Welcome back to ADHD-ish! I’m Diann Wingert, and in this episode, we’re addressing a question that many business owners with ADHD hesitate to ask themselves: Do you actually like the work that brings you your most reliable income?

Not just the money, but the day-to-day tasks, the routine, and the clients you serve month after month. Understanding neurodiversity means recognizing that what works for neurotypical business owners—predictable recurring revenue models—may actively sabotage your success.

Because so many of them hate to admit they don’t, I’m breaking down what I call the “recurring revenue trap”—the idea that true business maturity comes from stacking retainers, running memberships, or launching evergreen offers for that coveted, predictable income.

This myth is especially damaging for those of us navigating neurodiversity in business. But what happens when your ADHD brain, which craves novelty, challenge, and variety, clashes with the sameness and repetition these models demand?

If you’ve ever found yourself bored, resentful, or white-knuckling through work that “should” feel like a win, the problem isn't you—it's a structural mismatch between how neurodiversity is wired and traditional business models.

3 key takeaways for ADHD business owners:

• Predictability vs. Novelty: Recurring revenue models (like retainers and memberships) are built for brains that thrive on sameness and routine—not the dopamine-hungry ADHD brain, which craves novelty, challenge, and change. Understanding neurodiversity means designing around these realities, not fighting them.
• Structural Not Personal: Burning out on reliable income streams isn’t a failure—it’s a sign of structural mismatch. ADHD brains are wired to lose motivation with repetitive, predictable work. This is where value based pricing strategy becomes essential—charging for outcomes and transformation, not time.
• Design for Your Brain: You DON’T have to quit recurring revenue altogether. Instead, intentionally build novelty into your recurring offers—limited run cohorts, rotating scopes, themed “seasons,” and planned refreshes let you keep both financial stability and creative energy. A flexible retainer model can honor both your needs and your neurodiversity.

6 Dopamine-rich alternatives to boring recurring revenue models:

• Limited-run cohorts: Short sprints, not never-ending slogs
• Retainers with rotating scope: New focus each quarter keeps it fresh
• Memberships by season/theme: Built-in breaks & changing content
• Quarterly intensives: Ditch the monthly grind; go deep, then rest
• Planned sunsets: Don’t beat dead offers—set a clear end date!
• Built-in refreshes: Schedule reinventions before boredom strikes

The offer you’re white-knuckling today is NOT the offer that’ll get you to the next level. Try, tweak, or sunset—but make it on YOUR terms.

Mentioned during this episode:

Episode #238_Creative Sprint Days: One Entrepreneur’s Solution for an ADHD-Friendly Business, with Evan Sargent

Other episodes in the series:

Ep #315: How Successful ADHD Entrepreneurs Trigger Hyperfocus on Demand

Ep #317: Time Blindness is a Pricing Problem, Not Just a Productivity Problem

Your ADHD-ish ™ host, Diann Wingert Diann Wingert is a business strategist, coach, serial entrepreneur, former psychotherapist, and passionate thought leader at the intersection of ADHD and entrepreneurship. In addition to hosting the ADHD-ish ™ podcast, Diann is the creator of The ADHD-ish ™ Method, a practicing Buddhist, dog mom, and relentlessly curious human.

Want help to reimagine business with your ADHD traits in mind? Schedule a free consultation to explore 1:1 ADHD entrepreneur coaching with ADHD business strategist and coach, serial business owner, and former licensed psychotherapist, Diann Wingert.

For more ADHD-informed business strategies, follow ADHD-ish for the rest of the Reframing Your ADHD Traits as Business Strategies, as well as inspiring guest interviews and real client success stories! Subscribe/Follow ADHD-ish on Apple or Spotify

© 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Welcome back to ADHD-ish!

In this episode, I sit down with Paul Pape, a creative business coach who brings creativity and playfulness to entrepreneurship by turning business strategy into an adventure—literally.

Together, we explore the starving artist myth, the difference between creatives and artists, and why traditional business advice often falls flat for "cloud thinkers" with ADHD.

You'll hear behind-the-scenes stories about rescuing multi-million dollar businesses with a single round of "D&D Business Edition," how self-knowledge (and a character sheet!) can help you embrace your quirks, and find profit, purpose, and magic—on your own terms.

