ADHD-ish™

‍Kristina Flynn has had a psychiatrist since she was twelve, collected diagnoses like frequent flyer miles (anxiety, depression, OCD, bulimia, and more), and still didn't get an ADHD diagnosis until her thirties, after her daughter's birth blew up every workaround she'd been quietly running for two decades.
‍Now she runs Story EQ, where she helps people find the story underneath their work. Everybody tells you to stop overthinking. Kristina Flynn built a company on it.
‍We talk about why doing your own branding is a fool's errand (spoiler: your brain isn't primed for reality, it's primed for your perception of reality). We talk about the Mensa-level geniuses who sit across from her and say "I'm not that interesting."
‍We talk about the specific, weirdly universal terror of what your old colleagues will think. And we talk about AI — not as a voice replicator, but as something that can understand your context if you feed it properly.
‍Fair warning: if you're sitting on an abandoned rebrand, three different mission statements you don't believe, and a nagging sense that you should be further along by now — you're going to feel a little called out. Stay with us anyway. ‍
WHAT’S INSIDE: ‍
● Why Your Old Story Isn’t the Whole Story: How narrative identity, negativity bias, and corporate conditioning have shaped the way you show up ‍
● The 4 Stories Framework (Stealable Worksheet): Start mapping your old story, bridge story, and how to shift from “it’s about me” to “it’s about them”
● Radical Self-Acceptance Checklist: 5 mindset shifts to finally move past shame, imposter feelings, and waiting for permission ‍
● Overthinking as an Asset: Quick exercises to turn rumination into action, content, and connection (instead of procrastination) ‍
● Your First Move Blueprint: Micro-steps to start building story-driven content — without oversharing or burnout

FUN FACTS

Kristina and Diann are both pretty sweary and swear by the research that concludes swearing is a sign of intelligence. You decide!
‍Kristina & Diann met through Coach Vox - the platform where they both built their digital clones. If you haven’t signed up for Di AI yet - what are you waiting for? Here is the link to sign up for free.
ABOUT KRISTINA
Kristina (with a 'k') Flynn is an Overthinking High-Achiever (OHA) helping other OHAs turn their wild careers and stories into personal brands that feel like them and make sh*tons of money.
‍For 18+ years and across 11 roles in 8 industries, she's built brands for NBA All-Stars, Olympians, venture capitalists, Youtubers, founders, and executives.
The through-line across all of it: wildly capable people who are great at seeing other people's value, but can't see their own. In 2023, she built StoryEQ™ to close the gap.
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LINKS & RESOURCES
‍Kristina’s: ‍
WebsiteStory EQ Framework PDF LinkedIn ‍
The episode with Evan Sargent on branding ‍
20 Feet From Stardom (2013) — the backup singer documentary I mentioned
Brené Brown
Simon Sinek
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YOUR ADHD-ish™ HOST
‍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.
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WORK WITH ME
If this conversation hit a nerve — if you've been hiding behind your credentials and waiting to be discovered on the strength of good work alone — that's a strategy problem, not a character flaw. Let's fix the strategy problem together — schedule your call here.
ADHD-ish is hosted by Diann Wingert. If you got something out of this one, the single most useful thing you can do is send it to one person who needs it. Second most useful: leave a review.

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

Ever find yourself saying yes to a new collaboration, tool, or project—then months later wondering how you got there? If you run a business (especially with an ADHD-ish™ brain), you’re not alone.
‍In this episode, I break down why our brains confuse options for opportunities, how dopamine clouds our judgment at the moment of the ask, and share a practical “screen door” filter to make better decisions going forward.
‍Dopamine is a talent scout, not a bookkeeper: That rush of excitement we feel with something new? It’s all about anticipation—not reality. The cost and maintenance of a new yes don’t hit until much later. The trick is to slow the yes.
‍Clever ways options pretend to be opportunities:
‍The Flattering Ask: feeling chosen and visible can feel like opportunity, but might be just an option that doesn’t fit your goals.
‍The Closing Door: artificial urgency and manufactured scarcity prey on impulsive decision-making.
‍The Adjacent Idea: our shiny new ideas often show up exactly when important work becomes tedious, tempting entrepreneurs to jump ship.
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Why is this so hard for ADHD brains?
‍Because dopamine is LOUD and it fires at anticipation, not the actual result. That new offer or collab invitation? It’s pure possibility—no fatigue, no disappointment, no downside at first. The evaluation part comes much later, usually after you’re already committed.
Story Time
‍Diann once bought a high ticket course to “launch a high-ticket course,” and not only never opened it, but kept paying a monthly subscription for three (!) years (ADHD dopamine at work, folks—don’t feel bad, you’re not alone! 😂
‍Try this: The 4-Question "Screen Door" Filter
‍Before you say yes, ask yourself:
1. What existing goal does this serve?
2. What does it leverage that I’ve already built?
‍3. What are the terms of this commitment?
‍4. Does it survive 72 hours?

