Whenever Dylan Field’s face appears in the news—poised and framed by Figma’s success—my mind pulls me back to a memory of Dylan from 2016, climbing the stairs to our second-story office, arms straining under two bulky 24-packs of Charmin. Each one was nearly half his size. I remember chuckling to myself as I watched my CEO hauling toilet paper to restock the bathrooms. But the image stuck with me, and years later I understood this act as the underappreciated, steadying thread of effective leadership: the quiet willingness to carry what must be carried, no matter how small or heavy or unseen.

I joined Figma to build the world’s first collaborative design editor in the browser, not to manage anyone. A few months in, I was tasked with the team libraries project, which was a way for designers to share reusable components across files. It was technically ambitious, and I spent the early days designing backend APIs and debugging esoteric AWS S3 errors. I savored being in the weeds.

Just a few weeks into the project, Dylan asked how soon we could ship it. After two long days of mapping every dependency and date, I returned with a four-month plan for a single engineer, possibly a month or two less if we added more engineers. Before even glancing at it, Dylan said, “We can’t wait that long. We need it in less than half the time. How can we do that?”

My ego imploded. All my careful planning felt instantly obsolete. A quiet, hot current of resentment welled up within me. I thought I was in control of this project. When I vented to my manager, he asked, “Have you tried meditating?” I hadn’t, and I wasn’t planning to.

That weekend, running along the Bay, the pull of the tide gave me space to let go of my sunk-cost ego. I made peace with leading from the middle. In its place came a rush of harder questions about the project: What can we cut? How many people can work in parallel? Who can I ask to help? And beneath them all, one question I couldn’t escape: am I up to this?

I didn’t know it then, but an impossible deadline can be clarifying. It strips away the inessential and teaches you how to move through pressure—not by resisting it, but by learning to detach just enough to float atop it.

A few days later, right before the winter break, a handwritten thank-you note from Dylan appeared on my desk. He’d written one to every employee. I felt genuinely acknowledged at the time, but I also notice now how that gesture made it easier for him to ask for the impossible again next time—and easier for me to say yes. Maybe great leadership is knowing that urgency and gratitude can coexist, and maybe must, if a team is to carry impossible loads.

After the break, the project began to grow. One engineer became three, then five, then most of the company—all roughly 15 of us. My role shifted. I wrote less code, and my commits gave way to standups, one-on-ones, and status threads. I stopped solving problems directly and started absorbing them—the doubts, the blockers, the quiet unease that accumulates in a fast-moving team. As the project’s lead, I had become the person people looked to when they weren’t sure what to do next.

That’s how leadership often begins: not with a promotion, but with the gradual transfer of other people’s uncertainty into your hands.

There were nights when doubt kept me up. The new, complex feature we were building was untested and scrappy, held together by belief and several sleepless nights. Yet the team pushed forward relentlessly, aiming to ship the feature whenever it appeared ready for release. Then came Dylan’s next challenge: let’s launch in two weeks on Valentine’s Day so we can tweet “Here’s a little love from Figma.”

The team balked, and I worried morale would crack. The designs were unfinished and bugs still littered the code. Shipping in two weeks felt reckless. As team members came to me voicing their worries, I realized they weren’t afraid of ambition; they were afraid of overpromising a polished experience. The problem wasn’t the deadline; it was the contract. So I suggested we call it a beta, and the weight on the team lifted. That small word made a large difference: we could be ambitious and honest, and users would understand where we were in the journey. Dylan initially hesitated, worrying it would be an excuse for us to delay, but in the end, he came around. That single word bent the pressure just enough for us to move again.

On the evening of Valentine’s Day, we raced to complete the few tasks that still lingered. As Dylan walked toward the door, he stopped. “I appreciate how hard everyone’s working,” he said, “but it’s Valentine’s Day. Go home. We’ll launch tomorrow.” That moment taught me more about leadership than any all-nighter could. Knowing when to stop is as vital as knowing when to push. Urgent founders often confuse relentlessness with good judgment. The most valuable thing Dylan did wasn’t pushing us—it was knowing when pushing would break something that couldn’t be fixed.

When we launched the next day, we were tired, proud, and a little stunned that we’d made it. Afterward, a teammate handed me a box of chocolates and a card signed by the entire company. Inside the card, one note read, “You were a really helpful shit umbrella.” I laughed, having never heard that expression before. I also learned that leading from the middle doesn’t mean shielding your team from all pressure—that’s impossible; it means refracting the pressure and transforming diffuse anxiety into specific, solvable problems.

Looking back nearly a decade later, I see those formative months at Figma as a crucible. Leadership, I learned, is a series of impossible balances. It’s not just about driving people forward; it’s about carrying them without crushing them. It’s ambition held in tension with empathy. It’s knowing when to sprint and when to rest. It’s the willingness to carry the toilet paper and the team alike—the small burdens and the enormous ones, often at the same time.