If The Shoe Fits...

Fellow Shoe-Wearers,

The year was 1999.

The event: Dakota Rubin’s Bar Mitzvah.

The shoes: magenta hot pink platform strappy heels from the DSW sale rack.
It's safe to say that as a preteen and teen, I was pretty obsessed with shoes. My favorite place in the world was the DSW sales rack, hunting for the most ridiculous heels I could find. It was seventh grade, and I had a bar mitzvah to attend just about every weekend. Those shoes got a lot of wear—but they were ridiculously uncomfortable, and I'm honestly shocked I didn't break an ankle.

I was trying to find my identity in those days, like any young woman does. Figuring out who I was, what mattered to me, navigating friendships and more. Shoes were just part of that.
Fast forward to my early fundraising career. As I was learning how to ask for money, plan events, manage and be managed, I was also in desperate search for the perfect pair of black high heels to wear to galas. I refused to wear flats. Why wear flats when I could look fabulous all night—even if I paid the price later?

After one particularly grueling event I stopped at the dumpster outside my apartment, chucked my shoes in it, and walked barefoot down the alley. lk. My feet hurt so much. Why was I suffering like this?

But my shoe obsession continued.

It wasn't until my late thirties that I realized: I could wear flats to an event and no one would give a damn. I could even—most of the time—wear sneakers. These days, I have one pair of shoes I wear pretty much every day. One in black, one in white.For medium-fancy events, I've got a pair of sparkly sneakers. I can't remember the last time I wore heels.
It takes a long time to figure out what you're good at and who you are. And of course, that changes.

Which brings me to some news: starting this week, I'm stepping back into writing this newsletter.

For years, I wrote this newsletter myself. It was just me—then Kim Caldwell joined the team and changed everything. For the past few years, Kim has been the voice you've heard in your inbox every week—warm, funny, vulnerable, brilliant. Kim didn't just write newsletters. She pushed Giant Squid Group into new shoes entirely. We grew. We expanded. We became more than what I could have built alone. She created a space where we could be honest about how hard this work is while still believing it matters. Where we could talk about capitalism and candy corn in the same breath. Where feeling like you're doing it wrong could be reframed as evidence that the system is broken, not you.

And now, Kim is answering a new call. She's stepping into work that is urgent and important to her in this moment. Just like those magenta platform heels fit perfectly for seventh-grade Cat but would be absolutely ridiculous (and dangerous) for 40-something Cat, the role Kim played at Giant Squid Group fit beautifully for a season—and now she's trying on something new.

I couldn’t be more grateful, or more aware of the big shoes she’s left to fill.

When I started Giant Squid Group, my daughter had just been born. I was navigating new motherhood, a career transition, and the terrifying-exhilarating reality of building something from scratch. The business I built then fit the life I had and the person I was becoming.

Seven years later, both GSG and I have changed. My chronic illness became diagnosed and managed. My family grew. My understanding of what this work could be—should be—deepened. The shoes I was wearing didn't fit anymore, so I found new ones.

That's the thing about growth: it's supposed to be uncomfortable before it gets comfortable.

The role that fit you perfectly three years ago might pinch now. The work that energized you in one season might drain you in another. Your interests shift. Your life circumstances change. Your capacity evolves—sometimes expanding, sometimes necessarily contracting.

And that's not failure. That's being human.

We talk a lot in the nonprofit sector about "mission fit" and "organizational culture" and "the right seat on the bus." But we don't talk enough about how those things are moving targets. How the seat that was right for you in 2022 might not be right for you in 2026. How recognizing that and making a change isn't flaky or disloyal—it's self-aware and brave.

Kim reminded me (and all of us) that you can show up authentically in professional spaces. That vulnerability isn't weakness—it's connection. That the personal is professional when you're doing mission-driven work, because we don't leave our whole selves at the door.
So as I step back into this newsletter, I'm bringing all of that with me. You'll still get the warmth, the stories, the cultural references, the permission to be human while doing hard things. You'll still get the systemic analysis, the reframes, the reminders that burnout is a symptom of capitalism, not a personal failing.

But you'll be hearing it in my voice now. With my stories—about founding GSG while nursing a newborn, navigating chronic illness while running a business, serving on boards while parenting, finding sparkly sneakers that actually support my feet.
Because here's what I believe: comfort isn't about staying in one place. Real comfort is about finding what actually fits right now, even if it's different from what fit before. It's about trying on new roles, new shoes, new versions of yourself—and being willing to adjust when something stops working.

The magenta platforms had their purpose—they were exactly what seventh-grade Cat needed to figure out who she was. The black heels reminded me I could stop doing something that hurt. And the sneakers I wear now? They're perfect for where I am and what I'm building.

Kim's next chapter is going to be incredible. Giant Squid Group's next chapter is going to be different—and I think, even better. Your next chapter, whatever it looks like, deserves the same grace and possibility.

So here we go. New shoes, same mission: building a nonprofit sector that doesn't destroy the people trying to save the world.

Hit reply and tell me: what role or "shoe" are you wearing that doesn't quite fit anymore? What would it take to try on something new? I read every response, and I'd love to hear what's shifting for you.

Onward!
Cat