If you’ve ever been told your ADHD is either your biggest weakness or your greatest entrepreneurial superpower, this episode will challenge that narrative. I sit down with business coach, former psychotherapist, and ADHD-ish podcast host Diann Wingert to unpack the realities of building a business with an ADHD brain — from burnout and perfectionism to impulsivity and decision fatigue.

Diann shares honest, practical insights on scaling sustainably, managing rejection sensitivity, and creating a business that works with your brain instead of against it. If you’re tired of trying to fit into a neurotypical business mold, this episode is for you.

Episode Highlights

[0:38] - Why the “ADHD is a superpower” narrative can be harmful

[1:31] - Why Diann transitioned from psychotherapist to ADHD business coach

[3:43] - The difference between therapy and coaching for ADHD entrepreneurs

[9:00] - The overlooked connection between ADHD and trauma

[10:24] - Why ADHD traits are context-dependent in business

[13:14] - Why ADHD entrepreneurs struggle when it’s time to scale

[15:05] - Diann’s “idea parking lot” strategy for impulsive ideas

[18:42] - The “unholy trinity” of ADHD entrepreneurship: perfectionism, procrastination, and people pleasing

[21:09] - How rejection sensitivity fuels burnout and self-sabotage

[22:55] - Radical self-acceptance and why it matters in business

[26:39] - Diann’s 4 business pillars: positioning, packaging, pricing, and promoting

[29:53] - Why too many offers can hurt business growth

[33:22] - Creating a sustainable marketing strategy for ADHD entrepreneurs

[35:17] - How to stop chasing every shiny business idea

[37:27] - Impulsive vs. overthinking ADHD entrepreneurs

[43:08] - What most business coaches miss with ADHD clients

[46:04] - Building a business that works with your ADHD brain, not against it

Links and Resources:

Diann Wingert is a former psychotherapist, serial business owner, and ADHD business coach who helps entrepreneurs and creatives build businesses that work with their brains, not against them. Host of the ADHD-ish Podcast, Diann is passionate about helping neurodivergent business owners balance passion, purpose, and profit while embracing the creativity and innovation that come with ADHD.

ADHD-ish Podcast: ADHD-ish™

Diann Wingert Coaching website: ADHD Business Coach | Diann Wingert | For Entrepreneurs

Di AI - Diann Wingert's ADHD Business Coach Digital
Clone: Di AI is here.

LinkedIn account: https://www.linkedin.com/in/diannwingertcoaching/

Thank you for tuning into "SuccessFULL with ADHD." If this episode has impacted you, remember to rate, follow, share, and review our podcast. Your support helps us reach and help more individuals navigating their journeys with ADHD.

🚨Calling all aspiring ADHD coaches ▶️ https://www.coachingwithbrooke.com/coach-certification-and-training

Help your clients break free from paralysis and better manage their life with 3C Activation® coach training!

💥Gain a proven process for ADHD coaching

💥Earn 38 ICF Credits and 25.5 PAAC CCE’s

💥Learn the latest neuroscience to boost your practice

💥Qualify to be listed under ACO Directory

Learn more ▶️ https://www.coachingwithbrooke.com/coach-certification-and-training

Ever feel like friendships are way harder than they should be? In this conversation, I sit down with ADHD coach, educator, and author Caroline Maguire to unpack why so many neurodivergent adults struggle with connection—and what’s actually going on beneath the surface. We explore the hidden patterns that keep us stuck, from people-pleasing to rejection sensitivity, and why “just be yourself” isn’t always that simple.

Caroline shares powerful insights from her new book on friendship skills for neurodivergent adults, helping us rethink what authentic connection really looks like. If you’ve ever questioned your relationships, felt like “too much,” or wondered why friendships don’t stick, this episode will open your eyes—and give you hope for building connections that truly feel good.

Episode Timeline Highlights

[0:00] - The people-pleasing trap and why it sabotages authentic friendships

[2:17] - Masking, confidence issues, and the cost of trying to fit in

[5:20] - What actually fills your “social cup” (and why most advice gets it wrong)

[8:23] - The impulsive friendship cycle and dopamine-driven connections

[14:12] - What neurodivergent kids experience socially—and how it carries into adulthood

[19:25] - Why ADHDers are more likely to be bullied and excluded

[22:58] - How unhealthy friendship patterns continue into adult life

[28:32] - Practical tools: autopilot friendships, body doubling, and social systems

[35:33] - The difference between acquaintances, emerging friends, and real friendships

[41:19] - Rejection sensitivity, emotional flooding, and how to interrupt the spiral

[45:52] - What it really means when someone says “you’re too sensitive”

[49:49] - The ultimate friendship litmus test: how you feel after spending time together

Links & Resources

Caroline Maguire, M.Ed., ACCG, PCC, is an internationally recognized expert in ADHD, social-emotional learning (SEL), and relationship development. She’s the author of Why Will No One Play with Me? and Friendship Skills for Neurodivergent Adults (April 2026), focused on building authentic connections.

