ADHD-ish™ ADHD Business Strategy for Busy Brains

Juggling multiple services and overly complex offers often creates unnecessary operational fatigue for neurodivergent entrepreneurs. In this episode of ADHD-ish, host Diann Wingert examines how developing a signature offer framework helps an ADHD small business owner simplify client delivery and focus energy on core strengths.

Discover how refining your business operations around a single flagship offer establishes clarity, boosts profitability, and prevents burnout. If you are a business owner with ADHD looking for tailored ADHD business coaching to align your services with executive function, this episode outlines a streamlined path to sustainable growth.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:30 - ADHD Business Strategy and Offer Simplification

05:45 - Managing Cognitive Load with a Single Offer

10:15 - Streamlining ADHD Business Operations for Focus

15:00 - ADHD Decision Making and Sustainable Growth

19:40 - Building Scalable Systems for ADHD Entrepreneurs

Why more isn’t always better — Learn how the mental load of multiple offers can multiply (not just add) to your overwhelm.

When a single offer makes strategic sense — What life circumstances and business seasons call for focusing on one thing?

How a singular offer can clarify your marketing — No more juggling messages for different audiences. Say hello to SIMPLICITY and being memorable!

Building flexibility within one offer — Diann shares real tactics (payment plans, pacing choices, modular components) so “single” doesn’t mean “rigid.”

Taking care of your brain (and your business) — Get honest about energy, boundaries, and sustainable growth—especially if you’re neurodivergent.

Repetition actually builds mastery AND your reputation! Focusing on just one offer can skyrocket client results and make you the go-to expert—and much easier to refer to without a f*ck-ton of marketing.

About the Host

Diann Wingert is a former psychotherapist and serial entrepreneur turned business coach, specializing in helping entrepreneurs with ADHD and other “not-so-neurotypical” brains thrive.

Drawing from both her clinical expertise and business experience, Diann delivers actionable advice, real-world strategies, and a refreshingly honest perspective on building a business, balancing priorities, and protecting your most precious resources: your time and your creative energy.

Next steps:

Grab Diann's self-assessment to help you determine whether a single-offer model is right for your business right now. Click here for your free copy.

Coming soon:

Don’t miss the next episode! Diann is joined by Alan P. Brown of ADD Crusher to discuss what you’re doing every day that is making your ADHD worse. Hit subscribe so you never miss an episode.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Navigating overlapping identities often forces neurodivergent entrepreneurs into adaptive behaviors like ADHD masking and code-switching. In this episode of ADHD-ish, host Diann Wingert connects with leadership coach Ron Sosa to discuss how an ADHD small business owner evaluates safety, authenticity, and self-disclosure in professional spaces.

Understand how honoring neurodiversity and personal identity strengthens your overall business strategy and leadership style. If you are a business owner with ADHD looking for compassionate ADHD business coaching to foster self-acceptance while building a sustainable business, this conversation offers profound clarity and encouragement.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:15 - Neurodivergent Leadership and Identity Intersectionality

07:30 - Authenticity for the ADHD Small Business Owner

14:45 - Overcoming Masking in ADHD Business Strategy

21:10 - Managing Cognitive Load in Unfamiliar Environments

28:35 - Building Inclusive Systems for ADHD Entrepreneurs

35:20 - Real-Time Decision Making with Lived Experience

42:00 - Empowering the Diverse Business Owner with ADHD

48:15 - Sustainable Growth and Authentic Leadership Principles

Diann and Ron discuss the complicated layer of “family secrets”, the constant mental calculations neurodivergent and marginalized individuals make around safety and acceptance, and offer powerful insights about reclaiming agency in how we self-identify.

What you’ll hear in this episode:

• How Identities Stack and Interact: Ron walks us through how he thinks about and organizes his different identities—ADHD, autistic, white male, gay, and hard of hearing—and the personal and social factors that influence which aspects he shares in different situations.
• Navigating Safety and Disclosure: The conversation highlights the calculation involved in deciding which identity to disclose, considering factors like safety, context, and anticipated reactions from others.
• Invisible and Visible Disabilities: Ron shares honest experiences about masking, particularly with his hearing impairment, and the additional challenges posed by disabilities that are not immediately visible.
• Masking as Tool vs. Survival Mechanism: Diann and Ron discuss the difference between masking as a conscious, empowering choice and masking as a depleting necessity, including how the need to “pass” or “camouflage” can both protect and exhaust someone with multiple marginalized identities.
• Passing, Code-Switching, and Camouflage: The benefits and drawbacks of being able to “pass” in certain environments, including the emotional toll and moments of empowerment when one can choose how and when to reveal their authentic self.