Whether you’re a seasoned creative entrepreneur or wondering how to turn your neurodivergence into your greatest asset, this conversation is filled with wisdom bombs, real talk, and practical strategies for making business—and life—a game worth playing.

Here are my top 3 takeaways for creative entrepreneurs and fellow neurodivergents:

• Gamify for Engagement: Turning business challenges into quests (not just tasks!) makes even the most daunting to-do list approachable and—dare I say—fun. Paul swears by quest structures with tangible rewards to help ADHD brains stay motivated and follow through.

• Identity Is Your Superpower: Creating a "character sheet" for yourself enables candid self-reflection, minus the ego panic. It’s a way to step outside traditional business coaching and unlock rapid personal growth—especially for those who hide or mask their real selves.

• Redefine Success on Your Terms: Not every creative business needs to scale. chooses bespoke, deeply connected work over group programs and mass-produced results. The real magic? Custom approaches lead to legacy-building impact for both coach and client.

Ready to gamify your business? Take Paul’s personality quiz at www.gamifybusiness.com/quiz

About today’s guest, Paul Pape:

Despite the challenges of running an all-custom operation—a model many believe is doomed to fail—Paul Pape has been thriving, creating more than 3,000 original products for an impressive roster of clients, including Disney, Universal, and Nickelodeon, as well as individuals from around the globe. His unwavering dedication and inventive spirit have sustained his business for over 20 years, proving that passion and adaptability can defy the odds.

In addition to his custom design work, Paul runs Gamify Business, where he is the barkeep in a tavern for creatives. Tapping into his neurodivergent nerdery, Paul takes boring business practices and translates them into gaming themes and terminology. Character classes instead of customer avatars, quest lines instead of project plans. Want to chat with Paul about your business quest? The barkeep is in, so pull up a stool.

Paul’s Body of Work:

Gamify Business

TEDx Talk: Santa for Nerds

Paul’s Books:

Stop Selling Your Shit

The Creative Player’s Handbook to Business

Paul Pape Designs

Your ADHD-ish™ host, Diann Wingert

Diann Wingert brings decades of experience as a psychotherapist and serial business owner and is now a sought-after coach to entrepreneurs with ADHD traits.

Her style is direct, strategic, and always honest—peppered with the insight of someone who lives and breathes the neurodivergent experience.

Diann is a fierce advocate for self-acceptance and meaningful growth at the intersection of neurodivergence and entrepreneurship.

She is the creator of the ADHD-ish Method and host of the top-rated ADHD-ish podcast. Diann is many things, but she is not a gamer. She is, however, learning to tap into her nerdy side.

Mentioned during the episode:

Dragons & Beasties‍ ‍ Breaking Bad‍ ‍Dungeons & Dragons‍ ‍World of Warcraft‍ ‍Joe Dispenza: Breaking the Habit of Being Yourself‍ ‍‍ ‍Vincent Van Gogh‍ ‍Jackson Pollock‍ ‍The Industrial Revolution‍ Target‍ ‍TJ Maxx‍ ‍Tim Burton‍ ‍Nightmare Before Christmas‍ ‍Danny Elfman‍ ‍Johnny Lam’s You Are Player 1 ‍

Loved this episode? Leave a review and tell us why!

© 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

When many leave traditional employment to start their own business, they dream of freedom, creativity, and fulfillment. Yet the reality often looks eerily familiar.

Even after making that bold leap, it’s easy to recreate the same patterns and pitfalls from corporate life—scope creep, burnout, and that ever-present sense of chasing moving goalposts.

For today’s guest, Jabari Allen, a tech consultant specializing in AI reliability, the early entrepreneurial road was filled with the same energy-draining dynamics he’d hoped to escape.

But what makes Jabari’s story so unique is the intersectionality at play: building a business while navigating the realities of being Black and neurodivergent in the predominantly white tech industry.

Jabari shares what it feels like to be “the only one” in the room, and how owning every facet of his identity—rather than hiding or compensating—becomes the most radical business strategy of all.

This Client Success Story is a vulnerable and inspiring conversation about evolving your entrepreneurial identity and what is possible with a thought partner who challenges you to move beyond proving your worth into owning your power.