A coach, educator, and speaker, Caroline developed a widely used SEL methodology to support emotional regulation, self-awareness, and social confidence. She also hosts The ADHD Social Playbook podcast.

As a neurodivergent individual with ADHD, dyslexia, and learning differences, she brings both lived experience and professional expertise to her work.

Her work has been featured in ADDitude, WebMD, and TODAY Parenting. She’s also a TEDx speaker and keynote presenter at the International Conference on ADHD.

Instagram/Linkedin @authorcarolinem

Are you 18 or older with ADHD? Please help us collect data on adults with ADHD and bullying. In this less than 1-minute survey, you will also get $5 off of our store as a thank you > Bullying and ADHD https://docs.google.com/forms/d/e/1FAIpQLScOsxgorpei-2tzFEk-USZSXe9xETzbZIHQ4KM7P2YwG6x-tw/viewform?pli=1

Thank you for tuning into "SuccessFULL with ADHD." If this episode has im

🚨Calling all aspiring ADHD coaches ▶️ https://www.coachingwithbrooke.com/coach-certification-and-training

Help your clients break free from paralysis and better manage their life with 3C Activation® coach training!

💥Gain a proven process for ADHD coaching

💥Earn 38 ICF Credits and 25.5 PAAC CCE’s

💥Learn the latest neuroscience to boost your practice

💥Qualify to be listed under ACO Directory

Learn more ▶️ https://www.coachingwithbrooke.com/coach-certification-and-training

I’m joined by Chris Wang—co-founder and CEO of Shimmer and creator of the Indie ADHD support app—to explore the fast-moving world of AI and what it actually means for ADHD brains. We get real about the tension so many of us feel: can technology truly support executive function, decision-making, and organization, or is it just adding more overwhelm?

Chris shares how her late ADHD diagnosis completely shifted her perspective on productivity, and we dig into how to navigate tools, goals, and AI in a way that actually works for your brain. If you’ve ever felt stuck in analysis paralysis with too many options—or unsure how to use AI without spiraling—this conversation will help you simplify, refocus, and move forward with more intention.

Episode Highlights

[00:20] - Why AI feels both exciting and overwhelming for ADHD brains

[01:51] - Chris’s late ADHD diagnosis and how it reshaped her view of productivity

[04:14] - The real reason technology can increase overwhelm (and how to avoid it)

[05:56] - “Start with the end in mind” and why direction matters more than perfection

[07:31] - Odyssey planning: designing multiple futures instead of one rigid path

[10:23] - Letting go of all-or-nothing thinking and embracing flexible goals

[13:43] - Where AI actually helps ADHD (and where it adds noise)

[15:14] - Why “done is better than perfect” when choosing productivity tools

[19:20] - How Indie helps you prioritize what actually matters

[22:47] - Energy accounting: managing tasks based on your mental bandwidth

[24:10] - Guardrails to prevent AI from becoming a hyperfocus trap

[26:15] - When AI supports growth vs. when it replaces critical thinking

[30:21] - The future of ADHD + AI: leveling the playing field

[35:43] - The one mindset shift to reduce overwhelm with tech and tools

Links & Resources

Chris Wang is the co-founder and CEO of Shimmer, the leading coaching platform for teens and adults with ADHD, which has supported over 80,000 coaching sessions to date. She also leads Indy by Shimmer, a free ADHD support app that launched this January. After being diagnosed with ADHD as an adult, Chris founded Shimmer to help build a more neuro-inclusive world. She has been recognized as a Forbes 30 Under 30 honoree for her work transforming ADHD support.

IG: @adhd.christal

Thank you for tuning into "SuccessFULL with ADHD." If this episode has impacted you, remember to rate, follow, share, and review our podcast. Your support helps us reach and help more individuals navigating their journeys with ADHD.

🚨Calling all aspiring ADHD coaches ▶️ https://www.coachingwithbrooke.com/coach-certification-and-training

Help your clients break free from paralysis and better manage their life with 3C Activation® coach training!

💥Gain a proven process for ADHD coaching

💥Earn 38 ICF Credits and 25.5 PAAC CCE’s

💥Learn the latest neuroscience to boost your practice

💥Qualify to be listed under ACO Directory

Learn more ▶️ https://www.coachingwithbrooke.com/coach-certification-and-training