Guest Bio:

Ron Sosa is a neurodivergent, gay, hard-of-hearing leader who has walked unconventional paths through veterinary medicine, coaching, and leadership development. From the client service desk to executive roles, his story isn’t linear, and that's a testament to resilience, reinvention, and radical empathy.

Too many leaders feel like they’re wearing a mask and are exhausted from trying to fit into outdated expectations. They’re stuck managing overwhelm, struggling with conflict, and questioning whether they belong in leadership at all. They are not broken; the system is. Ron helps leaders unlearn what leadership “should” look like and rebuild from a place of clarity, confidence, and alignment with their neurotype, values, and rhythm through Syn-APT Neuroinclusive Leadership.

Find Ron Sosa online:

Website - LinkedIn

Mentioned during the episode:

Elizabeth Kubler-Ross' Stages of Grief model

The movie “Rainman” & how our views of autism have changed

Maslow's Hierarchy of Needs

Can’t get enough of insights from other neurodivergent experts?

Join Meredith Carder, Jesse J Anderson, Tayla Blair, Alice Draper and me for a FREE live roundtable discussion on “Visibility & Branding with ADHD” - October 15th at 9 AM Pacific/ 12 PM Eastern.

Register NOW to attend LIVE or watch the replay!

Ever wish you had been diagnosed with ADHD sooner? Want to open up a conversation about ADHD with your daughter, mother, or niece? Get your FREE copy of “Letters to My Younger Self” (22 letters from ADHD experts, including ME!) https://findtheadhdgirls.org/repository/

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Growing awareness around neurodiversity in entrepreneurship has led to an influx of generic guidance that fails to address executive function challenges. In this episode of ADHD-ish, host Diann Wingert breaks down what distinguishes true ADHD business coach services from standard productivity coaching, helping an ADHD small business owner select the right strategic support.

Discover how working with a specialized coach aligns business strategy, marketing, and operations with your unique cognitive style while protecting your time and energy. If you are a business owner with ADHD seeking experienced ADHD business coaching to build a sustainable enterprise, this episode provides a five-question framework for making an informed investment.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:15 - Role of an ADHD Business Coach

05:30 - ADHD Business Strategy versus Standard Coaching

09:45 - Tailoring Business Systems for ADHD Entrepreneurs

13:20 - Overcoming Cognitive Load and Business Burnout

16:50 - Sustainable Growth for the ADHD Business Owner

About the Host

Diann Wingert is a former psychotherapist and serial entrepreneur turned business coach, specializing in helping entrepreneurs with ADHD and other “not-so-neurotypical” brains thrive.

Drawing from both her clinical expertise and personal experience, Diann delivers actionable advice, real-world strategies, and a refreshingly honest perspective on building a business, balancing priorities, and protecting your most precious resources: your time and your creative energy.

Defining "ADHD Business Coach"

A major misconception is that being a certified ADHD coach with a coaching business is enough to qualify as an ADHD business coach.

The truth? The skills needed for managing ADHD and those needed to build sustainable business systems for an ADHD brain are worlds apart.

ADHD coaching typically zeroes in on organization, productivity, time management, and emotional regulation.

ADHD business coaching requires a deep understanding of how neurodivergent thinking plays out in the areas of business strategy, marketing, operations, and client delivery.

In other words, it’s about knowing not just that typical strategies fail for ADHD entrepreneurs, but why—and being able to offer effective alternatives.

Here’s my checklist for vetting an ADHD business coach—myself included:

• How do they run their business? Is it ADHD-friendly and sustainable, or are they “winging it” and modeling burnout?
• Can they answer nuanced questions about ADHD and business beyond the basics? How does rejection sensitivity impact marketing? Why do traditional sales funnels often fail?
• How do they talk about ADHD? Are they focused on deficits to “fix” or differences to leverage?
• Does their content feel ADHD-aligned? Or does it sound like a typical business guru tossing in some neurodivergent SEO keywords?
• Take a look at their boundaries. Strong boundaries signal true expertise and self-care—not codependency with a price tag.

