Welcome to the ADHD-ish Blog

ADHD-ish Blog

If you've ever Googled "why can't I just get my act together" at midnight, you're in the right place.

The ADHD-ish Blog is where business strategy meets brain science — written for entrepreneurs and small business owners who are tired of advice that wasn't designed for the way their minds actually work.

Whether you're officially diagnosed or just ADHD-adjacent, this is your no-fluff resource for building a business that works with your brain, not against it.

What You'll Find on the ADHD-ish Blog

Every blog is grounded in 20+ years of clinical experience and real-world business strategy — not toxic positivity and generic productivity hacks.

Browse the blog for episodes, frameworks, and straight-talk insights on focus, decision-making, pricing, boundaries, and everything else nobody warned you about when you started your business.

New to the ADHD-ish Blog? Start anywhere. That's kind of our thing.

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

Best Business Pivot Strategies for Creative Entrepreneurs

For neurodivergent entrepreneurs, small business ownership is rarely a straight line. The pressure to pick one thing and stick with it can leave us feeling stuck when our interests shift or we lose steam. I sat down with creative serial entrepreneur Megan Eckman, whose story of continual reinvention is a masterclass in sustainable entrepreneurship. Society idolizes grit, but that's a recipe for deep burnout. Megan's journey offers a nuanced model for creative entrepreneurs: multiple pivots, gradual swaps, and knowing when to stop. She shares three strategies: the test-and-build pivot (test, prototype, and build a new path while the old one winds down—this business pivot strategy methodically reduces risk); the hard stop (ending a successful project when it no longer aligns with who you are); and hibernate and evolve (pausing without panicking to explore new avenues). Ultimately, successful neurodivergent entrepreneurs thrive through relentless curiosity. Sustainable success in small business ownership depends on honoring your own cycles—experiment boldly, exit gracefully, and stay curious. Your business is allowed to evolve as quickly as you do.

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

Redefining Success After Loss: ADHD-Informed Support for Small Business Owner Burnout

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.

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

The Role of Thought Leaders in Shaping the Future

True thought leadership requires a willingness to engage in uncomfortable conversations and challenge long-held beliefs. It's not about preaching to the converted—it's about pushing boundaries and sparking debates that lead to growth and progress. Thought leaders bring a fresh viewpoint to their industries, challenging conventional wisdom and offering innovative solutions. Take Gabor Mate as an example—his unique perspective and bold communication position him as a sought-after authority who doesn't hold back from sharing controversial opinions. But being a thought leader goes beyond expertise—it's about creating projects and platforms that enhance your brand authority and amplify your message. It can be frustrating to see individuals with limited knowledge calling themselves experts and thought leaders, which is why you need a legitimate body of work and depth of knowledge before positioning yourself this way. Thought leadership is not about empty self-promotion but rather about sharing genuine insights, wisdom, and expertise that can impact people's lives. Your voice matters, and the time to make a difference is now.

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

Discovery Calls vs Free Consultation: What you need to know

If you're confused about the difference between a discovery call and a free consultation call, you're not alone. Discovery calls allow coaches to learn about potential clients' needs, but unfortunately, many coaches are trained to agitate pain points and present themselves as the obvious solution—which can feel manipulative and salesy. A free consultation call takes a broader look at your needs, and if the coach isn't the ideal fit, they can provide recommendations or referrals. This is how you demonstrate value even before working together. As a psychotherapist-turned-business strategist, I want to uncomplicate the process of choosing and hiring a coach. Because if you need shoes, you don't go barefoot when the first pair doesn't fit. It's worth taking the time to find your right-fit coach.

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