ADHD-ish™

In a world where technology promises to simplify our lives, how do those of us with ADHD – notorious for our resistance to structure – harness that promise without abandoning our critical thinking or our humanity?
Join me for this conversation with my client, Elizabeth Meyer - professor, coach, and self-described AI skeptic, who offers a roadmap for experimenting wisely with AI-powered tools, while staying loyal to our own brains, values, and need for connection.
When Elizabeth was first offered the opportunity to sign up for my digital clone, Di AI, she hesitated. Then she did something unexpected - she designed an experiment to put Di AI and herself to the test. Elizabeth brought a scientist’s rigor to the experience – scheduling regular sessions, setting clear goals, and running timers to structure her use, all to observe how the tool impacted her behaviors and mindset.
The episode explores:
How Elizabeth structured the experiment (including the infamous decision matrix and her “wildly unrealistic expectations”)
Surprising (sometimes maddening) moments where AI reflected “stupid common sense” she’d never considered
What ghosting an AI tool taught her about the difference between digital and human accountability
The unexpected role of values alignment and motivation for us “rebels”
Cautionary tales about outsourcing too much trust—or too much of ourselves—to technology
Why critical thinking and intentionality are the only way these tools ever work for ADHD-ish brains

Elizabeth and I share both the wins and the “facepalm” moments, plus an actionable tip sheet for anyone skeptical (or hopeful) about using AI for habit-building and organization.
Her pro tip: Judge the tool by the quality of questions it asks you
Don’t Miss:
Elizabeth’s three-question framework (adapted from Naturalistic Decision-Making) for deciding when and how to engage with AI tools—so you never cede too much power to an algorithm
If you’re tired of empty promises from productivity apps—or want a peek at what a scientifically-minded ADHD brain learns from kicking the tires on new tech—this episode is for you.
Fun Fact
Elizabeth shared a story about her 15-year-old niece who, when asked where they should go for dinner, responded: “I don’t know. Let me ask Chat.” The future is here and apparently it’s hungry for chatbot input

Your turn!
Make it practical: Use Di AI to help implement a tactic you picked up from the podcast, track specific goals, and follow up on progress.
Know your “why”: Consider the reason you are looking for accountability and fit AI into your schedule where you need a champion (hello, bookkeeping!)

If you haven’t signed up for Di AI yet - what are you waiting for? Here is the link to sign up for free.
Grab Elizabeth’s Tip Sheet for making the most of Di AI (or any AI app)

About today’s guest:
Elizabeth Meyers is an informatics professor, consultant, and owner of Deep Dive Strategies, where she advises early-stage startups and small companies on strategy and product design.
Driven by a fascination with how humans navigate complex environments, Elizabeth specializes in Naturalistic Decision Making (NDM), studying how experts make high-stakes choices in real-world settings.
As an entrepreneur who respects both human expertise and technology, she blends her deep background in technology and information science to explore how experts interact with AI.

Mentioned in this episode:
Conditions for intuitive expertise: a failure to disagree. Kahneman D, Klein G. Am Psychol. 2009 Sep;64(6):515-26. doi: 10.1037/a0016755. PMID: 19739881.
Naturalistic Decision Making Conference Michael Webb Presentation
Adam Mastroianni - “Bag of Words” post on Substack
DALL- E AI image generator
Ep #281: Find Your Flow: 3 Focus Days Models for ADHD Brains
Ep #212: Get More Done: How to Focus with ADHD & Take Real Action
The Four Tendencies - Elizabeth is a Rebel. What are YOU?
Identifying Your Core Values - self assessment
Jodie Cook, Founder of Coach Vox

Your ADHD-ish™ host, Diann Wingert
Diann Wingert is a former therapist turned coach, speaker, and consultant who blends her expertise in entrepreneurship and neurodiversity to help others thrive.
Host of the top-rated ADHD-ish™ podcast and creator of The ADHD-ish™ Method, Diann works with ADHD-ish™ business owners who are ready to create stand-out, sought-after, profitable businesses based on their unique brilliance.
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.

‍Welcome back to ADHD-ish! In this episode, host Diann Wingert closes out the five-part solo series, “Reframing ADHD Traits as Business Strategies.”
Today’s focus: the ADHD challenge of “out of sight, out of mind”—a.k.a. ADHD Object Permanence—and how it quietly drains money from your business. This is one of the most misunderstood ADHD strengths and struggles, and understanding it transforms your revenue.
Most people learned about object permanence as a developmental milestone in infants: it’s the reason peekaboo is so mind-blowing for toddlers. But for adults with ADHD, it’s not about missing a childhood milestone—it’s a “functional glitch” that endures throughout adulthood.
ADHD Object Permanence challenges aren't about immaturity; they're directly connected to how ADHD working memory functions differently from neurotypical brains.
If something isn't visible—literally in your line of sight—your ADHD brain tends to forget it exists.
In business, this means things like overdue follow-ups, unrevived client relationships, or forgotten services gather dust. This is one of the core ADHD strengths and struggles that impacts your bottom line.