My coach approach is simple and built on three principles:

Uncomplicate Your Business: ADHD brains get swamped by unnecessary complexity. Instead of piling on endless marketing channels or busywork, focus on what actually moves the needle. Eliminate the rest to avoid burnout.

Uncover Your Brilliance: ADHD entrepreneurs often have wildly innovative ideas, but years of hearing they should do things a certain way dims that spark. The real magic comes from aligning offers with your strengths and values, making sales a natural conversation rather than a high-pressure hustle.

Turn ADHD into an Asset: Instead of treating ADHD as something to manage, the right coach helps you turn traits like pattern recognition, hyperfocus, and flexibility into your business’s superpowers.

Do You Even Need an ADHD Business Coach?

Here’s a refreshing truth: not everyone needs specialized ADHD business coaching, especially if you’re still learning foundational business skills or are in the middle of a personal or professional crisis.

There’s a time and place—otherwise, you might benefit more from a mentor, a course, or ADHD life coaching. I think of it as the Goldilocks effect - not too much, not too little, but just right.

The ADHD business coaching field is growing, so you have more options than ever, but don’t let the noise drown out your intuition. Look for integrity, expertise, and a coach who practices what they preach.

If you want to explore coaching with me, I offer no-pressure consultations to see if we are a fit and if the timing is right. Click here to find out more.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Balancing multiple enterprises often leads neurodivergent entrepreneurs to doubt their capacity and leadership abilities. In this episode of ADHD-ish, host Diann Wingert sits down with client CherylAnn Crego to highlight how an ADHD small business owner can cultivate genuine confidence while running multi-passionate ventures.

Discover how embracing small windows of time, reframing a delayed diagnosis, and practicing targeted mindset tools help establish sustainable momentum. If you are a business owner with ADHD seeking empowering ADHD business coaching to step into leadership with clarity and ease, this client success story provides actionable inspiration.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:20 - Developing Confidence as a Business Owner

07:45 - Overcoming Imposter Complex for ADHD Entrepreneurs

15:30 - Tailoring Business Systems for ADHD Success

22:15 - Self-Trust and Decision-Making in Business

28:50 - Sustainable Growth for the ADHD Founder

Here are three key lessons from CherylAnn’s story for anyone managing multiple responsibilities while living with neurodivergence:

Embrace the “Nooks and Crannies” of Time:

You don’t always need a full day or a perfect schedule to make progress. CherylAnn leverages unexpected gaps in her day to move projects forward—proving that momentum can be built in the margins.

Growth Can Mean Letting Go:

Sometimes leadership requires making tough calls, like sunsetting a beloved business. CherylAnn shared how being honest about capacity and leading family and team members through disappointment is true leadership—and it’s okay to grieve business decisions. She also shares some vulnerable moments while talking about letting go of ego in service to growth.

Confidence Can Be Cultivated (at Any Stage):

Even as an experienced therapist, CherylAnn found new confidence by being open to coaching, embracing affirmations, and reframing challenges as opportunities to grow.

A Different “Take” on a Delayed ADHD Diagnosis

Cheryl Ann reflects on her midlife ADHD diagnosis and discusses how learning to build life strategies before even knowing she had ADHD turned out to be a hidden blessing.

For me, some of the most satisfying things about sharing the experience and outcomes from our work are how CherylAnn came to see herself in a new way, how she embraced the role of being “the boss,” and why finding the right support (and having a little fun) is essential when choosing the right coach, especially for someone who is accustomed to figuring things out on their own.

Client Bio

CherylAnn Crego is the co-founder of Chef Kent Getzen, a consulting business she started with her husband, whom she lovingly refers to as “the talent.” Together, they travel across the country teaching schools how to cook from scratch, source ingredients locally, and develop essential cooking skills.

Like many individuals with ADHD, CherylAnn is multi-passionate and multi-talented. In addition to being the CEO (and business brain) of the consulting business, CherylAnn is also a licensed psychotherapist in private practice, is in the midst of writing her first book, and has an extensive background in the performing arts.

Mentioned during the interview

• John Sovec - Diann’s friend and therapist who used to work for Disney
• Disney Front of House & Back of House distinctions
• Neurodiversion 2025 - the conference in Austin, where we hung out in person
• ADDitude Magazine - the leading website for resources and support for ADHD

Want to hear more Client Success Stories? Click here for the custom playlist

Is it time to build YOUR confidence as a business owner with ADHD?

