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.

For ADHD entrepreneurs, traditional productivity hacks often create more frustration than focus. Our brains don’t switch tasks like TV channels—they reset like vinyl records, losing momentum with every change. That’s why the Focus Day model is such a game-changer. By structuring your week around task batching, you reduce context switching and give your brain the space to hit its flow. Whether it’s the Single Focus Scheduling model, the Essential Three, or the Split Screen approach, each option allows you to match your energy to your work instead of forcing yourself into a neurotypical system. Protecting your focus days with clear boundaries not only boosts productivity but also builds confidence and sustainability in your business. The beauty of this strategy is that it’s not about perfection—it’s about progress and creating a system that works with you, not against you.

ADHD is often misunderstood as mere distraction or restlessness, yet for women it frequently shows up in more invisible ways: emotional overwhelm, chronic masking, and a lingering sense of being misunderstood. Emotional dysregulation—the quick shifts between joy, frustration, and sadness—can complicate relationships and fuel rejection sensitivity, often leading to misdiagnosis as anxiety or mood disorders. But alongside these struggles lie remarkable strengths: curiosity, creativity, and a playful perspective that drives innovation and resilience. By naming and validating these experiences, we not only rewrite the ADHD narrative for women but also highlight the strengths that make neurodivergent minds essential in work, life, and leadership.

Ghosting can feel crushing for ADHD entrepreneurs, triggering rejection sensitivity and endless mental “open loops.” But most of the time, it’s not personal—it’s about the prospect’s circumstances, not your skills. The key is reframing ghosting as data, setting clear expectations, and closing loops for yourself with professional follow-ups and boundaries. By strengthening your pipeline, limiting rumination, and leaning on systems, you protect your energy while staying focused on what you can control. Ghosting doesn’t diminish your value; it’s just part of the process of finding the right clients.

Entrepreneurs often dream of cloning themselves to keep up with growth, but real scaling comes from pairing opposites and leveraging automation. ADHD founder Will Christiansen learned that exact “clones” only multiplied chaos, while hiring complementary talent brought balance and sustainability. His approach combines finding integrators—apprentices who thrive under visionaries—with automation that removes repetitive work, freeing up space for creativity and strategy. By letting go of what doesn’t serve and embracing systems, entrepreneurs can scale without losing their spark.

For ADHD entrepreneurs, every new business idea can feel like “the one,” igniting a rush of passion and possibility. Fueled by dopamine, this cycle of attraction, infatuation, honeymoon, and reality often leads to shiny object syndrome—abandoning projects once the excitement fades. But this isn’t a flaw; it’s how ADHD brains are wired. The key is learning when to channel that creative burst into meaningful progress and when to commit for the long haul. By “dating” your ideas, testing them as side projects, and integrating them into your existing work, you can capture the thrill of novelty while building sustainable, long-term success.

High-achieving women are often missed when it comes to ADHD diagnosis, only discovering it in adulthood or midlife when the weight of hidden struggles becomes undeniable. Therapists Diann Wingert and Lisa Lackey share their personal journeys of realizing they had ADHD after years of helping others, revealing how intelligence and adaptability can mask symptoms for decades. Their stories highlight how menopause and midlife often intensify ADHD challenges but also open the door to what Lisa calls the “second knowing”—a return to self, authenticity, and purpose.

This awakening is not just about diagnosis; it’s about transformation. By shedding perfectionism, embracing self-acceptance, and building community, women are redefining success on their own terms. As Lisa says, “You’re not unraveling or falling apart, you’re actually coming together.”

For many entrepreneurs with ADHD, the word “business plan” brings up memories of 40-page documents, rigid structures, and endless details that feel more like homework than help. But building a business plan doesn’t have to be exhausting or overwhelming. In this episode of ADHD-ish, Diann Wingert introduces the Minimalist ADHD Business Plan, a flexible four-step framework designed to align with the way ADHD brains naturally work. Instead of long-term forecasting and jargon, this approach emphasizes clarity, focus, and sustainability, helping you move forward without burning out.