Here’s What You’ll Learn in This Episode

• Trusting Your Intuition Matters: What it really means to listen to your gut in business, especially when everyone else seems to know better
• People-Pleasing Isn’t Always Obvious: Discover the sneaky ways people-pleasing shows up for entrepreneurs—and why setting boundaries is actually better for you and your clients
• Intersectionality & Self-Advocacy: Gain insight into what it’s like to navigate tech as a Black neurodivergent professional, and how those layers shape confidence and communication
• Embracing Your Thought Leadership: Learning how to shift from “technician” to “expert”—and how the simplest offer can be both disruptive and profitable

Fun Fact from the Episode

There’s a term in the tech industry for endlessly fussing with tiny details called “yak shaving.” Turns out, it’s not just about perfecting code—but can be a major sign you’re avoiding a bigger decision. Jabari calls it circling the drain, and I refer to it as fluffing the pillows.

Whether it's the obsessive nature of ADHD perfectionism, anxiety about feeling we need to prove ourselves, or keeping ourselves too busy with the small stuff to confront the big stuff, or a combination plate of all of the above, set a limit on this tendency to keep from holding yourself back while feeling productive.

Connect with Jabari Allen: Website - Substack - LinkedIn

Is it time to redefine your success as a business owner with ADHD, and shift from proving your value to owning your expertise?

The first step is scheduling a free consultation where we talk about your goals and see if we are a good fit. Click here to book yours now.

Click here for the custom playlist of more ADHD-ish™ Method Client Success Stories

And, don’t forget to leave a comment on Spotify (I personally respond to every one) or leave a review so more ADHD-ish business owners can find THE podcast full of real talk and real solutions for neurodiverse business brains.

© 2026 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

‍From her unexpected rise as an ADHD comic creator to pouring over 3,000 hours into designing The Anti-Planner, a "productivity spell book," Dani Donovan is a force of nature.

In this lively interview, Dani shares her unfiltered journey of building a tool for people tired of feeling like failures, dealing with the emotional roller coaster of intellectual property theft, and navigating impostors selling shoddy knockoffs of her labor of love.

‍We discuss what goes into protecting your intellectual property as an entrepreneur, why valuing your own creative work is vital, and what Dani wishes she’d known before dealing with copycat chaos and the steep cost of defending her business.

Her story underscores why trademark protection and legal safeguards aren't luxuries—they're essential armor for small business ownership.

‍If you’ve ever obsessed over planners you never use, struggled with perfectionism and procrastination, or wondered what it really takes to launch and protect something one-of-a-kind—this episode will resonate.

‍Get ready for hard truths, laughter, and transparency about the messy realities of ADHD entrepreneurship.

‍

Key takeaways for fellow creators and founders:

‍Protect Your IP Early - Dani Donovan’s story underscores the importance of copyrighting your content and considering trademarks before you reach mass awareness—even an overseas copyright or trademark if necessary.

Counterfeiting Can Happen to You - Whether you’re just starting out or have a viral hit, don’t assume your business is “too small” to be targeted. Copycats watch for what’s trending, and success makes you a target.

‍Community & Transparency Matter - Sharing the messy, challenging parts (like publicly addressing counterfeiting) can activate support from customers and fellow entrepreneurs—and may even lead to further growth and visibility.

‍Fun Fact From The Episode

‍When the first shipment of the Anti-Planner arrived, people (including myself) literally hugged it to their chest—and it wasn’t by accident! Dani intentionally made it “therapy pillow-sized” based on how she wanted users to feel about it.

‍

About today’s guest, Dani Donovan:

‍Dani Donovan is an award-winning designer and creator of the viral hit product, "The Anti-Planner: How to Get Sh*t Done When You Don't Feel Like It." Known for her relatable ADHD comics, tweets, and TikToks, she's been helping shape the online neurodiversity community since 2018.

Dani was the closing keynote speaker at the 2021 International ADHD Conference, and her work has helped thousands of people seek an ADHD diagnosis and treatment.

Mentioned during the episode:

‍Alibaba ‍ - Steve Peha - Copyscape Plagarism Checker ‍- MarqVision Brand Protection Agency

‍

About the Anti-Planner:

‍Tapping into her own frustrations and the lived experiences of ADHD peers, Dani Donovan spent over 3,000 hours creating The Anti-Planner, a “productivity spellbook”—a lovingly designed, non-linear, highly personalized compendium of over 100 strategies for overcoming procrastination and building emotional resistance.