I have two openings for one one-on-one coaching engagements, starting in October. 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.

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.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Every time you switch between calls, emails, and content creation, your brain loses momentum to context switching. For an ADHD entrepreneur or small business owner with ADHD, rigid time management systems often lead to task paralysis, overwhelm, and multitasking burnout. Protecting your energy requires a system built for neurodivergent focus.

In this episode, Diann Wingert shares three tailored "Focus Day" task-batching models to help you find your flow. Discover practical strategies to protect your boundaries, step into proactive ADHD leadership, and implement an ADHD business strategy that honors your natural energy patterns and stops daily interruptions.

EPISODE HIGHLIGHTS & TIMESTAMPS:

00:00 - ADHD Business Strategy: Finding Your Flow State

05:30 - The Traditional Theme Day Model for Focus

12:15 - The Energy-Driven Focus Model for ADHD

19:40 - The Sprint and Rest Method for Entrepreneurs

25:00 - Implementing Focus Day Models in Your Business

About the Host

Diann Wingert is a former psychotherapist and serial entrepreneur turned business coach, specializing in helping entrepreneurs with ADHD and other “not-so-neurotypical” brains thrive.

Drawing from both her clinical expertise and personal experience, Diann delivers actionable advice, real-world strategies, and a refreshingly honest perspective on building a business, balancing priorities, and protecting your most precious resources: your time and your creative energy.

Here’s your quick guide to Focus Days, ADHD-style:

The Single Focus Scheduling Method

Think of this as giving every day its own “job”—Mondays are CEO days (big picture, strategy only!), Tuesdays and Thursdays are for clients, Wednesdays for content creation, and Fridays for building connections.

The magic? You get to deeply immerse in one type of work at a time—no more multitasking burnout.

The Essential Three Model: Create, Connect, Consume

Perfect if you don’t want to lock yourself into a five-day structure. Allocate days based on energy: Create (any kind of output work), Connect (people-focused work like client calls), and Consume (input tasks like learning or admin).

You can spread these across your week however you like—and it totally honors both structure and spontaneity.

The Split-Screen Approach

Not all of us can devote a full day to a single focus. With the Split Screen model, you match tasks with your daily energy: deep work when your brain’s sharpest, creative or relational work when it feels right, and breaks when you need them. It’s about flowing with your energy patterns, not fighting them.

Which one to try?

• Are your days packed with interruptions? Go for the Essential Three.
• Thrive with structure? Try Single Focus Scheduling.
• Need max flexibility or have health/family stuff? Split Screen’s your friend.

Protect your boundaries (and sanity):

Most “emergencies” can actually wait. Create clear expectations and communicate your availability so you’re not always on call—this protects your energy, time, and creative spark.

Embrace experimentation over perfection:

Whether you need more structure or more flexibility, give yourself permission to tweak any system. Growth comes from iteration, not rigid adherence. Try one approach for a few weeks, then adjust as needed.

Not-so-fun fact:

Research shows it can take UP TO 25 MINUTES to fully recover your focus after switching tasks. And with ADHD? Yep, it can take even longer. It’s like trying to cook five different cuisines at once—the results are always a little…messy.

Mentioned in this episode:

Changes Diann made based on her quarterly review during a CEO Day:

• Zoom Pro to Google Meet_savings: $160
• Loom to Konvey_savings: $71
• Calendly to TidyCal: $91

Links to Diann’s three-part momentum series:

• Starting Strong
• Stopping Smart
• Shifting Smoothly
• Start, Stop, Shift Toolkit for ADHD Entrepreneurs

If you tried one of the three Focus Day models shared in this episode, let Diann know! Leave a comment on Spotify or leave a review on Apple Podcasts

Whether you crave more structure or more flexibility, you’ll leave this episode with permission to tailor your week—and your business—to what actually works for your ADHD-ish brain.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Emotional intensity and rejection sensitivity often remain overlooked in traditional discussions around neurodiversity. In this episode of ADHD-ish, host Diann Wingert connects with clinical psychologist Dr. Gilly Kahn to examine why women with ADHD frequently feel misunderstood, misdiagnosed, or dismissed in professional and personal settings.

