Podcast Summary: ADHD for Smart Ass Women with Tracy Otsuka

Episode 352: "AI, Delegation, and ADHD: Work Smarter, Stress Less with Skye Waterson"
Guest: Skye Waterson, ADHD Strategist and Founder of Unconventional Organization
Release Date: October 1, 2025

Episode Theme and Purpose

This episode centers on working smarter—not harder—with ADHD, and how tools like AI and delegation can help entrepreneurial women with ADHD build practical systems that reduce overwhelm, maximize strengths, and create sustainable success. Host Tracy Otsuka and guest Skye Waterson dig deep into strategies tailored for neurodivergent brains, debunk common productivity myths, and share actionable tips for business owners, professionals, and anyone seeking a better way to thrive with ADHD.

Key Discussion Points & Insights

Skye’s ADHD Story & Professional Pivot (05:36–15:41)

• Early Academic Burnout:

  • Skye shares how chronic cycles of burnout throughout her academic career ultimately led to her ADHD diagnosis at the start of her PhD.
    • "All of my trying to outwork my ADHD symptoms, it just was not working." (08:28, Skye)
  • Pressure to overachieve came from a strong grade-oriented family and the belief that hard work could solve any problem.

• Diagnosis and Turning Point:

  • Diagnosis came via her university’s learning center, where inattentive and inconsistent performance revealed the possibility of ADHD.
    • "I literally went home and Googled ADHD in adults. And it was just bad, bad, bad, bad, bad..." (11:58, Skye)
  • Instead of feeling defeated, Skye dove into research and community-building, which blossomed into her global ADHD-focused business.

• Choosing Business over Academia:

  • Skye eventually left her PhD behind—by then, her ADHD-friendly business had become so successful she could no longer ignore her true calling.
    • "Sometimes you can't do both things. Sometimes you have two giant things in front of you..." (15:41, Skye)

Debunking Productivity Myths and Building ADHD-Safe Systems (24:21–29:16)

• One-Size-Fits-All Productivity Fails:

  • Skye addresses why classic methods (like the Pomodoro Technique) are often touted for ADHD folks, despite their origins serving neurotypical brains.
    • "The Pomodoro method was designed to help Italian students study...but we still see that all the time in advice for ADHD brains." (24:34, Skye)

• Reward System Adjustment:

  • ADHD brains often need a reward upfront just to get started—not just as a treat for finishing.
    • "We have to break those things down to get the task started." (25:52, Skye)
    • Example: Creating a pleasant 'vibe' (music, coffee, comfy environment) before tackling a boring/complex task.
    • "I use the recipe metaphor a lot because people can understand that..." (28:48, Skye)

• "Recipe" Approach for Overwhelm:

  • Create small, clear, step-by-step 'recipes' (task breakdowns) each time to combat working memory overload and resistance.

Prioritization and Cutting Through Urgency (29:16–34:09)

• Urgency vs. Importance:

  • Skye teaches a "prioritization filter" for making sense of overwhelming to-do lists:
    • Write down everything on your mind
    • Identify what’s TRULY urgent (i.e., has a negative consequence if not done tomorrow)—usually no more than 5 items
    • Focus first on true urgencies, then on 80/20 business "momentum-movers."
    • "Your job as an entrepreneur is to do the truly urgent tasks and then create space for the important." (30:28, Skye)

• Focus Over Scatter:

  • Using 30-day 'focus to growth' challenges gives entrepreneurs a single clear objective and measurable outcome, fostering real results.
    • "The first thing we do is a 30 day focus to growth challenge... People have tripled their previous month's revenue going, oh, if I focus this, I can do this." (33:01, Skye)

Delegation and Overcoming ADHD Barriers (34:09–39:47)

• The Emotional Block of Delegation:

  • Tracy and Skye commiserate on how uncomfortable it is to explain tasks to someone else.
    • "Nothing is more uncomfortable... than having to explain to someone how to do something." (34:34, Tracy)

• Skye’s AI-Driven Delegation System:

  • Use AI (with a voice feature) to create quick-and-dirty process docs—record yourself explaining a task, then let AI organize the information.
  • Empower assistants to iterate, improve, and own the process, reducing the pressure for perfection.
    • "The process I teach doesn't involve ever doing the task again." (36:05, Skye)
    • "You're empowering them in that moment and come back with questions..." (37:05, Skye)

Practical AI Strategies for ADHD Entrepreneurs (39:47–50:36)

• AI as Assistant, not Just Tool:

  • Automate repetitive processes using AI, but don’t let it become another “DIY bottleneck”—repeated AI tasks should be handed off to human assistants.

