I Have a Serious Problem with To-Do Lists (And You Probably Do Too)
Okay, I need to be completely honest with you about something that's been running my life since I was old enough to own a neon-colored Lisa Frank planner. And yes, I was absolutely “that kid”—the one with different colored markers for different subjects, scheduling everything every day of the week by hour from homework time to friend hangouts to tests and soccer practice. (My high school best friend still brings this overbooked up at least once a year, by the way.)
Get my point? I have a serious problem with to-do lists.
Like, the kind of problem where I look at my daily list and think, "Holy shit, am I secretly three people?" You know that feeling? When you've written down enough tasks for a small army, and somehow you still think you can get it all done before dinner?
Right. That's been my entire life…
This isn't one of those stories where I figured it all out and now I have the perfect relationship with right-sized expectations around time, work and productivity now (spoiler alert: I definitely don't). This is me, sitting here at my desk with my favorite black Pilot V7 pen (because of course I have a favorite pen), sharing what I'm learning while still very much in the thick of it. If you've ever wondered why your brain seems to think you can accomplish seventeen big things between 7 hours on a Tuesday... welcome to the club. Population: way too many of us driven and ambitious women with relational trauma histories.
It Started Early (Like, Embarrassingly Early)
Picture this: a seventeen-year-old on this tiny island off the coast of Maine—I mean, we're talking 3,000 people, one grocery store that closes at 6 PM, and where if you sneezed on one side of the island they would say “Gesundheit!” on the other side— this girl wasn't just aiming for valedictorian. She was doing it while running student council, serving as senior class treasurer, playing two sports (badly, but still showing up), participating in civil service programs, and somehow finding time to represent Maine in Washington D.C. at youth leadership conferences.
I know. I know. Even writing it out makes me tired.
From the outside, it probably looked like impressive ambition, right? From the inside? It felt like I was constantly trying to outrun something I couldn't name, something that whispered "not enough" no matter how many boxes I checked off my ever-growing lists.
My best friend used to joke—and honestly, she wasn't wrong—that watching me plan a weekend was like watching someone coordinate a military operation. She'd suggest we "just hang out," and I'd show up with this color-coded itinerary for Saturday afternoon. Four different activities. Timed to the hour. (I wish I was kidding, but I'm really not.)
She—built more like a housecat who likes to lay in the sun and nap vs me the somewhat frantic Belgian drafthorse who always needs to be working in the fields—was always encouraging me to rest, to take breaks, to just... be. I never, ever would. Because sitting still felt dangerous in a way I couldn't explain back then.
Sound familiar? That pattern of loading your schedule like you're preparing for battle—it's been with me my entire life.
Where It Really Comes From (The Part That's Hard to Admit)
Here's what's challenging for me to own, especially as someone who literally helps other people understand their patterns: I keep taking on projects that make absolutely no logical sense given what's already filling my calendar to the brim.
I mean, the most glaring example? Launching a therapy center when my daughter was three months old. Three. Months. Old. What the hell was I thinking?
I can rationalize it six ways to Sunday—prime Berkeley real estate doesn't come up often (especially pre-pandemic when therapists were basically fighting over closet-sized offices), the opportunity was rare, the timing was "perfect" from a business perspective. Blah blah blah.
But if I'm being brutally honest with you? I was addicted to the safety that came from a completely packed calendar. And that safety has almost always been rooted in one specific terror: financial ruin.
Growing up disowned by my biological father (yes, that happened—more on that in future letters), watching my mother struggle financially and being completely on my own from a ridiculously young age with zero family safety net... the original motivation was proving my worth and getting off that island. But later, when I was financially independent and still loading my schedule like creditors were chasing me with pitchforks, it became about never, ever ending up on the streets.
That was my biggest fear. Without family as an umbrella or a social network to catch me if everything fell apart, staying busy felt like survival itself.