Welcome to the 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.


Oh, and if you’re more of a listener than a reader, check out the top-rated ADHD-ish™ podcast!

Diann Wingert Coaching, LLC Diann Wingert Coaching, LLC

Why You Need a Strategist Before You Hire an Operator or COO

Hiring a COO for a small business — or an operations manager, or an online business manager (essentially a really good VA) — is the most reasonable-sounding but fundamentally wrong move I see business owners with ADHD make. It looks logical. It looks like the next best step. It looks like the thing a “serious” business owner does. And a significant percentage of the time, it's an expensive way to postpone dealing with the real problem.  

And before you come for me, let me be clear. I'm not anti-operations. I recommend operational hires all the time. But the order matters more than most business owners realize and getting it backwards costs them double.

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Diann Wingert Coaching, LLC Diann Wingert Coaching, LLC

Why Your Last ADHD Business Coach Didn't Work Out the Way You Expected

If you hired an ADHD business coach and things didn't work out the way you imagined, and you've come to the conclusion that you're the problem or the coach wasn’t “the one”, I'd like to offer an alternative explanation. 

I hear this a lot, usually in a first conversation, typically delivered in the flat voice people use for things they've decided are their fault. “I've worked with three coaches. Maybe four, depending on whether you count the group program.  Maybe I’m just not coachable.”

Chances are you are coachable and maybe you've been hiring the wrong type of help, repeatedly, for a reason that makes complete sense once you see it.

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Diann Wingert Coaching, LLC Diann Wingert Coaching, LLC

How Your ADHD Coach Prepares You to Work With a Business Strategist

If you're trying to figure out the difference between an ADHD coach and a business strategist, there's an excellent chance you’re not just doing research or obsessed with semantics. You're most likely six months to two years into coaching that genuinely helped and you've hit a wall you can't quite name. You're doing the things. You're doing them consistently. And something is still off.

I want to tell you what that wall is, because it’s not your imagination and it’s also not what you might think it is. 

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Diann Wingert Coaching, LLC Diann Wingert Coaching, LLC

Why Your Best Offer Died in Draft Mode

You wrote it. That's the part that makes this different from every other marketing problem you have.

The post existed. The launch email was finished, and it was good — better than most of what you've actually sent, and even your inner critic agrees with that. It sat in draft mode while you told yourself you wanted to look at it again with fresh eyes. Then it sat another day. Then the timing wasn't right anymore, and eventually you deleted it or quietly repurposed the good parts into something smaller and safer.

If you've ever felt a genuine flood of relief when a launch got postponed, an email wasn’t sent or an offer never made it out of draft mode, you already know what this article is about. Take a deep breath, skip the shame spiral and keep reading. 

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Diann Wingert Coaching, LLC Diann Wingert Coaching, LLC

How to Build a Marketing System That Works on Your Low-Dopamine Days Too

Almost every marketing system you've been sold was designed by someone neurotypical or a neurodivergent having a good week.

They had the idea, tested it while they were energised and interested, saw it work, and wrote it up. What they probably didn’t do was stress-test it against a week where getting dressed was the sole accomplishment. So the system arrives in your red-hot hands with a hidden requirement in the very fine print; this works if you can show up like I did when I made it.

Then you have a low stretch  (low mood, energy and motivation) — and every entrepreneur with ADHD traits has them, including me, and the system produces nothing. Not less. Nothing at all. Because it had no version of itself that runs at reduced capacity.  The one I call the MVV - Minimum Viable Version. 

That's not a discipline failure. That's a system that doesn’t take fluctuating capacity into account, and fluctuating capacity is something you can count on with ADHD, so we might as well count on it and plan for it. 

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Diann Wingert Coaching, LLC Diann Wingert Coaching, LLC

Why Your Promotion Strategy Should Be Boring on Purpose

At some point in the last few months, you looked at your own marketing and thought: this is stale. I've said this a hundred times. People must be sick of hearing it. I need a new angle.

That thought felt like strategic insight. It almost never is.

What it usually is: your appetite for novelty, which has nowhere useful to go at the moment, redirecting itself at your messaging. And messaging is a terrible place to spend it, because the thing you're bored of is very likely the thing that's finally starting to work. Stay with me. 