• Prompt Logs and Organization:

  • Keep a running doc of AI prompts for repeated use—structure beats chaos.
  • Use Notion + Notion AI for organization, meeting transcription, and summary—Skye and Tracy both admit it was a learning curve, but transformational.
    • "My assistant was like, you have to try Notion, and I was like, no. And then the AI turned up and it's been so much, so cool." (48:48, Skye)

• Prompts over Rambles:

  • Develop clean, specific prompts for AI rather than rambling, multi-topic requests.

Motivation for Aspiring ADHD Entrepreneurs (52:07–54:27)

• Start Simple: Sell Something:

  • The first step to entrepreneurship: Sell one thing to one person.
    • "You are a business owner when you sell something to someone. ...What is the fastest and easiest way that I can sell something to somebody right now?" (52:07, Skye)
  • Don't get lost in branding, websites, or endless prep—action creates momentum.

• Progress Trumps Perfection:

  • Both Skye and Tracy recount how messy and awkward their own business launches were—but it didn’t matter. Just start.

The Secret to Success with ADHD (54:27–57:30)

• Own Your Brain:

  • Success comes from understanding your strengths and weaknesses, disregarding unfit advice, and building confidence in your own style of working.
    • "Ignore advice that isn't built for your brain, and then feeling confident to go out and do things the way that they work for you." (54:35, Skye)

• Major Client Transformations:

  • Skye shares client stories: from tenure-track professors and sponsored athletes to $200k playwright grants, all achieved through custom ADHD systems.
  • "You water that seed, you plant that, you water that, you grow that... and that's how everyone starts." (56:37, Skye)

Notable Quotes & Memorable Moments

• On ADHD and Systems:
  • "You don't need more willpower. You need the right system." (02:39, Tracy introducing Skye’s message)
• On Rewards for ADHD Brains:
  • "While people who are more typical will get boosts at the start of a task, we will just get a bit of a womp. Womp. Why are we doing this?" (24:57, Skye)
• On Delegation with AI:
  • "The process I teach doesn't involve ever doing the task again." (36:05, Skye)
  • "They're going to be like, 'oh, thank goodness, she's finally delegating something to me.' And this is written with AI, it's not written by me." (37:02, Skye)

Important Tools and Tactics with Timestamps

Stardew Valley & Cozy Gaming (04:18–04:55)

• Skye decompresses with "cozy games" like Stardew Valley, helping her dopamine regulation.

Delegation via AI (35:56–39:47)

• Use the AI voice feature to make a rough process doc.
• Let your assistant pilot, troubleshoot, and refine for you.

Using Notion with AI (48:48–50:10)

• Notion AI can transcribe meetings, summarize action items, and makes organizing business life with ADHD much easier.

System for Reducing Overwhelm (29:16–31:59)

• Use a single prioritized task document
• Limit "truly urgent" items (rarely more than 5)

30-Day Focus Challenge (33:01–34:09)

• Sign on to ONE measurable focus/growth task for 30 days; this transforms productivity.

Actionable Takeaways

• Start with your strengths: Accept and design systems for your unique ADHD brain.
• Reward early and often: Build "pleasure" into the START of hard tasks.
• Get out of your head: Write everything down, then limit urgent tasks ruthlessly.
• Delegate with the help of AI: Speak your instructions, get AI to organize, and empower your assistant to iterate—don’t aim for perfection.
• Build Prompt Logs: Keep AI interactions structured and retrievable.
• If you want to start a business, JUST SELL SOMETHING: The rest can follow.

Where to Find Skye

• Website & resources: Unconventional Organization
• Instagram DM for overwhelm resource: @unconventionalorganization (DM “WOMAN” or “WOMEN”)
• Podcast: ADHD Skills Lab

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