Where Are You Leaking Money? ‍
I break it down into three layers:
1. Past Clients: Amazing people who loved working with you, would buy again, and just need a nudge. But if they’re not in your calendar or inbox—they don’t exist to your brain. Your ADHD working memory isn't the problem; your system is.
2. Leads in the ‘Dark Pipeline’: Warm prospects you were this close to converting…now forgotten until you randomly find that old email weeks later (and then feel the shame spiral). ‍This is ADHD Object Permanence in action—out of sight, completely out of mind.
3. Your Own Offers: Courses, workshops, or services you actually could be selling—but forgot you even have. How many revenue streams are invisible because of ADHD Object Permanence?
What’s the Fix? Structural Visibility ‍
Don’t go buying a new planner or promising to “try harder.” That’s not a strategy—it’s just more stress.
Instead, build software (aka systems!) around your brain’s “hardware” constraints. This is how you turn ADHD strengths and struggles into actionable business strategy.
Here’s How: ‍
● Use a CRM to remember leads for you—don't let your ADHD working memory be your only sales tool! This is structural support for ADHD Object Permanence.
● Block off time every week to review offers, check in on clients, and nudge those dark leads back into the light. Regular visibility beats relying on memory.
● Pre-schedule re-engagement emails for past clients + warm leads. Automation handles what ADHD Object Permanence makes invisible.
Where to start: ‍
Don’t overhaul everything at once. Pick one area—past clients, dark leads, or forgotten offers—and add a single piece of visibility this week. ‍
It could be as simple as pulling your last 20 clients into a spreadsheet or writing a list of every product you currently offer.
The important part is making invisible opportunities visible again. This is how you leverage ADHD strengths and struggles for revenue growth.

Mentioned in this episode: ‍
Laura Schulte - LinkedIn ‍
The Pipeline Compounder

Kit email marketing platform (affiliate link)
‍ ‍
Other episodes in the Reframing ADHD Traits as Business Strategy series: ‍
Ep #315: How Successful ADHD Entrepreneurs Trigger Hyperfocus on Demand ‍
Ep #317: Time Blindness is a Pricing Problem, Not Just a Productivity Problem ‍
Ep #321: The Recurring Revenue Trap: The Hidden Cost of Stable Income
Ep #323: What Procrastination, Resistance & Avoidance are Trying to Tell You About Your Business
‍
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.

In this episode of ADHD-ish, host Diann Wingert is joined by client, Kathryn Bird, a successful travel content creator and entrepreneur, as she opens up about the reality behind her seemingly enviable career.
Despite speaking at major shows and building an impressive business, Kat wrestled with overwhelm, time blindness, guilt, and the relentless expectations she placed on herself—classic hallmarks of living and working with ADHD.
Join us for an honest conversation about unraveling the tangled threads of passion, drive, and self-worth, and how doing "less but better" can transform both business and well-being.
Here are my top 3 takeaways for anyone feeling stuck in their own “success”:
You don’t have a million problems—just a few powerful patterns. Identifying and naming them makes change possible.
Your worth is not tied to your to-do list. Planning for realistic work hours, protected downtime, and recovery is the key to sanity and sustainability.
You get to define your boundaries. Say no, let go of what drains you, and protect your energy—even when it means “hiding” some of your projects from yourself if deleting them feels too scary.

If you find yourself working nonstop, feeling guilty about taking a break, or recreating old corporate patterns in your “dream job,” remember: nothing on your list is more important than your well-being.

About today’s guest, Kathryn Bird
Kat (she/her) is a former Royal Navy helicopter observer and London airspace air traffic controller turned travel blogger and entrepreneur. After leaving her high-pressure career to travel the world, Kat turned her passion into a thriving business, teaching and inspiring fellow adventurers through her content and memberships.
Her journey has been marked by remarkable achievements—and the hidden struggle of managing ADHD, perfectionism, and the pressures of self-employment.
Connect with Kat:
Website: https://www.wandering-bird.com/
Instagram: @wanderingbird.adventures.
YouTube: https://www.youtube.com/@WanderingBird

Your ADHD-ish™ host, Diann Wingert
Diann Wingert is a former therapist turned coach, speaker, and consultant who blends her expertise in entrepreneurship and neurodiversity to help others thrive.
Host of the top-rated ADHD-ish™ podcast and creator of The ADHD-ish™ Method, Diann works with ADHD-ish™ business owners who are ready to create stand-out, sought-after, profitable businesses based on their unique brilliance, while eliminating the extremes of boredom and burnout.

Inspired by Kat’s results & want to chat about what success can look like for YOUR business? Book a free consultation and let’s talk!

Want to listen to other Client Success Story episodes before booking that consultation appointment? I’ve got you. Here is the playlist.

Practical Takeaways
Be honest about what’s really on your plate. Track your time and get real with your expectations
“Nothing on this list cannot wait.” Borrow Kat’s mantra - perfect for ADHD overachievers
Rest is productive. Building in recovery weeks and being intentional about your workload makes all the difference
Let go (just a little). Not every idea, offering, or piece of content needs to be perfect or even used

Not ready for my six-month, one to one coaching program, but want an ADHD-informed, business savvy coach on demand? My digital clone, Di AI is free in beta.Just click the link and start chatting now!