Gain clarity on how emotional dysregulation influences confidence, leadership, and workplace dynamics. If you are a business owner with ADHD looking for compassionate ADHD business coaching to process past misdiagnoses and harness your emotional strengths, this conversation offers validation and self-acceptance.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:15 - Feeling Chronically Misunderstood with ADHD

06:45 - Unpacking Masking in ADHD Business Operations

12:30 - Managing Cognitive Load in Professional Environments

18:10 - Building Self-Trust as a Business Owner

24:00 - Neurodivergent Leadership and Authentic Communication

29:45 - Navigating Relational Dynamics with ADHD

35:20 - Sustainable Growth and Personal Empowerment

41:10 - Embracing Authenticity as an ADHD Founder

What you’ll hear in this episode:

Emotional Dysregulation is Fundamental (and Overlooked): While most people associate ADHD with distractibility and impulsivity, Diann and Dr. Kahn remind us that emotional sensitivity and reactivity are just as central—especially for women. Emotional outbursts, rejection sensitivity, and the complexities of self-regulation often remain unaddressed but profoundly impact daily life and professional relationships.

Misdiagnosis & Misunderstanding Persist: Many women spend years feeling misunderstood, misdiagnosed with anxiety, depression, or even personality disorders, before discovering ADHD’s unique presentation in females. Trauma from chronic misunderstanding—whether “big T” or “little t”—leaves lasting scars on self-esteem and career confidence.

Diversity of Thought = Business Advantage: The strengths that come with ADHD—creativity, expansive curiosity, resilience in the face of rejection—aren’t just “superpowers” for individuals. As Dr. Kahn eloquently puts it, teams excel when they have true diversity of thought. Those who think differently spark innovation and challenge the status quo.

“You can’t have strengths without also having weaknesses, especially when the strengths are extreme.” – Gilly Kahn, PhD

Gilly Kahn, PhD, is a clinical psychologist, ADHD advocate, researcher, and author in private practice in Atlanta, GA, USA. Before pursuing a master's in experimental psychology and a doctorate in clinical psychology, Gilly studied creative writing, a passion since childhood, and regularly publishes articles on Psychology Today and ADDitude Magazine. Gilly and Diann are both members of the Committed Partners of FindTheADHDGirls.org, an advocacy group for ensuring that future generations of girls with ADHD are not overlooked.

Find Gilly Kahn, PhD, online:

Website: https://www.drgillykahn.com/

Book: Allow Me to Interrupt: A Psychologist Reveals the Emotional Truth Behind Women’s ADHD by Gilly Kahn, PhD.

Instagram and LinkedIn

ADHD experts mentioned during the episode:

William Dodson

Russell Barkley

Want to know more about ADHD in girls and women? #FindTheADHDGirls.org

Don’t forget to subscribe/follow the podcast, and leave a review so more ADHD-ish business owners can find THE podcast full of real talk and real solutions for neurodiverse business brains.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Navigating corporate or entrepreneurial environments with ADHD often brings an intense urge to seek approval and avoid perceived criticism. In this episode of ADHD-ish, host Diann Wingert shares practical lessons from Alfred Adler's philosophy to reveal how approval-seeking behaviors and fear of judgment trigger professional burnout.

Discover how separating tasks, establishing intentional boundaries, and cultivating self-acceptance reduce the emotional weight of workplace interactions. If you are an entrepreneur looking for targeted ADHD business coaching to navigate professional relationships with grounded self-assurance, this discussion provides a roadmap toward sustainable peace of mind.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:15 - When a Prospect Ghosts You with ADHD

05:30 - Overcoming Rejection Sensitivity in ADHD Business Operations

09:45 - Reclaiming Focus and Managing Cognitive Load

13:20 - ADHD Follow Through and Sales Communication Systems

16:50 - Building Self-Trust as an ADHD Entrepreneur

ABOUT THE HOST

Diann Wingert (she/her) is a former psychotherapist turned ADHD entrepreneur coach and business strategist, as well as the insightful host of ADHD-ish.

With both lived experience and deep professional expertise in ADHD, Diann guides neurodivergent entrepreneurs toward greater self-awareness, creativity, and sustainable success— with her signature blend of no-nonsense advice, compassionate understanding, and a dash of sass.