‍Dani obsessed over every detail: the comforting size, playful illustrations, durable faux-leather binding, gold foil, thick paper, pen loop, and rounded corners. It is gorgeous, practical, and nothing like all the planners you’ve bought and abandoned two weeks later. I absolutely love mine!

‍Buy your copy of the Original Anti-Planner here. (Dani also has a Clean version if you are not so sweary…)

‍ ‍

Your ADHD-ish™ host, Diann Wingert

‍Diann Wingert brings decades of experience as a psychotherapist and serial business owner to coaching entrepreneurs with ADHD traits. Her style is direct and strategic, with a dash of humor, and filled with the insights of someone who lives and breathes the ADHD-ish™ experience. Diann is the creator of the ADHD-ish™ Method, host of the top-rated ADHD-ish™ podcast and proud mom of three neurodivergent adults.

‍ ‍‍ ‍

Should I have Dani back again?

Want Dani Donovan to return to ADHD-ish™ to talk about what actually happens when your business scales way faster than you expected? Let us know by leaving a voice message here or sending an email here. Thanks!

‍ ‍

© 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

‍Traditionally seen as a productivity flaw, time blindness is revealed here as a money problem, quietly undermining pricing, profits, and self-worth for solopreneurs with ADHD.

This episode explores why common fixes like timers and time blocking miss the deeper issue, and instead, offers practical ways to design around the unique ADHD brain.

Listeners can expect actionable tools—like range pricing, value-based pricing, and multipliers—to help create smarter, ADHD-friendly business practices.

Key Takeaways:

1. Why time blindness is more of a money issue than a productivity problem

Missed deadlines are visible, but it’s the underpriced projects and unseen labor that are draining your profits.

2. How the ADHD brain’s sense of time impacts your pricing (and sends you into the red)

3. Why accurate estimation is a myth—and what to do instead

Spoiler: The strategic move is to build pricing that works with your brain

The Three Places You’re Losing Money

The invisible cost of time blindness shows up in three big ways in most service-based businesses—and maybe in yours too:

● Quoting New Work: Saying “yes” to projects we’ve never done, referencing a project that only looks similar, and then confidently (but cluelessly) assigning a price. Inevitably, unknowns explode, and you end up working for free

● Scoping Familiar Work: Every project you think you know by heart, but memory only shows you the highlight reel.

● Hidden Labor: The worst offender. All the little admin tasks, endless revisions, back-and-forth emails, and extra meetings never get included in my quote. They don’t feel like “billable” work, but they devour hours and energy in unpaid work.

Six Pricing Strategies that Correct The Effects of Time Blindness:

● Range Pricing: Quote within a range, not a fixed number.

● Value-Based Pricing: Charge for outcomes, not hours.

● Multipliers & Buffers: Take your default quote and multiply it (1.5x, 2x, even 2.5x if you’re feeling brave).

● Project vs. Hourly Pricing: Bill by project, not hours, so you’re aren’t penalized for hyperfocus sprints

● Built-In Revision Rounds & Communication Caps: Set clear boundaries on extra work and comms, and make it official.

Time blindness isn’t going away—but by meeting your brain where it is, you can transform ADHD traits from liabilities into business assets. Design your pricing not despite your ADHD, but in partnership with it—and start keeping your hard-earned money where it belongs: in your business.

Try The Multiplier Experiment on your next proposal:

1. Write down the number you want to send.

2. Multiply it by 1.5x (or higher—it should feel just a bit stretchy).

3. Send that quote. Notice the resistance, the stories, the “what ifs.”

4. Collect the data: Did the client say yes? No? What did you learn?

Every proposal is a data point for better pricing decisions. Stop leaving money on the table!

Research on ADHD & time blindness

Your ADHD-ish ™ host, Diann Wingert

Diann Wingert is a business strategist, coach, serial entrepreneur, former psychotherapist, and passionate thought leader at the intersection of ADHD and entrepreneurship. In addition to hosting the ADHD-ish ™ podcast, Diann is the creator of The ADHD-ish ™ Method, a practicing Buddhist, dog mom, and relentlessly curious human.

Diann explains neuroscience in a relatable way. Through her accessible storytelling, Diann empowers others to understand their brains, manage their energy, and show compassion to themselves as they navigate the demands of being a business owner and in their everyday lives.

