Diann Wingert

ADHD-ish™

Business EN ↓ 300 episodes

ADHD-ish is THE podcast for business owners who are driven and distracted, whether you have an “official” ADHD diagnosis or not. If you identify as an entrepreneur, small business owner, independent professional, or creative, and you color outside the lines and think outside the box, this podcast is for you. People with ADHD traits are far more likely to start a business because we love novelty and autonomy. But running a business can be lonely and exhausting. Having so many brilliant ideas means dozens of projects you’ve started and offers you’ve brainstormed, but few you’ve actually launched...

Author

Diann Wingert

Category

Business

Latest episode

Jul 7, 2026

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Episodes

Celebrating Our Imperfections as a Business Strategy 22.07.2025

In this episode, I sit down with Mikey Schumacher, the 29-year-old creative entrepreneur behind “but cute”—a start-up brand of plush toys designed to celebrate mental health and celebrate our imperfections. In this episode, Mikey & I discuss his entrepreneurial journey, the healing power of community, and how comfort objects can open up much-needed conversations around anxiety, ADHD, and more....

Shifting Smoothly with ADHD: Stop Task Switching Stress – ADHD Tips That Actually Work 15.07.2025

If you’re a solopreneur, consultant, creative, or independent professional, you know there’s more to running a business than hustling between deadlines and client meetings. The real challenge? Moving reliably and efficiently between your various roles, priorities, and ideas, especially if you relate to the “ADHD-ish” brain.  In this final episode of the three-part Momentum Series, the focus i...

Stopping Smart with ADHD: Break Free from ADHD Hyperfocus & Perfectionism – Simple Strategies 08.07.2025

Welcome back to ADHD-ish! I’m your host, Diann Wingert, and today we’re diving into the “Stopping Smart” episode—a must-listen for any ADHD entrepreneur who’s ever struggled with getting projects across the finish line.  If you’ve ever found yourself in the dreaded “improvement vortex”—tweaking, reworking, and researching just a little bit more instead of actually finishing, publishing or lau...

Starting Strong with ADHD: Overcoming Procrastination & Task Avoidance to Get the Ball Rolling 01.07.2025

Welcome to ADHD-ish , the podcast for ambitious entrepreneurs whose brains work a little differently. I’m your host, Diann Wingert, and today we’re kicking off “The Momentum Series,” a deep-dive into what I like to call the “unholy trinity” of ADHD business struggles: starting, stopping, and switching gears. Ever find yourself stuck in a never-ending planning phase, or maybe leaping headfirst into...

How to Stop People Pleasing and Manage ADHD Rejection Sensitivity at Work 24.06.2025

Welcome back to ADHD-ish! In today's episode, I sit down with my friend, author, writer, and ADHD coach, Dave Greenwood, for another honest, thought-provoking conversation—this time exploring the powerful lessons of The Courage to Be Disliked , a book rooted in the teachings of 19th-century psychotherapist Alfred Adler. While not specifically an ADHD book, Dave shares how this book packs a punch o...

ADHD & Justice Sensitivity: From Overwhelm to Advantage in Business 17.06.2025

Do you ever feel like you’re walking around with your emotional skin turned inside out whenever you spot unfairness? This week’s podcast episode is for you!  I’m Diann Wingert, your neurodivergent navigator, and in this episode, we are unpacking the lesser-known ADHD traits of justice sensitivity—what it really is, why it matters, and how it could become your business’s hidden strength instea...

ADHD Business Coach Tips: Finding Your Flow as a Creative Solopreneur 10.06.2025

If you’re a multipassionate ADHD-ish creative who tends to be much better at starting a project than finishing it, wonders if it’s really possible to stand out in a crowded market, and struggles to figure out how to make a living from art and make a difference in the world,  this Client Success Story episode will resonate with you, big time.  My guest today is one of my favorite people,...

Mind Traps & Thought Loops: Identifying Cognitive Bias in the ADHD Brain 03.06.2025

If you’ve ever invested time or money into a “sure thing” that fizzled, or found yourself insisting, “this time I’ll stick to my schedule!” (despite plenty of evidence to the contrary), you’re not alone. We are talking about cognitive biases, those sneaky mental shortcuts that shape our decisions, our stories, and, often, our downfalls. Cognitive biases aren’t unique to ADHD brains; they’re a univ...

When Ambition Overtakes Performance: A Guide for ND Founders 27.05.2025

Learning to align our drive and ambition with our genuine capacity tends to be one of those lessons that ADHD entrepreneurs learn the hard way - through cycles of shame, regret, and burnout.   But what if there is a better way, like listening to this conversation between two seasoned ADHD coaches? Meredith and I have both struggled with our own untamed ambition and learned that not all i...

Wicked Wisdom: Real Talk on Neurodiversity & Self Acceptance 20.05.2025

I decided to do something special for this episode, because this week is our 5th podcast anniversary (and it's also Mental Health Awareness Month.) One of the most challenging things about being neurodivergent is learning to accept ourselves in a world where being different often marks you as an outsider.  Using my obsession with Wicked and exploring four of Stephen Schwartz’s iconic songs&nb...

The Psychiatrist’s Take on Vulnerabilities in ADHD Entrepreneurship 13.05.2025

Ever wondered why the idea of working for someone else just never quite fit, or why chaos seems to call your name (and you answer with gusto)? If you’re an entrepreneur who’s found yourself drawn to the thrill of building your own path—and maybe even stumbled more than a few times along the way—you are going to love this week’s guest interview.  I recently sat down with Dr. Michael A. Freeman...

