Organizing an ADHD Brain

GUEST BIO
Bailey Pilant is a New York and Florida-licensed therapist, ADHD-CCSP certified, and the founder of The Wave Counseling, a practice specializing in neurodivergent affirming therapy for women navigating ADHD, anxiety, burnout, and life transitions. She brings both clinical expertise and lived experience to her work, helping women understand themselves more deeply and advocate for the support they actually need. Find her:
Website: https://thewavecounseling.com 
Instagram: https://www.instagram.com/thewavecounseling 
TikTok: https://www.tiktok.com/@thewavecounseling
SHOW NOTES
Have you ever felt like your ADHD symptoms get dramatically worse at certain times of the month, and wondered if it was all in your head?
On this episode of Organizing an ADHD Brain, ADHD coach Megs welcomes back therapist Bailey Pilant to break down the connection between ADHD, hormones, and women's health, including cycle tracking, perimenopause, and PMOS. Whether you're looking for ADHD coaching, a supportive ADHD community, or practical ways to get organized, this episode meets you where you are.
By the end, you'll understand why women's ADHD is so often missed, how your hormones are directly affecting your symptoms, and what you can start doing right now to track, plan, and advocate for yourself.
Bailey explains how estrogen affects dopamine and why that means ADHD symptoms can shift dramatically across the menstrual cycle, worsen with age, and intensify during perimenopause. She walks through why women's ADHD is so frequently dismissed as personality traits rather than a neurological difference, the knowledge gaps that exist around diagnostic criteria and co-occurring conditions, and why girls often mask in ways that hide their symptoms entirely. They also dig into emotional overwhelm, what borderline hormone test results can mean, and why "normal" results don't always tell the full story.
Bailey shares her own experience with PMOS (formerly PCOS), the value of at-home hormone tracking, and how using real data can help you plan supports, communicate your needs, reduce reactivity, and extend yourself genuine self-compassion, through what she calls "experiments" rather than expectations.
The good news? Once you understand what your hormones are doing and when, you stop wondering if something is wrong with you and start working with your body instead of against it.
Previously on Organizing an ADHD Brain — Bailey's earlier episodes: 
Cravings & Cognitive Chaos: Decoding the ADHD-Eating Disorder Connection for Women
Cognitive Chaos: Interview with Bailey (Part 2)
This episode is for any woman with ADHD who has ever felt like her symptoms were a moving target — and is ready to understand why.
3:31 — Why women's ADHD is so often missed and dismissed as personality traits 
8:18 — How ADHD presents differently in girls versus boys due to socialization and masking 
14:18 — How estrogen affects dopamine and what that means for ADHD symptoms across your cycle 
17:49 — When to test your hormones and what to look for 
20:39 — When test results look "normal" but something still feels off 
26:26 — Cycle tracking as a self-support tool, using data to plan and regulate 
36:03 — Perfectionism, self-compassion, and reframing progress as experiments 
44:03 — What PMOS means and Bailey's personal experience with her diagnosis 
50:55 — How to work with Bailey and closing thoughts
Share your thoughts with Megs!
Would you like to learn more about hiring Megs as your ADHD coach? Start here> The Perfect Place to Start
The Community is OPEN! Join right here: Organizing an ADHD Brain
You can also learn more about the community HERE> OrganizinganADHDBrain.com

On this episode of Organizing an ADHD Brain, ADHD coach Megs breaks down the "deadheading" analogy, removing what's no longer living so your energy and resources can go toward what will actually thrive. Whether you're looking for ADHD coaching, a supportive ADHD community, or practical ways to get organized, this episode meets you where you are.
By the end, you'll have a new framework for making decluttering decisions that feel regulated, intentional, and aligned with where you're actually going, not where you've been.
Megs shares the real story behind letting go of most of her family's belongings before their move from Colorado to Massachusetts. When she and Adam learned that moving pods could cost up to $16,000, they made a different call, sell, gift, donate, and occasionally discard. What followed was an unexpectedly emotional process of untangling identity, memory, and nervous system strain from the objects filling their home.
She reflects on the time cost of selling, the weight of repeated decision-making, and how Dana K. White's decluttering questions helped her make choices that felt grounded rather than reactive. She shares memorable exchanges with buyers and neighbors, what they chose to keep (sentimental ornaments made the cut), and how renting furnished places freed them from the pressure of building a "perfect" space, and let them focus on what was actually next.
The good news? You don't have to let go of everything. You just have to get clear on what you're growing toward, and deadheading gets a lot easier from there.
This episode is for anyone with ADHD who is holding onto more than they need and is ready to make peace with letting go.
Products mentioned in this episode: Colorful storage drawers with gold knobs: https://amzn.to/3Pxt9oY 3-tier rolling cart: https://amzn.to/3PgYDQm
Organizing an ADHD Brain is supported by its audience: when you purchase through links on our site, we may earn an affiliate commission.
Share your thoughts with Megs!
Would you like to learn more about hiring Megs as your ADHD coach? Start here> The Perfect Place to Start
The Community is OPEN! Join right here: Organizing an ADHD Brain
You can also learn more about the community HERE> OrganizinganADHDBrain.com