Resources Mentioned in This Episode:

Sign up for Di AI, my ADHD business coach digital clone, for free: https://bit.ly/di-ai-access

Make sure you don’t miss the next episodes in this “Reframing Your ADHD Traits as Business Strategies” series. Subscribe/Follow ADHD-ish on Apple or Spotify

Want my help to build your business with your ADHD traits in mind? Schedule a free consultation to explore 1:1 ADHD entrepreneur coaching.

‍ ‍

© 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Ever wondered how someone with a full plate—a thriving business, a family, a neurodiverse household, AND a stack of published books—still finds time to sleep?

Or better yet… how they use their ADHD to power all of it? If you’ve ever felt overwhelmed by your own creativity or wondered if you’re “too much,” you’re going to love this interview with returning guest and my SEO consultant, Meg Casebolt. Her approach to neurodiversity in business proves that ADHD can be a strategic advantage, not a limitation.

Meg is an entrepreneurial powerhouse who perfectly embodies the phrase “multi-passionate with a mission.” I’m talking about building a successful SEO consultancy while cranking out several romance novels, nonfiction books, and helping others find their voices—all with the magic (and occasional mayhem) of an ADHD brain. Her writing strategy and approach to creative writing offer a blueprint for managing multiple projects without burning out.

This is not a conversation about “doing it all.” It’s about how to let your brain’s unique wiring become your greatest asset. Meg shares candidly about her writing journey: from being a childhood word nerd, to losing the joy of writing through academia’s rigidity, and then rediscovering the creative spark during the uncertainty of the pandemic.

Ever felt like your nervous system is on overdrive? You’re not alone—turns out writing romance novels was exactly what Meg needed to dial down anxiety and reclaim hope. This is neurodiversity in business at its most authentic.

Here are my top 3 takeaways from our chat:

• Creativity Needs Structure:

Meg breaks big projects like writing novels and business books into manageable, bite-sized sessions—30 minutes a day can add up to published work and reduced overwhelm.

• Curate Your Input to Cultivate Your Output:

Both of us have found that reducing media consumption and focusing on our unique perspectives boosts creativity and clarity—whether you’re writing, building, or rebranding.

• Honor Your Brain (and Your Needs):

It’s not about doing it all—it's about doing what fuels you. Speaker B balances left- and right-brain work, has learned to say no to platforms that drain her energy, and finds flow by following her interests and intrinsic motivations.

About today’s guest, Meg Casebolt:

Meg Casebolt helps experienced founders, consultants, and creators become findable in AI-powered search—not through keyword tactics, but through strategic authority positioning.

As founder of Love At First Search, she works with experts who don’t need more SEO advice but do need a new way to be understood by modern search systems.

Her approach focuses on helping people become quotable and recommendable: teaching them to claim specific expertise territory and build the signals AI uses to evaluate credibility.

Diann’s Note: After I lost 10k followers on social media accounts overnight due to hackers, I was determined to learn SEO and started working with Meg. Within 1 year, I rank at the top of all search engines in my niche, and 50% of my clients now find me through online search.

Meg’s Body of Work:

Love at First Search / Signal - SEO membership program (affiliate)

Aggressively Human podcast with Jessica Lackey

Social Slowdown Meg’s podcast and book

Happily Ever Indie - for self-published romance authors

Meg’s romance novels under her pseudonym Bailey Seaborn

Recommended by Meg during the episode:

Lacy Boggs, The Content Direction Agency

Joanna Wiebe - 12 Books That Will Make You Insanely Smart

Your ADHD-ish™ host, Diann Wingert

Diann Wingert brings decades of experience as a psychotherapist and serial business owner and is now a sought-after coach to entrepreneurs with ADHD traits.

Diann is a fierce advocate for self-acceptance and meaningful growth at the intersection of neurodivergence and entrepreneurship. She is the creator of the ADHD-ish Method and host of the top-rated ADHD-ish podcast.

Connect with Diann

Ready to work with an ADHD-informed business strategist and coach? Book a free consultation with me.

© 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Welcome back to ADHD-ish™, where we're kicking off a five-episode series reframing the most talked-about ADHD traits as tools for entrepreneurial success, starting with hyperfocus.

Forget the myth that hyperfocus is a rare, unpredictable gift. ADHD-ish™ host, Diann Wingert, reveals that the most successful ADHD entrepreneurs create the conditions for hyperfocus rather than hoping it just shows up.