Shiny New Object Syndrome? Here’s How to Stop It From Sabotaging Your Success 06.05.2025

Our edge as entrepreneurs comes from spotting trends and launching fresh ideas. The problem? Most of us have a graveyard of half-baked projects, forgotten launches, half-written newsletters, and more orphaned tech tools than we care to admit.  Let’s face it: innovation is our ADHD advantage, but execution moves the needle.  Shiny Object Syndrome is not a quirky personality trait; our ADH...

Staying Strategically Solo as a Neurodivergent Entrepreneur 29.04.2025

If your head is spinning with marketing messages from high-profile coaches insisting you need a team, a course, a 6 or 7 figure business, when what you really want is flexibility and the freedom to do something you love on your own terms, this episode is your permission slip to have a simple, sustainable solo business. My returning guest, Maggie Patterson, joins me to chat about the significance o...

Beyond People Pleasing: Unlearning the Default Yes 22.04.2025

How often do you find yourself agreeing to something and later regretting it? Yeah, me too.  In fact, the majority of adults with ADHD identify as people pleasers, but there’s more to this knee-jerk reflex than meets the eye.  This solo episode is packed with actionable tips for unlearning the Default Yes, starting with identifying the role of our unique neurological wiring in this dynam...

Creative Sprint Days: One Entrepreneur's Solution for an ADHD-Friendly Business 15.04.2025

Trying to figure out what you need to do to make your small business more ADHD-friendly?  In today’s episode, I sit down with ambitious outlier, Evan Sargent to discuss how she built a business that allows her to thrive, stand out from the competition and honor her ADHD attributes and gifts.   With a background in graphic design and advertising, Evan transitioned from a fast-paced a...

Paying Less ADHD Tax: A Solopreneur's Guide 08.04.2025

It’s tax time here in the US, and those of us with ADHD traits are paying extra! Have you heard of the ADHD tax?  I’m referring to those invisible costs that affect entrepreneurs and solopreneurs with ADHD, draining not only finances but also well-being and relationships.  From late fees and impulse buys to missed deadlines and opportunities, these ADHD-related financial and time-related...

Innovative Solutions for ADHD Executive Functioning Challenges 01.04.2025

Sometimes, we don’t have the option of masking, hiding, and attempting to fit in.  As a female of color from an unstable family, today’s guest Mina Raver dropped out of high school after being identified as gifted and diagnosed with ADHD, Autism, and Oppositional Defiant Disorder.   This set her on a non-conventional path that has dramatically accelerated her growth. Mina has been d...

Becoming The Leader Your Business Needs 25.03.2025

If you are a neurodivergent business owner, one of the biggest challenges can be leading a team, especially if you lead an all-female team in a female-dominated industry like occupational therapy.   Today’s Client Success Story features Kirsten Beukes, who is the owner of an OT group practice in South Africa. Through our work together, Kirsten came to understand how her ADHD affects her...

Let Them See You: Marketing with Courage for Neurodivergent Business Owners 18.03.2025

So many small business owners obsess about how their ADHD struggles make things more challenging, but there is a bigger picture at play.  When you identify your ADHD strengths and use them as your competitive advantage, now you are cooking with gas.   My friend, Iris Goldfeder is a marketing strategist and owner of Gas Stove Creative.  She joins us today to talk about how she l...

Inbox Strategies That Work for Your ADHD Brain 11.03.2025

In today's fast-paced world, email management is a critical skill, but for those with ADHD,  constantly checking email can become an addictive habit and the source of our greatest distraction. Email acts as a digital slot machine for those with ADHD, creating a dopamine-driven cycle of constant checking in search of novelty and stimulation.  This behavior is about immediate gratification...

From Idea to Impact: Start a Revolution with Your Business 04.03.2025

Most soloists I know want to make a living on their own terms, but many are also driven by a bigger vision of making a difference,  infusing both passion and purpose into their work. Have you ever wondered if you and your business could start a revolution?   I sat down with Rochelle Moulton, a brand strategist, author, podcaster, and advocate for soloist consultants doing work that...

From Setback to Comeback: Strategies for Dealing with Disappointment 25.02.2025

Does disappointment seem to follow you at every stage of your entrepreneurial journey? In this episode, I’ll be sharing why running your own business can set the stage for letting yourself and others down, especially when ADHD is in the mix.  In this episode, I share common triggers for disappointment, from overloading yourself with too many clients to underestimating how long things will tak...

Pivot Your Way to a Stand-Out Business 18.02.2025

Brittany grew up in a family with a history of entrepreneurship. Both grandfather and father were small business owners, but, after witnessing the instability and uncertainty of self-employment firsthand, Brittany shied away from entrepreneurship, at least at first.   Over time, and by allowing herself to follow her curiosity and pivoting in response to changing market conditions, Britta...

The ADHD Entrepreneur's Guide to Confident Decision Making 11.02.2025

I love Cirque du Soleil, but running a business with ADHD can feel like a 3-ring circus inside your brain that’s not so fun.   We have countless decisions to make and without a decision strategy in place, our defaults of impulsivity, overthinking, and self-doubt will be running the show. The good news is that there are simple ways to not only make better decisions now, but gain decision...

ADHD-friendly Ways to Outsmart Procrastination 04.02.2025

When you have ADHD, you are no stranger to struggles with task avoidance, task completion, managing energy levels, and finding balance in your daily life. If you are self employed or run a business, these struggles can really eat into your productivity, passion and profits.   After hearing today’s guest share insights from her latest best seller, The Procrastination Playbook , in a webin...

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