What if the hardest part of a big life change isn't the logistics, it's everything that happens while you're in the middle of it?
On this episode of Organizing an ADHD Brain, ADHD coach Megs walks through what it really looks like when a carefully made plan meets real life; grief, fear, and all. Whether you're looking for ADHD coaching, a supportive ADHD community, or practical ways to get organized, this episode meets you where you are.
By the end, you'll have a new way to think about the messy middle, not as failure, but as temporary data pointing you toward what matters most.
Megs gets real about her fourth move of the year, relocating from Colorado to Massachusetts after selling their home in July 2025. She came prepared: early packing, labeled boxes, a full week off to settle in. Then the plan met life. What followed was a week of grief, anxiety, and move-related chaos that no amount of planning could have prevented.
She explores why change is uncomfortable even when it's good, how clutter and unfinished logistics amplify emotional overwhelm for ADHD brains, and why regulation in those moments comes down to something simple, reminding yourself that you are safe. She shares the choice she kept making that week: putting down the unfinished tasks to be present with her kids, even when everything around her felt undone.
The good news? The messy middle isn't a sign that something went wrong. It's information. And choosing presence over perfection, even once, even imperfectly, is always the right move.
This episode is for anyone with ADHD who is navigating a season of change and needs permission to put down the to-do list and just be okay for a minute.
TIME MARKERS 
2:45 — How Megs planned the move: early packing, labeled boxes, a week to settle in 
4:39 — When life hits: a friend's death, a community crisis, and Charlotte's hospital visit 
7:22 — Finding home again in the middle of grief and chaos 
10:23 — How clutter and unfinished logistics amplify ADHD overwhelm, and what regulation actually looks like 
14:45 — Choosing presence over productivity, putting down the tasks to be with her kids 
18:14 — Lessons from the week: what the messy middle was actually teaching her 
22:17 — Permission to pause, why stopping is sometimes the most regulated choice 
Share your thoughts with Megs!
Would you like to learn more about hiring Megs as your ADHD coach? Start here> The Perfect Place to Start
The Community is OPEN! Join right here: Organizing an ADHD Brain
You can also learn more about the community HERE> OrganizinganADHDBrain.com