Here’s the game-changing insight:

Hyperfocus is a state, not a fixed trait—and you can stack the deck to get into it on demand.

3 Key Takeaways:

Engineer Your Hyperfocus: Don’t wait for the muse—set up conditions like real deadlines, novel environments, meaningful rewards, supportive sensory cues, and a nourished body to invite focus on demand.

Body Doubling is a Real Strategy: Working alongside others—friends on Zoom, coworking sessions, or even a busy coffee shop—provides social accountability and can reliably spark focus.

Stack Conditions, Not Guilt: Hyperfocus isn’t about willpower; it’s about stacking multiple supportive factors. Even intentionally stacking just two of these can create momentum in your business.

Hyperfocus can be a genuine business asset—if you learn to direct it. But, there are hidden costs to hyperfocus, too:

• Mental exhaustion and decision fatigue
• Neglected relationships
• Other parts of your business are left idle

Remember: Hyperfocus is a power tool. Use it wisely—and plan for the comedown.

What’s My Hyperfocus Setup?

In my own business, I decide, ahead of time, exactly what needs my hyper-focused attention and how much time I’ll devote to it.

The routine is precise: comfortable clothes, a high-protein breakfast, natural light, a pre-game ritual of exercise, sunshine, and social connection. And hydration throughout the hyperfocused state. No brain jerky for me.

What’s not in my routine: willpower, white-knuckling, bullying myself or shame. The environment is repeatable, the stakes are real, and the body, mind, and brain are primed and ready. After it's over? Rest, recalibration, and reconnection.

Hyperfocus as Skill - Start Here:

Pick one 90-minute block of business-critical work.

Deliberately create at least two of the five conditions above.

Do the work—and observe the impact on your focus.

Don’t be an overachiever and do all five. Start small, track the effect, and iterate. It’s not a productivity contest—it’s your personal hyperfocus experiment.

Resources mentioned in this episode:

Focus Mate

Focused Space (affiliate link)

Zoom

Spotify playlists

Your ADHD-ish ™ host, Diann Wingert

Diann Wingert is a business strategist, coach, serial entrepreneur, former psychotherapist, and passionate thought leader at the intersection of ADHD and entrepreneurship.In addition to hosting the ADHD-ish ™ podcast, Diann is the creator of The ADHD-ish ™ Method, a practicing Buddhist, dog mom, and relentlessly curious human.

Diann explains neuroscience in a relatable way. Through her accessible storytelling, Diann empowers others to understand their brains, manage their energy, and show compassion to themselves as they navigate the demands of being a business owner and in their everyday lives.

Want more strategies for time blindness, novelty chasing, object permanence issues, and procrastination? Make sure you don’t miss the next episodes in this “Reframing Your ADHD Traits as Business Strategies” series. Subscribe/Follow ADHD-ish on Apple or Spotify

Want my help to build your business with ADHD in mind? Schedule a free consultation to explore expert ADHD entrepreneur coaching with Diann Wingert

© 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

ADHD fundamentally impacts executive function—the mental skills for planning, prioritizing, delegating, and following through. So, when an entrepreneur hires a VA and is expected to onboard, direct, and give detailed instructions, they’re faced with a mismatch: the very skills they struggle with are those they now must use to instruct their assistant.

Traditional VAs, trained to “do what they’re told,” end up sitting idle, waiting for direction, while the entrepreneur is paralyzed by indecision and shame. The result? Money is wasted, little is accomplished, and increased frustration, making it even harder to try again.

What if support could be different? What if, instead of looking for a “unicorn” VA who can do everything, ADHD entrepreneurs sought out “distant assistants”—human lifelines who specialize in executive functioning, regulated communication, and operationalized thinking?Today’s guest is Avigail (Avy) Schondorf, fellow ADHD entrepreneur, podcaster, and owner of the Alisto agency that trains and outsources distant assistants who understand what neurodivergent business owners really need.

This conversation is full of insights, humor, cringeworthy moments, and a new paradigm for shame-free support.

Here are 3 key takeaways for anyone considering hiring support:

• A “bad” solution is not worse than no solution. Many ADHD entrepreneurs avoid help out of fear that it won’t work, but that only fuels more shame and wasted energy.
• Don’t wait for the “perfect” moment or system. The real tipping point isn’t having more work—it’s being ready to ask for what you need, without shame.
• Stop looking for unicorns—lean into teams. Expecting one assistant to do everything sets everyone up for failure. Specialized support means you (and your VA) can play to your strengths.