WHAT TO LISTEN FOR:

Ghosting = Brain Spiral Town.

Most of us with ADHD are natural connectors, really tuned in to people’s emotions and needs (sometimes to a fault!). So when a prospect suddenly ghosts, our brain doesn’t just let it go. We cycle through: Did I misread everything? Did I say something wrong? Should I follow up? The open mental tabs never close!

Why Does It Hit So Hard?

It’s about more than lost potential business — it chips away at our confidence and identity. Thanks, rejection sensitivity! Our brains crave closure, and ghosting feels like an unsolvable mystery that burns a hole in our mental inbox.

3 Practical Ways to Prevent & Recover:

1.Set Clear Expectations on the Call:

Instead of ending with vague “I’ll send info and we’ll go from there,” clearly address what comes next. Give the prospect space to say if they need to think or consult someone else. Your brain will thank you later.

2.Summary Follow-Up Email:

After the call, send a recap: “Here’s what I heard you need, and how I’d help.” It’s not just professionalism — it helps you remember details if the anxiety spiral hits.

3.One Professional Follow-Up (Then Let Go):

Send a single, polite check-in. Example:

“Hi X, just following up on the proposal. Totally understand if timing isn’t right. Let me know if you have questions!”

Then, mentally… close that tab. Their silence is about their stuff, not your value.

Bonus Brain Hack:

If you catch yourself spiraling, say out loud, “My brain is trying to solve an unsolvable puzzle.” Set a 15-minute timer to ruminate if you must, then move your body — walk, jump, play with the dog, whatever. Shifting gears really does help!

Real Talk:

Ghosting is not a judgment of your worth or skill. Often it’s got nothing to do with you. Life happens. Budgets cut. Crises pop up. Sometimes people just freeze on big decisions.

Focus on what you can control: being a pro, building your pipeline (more prospects = less sting), and separating your self-worth from any one client’s decision. And, always redirect energy into new opportunities — don’t dwell on what’s done.

If you’re ready to get found everywhere online, check out Meg Casebolt’s “Findable Everywhere” 5-Day challenge — Sept 15th - 19th. It could be the redirect your brain and business need! Meg is the SEO expert who saved my bacon after my social media accounts disappeared, and this is your chance to work with her for under $100!

Click here to register

Don’t forget:

You. Are. Not. Alone.

And you’re honestly better at this than you think. ❤️

Stay tuned for more empowering conversations and practical tools for thriving in business with ADHD—right here on ADHD-ish! Be sure to follow/subscribe so you don’t miss a thing!

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Wearing every hat in a growing business quickly drains executive functioning and leads to severe cognitive fatigue. In this episode of ADHD-ish, host Diann Wingert connects with automation expert Will Christensen to detail how neurodivergent founders can leverage modern technology and key talent to build sustainable momentum.

Discover how combining AI workflows with complementary team support streamlines daily operations without burning out. If you are a visionary founder seeking specialized ADHD business coaching to transition from solo execution into strategic leadership, these practical strategies provide a clear framework for expansion.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:15 - How to Clone Yourself as an ADHD Entrepreneur

07:30 - Streamlining ADHD Business Operations with AI

13:45 - Building Business Systems for ADHD Success

20:10 - ADHD Delegation and Accountability Frameworks

25:40 - Sustainable Growth with Automation and Apprentices

Will Christensen (he/him) is a systems thinker and automation expert who helps entrepreneurs take back their time and scale their business. Will is the founder of The Entrepreneur’s Apprentice and host of Automation Hunter. He specializes in building teams and tech stacks that let visionary minds focus on what they do best.

Will is also a champion of the “Automate, Delegate, Eliminate” approach and has a brilliant strategy for hiring “entrepreneurial apprentices” who help founders scale without burning out. Will’s revolutionary“15-1-1-5” framework, which he developed to manage his own executive functioning challenges, is an ADHD-friendly alternative to traditional time management strategies.

Episode Highlights

• You Don’t Need a Clone—You Need Your Opposite: Will reveals that hiring someone just like you might double your chaos, not your output. The real solution? Find an apprentice or two who complements your weaknesses and excels where you struggle. Sometimes, your best partner is someone with a different brain!
• Automate, Delegate, Eliminate—In That Order: Learning to let go is harder than it looks, so start with identifying what can be automated (especially now that AI makes it easier than ever). Save your executive functioning and cognitive energy for the big, creative stuff rather than routine busywork.
• Equity and Ownership Breed Commitment: Want your team to “own” their work? Will recommends offering phantom equity to empower top-tier talent to act as “mini-CEOs.” This transforms their sense of responsibility and buy-in, leading to loyalty and drive you can’t just hire for.