Nothing new gets a same-day yes. That 72-hour pause is where the real magic happens (and where many “opportunities” evaporate).
‍Start here:
*Make an idea parking lot for every new ask or idea.
*‍Practice the pause: “Let me check a couple things and get back to you.”
‍*After 72 hours, run the 4-question test.

Some asks will quietly disappear. Others will become real, intentional decisions. Give it a try and notice how different your “yes” feels and the discomfort of waiting. That’s data.
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Mantra for the week:
Every yes is not a purchase—it’s a subscription. Read the terms before you sign.
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But what about all the past decisions you’ve made that have made your business messy and chaotic?
‍I’ve got you! Click here to read the companion blog post “How to Know When Your Business is Too Complicated: A Right-Sizing Guide for ADHD Entrepreneurs.”
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Your ADHD-ish ™ host
‍Diann Wingert, MSW is the insightful host of ADHD-ish™, where she helps entrepreneurs and professionals navigate the challenges of running a business with an ADHD brain.
‍Known for her practical wisdom, Diann regularly explores topics like decision-making, teaching her audience how to filter choices more effectively.
‍Through her relatable storytelling and expertise, Diann shares lessons gained from serial business ownership, a 20 year career as a psychotherapist and a lifetime with ADHD.
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Want deeper support untangling your yeses and rebuilding your decision-making? 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, MSW.
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New to ADHD-ish™? Subscribe/Follow ADHD-ish on Apple or Spotify for more ADHD-informed business strategy, inspiring guest expert interviews and client success stories.
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© 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Traditional business coaching falls short when late-night decision-making spirals hit, leaving many ADHD entrepreneurs feeling isolated and tired of generic productivity advice. As a stubbornly self-sufficient business owner, your urgent questions, pivot ideas, and friction points rarely line up with a pre-scheduled coaching call.
In this episode, Diann Wingert shares how her digital clone, Di AI, serves as a 24/7 thought partner to streamline your ADHD business strategy and lighten your daily cognitive load. Discover how on-demand support improves ADHD decision making, strengthens entrepreneur accountability, and optimizes ADHD business operations all without losing the essential human connection.
EPISODE HIGHLIGHTS & TIMESTAMPS:
00:00 — Introduction: AI Tools for the ADHD Entrepreneur
03:15 — Testing Digital Coaching and ADHD Decision Making
08:40 — Business Systems for ADHD Entrepreneurs
14:20 — Managing Cognitive Load in Business and Tech
19:50 — AI vs Human Entrepreneur Accountability
25:10 — ADHD Productivity for Entrepreneurs: Evaluating AI
31:05 — ADHD Executive Function in Business and Values
35:00 — Roadmap for Business Owners with ADHD
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! For many ADHD entrepreneurs, "out of sight, out of mind" is a daily reality, whether that means active client projects, strategic goals, or vital admin tasks. When working memory struggles to keep priorities front and center, simple operational gaps quickly turn into overwhelming friction, trapping business owners in cycles of panic work and unnecessary stress.
In this episode, Diann Wingert explores how ADHD object permanence uniquely impacts business operations and daily execution. You’ll discover practical strategies to build visible business systems for ADHD entrepreneurs, improve ADHD follow through, and protect your mental bandwidth—helping you maintain consistent momentum without adding to your cognitive load in business.
EPISODE HIGHLIGHTS & TIMESTAMPS:
00:00 - Options vs Opportunities for the ADHD Entrepreneur
06:15 - Dopamine and ADHD Decision Making in Business
13:30 - Three Disguises that Overload Cognitive Load
20:45 - The Screen Door Filter for Entrepreneur Accountability
27:10 - Sustainable Systems for Business Owners with ADHD

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

Standard productivity frameworks and hustle culture often sell a rigid, neatly divided version of work-life balance that rarely works for high-achieving neurodivergent brains. When you try to force hyperfocus into conventional schedules, attempting to balance intense professional drive with personal well-being frequently leads to emotional exhaustion and severe ADHD burnout in entrepreneurs.
To break this cycle, Diann Wingert dismantles the myth of traditional balance to reveal an approach built for neurodivergent momentum. Learn how resetting your operational baseline, reducing cognitive load in business, and enforcing clear boundaries can optimize your ADHD business operations while protecting your energy for sustainable growth with ADHD.
EPISODE HIGHLIGHTS & TIMESTAMPS:
00:00 - The Truth About ADHD Executive Function in Business
04:30 - Operational Bottlenecks Facing the ADHD Small Business Owner
09:15 - ADHD Decision Making Under Heavy Working Memory Load
15:40 - Streamlining ADHD Business Operations and Daily Systems
21:10 - Delegation for Entrepreneurs Managing Small Teams
26:35 - Overcoming Executive Dysfunction and ADHD Burnout Prevention
32:00 - Real-World Entrepreneur Accountability Strategies for Growth
36:45 - Sustainable Success Frameworks for the ADHD CEO

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.