context chaos and start shifting smoothly.

ADHD entrepreneurs know how to start things with passion and intensity—but finishing them? That’s another story. If you find yourself trapped in endless tweaks, consumed by research, or held back by fear of judgment, you might be stuck in what Diann Wingert calls the "Stopping Problem." In this episode of the ADHD-ish Podcast, Diann unpacks the perfectionism, hyperfocus, and rejection sensitivity that keep brilliant ideas stuck at 85% done. You’ll meet three archetypes—Lenor the Tweaker, David the Protector, and Marta the Researcher—and learn how to break free using the “Completion Compass.” It’s time to redefine “done,” embrace real-world feedback, and start finishing what matters. Because done is not just better—it’s better for you.

If you’re an ADHD entrepreneur stuck in either over-researching or reckless launching, you’re not lazy or broken—you’re caught in the ADHD starting paradox. In this episode of the ADHD-ish Podcast, Diann Wingert introduces the “Messy Start Method,” a refreshingly doable approach to beat analysis paralysis, manage performance anxiety, and build momentum with less burnout. Tune in to learn how 2% effort and 20% planning can help you stop spinning your wheels and finally move forward.

In this compelling episode of the ADHD-ish Podcast, Diann Wingert dives into justice sensitivity—a trait many ADHD entrepreneurs carry quietly and intensely. Learn how to turn your fierce sense of fairness into a values-driven brand, connect with aligned clients, and avoid the emotional burnout that comes with caring a lot. With Diann’s 3-part framework, you’ll discover how to channel your passion without draining your power—and why neurodiverse businesses that give a damn are exactly what the world needs.

Entrepreneurship is rarely a straight path, and for those of us with ADHD, it often feels like a winding road full of detours, dead ends, and unexpected scenic routes. Yet, it’s on these unconventional paths that our unique strengths shine brightest. Early in my journey, I struggled to fit into standard business practices—long meetings, linear plans, and rigid expectations left me restless and frustrated. It wasn’t until I embraced my ADHD that I realized my brain’s natural tendencies could become powerful business assets.

ADHD gives us the ability to see possibilities where others see obstacles. My mind thrives on novelty, spontaneity, and creative problem-solving, which has allowed me to craft innovative solutions and build systems that align with my natural workflow. Facilitated sprint sessions, a technique I learned from Evan Sargent, became a game-changer. Structuring work in quick, focused bursts with intentional breaks allows ADHD entrepreneurs to channel restlessness into productivity without burning out.

Being part of a community of like-minded, neurodivergent entrepreneurs has been equally transformative. Sharing strategies, celebrating wins, and navigating setbacks together fosters camaraderie and reinforces the value of our ADHD strengths. The biggest revelation? “Weird” is not a liability—it’s a competitive edge. By leaning into our differences and designing systems that honor our neurodivergent wiring, we can redefine success on our own terms and turn challenges into opportunities for creativity, innovation, and growth.In this episode of the ADHD-ish Podcast, I explore why embracing your so-called “weirdness” is the secret to thriving as a neurodivergent entrepreneur. Joined by Evan Sargent, we dive into strategies like facilitated sprints, self-acceptance, and building systems that amplify your creativity instead of fighting against it. If you’ve ever felt like you didn’t fit the traditional business mold, this episode is for you.