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

Feeling stuck in a cycle of procrastination, resistance, and avoidance?
If you’re running a business with an ADHD brain, it’s time to stop fighting your nervous system and start listening to it. Understanding ADHD means recognizing that your resistance is data.
In this episode of the ADHD-ish™ Podcast, part of the Reframing ADHD Traits as Business Strategy series, I challenge the mainstream productivity tips, and offer a new perspective: Procrastination isn't always the enemy—it's often vital business information.

3 Key Takeaways:
Procrastination is a signal, not a personal failing. Your nervous system might be telling you something important about your business, like a task you’ve outgrown or a decision you haven’t fully made. This is how ADHD neurodiversity communicates through resistance.
Five “signals” behind resistance: Delegation (tasks you should hand off), Decision (incomplete choices), Sunset (offers you need to let go), Revenue (underpriced work), and Clarity (undefined scope/stakes). Most productivity tips miss these underlying issues entirely.
Don’t override, diagnose first. Before pushing through with more discipline, ask “What is this resistance telling me?”—then act on the real issue behind your avoidance. This diagnostic approach honors ADHD neurodiversity.

The Reframe: Procrastination is regulatory, NOT motivational.
Your nervous system is sending a protective signal, not exposing a character flaw or lack of discipline. For ADHD neurodiversity, this shows up when something is off below the surface—even if you don't consciously know what it is. This is why traditional productivity tips often fail.

Next time you find yourself stuck, don’t reach for another productivity hack. Instead, ask: “What is my resistance trying to tell me?”
Then act on the message, not just the task. Your business, and your brain, will thank you. This is what working with ADHD neurodiversity—rather than against it—actually looks like.

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
Ep #321: The Recurring Revenue Trap: The Hidden Cost of Stable Income
Looking for an ADHD-informed business coach that is available on demand? Sign up for my digital clone, Di AI Beta access is still free and available now!

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. 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 to another episode of ADHD-ish, where we explore the lived realities, hidden challenges, and unique gifts of being neurodivergent in business and life.
Today’s episode is an intimate conversation between friends, colleagues, and fellow neurodivergent entrepreneurs.
Returning guest, Dr. Naketa Ren Thigpen, is an expert at the intersection of relationships and entrepreneurship, who has made the decision to forgo a formal diagnosis, while fully accepting her ADHD traits.
Together, we explore how trauma, workarounds, and unapologetic authenticity shape both personal growth and professional impact.

3 Key Takeaways:
Workplace Dynamics Are Deeply Human: So many organizational challenges stem from unresolved personal issues that show up at work. As Naketa says, bringing relational intelligence into organizations is the next frontier for trust, performance, and true inclusion.
Diagnosis Isn’t Required for Legitimacy: You don’t need a formal diagnosis to embrace your neurodivergent identity. For some, building effective "workarounds" is enough to thrive—labels can be empowering for some and unnecessary for others, as powerfully shared.
Hyperfocus Is a Super Tool—With Boundaries: Our ability to “hear the words and the music”—to focus deeply and be truly present—is a neurodivergent gift. Guarding these focus states with strong boundaries is key to making the most of them, both in business and personal growth.

About today’s guest, Dr Naketa Ren Thigpen
Dr. Naketa Ren Thigpen is the Architect of Intimacy in Innovation, the world's foremost Balance (and) Relationship Advisor, and Co-Founder and CEO of ThigPro Balance (and) Relationship Management Institute.
Embodying her wild & rare nature, she moved beyond traditional therapy into something the industry hadn't seen.
Double Board Certified and doctorate-trained in Relationship Dynamics, Dr. Naketa licenses Applied Relational Intelligence Systems to mid-market organizations, certifying their own leaders to reduce turnover, stabilize trust, and accelerate decisions from the inside.
Her private advisory, BAR COTERIE, serves a select few bold enough to recalibrate success without regret. Named among 100 Women to Watch in 2026 and honored by the NAACP, she proves one thing: intimacy fuels innovation.
Connect with Dr Naketa:
Website: https://thigpro.com/
LinkedIn: https://www.linkedin.com/in/naketathigpen/
Instagram: https://www.instagram.com/asknaketa
Naketa’s framework: Applied Relational Intelligence System (ARIS)
Substack: https://thigproquo.substack.com/

Your ADHD-ish™ host, Diann Wingert
Diann Wingert is a former therapist turned coach, speaker, and consultant who blends her expertise in entrepreneurship and neurodiversity to help others thrive.
Host of the top-rated ADHD-ish™ podcast and creator of The ADHD-ish™ Method, Diann works with ADHD-ish™ business owners who are ready to create stand-out, sought-after, profitable businesses based on their unique brilliance.

What’s the first step for turning the business you have into the business you want? Take the ADHD-ish™ Business Blindspot quiz
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.