The ADHD Business Strategist Who Turns Chaos into Focused Growth (Sky Waterson)

2026-01-05

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You don’t need more discipline. You need a system built for your brain. In this powerful conversation, ADHD strategist and founder of Unconventional Organization, Sky Waterson, reveals why most traditional productivity and business systems silently fail ADHD entrepreneurs—and what to do instead. If you’ve ever felt “broken” because you can’t stick to lists, planners, or funnels that seem to work for everyone else, this episode will feel like finding the manual you never got. Sky breaks down her “step into focus” routine, how to escape the ...

You don’t need more discipline. You need a system built for your brain. In this powerful conversation, ADHD strategist and founder of Unconventional Organization, Sky Waterson, reveals why most traditional productivity and business systems silently fail ADHD entrepreneurs—and what to do instead. If you’ve ever felt “broken” because you can’t stick to lists, planners, or funnels that seem to work for everyone else, this episode will feel like finding the manual you never got.

Sky breaks down her “step into focus” routine, how to escape the feast-or-famine cycle, and why dopamine, time blindness, and working memory must sit at the center of any system you use. From post-it recipes to front-loading rewards, she shows you how to create sustainable focus, predictable revenue, and space for hobbies and real life—without trying to become someone you’re not.

What You'll Learn:

Traditional systems fail ADHD brains because they ignore dopamine, working memory, and time blindness. They weren’t designed for you.
Feast-or-famine is a systems problem, not a character flaw; you need focus filters and clear revenue visibility, not more willpower.
The “step into focus” routine starts with a reward before the hard task, then uses a simple written “recipe” to defeat distraction.
Post-it note planning helps counter time blindness and tab-hopping by defining exactly what you’ll do this session—no more getting lost in rabbit holes.
Immersive hobbies are essential, not optional; intense, project-like hobbies help ADHD entrepreneurs switch off, reset, and come back sharper.

Timestamps

00:01 – Why ADHD entrepreneurs burn out on traditional systems
Sky explains why “proven” business frameworks keep ending up on the shelf for ADHD minds.
02:15 – The hidden cost of forcing yourself into neurotypical systems
How misaligned systems create shame, exhaustion, and constant restarting.
04:15 – The feast-or-famine trap and the “focus filter” fix
Sky shares how to stop reacting to everyone else’s crises and start building real momentum.
05:03 – The secret: reward yourself before you start
Dopamine transfer deficit theory and why standard “reward yourself after” advice doesn’t work for ADHD.
06:34 – The step into focus routine: post-its, recipes, and no more rabbit holes
A practical breakdown of how to write out your focus like a recipe and protect it from distractions.
09:04 – From crisis to clarity: turning ADHD strategy into time and revenue
How combining ADHD tools with business strategy unlocks hours back each week.
10:35 – 30 keynotes in one month: a client case study
How one speaker used Sky’s method to cut his prep time in half, consistently.
11:19 – Why intense hobbies (like Warhammer) can save your focus
The power of immersive, project-based hobbies for switching off from business without numbing out.
15:16 – Calendar hacks: scheduling rewards, not just tasks
Why writing the reward in your calendar might be the switch your brain actually responds to.
17:17 – ADHD, energy, and human design: a new frontier?
A teaser into exploring the overlap between ADHD, energetic types, and how we work best.