If “doing it all myself” isn’t scalable OR sustainable, maybe it’s time to delegate differently—and embrace asking for help as a sign of strength.

About today’s guest, Avigail (Avy) Schondorf:

Avigail (Avy) Schondorf is a social worker turned entrepreneur who built two companies around the way her brain actually works.

She's the founder of Alisto Virtual Workforce, a team of Distant Assistants who specialize in supporting neurodivergent entrepreneurs — and AvyHD, her strategy and thought leadership brand where she gets real about ADHD, delegation, and building a business without burning out.

When she's not running her team or hosting the AvyHD Podcast, she's lifting weights, reading, or wrangling two very energetic daughters.

Connect with Avy:

• Website
• AVYHD podcast
• LinkedIn

Mentioned during this episode:

Avigail’s Octopus prompt

Jamie from Bottleneck Distant Assistant

My interview on Avi’s podcast, “Consistency, the Other C Word for ADHD Entrepreneurs”

Your ADHD-ish™ host, Diann Wingert

Diann Wingert brings decades of experience as a psychotherapist and serial business owner and is now a sought-after coach to entrepreneurs with ADHD traits. Her style is direct, strategic, and always honest—peppered with the insight of someone who lives and breathes the neurodivergent experience.

Diann is a fierce advocate for self-acceptance and meaningful growth at the intersection of neurodivergence and entrepreneurship. She is the creator of the ADHD-ish Method and host of the top-rated ADHD-ish podcast.

Links:

Follow / Subscribe to ADHD-ish so you don’t miss an episode

Ready to work with an ADHD-informed business strategist and coach? Visit my website.

© 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

You’ve scrolled past Mental Health Awareness Month posts thinking, “That doesn’t apply to me.”

Your business looks fine. On the surface, YOU look fine. But what if the very skills driving your success are quietly putting your mental health at risk?

The ADHD-ish ™ Podcast tackles the conversations mainstream mental health awareness misses—especially for high-functioning ADHD entrepreneurs.

For those with ADHD, the world often evaluates “functioning” based on visible output, and being able to run a business is seen as “high functioning.”

But the trap is that the more capable and outwardly composed you appear, the less likely you—and others—are to notice when your mental health is slipping.

This isn’t about denial. It’s the same creativity, drive, and resilience that helped build your business that masks the warning signs.

What looks like ambition could be an ADHD brain that never learned to stop, rest, or celebrate. This is the hidden reality of ADHD entrepreneur chronic stress.

Your ability to “power through” is precisely what puts you at risk for long-term exhaustion, burnout, and a quiet form of isolation.

Four hidden risk categories:

These are thinking patterns that feel like logic but quietly work against us. Do any of these sound familiar?

• The perpetually moving finish line (rest is always “after the next thing”)
• “I work better under pressure” — sound familiar? It’s a seductive trap, not a strategy!
• Comparing your struggles to others and invalidating your own needs

You might think you’re resting when you’re actually just switching to a different kind of stimulation (hello, endless content consumption!).

Genuine restoration often looks like boredom at first, but it’s what your mind and body actually need.

High-functioning ADHD people are notorious for skipping the habits that keep us steady, especially when we need them the most.

• Jumping right back into work after time off? That’s the “vacation tax.”
• Ditching sleep, movement, and real food when stress rises? That’s called “stress inversion.”
• Having no interests or life outside your business? That’s a hidden drain on your energy and identity.

Busyness can become a mask for loneliness. Relationships that aren’t transactional quietly disappear, and your sense of self can erode until it’s fused with your business.

If your only role is “the one who has it together” for everyone else, this one may hit home especially hard.

You are not broken. These patterns are the predictable result of managing ADHD in a career that rewards output and intensity.

If you recognize yourself in this description, don’t make it another to-do item. Instead, let this be an invitation: Pause. Notice. Take your own needs seriously, even—and especially—when you’re “doing well.”

Your mental health is always worth protecting, no matter how high-functioning ADHD you appear to others.

Your ADHD-ish ™ host, Diann Wingert

Diann Wingert is a business strategist, coach, serial entrepreneur, former psychotherapist, and passionate thought leader at the intersection of ADHD and entrepreneurship.