• Automation Hunter YouTube Channel
• Entrepreneur’s Apprentice
• Kolbe Assessment
• RemoteWork.com
• Books referenced:
• The E-Myth by Michael Gerber
• The One Thing by Gary Keller & Jay Papasan
• Buy Back Your Time by Dan Martell
• The 6 Types of Working Genius by Patrick Lencioni
• Never Split the Difference by Chris Voss

Want to Find Out More?

Will is offering a FREE 15-minute call for ADHD-ish listeners to jumpstart your “Automate, Delegate, Eliminate” journey. And if he doesn’t blow your mind, he’ll give you a $50 Amazon gift card. (Spoiler: it never happens!)

Book your call now, for listeners of ADHD-ish only: EntrepreneursApprentice.com/adhd-ish/

Don’t forget to subscribe/follow the podcast, and leave a review so more ADHD-ish business owners can find THE podcast full of real talk and real solutions for neurodiverse business brains.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

Business growth for neurodivergent founders depends heavily on understanding how neurotransmitters influence daily focus and decision-making. In this episode of ADHD-ish, host Diann Wingert details how relying solely on novelty-driven motivation creates unpredictable cycles in business operations.

Learn how aligning daily workflows with natural brain chemistry creates consistent progress on both high and low-energy days. If you are an entrepreneur seeking specialized ADHD business coaching to build a sustainable enterprise that honors your neurodivergence, this episode offers practical, science-backed guidance.

EPISODE HIGHLIGHTS & TIMESTAMPS:

01:15 - Idea Infatuation and ADHD Business Strategy

05:20 - Managing Cognitive Load with New Ideas

09:40 - Evaluating Focus in ADHD Business Operations

13:15 - Overcoming Shiny Object Syndrome as Founders

16:50 - Building Sustainable Systems for ADHD Entrepreneurs

ABOUT THE HOST

Diann Wingert (she/her) is a former psychotherapist turned ADHD entrepreneur coach and business strategist, as well as the insightful host of ADHD-ish. With both lived experience and deep professional expertise in ADHD, Diann guides neurodivergent entrepreneurs toward greater self-awareness, creativity, and sustainable success— with her signature blend of no-nonsense advice, compassionate understanding, and a dash of sass.

WHAT TO LISTEN FOR:

How the "Soulmate Phenomenon” shows up for entrepreneurs with ADHD

• Romancing the Idea: attraction, infatuation, honeymoon, and reality
• Why falling for new ideas isn't about lack of commitment or follow-through
• How dopamine cravings and novelty-seeking drive this cycle
• Concrete examples: coaching, consulting, and creative service businesses
• Key questions to ask yourself when a new idea lands
• Why the honeymoon phase is creative gold and how to use it intentionally
• Four actionable frameworks for managing new ideas:
• The "dating period" (test ideas before big changes)
• The side project approach (explore without derailing your main business)
• Integration (fold new ideas into what you already do)
• Relationship maintenance (recommit and work through boredom and obstacles)
• How to distinguish between ideas worth a long-term run vs. a temporary high

TIMESTAMPS

• 00:00 — Getting Obsessed: The Soul Mate Phenomenon Hits Hard
• (Falling for the idea, dopamine rollercoaster, full rom-com montage)
• 02:10 — Why This Happens: Dopamine, Novelty, and Hyperfocus
• (Science of ADHD meets daily business life, shiny object syndrome explained)
• 05:15 — Pattern Recognition: Attraction, Infatuation, Honeymoon, Reality
• (Breaking down the idea romance step by step)
• 09:40 — Classic ADHD Business Moves: Case Studies
• (Real-life business examples with coaches, consultants & service providers)
• 14:35 — The Crash: When the Fizz Fades and the Next Idea Calls
• (Losing steam, misreading the end of infatuation, jumping ship too soon)
• 17:50 — Deep Truth: The Real Problem Isn’t Commitment
• (It’s unrealistic expectations, not a lack of grit — and what to do instead)
• 21:40 — The Gold in the Honeymoon Phase: How to Use It
• (Why that first burst of energy is actually your secret weapon)
• 24:20 — Four Frameworks for Working With ADHD, Not Against It:
• The Dating Period
• The Side Project Approach
• The Integration Question
• Relationship Maintenance Plan
• 32:10 — The End Game: Choosing Long-Term Commitment (Or Not)
• (Learning to spot quick dopamine hits versus real growth opportunities, radical self-acceptance)
• 35:10 — Final Pep Talk and How to Get In Touch
• (Reminders, contact info, encouragement, closing thoughts)