Does it ever feel like you're constantly running on empty, rushing, crashing, and starting the whole cycle over again?
On this episode of Organizing an ADHD Brain, ADHD coach Megs welcomes back therapist and author Jenna Free to talk about her book, The Simple Guide to ADHD Regulation, and what it actually means to heal your nervous system instead of just managing it. Whether you're looking for ADHD coaching, a supportive ADHD community, or practical ways to get organized, this episode meets you where you are.
By the end, you'll understand why so many ADHD coping strategies keep you stuck, and what a different approach to regulation could make possible for your everyday life.
Jenna explains how many ADHDers live in chronic fight-or-flight, caught in frantic crash cycles that quietly make executive functioning and symptoms worse over time. Her approach isn't about more homework, better organization systems, or forcing your way through, it's about retraining your nervous system toward genuine balance. They dig into why rushing, rigid cleanliness, hustle culture, and constant news and social media scrolling can all function as attempts to soothe dysregulation rather than actually resolve it..
The good news? Regulation isn't about becoming a different person or achieving a perfect life. It's about building enough internal stability that you can stay okay — no matter what the messy middle throws at you.
Grab Jenna's book, The Simple Guide to ADHD Regulation, on Amazon: https://amzn.to/4w7Z14d
This episode is for anyone with ADHD who is exhausted by the cycle of hacking and crashing and is ready to try something that goes a little deeper.
Jenna Free is a therapist, ADHD specialist, and the author of The Simple Guide to ADHD Regulation, a practical, structured approach to retraining the nervous system for people who are tired of hacks and ready for something that actually sticks. Diagnosed with ADHD herself at 32, Jenna brings both lived experience and deep clinical expertise to her work helping ADHDers move out of chronic fight-or-flight and into a life that feels more balanced, more spacious, and a lot less frantic. 
instagram: @adhdwithjennafree
website: ADHDwithJennafree.com
1:25 — From coping and hacking to actually healing 
3:16 — The eureka moment behind her method 
9:35 — The "messy middle" 
15:34 — Control, perfectionism, and how they show up as dysregulation in disguise 
19:05 — The power of doing one thing at a time for an ADHD nervous system 
22:46 — What it actually means to be dysregulated 
25:09 — How Jenna's method differs 
29:35 — ADHD dysregulation vs. trauma dysregulation 
34:40 — How regulation creates space for ambition instead of replacing it 
39:11 — News, doomscrolling, and the beliefs quietly driving the habit 
44:22 — Choosing presence as a daily practice — what that looks like in real life 
47:56 — Kids, screens, and the underrated value of boredom 
54:07 — No shame, just curiosity — how to wrap it all together
Share your thoughts with Megs!
Would you like to learn more about hiring Megs as your ADHD coach? Start here> The Perfect Place to Start
The Community is OPEN! Join right here: Organizing an ADHD Brain
You can also learn more about the community HERE> OrganizinganADHDBrain.com

Have you ever looked at a blank weekly planner and thought, I don't even know where to start?
On this episode of Organizing an ADHD Brain, ADHD coach Megs teaches how to make a plan that actually works for an ADHD brain, without needing it to be perfect. Whether you're looking for ADHD coaching, a supportive ADHD community, or practical ways to get organized, this episode meets you where you are.
By the end, you'll have a new way to think about planning, one that bends instead of breaks, and actually helps you feel more regulated instead of more overwhelmed.
Megs gets real about a hard day juggling two young kids and another move, then pushes back on the idea that ADHD brains just can't plan. Plans, rhythms, and routines can absolutely work, when they're simple, written down, and treated as flexible guides instead of rigid rules to fail at.
Using meal planning as her anchor example, she shares what she learned living temporarily on a mountain in Georgia (far from any grocery store), and how she eventually built a Sunday meal-planning habit in Massachusetts that reduced both overwhelm and overspending, even on the weeks it still fell apart. She walks through how to notice what isn't working, break goals into small steps, set intentions with reminders and support like body doubling, and build a "bare minimum" plan for your worst days so you stay regulated even when life gets chaotic.
The good news? A plan doesn't have to be beautiful or complete to work. It just has to exist, and this episode shows you exactly how to build one you'll actually use.
This episode connects to an earlier conversation about all-or-nothing thinking, if that resonates, check out the "Burn It All Down" episode here: https://podcasts.apple.com/us/podcast/organizing-an-adhd-brain/id1728728980?i=1000760213135
Looking for more meal-planning and organizing support? Join Megs' Circle community, a space built for ADHD brains who want accountability and connection without the pressure. > Join Here
This episode is for anyone who has ever given up on planning because it felt too hard to do it perfectly, and is ready to try a different way.
Time Stamps:
2:03 — An Instagram video about ADHD planning sparks a reframe 
3:23 — Why plans fail: and why that's not the whole story 
4:26 — The Georgia meal planning story: planning on a mountain far from groceries 
7:46 — Building a Sunday meal-planning routine in Massachusetts 
11:26 — Keeping plans simple, written, and flexible 
13:25 — Beliefs, small wins, and what actually builds momentum 
17:04 — What a plan really is — and what it doesn't have to be 
18:25 — How to reverse-engineer a goal into something doable
4:03 — Setting intentions, reminders, and using body doubling for support 
29:27 — Expecting imperfection: treating plans like projects, not promises 
32:12 — Building a bare minimum plan for your hardest days 
35:52 — Community invite and closing thoughts
Share your thoughts with Megs!
Would you like to learn more about hiring Megs as your ADHD coach? Start here> The Perfect Place to Start
The Community is OPEN! Join right here: Organizing an ADHD Brain
You can also learn more about the community HERE> OrganizinganADHDBrain.com