In this episode, Diann Wingert and guest Phil Drinkwater dive deep into the intersection of the ADHD brain, neurodivergent shame, and business leadership. They explore how years of masking and internalized stigma impact founders, and why understanding these hidden layers is crucial for growth.
The conversation highlights powerful mental shifts, focusing on moving away from self-limiting doubts and transitioning from "can I?" to "how can I?". Tune in to discover actionable insights and strategies designed to help neurodivergent entrepreneurs overcome perfectionism, leverage cognitive frameworks, and build a business that truly supports their mind.
EPISODE HIGHLIGHTS & TIMESTAMPS:
0:00 - What running a company teaches you that coach training can't
4:15 - ADHD presentations and entrepreneurship: why combined type shows up more often
11:30 - "Can I?" versus "How can I?" and your only job as a founder
18:45 - Shame: Do you point it inward or outward?
25:10 - Attachment style at work, and the copy that attracted the wrong clients
33:20 - Pull the decisions forward: Procrastination has layers
41:05 - Working memory, the 32-path problem and mirrorboarding
48:30 - Perfectionism: Where it helps, where it doesn't, and hiring for attachment style
Phil and I get into it:
- Phil's one-word shift that named the episode for us: "Can I?" is the fear. "How can I?" turns it into agency, and solves the ADHD inertia problem
- Your only job as a founder. You don't have to do everything. You have to make sure everything gets done. Phil's advice is to fire bits of yourself, starting with the work you don't like and aren't good at.
- Shame, and whether you point it inward or outward, and why Phil hears "high performance" as "I mask a lot."
- Attachment style as a business issue. The founder whose copy kept attracting the wrong clients, the one whose Open Door Tuesday handed him ten extra spinning plates a week, and why your best team member may have a different attachment style than yours.
- Designing an AuDHD work week. Phil's version of ADHD energy management when the ADHD half wants stimulation and the autistic half wants quiet: coaching days cut from five to four to three, plus a sleep mask and noise-canceling headphones between calls.
Fun fact from the episode: When a therapist first suggested Phil might be neurodivergent, he joined an online community and asked, "Do I just need to drink more coffee?" They told him, very kindly, that it's a different kind of stimulation he needs.
Mentioned in this episode:
Alan Watts: The Story of the Chinese Farmer (video) - Mirrorboarding - The Highly Sensitive Person (Elaine Aron) - ADHD presentations (CHADD) - Attachment styles (Cleveland Clinic) - Body doubling (CHADD) -ClaudeCowork
About today's guest:
Phil Drinkwater is a business coach for founders, executives and leaders with ADHD, autism, or both. He started out as a computer games programmer, scaled his previous company to $20M in sales, and has a psychotherapy background. He's accredited by the Association for Coaching (UK), has coached more than a hundred business owners and leaders, and is AuDHD himself. Phil is based in Manchester, England, and works with clients online.
Connect with Phil:
Website LinkedIn Running on Friction (free book) Thinking Out Loud blog
Your ADHD-ish™ host, Diann Wingert, MSW
Drawing from her own experiences as a serial business owner, former psychotherapist and fellow ADHDer, Diann Wingert developed The ADHD-ish™ Method, her six-month, 1:1 business strategy and coaching program, the ADHD-ish™ podcast, and Di AI, her digital clone.
Di AI is available free in beta through the end of ADHD Awareness Month and ends on October 31st. Got something in your business you've been filing under "can't"? Take it to my digital coaching clone and ask her "how can I?" Sign up now and start chatting!
Got a pile of unmade decisions sitting between you and the work? Book a free consultation with Diann and let's talk about how I can help.
© 2026 ADHD-ish™ Podcast. Intro music by Ishan Dincer / Melody Loops / Outro music by Vladimir / Bobi Music / All rights reserved.