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Diann Wingert Coaching, LLC Diann Wingert Coaching, LLC

The Balanced Marketing Strategy: 3 Components That Keep You Top of Mind for Your Best-Fit Clients

There are two ways entrepreneurs and small business owners with ADHD typically get it wrong when it comes to marketing, and they look like opposites from a distance. 

The first is chasing everything at once. Four social media platforms, a newsletter, a lead magnet, a networking group, and a podcast started in a burst of enthusiasm and abandoned a few months in. It feels like coverage. It's actually one energy source spread so thin that all of it goes silent at the same time.  

The second is locking onto a single channel and treating it as the whole strategy. That one at least produces results — up until the week you can't produce anything, and then your visibility drops to zero with nothing underneath it.

Neither is actually a system. Both are one drop in capacity away from total collapse.

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Diann Wingert Coaching, LLC Diann Wingert Coaching, LLC

Why Entrepreneurs with ADHD Can't Market Consistently (It's Not a Discipline Problem)

Every piece of marketing advice aimed at ADHD entrepreneurs assumes the problem is willpower — post more, stick to the calendar, build the habit. That's backwards. The problem isn't that you can't be consistent. It's that you built a promotion strategy that requires a version of consistency your brain was never going to sustain, on a schedule that ignores how your energy actually moves.

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Can AI Replace Your Human Coach?

ADHD-ish ™ Blog: I never shy away from complexity—whether it's talking about neurodiverse brains or the new tech shaping our lives. When it came time to talk about Di AI, an ADHD AI coaching tool I created and have poured so much of myself into, I didn't want a cheerleader. I wanted a discerning, thoughtful skeptic with both feet firmly on the ground. Enter Dr. Elizabeth Meyer. As a professor, researcher, and one of my former coaching clients, Elizabeth came to this episode not as a fan, but as someone with a "love-hate" relationship with Generative AI—someone perfectly equipped to interrogate what Di AI could actually offer.

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3 Hidden Revenue Leaks in Your ADHD Business

ADHD-ish ™ Blog: If you're an entrepreneur with ADHD, you already know how many "hacks," life tips, and motivational speeches we're bombarded with. They tend to sound the same: work harder, try more, get organized, plan, focus. After years doing this work with entrepreneurs like you—and, honestly, after years struggling and triumphing with my own ADHD—I've learned that what actually helps us isn't more willpower or better reminders. It's structural change. 

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ADHD Entrepreneur Burnout: When Success Feels Like Survival

ADHD-ish ™ Blog: When I first connected with Kathryn Bird, she genuinely seemed to have it all: traveling the world, running a highly successful business, celebrated as an expert in her arena, even stopped by strangers like a celebrity. But as is so often the case with ADHDers, the external perception couldn't have been further from her internal reality. She described it as "feeling like a swan"—serene on the surface, but furiously paddling underneath, continually battling a sense of drowning in her to-do list and never earning the space to rest or enjoy personal time.

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ADHD Entrepreneur Procrastination: Resistance Is a Message

ADHD-ish ™ Blog: I've spent years challenging the narratives that surround common ADHD traits, especially in the context of entrepreneurship and business ownership. In this post, which is part four of my series, “Reframing ADHD Traits as Business Strategies”, I wanted to take a deeper look into ADHD procrastination—and the resistance and avoidance that travel alongside it—three words that have a stranglehold on many of us with ADHD, both as entrepreneurs and as individuals.

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A Diagnosis Isn't Required for Neurodivergent Self-Trust

ADHD-ish ™ Blog: As the host of the ADHD-ish™ Podcast, I've had the privilege of having conversations with courageous, insightful, and truly memorable people, but my latest episode with my friend Dr. Naketa Ren Thigpen, lingers in my mind in the best possible way. Naketa has worn many professional hats—the therapist's hat, the coach's hat, the transformational speaker and consultant's hat—and beneath each is an unwavering devotion to strengthening relationships in both life and business.

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Why ADHD Entrepreneurs Struggle With Recurring Revenue

ADHD-ish ™ Blog: As an ADHD entrepreneur coach I find myself returning to one deceptively simple question when I work with business owners who have ADHD: “Do you actually enjoy the way you make your most reliable income?” Not just how much you make, but the day-to-day, month-to-month rhythm of the work itself.

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