In addition to hosting the ADHD-ish ™ podcast, Diann is the creator of The ADHD-ish ™ Method, a practicing Buddhist, dog mom, and relentlessly curious human.

Diann explains neuroscience in a relatable way. Through her accessible storytelling, Diann empowers others to understand their brains, manage their energy, and show compassion to themselves as they navigate the demands of being a business owner and in their everyday lives.

Try out “Di AI”—my digital ADHD business coach

I have spent the last several months training and fine-tuning Di AI with The ADHD-ish ™ Method frameworks, strategies, and mindset tools. Not quite ready to work with an ADHD business coach? Di AI is currently in beta, and you can get access for free.

Ready to work with an expert ADHD entrepreneur coach? Most of us started out bootstrapping our business and raw dogging everything on our own. But that approach will only get you so far.

If you want to get further and faster, it might be time for the guidance, support, and accountability you can only get from working with an expert strategist and coach. Book a free consultation to see if we are a fit.

And remember: You are never too high-functioning for your own mental health to matter.

© 2026 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Welcome back to ADHD-ish! In this episode, my guest Ian Wilson, a creative agency owner of over 16 years, is what I call a natural-born entrepreneur.

From hustling for his first job at age eleven to building a unique partnership with his neurodivergent business partner Eric, Ian sheds light on why traditional approaches to team building rarely work for people whose brains are wired a bit differently.

We’ll hear how Ian and Eric’s complementary neurotypes—ADHD and autism - have enabled them to build a successful agency grounded in autonomy, mastery, and ownership.

Ian shares lessons learned on building a team of “hurricane chasers,” hiring for attitude over experience, and why the bold move of unapologetically charging what you’re worth doesn’t just benefit the business—it creates a thriving company culture.

Whether you’re a founder who is churning and burning team members or a solopreneur anticipating that first hire, this episode is packed with practical advice, refreshing honesty, and plenty of laughs about what happens when you fully embrace the ADHD-ish way of doing business.

Three key takeaways:

• Self-awareness and self-acceptance matter more than “best practices.” Knowing what you’re brilliant at—and what you hate—makes it so much easier to build a business (and find team members) that complement your strengths and support your growth.
• Hire for traits, not just skills. Ian’s team isn’t made up of “perfect resumes” but of entrepreneurial thinkers who enjoy solving problems and don’t need to be micromanaged. Find the ones who vibe with your approach and love challenging themselves to figure things out.
• Be bold about your value. Ian & Eric tell prospects: “We’re probably the most expensive quote you’ll get—and here’s why.” Setting unapologetic boundaries not only draws the right clients but also creates a culture of excellence and transparency.

Mic Drop Moment:

Ian & Eric deliberately hire people who crave these three things, no matter their resume. Their neurodivergent advantage? Investing in traits, not credentials.

• Autonomy: Freedom to do things your way.
• Mastery: The drive to get better and own your craft.
• Ownership: Feeling like your contributions actually matter.

About today’s guest, Ian Wilson:

Ian is the Co-Founder and Creative Director of buildcreate, a full-service B2B marketing agency for manufacturing, technology, engineering, and industrial clients in Ann Arbor, Michigan.

Home-schooled and entrepreneurial from childhood, Ian discovered his ADHD as an adult. He and his business partner, Eric Lynch, who is autistic, have discovered that their secret sauce as neurodivergent leaders is to hire smart people and let them work to their strengths.

Connect with Ian:

LinkedIn- Company Website - Email

Your ADHD-ish host, Diann Wingert

Diann Wingert brings decades of experience as a psychotherapist and serial business owner and is now a sought-after coach to entrepreneurs with ADHD traits.

Diann is a fierce advocate for self-acceptance and meaningful growth at the intersection of neurodivergence and entrepreneurship. She is the creator of the ADHD-ish Method and host of the top-rated ADHD-ish podcast.

Mentioned during this episode:

Ep # 303: Which Company Culture is Your ADHD Brain Building?

Links:

Follow / Subscribe to ADHD-ish so you don’t miss an episode

Know another entrepreneur with ADHD who thinks there is only one way to build a team - the neurotypical way? Share this episode.

Ready to work with an ADHD-informed business strategist and coach? Visit my website.

© 2026 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops/ Outro music by Vladimir / Bobi Music / All rights reserved.