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.

ADHD has long been framed as a dopamine problem, but embodied neuroscience paints a far more complex—and empowering—picture. In this episode, Dr. Miguel Toribio-Mateas explains why ADHD isn’t just happening in the brain, but across the entire mind-body system. From gut-brain chemistry to interoception, movement, intuition, and emotional regulation, ADHD shows up through signals that most adults have been conditioned to ignore. Instead of trying to “fix” yourself with productivity tools, this conversation invites you to rebuild self-trust, tune into your body’s cues, and support your brain through rest, nourishment, and nervous system regulation. You’ll walk away with a deeper understanding of how ADHD actually works—and why honoring your rhythms is the key to thriving.

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.

ADHD isn’t just about focus—it’s about the habits that quietly shape how your brain functions day after day. In this powerful conversation with ADHD coach Alan P. Brown, we uncover the everyday behaviors that sabotage your energy, focus, and mood, from sugar crashes to revenge bedtime procrastination. You’ll learn why sugary snacks and late-night screen time drain your brain power, and how small shifts—like prepping protein-rich snacks, celebrating micro-movements, and improving sleep hygiene—can dramatically enhance your executive functioning. With realistic, science-backed strategies, this guide shows how to build adhd healthy habits wellness that actually fit your lifestyle. The goal isn’t perfection—it’s getting 1% better every day, with compassion and consistency.

In a business culture obsessed with “more,” neurodivergent entrepreneurs can find freedom, clarity, and consistency by doing less—through one signature offer that captures the full depth of their genius. This blog explores why the old “offer suite” model often leads to burnout and confusion, especially for ADHD business owners juggling executive function limits. Multiple offers don’t just multiply income opportunities—they multiply decisions, marketing plans, and emotional strain. By shifting to a singular, focused offer, you simplify operations, refine your messaging, and amplify your results. You’ll learn how to build flexibility within your offer through pacing and payment options, how to price based on capacity, and how to streamline your marketing so every message points to one powerful transformation. The result? Less chaos, more clarity, and a business that fits your brain—and your life.

For many ADHD and neurodivergent professionals, success in business often comes with an invisible cost: the effort of masking. What’s often misunderstood as a conscious choice to “fit in” is, for most, a deeply ingrained survival mechanism—learned early and performed instinctively. In this blog, we explore what it means to live and work authentically in a world designed around neurotypical expectations. Through my conversation with ADHD coach and entrepreneur Ron Sosa, we delve into the realities of unmasking, intersectionality, and redefining productivity on your own terms. Ron’s story—spanning early misdiagnosis, identity discovery, burnout, and resilience—reveals how authenticity is rarely linear, but always powerful. From the tension between “superpower” narratives and real lived struggle to the importance of self-acceptance in neurodiversity in business, this piece invites readers to reflect on what standing tall in one’s truth truly means. Because for many of us, authenticity isn’t rebellion—it’s survival.

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.

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.