Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

ADHD Hyperfocus & Perfectionism: Real Strategies to Finally Finish What You Start

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.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

Analysis Paralysis Stopping You? How to Beat Performance Anxiety and Just Get Started

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.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

The Surprising Link Between ADHD Rejection Sensitivity, Burnout and Genuine Confidence

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.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

ADHD Entrepreneurs: Use Your Strong Sense of Justice to Grow Your Brand

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.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

Work-Life Harmony for the Creativity Entrepreneur Who Hustles Too Hard (Try This)

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.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

Is It Time to Rethink That Decision? How Cognitive Bias Shapes the ADHD Entrepreneur’s Choices

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.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

When Ambition Overtakes Performance & What to Do About It

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.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

Why “Fitting In” Keeps You Stuck And Embracing Your ADHD Sets You Free

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.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

Mindset and Performance Tips for Neurodivergent Entrepreneurs: The ADHD Advantage

In this powerful episode of the ADHD-ish Podcast, I sit down with psychiatrist and entrepreneurship researcher Dr. Michael Freeman to unpack how ADHD traits—often seen as deficits—can actually be superpowers in business. From crisis-thinking to creative resilience, we explore how neurodiverse entrepreneurs (especially women) thrive in fast-paced, high-stakes environments. If you’ve ever wondered whether your brain is wired for success on your own terms, this is a must-listen.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

How to Finally Finish What You Start (No More Shiny Object Syndrome)

In this episode of the ADHD-ish Podcast, I pull back the curtain on how ADHD entrepreneurs can move from brilliant-but-buried ideas to real, repeatable success. From dopamine scheduling to shiny object parking lots, I’m sharing the exact strategies that have helped me (and my clients) finally finish what we start—without smothering creativity or burning out. If your brain lights up with every new idea but struggles to see things through, this one’s for you.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

Why Your Solo Entrepreneur Business Doesn’t Need to Scale to Succeed

Many neurodivergent entrepreneurs feel pressured to scale, hire teams, or chase seven-figure dreams—but that’s not the only path to success. In this conversation with Maggie Patterson, host of the ADHD-ish Podcast explores why staying solo can be the ultimate form of freedom and self-care. Maggie shares how designing a business around your actual life, capacity, and values can protect your energy, reduce stress, and create a more sustainable future. By challenging the hustle culture and rejecting one-size-fits-all business models, she empowers entrepreneurs to embrace simplicity, autonomy, and meaningful work over endless growth.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

Unlearn People Pleasing: Change How You Work by Saying No With Confidence

For many entrepreneurs—especially those with ADHD—the "Default Yes" can be a fast track to burnout. Years of people pleasing, driven by rejection sensitivity, fear of disappointing others, and impulsivity, can leave you overextended and undervalued. In this blog, you'll discover how to replace automatic yeses with intentional boundaries using strategies like buffer phrases, guilt-free responses, and practical follow-up habits. By learning to pause, assess requests, and protect your time, you’ll not only reduce stress but also gain more respect from clients and collaborators. The journey isn’t about perfection—it’s about progress, self-respect, and creating space for what matters most.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

Why Weird Works: Neurodivergent Entrepreneurs, ADHD Strengths, and Real Success

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.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

How to Master Task Initiation and Quit Paying the ADHD Tax Forever

Living with ADHD as a solopreneur often comes with what’s called the “ADHD Tax”—those hidden costs in time, money, and energy caused by missed deadlines, late fees, or overlooked opportunities. For years, I thought these mistakes reflected personal failings, but what I’ve learned is that they’re tied to how the ADHD brain approaches task initiation. Instead of fighting against it, I discovered how to design systems that work with my wiring, allowing me to show up with more clarity, creativity, and confidence.

Through intentional rituals, cues, and calendar blocking, task initiation stopped being a roadblock and became a launchpad for meaningful progress. Scheduling well-being blocks and recovery runways not only preserved my energy but also created natural transition points that made starting tasks far less overwhelming. By reframing ADHD task initiation as a neurological challenge instead of a flaw, I built strategies that support my strengths while honoring the ebb and flow of focus.

This shift hasn’t just saved me from paying the ADHD Tax—it’s given me a framework for sustainable entrepreneurship and self-compassion. And I’ve learned that connection is just as important as systems; being part of a community of ADHD entrepreneurs offers solidarity, encouragement, and collective wisdom. With the right tools and mindset, task initiation doesn’t have to drain your energy or your wallet—it can become the foundation for a thriving business built on your unique strengths.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

Healthy Startups: Beyond Profit, Mental Health Matters

Entrepreneurship often glorifies hustle, profit, and relentless growth—but Mina Raver’s story shines a light on a different path. As a trailblazing female entrepreneur and innovator, she has transformed personal adversity into a mission to redefine productivity, authenticity, and mental health in the startup world. Her journey demonstrates that success is not only about scaling quickly or satisfying investors, but also about creating sustainable systems that honor our well-being—especially for neurodivergent minds navigating executive functioning challenges.

