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September 30, 2026
Some jobs make you feel brilliant. Others make you wonder what happened to your brain.
Rosemary Hollinger is a certified ADHD coach who works with female lawyers and other analytical professionals. Before coaching, she spent 32 years at the Commodity Futures Trading Commission, eventually becoming Head of the Chicago Regional Office and Deputy Director in Enforcement. She was trying cases, shutting down Ponzi schemes, working alongside people she liked, and getting plenty of stimulation from the work itself.
Now she coaches lawyers who are every bit as smart and capable, but sometimes feel like they’re failing at the very careers they worked so hard to build.
And this is where it gets really interesting. Because what happens when the problem isn’t whether you can do the work, but the way the work is set up?
In this episode, Rosemary and I get into the parts of the legal profession that can be especially brutal for an ADHD brain, why the usual advice about priorities doesn’t always help, and something she discovered about her ADHD lawyer clients that genuinely surprised me. We also talk about what her own 32-year legal career taught her about the kind of work, people, and environment that can completely change how a brain performs.
“It took me a long time to get to the point of thinking, ‘it is okay to be different.”
-Rosemary Hollinger
“We can do very hard things in the right environment. Sometimes the people around us make even boring work engaging enough to do."
-Rosemary Hollinger
“I think ADHD professionals are the canaries in the coal mine. If something is wrong in the workplace, we are often going to notice it first.”
-Rosemary Hollinger
"Sometimes the real question is not, why aren’t you billing enough? It is, are you burned out, in the wrong job, or unable to bring yourself to do work you hate?"
-Rosemary Hollinger
"Body doubling helps with billing because everybody is doing the same miserable task together. Sometimes that alone makes it much easier to start and finish."
-Rosemary Hollinger
"Delegating, saying no, and getting unnecessary tasks off your plate are part of prioritizing too."
-Rosemary Hollinger
- Rosemary Hollinger reflects on lifelong ADHD traits, from restlessness and inconsistent grades to talking too much and feeling different.
- She explains how interest, supportive people, and the right team environment helped her thrive throughout her legal career.
- After seeing coaching transform workplace culture, she trained as a coach and eventually specialized in ADHD professionals and lawyers.
[18:25 – 36:29] Billable Hours, Procrastination, and ADHD at Work
- Rosemary explains why billable hours are especially difficult for ADHD lawyers, with constant task switching, time tracking, and working-memory demands.
- She describes the procrastination, shame, ghosting, and last-minute sprint cycle she regularly sees in legal professionals.
- Her character-strength research suggests ADHD lawyers highly value close relationships, helping explain why supportive teams and coaching can be so effective.
[36:29 – 57:21] Prioritizing Differently, Delegating, and the Power of the Pause
- Rosemary replaces vague “urgent versus important” prioritizing with concrete deadlines, delegation, and deciding what truly needs to be done by you.
- She and Tracy discuss perfectionism, outsourcing, workaholism, and using AI as a thinking partner to reduce overwhelm and get into action.
- Rosemary says thriving with ADHD means doing meaningful work with people you enjoy, and her current workaround is pausing before impulsively reacting.
ADHD isn’t a productivity problem. It’s an identity problem.
That’s why most strategies don’t stick—they weren’t designed for how your brain actually works. Your ADHD Brain is A-OK Academy is different. It’s a patented, science-backed coaching program that helps you stop fighting your brain and start building a life that fits. 👉Learn more here
- Website: partnerupcoaching.com
- Facebook: Partner Up LLC
- Instagram: @partnerup.llc
- Tiktok: @partnerup.llc
- LinkedIn: RosemaryHollinger