The plan rests on four simple pillars: your North Star (your guiding “why”), a Revenue Reality Check (understanding the numbers that actually matter), your Zone of Genius (focusing on strengths while minimizing energy drains), and your Next Three Moves (actionable steps that keep momentum going without overwhelming you). By making your plan visual, flexible, and imperfect, you create a living tool that supports your creativity while giving you enough structure to stay on track.

Diann also emphasizes the importance of working with your brain instead of against it: short planning sprints, visual dashboards, and regular reviews make the process doable and even energizing. This is planning reimagined—not about controlling your every move, but about creating a compass to guide your decisions. For ADHD entrepreneurs, this means less burnout, more intentional growth, and the confidence that comes from knowing you’re moving toward your goals with clarity.

Running a business with ADHD can feel like a rollercoaster—thrilling highs, sudden pivots, and moments of burnout that leave you scrambling to catch up. In this ADHD-ish Podcast episode, Diann Wingert and guest Diane Mayor dive deep into how neurodivergent traits show up in business models, from dopamine-driven decision-making to executive dysfunction and open loops. Together, they unpack why traditional business advice often fails ADHD entrepreneurs and share practical tools like idea parking lots, structured flexibility, and “sandbox time” to balance creativity with consistency. More than a conversation about impulsivity, this episode offers a roadmap to build ADHD-friendly systems that fuel growth while honoring your unique brain. If you’ve ever felt like your business was built with duct tape and dopamine, this is your reminder that resilience, adaptability, and grit are your superpowers.

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 deeply resonant episode of the ADHD-ish Podcast, Diann Wingert and guest Dave Greenwood unpack the liberating ideas behind The Courage to Be Disliked—and why its roots in Adlerian psychology are so powerful for ADHDers struggling with rejection sensitivity, burnout, and self-doubt. From radical self-acceptance to learning how to separate your responsibilities from others’ reactions, this episode is a must-listen for anyone ready to stop people-pleasing and start building real confidence, on their terms.

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.

In this inspiring ADHD-ish Podcast episode, Diann Wingert and brand strategist Jess Malli Mercier explore how creative entrepreneurs can redefine productivity, embrace rhythm over rigidity, and use collaboration as a tool for transformation. They discuss why an ADHD diagnosis is optional, but self-understanding is essential—and how building a brand (and business) that reflects your truest self leads to real work-life harmony. Whether you’re sprinting through inspiration or slowing down for self-care, there’s a better way to create, heal, and thrive.

In this episode of the ADHD-ish Podcast, Diann Wingert breaks down how cognitive biases—like optimism bias, fundamental attribution error, and the sunk cost fallacy—shape the way ADHD entrepreneurs make decisions. With insights from Vicky Tan’s Ask This Book a Question, Diann offers a practical framework to spot these sneaky patterns, rethink your choices, and build a business that’s both bold and intentional. If your big ideas often outpace your outcomes, this episode will help you pause, pivot, and reframe with clarity.

In this episode of the ADHD-ish Podcast, Diann Wingert and guest Meredith Carder get real about the double-edged sword of ambition for ADHD entrepreneurs. From chasing big ideas to hitting burnout, they unpack the unique highs and lows of building a business with a neurodivergent brain. Together, they explore how radical self-acceptance, idea vetting, and honoring your life’s seasons can help you redefine success—on your terms. If you’ve ever felt overwhelmed by your own potential, this episode is your permission slip to pause, pivot, and protect your energy.

This episode of the ADHD-ish Podcast dives deep into what it really means to stop masking and start embracing your ADHD—especially as a female entrepreneur. Through the powerful metaphor of Wicked's Elphaba, we explore the stages of trying to “fix” and “fit in” before finally breaking free and building a business that honors your neurodivergent brain. If you’ve ever felt like success demands pretending to be someone else, this conversation will remind you: you were never meant to blend in—you were meant to fly.