SHARE YOUR STORY:

What’s the big “soulmate idea” that got away? Did it deserve a second chance, or was it just a quick dopamine hit? Hit me up by email, send me a DM on LinkedIn or leave a voice message on my website.

SUMMARY

ADHD brains light up for new ideas…and then we feel like changing everything for that rush. Don’t fight the pattern, work with it. Date your ideas. Don’t move in with them at first sight. Keep your current business healthy and figure out what deserves real commitment. That’s how you survive idea infatuation and the “Soulmate Phenomenon” and make your next hyperfocus phase count for something.

Your brain is a brilliant and busy place. Let’s make it your greatest business asset. Stay tuned for more empowering conversations and practical tools for thriving in business with ADHD—right here on ADHD-ish! Be sure to follow/subscribe so you don’t miss a thing!

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.

What happens when high ability and late-diagnosed ADHD intersect in midlife? In this episode, Diann Wingert sits down with licensed psychotherapist Lisa Lackey to explore the unique journey of a high-achieving business owner with ADHD receiving a diagnosis later in life. High intelligence often masks executive function struggles for decades until life transitions like menopause make traditional coping mechanisms unsustainable.

For every ADHD entrepreneur exhausted from compensating for hidden challenges, this conversation offers clarity and validation. Discover how ADHD business coaching, self-compassion, and intentional community foster sustainable success and elevate neurodivergent leadership without burnout.

EPISODE HIGHLIGHTS & TIMESTAMPS:

00:00 - Delayed ADHD Diagnosis in High-Achieving Women

06:45 - Why High Ability Can Hide ADHD

13:30 - ADHD, Perimenopause, and Midlife Changes

20:15 - The Second Knowing: Rediscovering Yourself

27:30 - Redefining Success Beyond Society’s Expectations

34:45 - Black Women, Burnout, and Legacy Healing

42:00 - Sankofa, Identity, and Midlife Transformation

48:30 - ADHD, Self-Acceptance, and Neurodivergent Strengths

Guest Bio: Lisa Lackey (she/her)

Lisa Lackey is a licensed psychotherapist, coach, and speaker with decades of experience supporting high-achieving individuals facing addiction, anxiety, depression, and now, navigating the complexities of neurodiversity and midlife transitions.

After being diagnosed with ADHD later in life, Lisa transformed her approach—creating supportive spaces for women, particularly Black women, to rediscover their authentic selves, reclaim joy, and build community in the second half of life. Lisa is passionate about spiritual growth, legacy work, and helping others write their own rules for fulfillment.

Episode Highlights – What You’ll Learn

• Why ADHD is often missed in high-achieving women, and how self-awareness—and even reading the “right” book—can be a game changer.
• How hyper-competence, overachievement, and the ability to "make it work" can hide ADHD symptoms for decades.
• Understanding how hormonal changes bring ADHD and identity struggles front and center for so many women in midlife.
• Lisa’s concept of the “second knowing”- waking up in midlife, letting go of societal shoulds, and connecting to your true purpose and inner wisdom.
• How women—especially women of color—can build new definitions of success, heal generational burdens, and lift each other up.

Connect with Lisa Lackey

• Website: Inside Out Recovery
• LinkedIn: Lisa Lackey on LinkedIn

Mentioned by our guest:

Driven to Distraction by Ned Hallowell, MD - the book Lisa read in 2 hours & recognized her own ADHD

Bell Hooks - Black author, best known for her work on race, feminism & social class

Sankofa - a word in the Twi language of Ghana, meaning “to retrieve”

If something in this episode struck a chord, share it with a friend, leave us a review, or drop a comment on Spotify about your own late diagnosis and mid life awakening.

© 2025 ADHD-ish Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.