Filling the Pitcher Without Poking Holes
When I was in high school, there was an award—or maybe a recognition, maybe even a ceremony—centered around a pitcher.
Not the baseball kind.
It was something about being a person who filled others’ pitchers. I remember the phrase “you can’t pour from an empty cup,” and I’m fairly certain it had a “fill yourself with the Holy Spirit” angle (all-girls Catholic school, after all).
That was far from the first or last time I heard the phrase “fill your own cup.” I’ve repeated it back over the years, almost like a reflex mantra. But the truth is—don’t we all struggle to actually do it?
When we take time for ourselves, guilt often creeps in (“guilty pleasure” didn’t get coined accidentally). Or maybe it’s not guilt—it’s that nagging voice saying, you should be doing something else right now. And if we’re mentally scolding ourselves while we’re trying to fill our cup, we’re not really filling it at all.
It’s like we’re pouring into our own pitcher while poking holes in the sides.
Recently, my therapist and I talked about habit tracking. I’d been tracking things like exercise, mobility work, writing, reading, and symptom check-ins (helpful for my doctors since I live with chronic illnesses).
But here’s the problem: even on a day I felt great, I’d get to my evening checklist and think, Crap—I didn’t hit any of my habits today. That one thought could take me from feeling proud to feeling like I hadn’t done enough.
Clearly, not the point of habit tracking.
So we pivoted.
My Passion Planner only has six habit-tracking slots (no, I’m not sponsored—though at this point, maybe I should be; I’ve been a fan since 2014). I realized I needed to rethink the purpose behind my habits. Because ultimately, they all had the same goal: pour back into my own pitcher.
Instead of tracking rigid, task-specific habits (read for 20 minutes, do mobility routine, log Bearable app), I shifted to categories—flexible ways I can care for myself each day without turning it into another to-do list.
Here’s what I landed on:
Movement
Move—big or small, gentle or intense.
Walking, lifting, yoga, bike rides, hikes, yard work, kayaking.
Mindfulness
Slow down, turn inward, find breath.
Guided meditation, tarot pull, journaling, deep breathing.
Creativity
Make something—small, messy, weird, beautiful.
Writing, watercolor or doodles, wood burning, sewing, baking.
Input
Take something in—nourishing or curious.
Reading, documentaries, podcasts, music, parts work (therapy), time outdoors, time with the right people.
Restore
Take care of my body—gently and kindly.
Mobility work, foam rolling, deep stretch, luxury shower, nap without guilt, evening routine with soft lighting.
Track
Notice patterns—for care, not control.
Food logs, symptom journals, energy tracking.
When I stopped making “fill my cup” into a rigid, quantifiable set of tasks and started thinking in categories, something shifted.
It became less about doing it “right” and more about asking: What would pour into my pitcher today?
And maybe that’s the thing—our pitchers aren’t always filled by the same water. Sometimes it’s a big hike. Sometimes it’s tea with a friend. Sometimes it’s lying in bed watching the rain.
Filling our cups isn’t a one-size-fits-all recipe. It’s a daily conversation with ourselves—one that should feel nourishing, not nagging.
So, what’s pouring into your pitcher today?
H.R. Gordon is the author of children’s and adult works of fiction and nonfiction. She is also the founder of Gordon Publishing and its imprints Spilt Ink Press and Beach Bum Books and an adjunct professor at SUNY University at Buffalo and Fredonia, St. Bonaventure University, and a number of other colleges. Outside of writing, Hannah is a dedicated competitive powerlifter, with current PRs (personal records) at: Squat: 375 lb; Deadlift: 445 lb; Bench: 210 lb. When she’s not writing, teaching, or working out, she enjoys cooking, reading, hiking, DIYs and refurb projects, and smashing the patriarchy.
Hannah welcomes connections through @HR_Gordon on all major social media platforms and on her website HannahRGordon.com. She lives in Buffalo, New York, with her partner Bryan, a librarian, a three-legged super mutt therapy dog Charley, his little sister Iggy, who is basically a dingo, and their baby brother Meeko, who is a menace to society.