Through her work, including the creation of adaptive tools like the Better CEO app, Mina is pushing for inclusivity in industries that often overlook the unique needs of neurodivergent individuals. Her perspective challenges the status quo, offering an alternative vision where resilience, authenticity, and balance drive innovation. Mina’s philosophy reminds us that the health of a founder is just as vital as the success of their business—and perhaps the most important foundation for long-term impact.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

ADHD Leaders: Powerful Strategies for Women in Charge

Leadership can feel overwhelming for women entrepreneurs with ADHD, but stories like Kirsten Beukes’ prove that balance and impact are possible when we lean into our strengths. As the owner of a thriving group occupational therapy practice in South Africa, Kirsten has learned to navigate the challenges of being both practitioner and business leader, while also honoring the realities of ADHD. Her journey highlights the tension many ADHD leaders face—managing the demands of daily operations while still making time for big-picture strategy.

Through trial and insight, Kirsten discovered the importance of setting boundaries, adjusting expectations for her team, and creating intentional “owner days” for strategic focus. Her story is a powerful reminder that ADHD leadership is not about fitting into traditional molds, but about channeling creativity, empathy, and resilience into building organizations that reflect both personal values and team well-being. For women in business, especially those navigating ADHD, this narrative offers strategies, encouragement, and proof that our unique wiring can be an asset when we embrace it fully.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

ADHD Traits For Business: Strategic Listening & Systems Thinking

Entrepreneurship with ADHD often means navigating challenges while uncovering unique strengths that can transform the way we do business. In this episode, Iris Goldfeder shares how she leverages her ADHD traits as entrepreneurial superpowers. From hyperfocus and systems thinking to strategic listening and authenticity, Iris demonstrates how neurodivergent strengths can fuel creativity, innovation, and stronger client relationships.

One of her most powerful insights lies in the concept of client fit—choosing to work only with clients who align with her values and business vision. By embracing authenticity, even if it means walking away from misaligned opportunities, she’s built a practice rooted in integrity and sustainability. Iris’s approach reminds us that success isn’t just about hard skills or scaling faster—it’s about cultivating courage, empathy, and emotional intelligence to create partnerships that thrive. For neurodivergent entrepreneurs, these qualities aren’t just helpful; they’re essential tools for building meaningful, lasting businesses.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

Inbox Organization Strategies for an ADHD Brain

For ADHD solopreneurs and small business owners, the inbox can quickly become a trap—a place where urgency and novelty hijack focus and derail productivity. Emails feel important, but in reality, they’re often just other people’s priorities. With ADHD, the brain craves stimulation, making constant email checking a hard-to-break cycle that drains energy and executive functioning.

In this post, I share simple, ADHD-friendly inbox organization strategies that shift your relationship with email from reactive to intentional. From scheduling specific check-in times, to using folders, templates, and autoresponders, these strategies help you set boundaries, protect deep work time, and reduce task-switching fatigue. The goal isn’t just inbox zero—it’s reclaiming your time, focus, and confidence as a business owner. Because when you stop letting emails run your day, you finally create the space to focus on what matters most.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

Small Business? Use a Business Transformation Strategy That Sparks Action

For solopreneurs, running a business isn’t just about selling a service—it’s about standing for something bigger. This blog dives into how adopting a business transformation strategy can turn your business into a revolution rooted in purpose, passion, and impact. Drawing inspiration from consultant Rochelle Moulton’s insight that “a revolution begins with an idea for change you’re willing to lead,” the piece explores how small business owners can transform from self-starters into thought leaders through alignment, experimentation, and authenticity. From embracing your “genius zone” to narrowing your niche, facing fear, and cultivating genuine community, this approach reframes transformation as a creative and deeply personal process. Through my own experience as a neurodivergent coach and host of ADHD-ish, I’ve learned that revolutions aren’t about chaos—they’re about clarity, courage, and connection. When you align your purpose with your business, you don’t just work for profit—you work for change.

Read More
Blog Diann Wingert Coaching, LLC Blog Diann Wingert Coaching, LLC

ADHD Entrepreneur: Dealing with Disappointment and Time Blindness

Disappointment hits differently when you’re an ADHD entrepreneur—it’s louder, heavier, and often tangled up in time blindness and perfectionism. This blog explores why that happens and how to bounce back faster. From the emotional amplifier effect and the time blindness tax to the hyperfocus paradox, understanding these patterns is the first step toward resilience. Learn how to build scaffolding systems, automate tasks, and design visual workflows that anchor your focus. Discover how energy management and the “Minimum Viable Day” approach can keep your business moving even on low-focus days. And most importantly, explore how self-compassion, time buffering, and proactive communication can turn disappointment into a growth strategy. Managing ADHD in business isn’t about avoiding failure—it’s about designing supports that make success sustainable.

Read More