ADHD, Parenting, and the Pressure of Entrepreneurship (With Jessica Shaw)

The ADHD Skills Lab

The school sent her daughter to a desk with her head down because she could not sit still during circle time. That was the moment Jessica stopped waiting for someone else to figure it out.

Jessica Shaw is an award-winning journalist whose work has appeared in the New York Times, Entertainment Weekly, and Vanity Fair. She is the host of Everyone Gets a Juice Box, Understood.org's podcast for parents raising neurodivergent kids. She is also a mom of two teens who think differently, and someone who recognized her own ADHD only after researching her children's.

Skye and Jessica get into what the detective process actually looks like. Why parents are often dismissed first and believed later. How the school system's default response to a kid who cannot conform is to remove them rather than support them. What guilt sounds like when you feel like you should have seen it coming sooner. And why the window between noticing something and getting real support is longer, more expensive, and more isolating than it should be.

What We Cover:

  • Why parents are often the last ones taken seriously, and what it takes to keep pushing anyway
  • How school systems send a conformity message to neurodivergent kids and what it costs them long-term
  • The financial and time barriers to evaluation, and why they fall unevenly across families
  • What the detective process looks like when the parent doing the investigating also has undiagnosed ADHD
  • Why one parent's decision to reduce work hours for her neurodivergent child was called "trad wife" by colleagues, and what that reveals about the support gap

Connect With Jessica Shaw

About ADHD founders for ADHD founders.

Interesting in working together? You can click here to receive a free bottleneck audio session and learn more about what we do. https://www.unconventionalorganisation.com/unstuckaudiosession

Diagnosed with ADHD at the start of her PhD, Skye Waterson spent years researching what actually works and writing about it for thousands of founders. The pattern she kept finding: ADHD business owners don't have a focus problem, they have an operations problem, because the whole business runs through their own head. Now she and her husband, former programmer Robert Waterson, work as fractional COOs for those founders. They find the bottleneck, hire the fix, and build the system that holds.

Subscribe to our Newsletter - https://unconventionalorganization.substack.com/

Follow us on Instagram - @unconventionalorganisation

Visit our website - https://www.unconventionalorganisation.com/

More description

The school sent her daughter to a desk with her head down because she could not sit still during circle time. That was the moment Jessica stopped waiting for someone else to figure it out.

Jessica Shaw is an award-winning journalist whose work has appeared in the New York Times, Entertainment Weekly, and Vanity Fair. She is the host of Everyone Gets a Juice Box, Understood.org's podcast for parents raising neurodivergent kids. She is also a mom of two teens who think differently, and someone who recognized her own ADHD only after researching her children's.

Skye and Jessica get into what the detective process actually looks like. Why parents are often dismissed first and believed later. How the school system's default response to a kid who cannot conform is to remove them rather than support them. What guilt sounds like when you feel like you should have seen it coming sooner. And why the window between noticing something and getting real support is longer, more expensive, and more isolating than it should be.

What We Cover:

  • Why parents are often the last ones taken seriously, and what it takes to keep pushing anyway
  • How school systems send a conformity message to neurodivergent kids and what it costs them long-term
  • The financial and time barriers to evaluation, and why they fall unevenly across families
  • What the detective process looks like when the parent doing the investigating also has undiagnosed ADHD
  • Why one parent's decision to reduce work hours for her neurodivergent child was called "trad wife" by colleagues, and what that reveals about the support gap

Connect With Jessica Shaw

About ADHD founders for ADHD founders.

Interesting in working together? You can click here to receive a free bottleneck audio session and learn more about what we do. https://www.unconventionalorganisation.com/unstuckaudiosession

Diagnosed with ADHD at the start of her PhD, Skye Waterson spent years researching what actually works and writing about it for thousands of founders. The pattern she kept finding: ADHD business owners don't have a focus problem, they have an operations problem, because the whole business runs through their own head. Now she and her husband, former programmer Robert Waterson, work as fractional COOs for those founders. They find the bottleneck, hire the fix, and build the system that holds.

Subscribe to our Newsletter - https://unconventionalorganization.substack.com/

Follow us on Instagram - @unconventionalorganisation

Visit our website - https://www.unconventionalorganisation.com/

2026-05-18 31 min Transcript
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