Good Things Come in Threes

Moving on, finding a forward path, and not settling

Welcome to Frank Takeaways. I'm Frank, writing the notes worth keeping from decades at companies like Slack, Etsy, and Google. I run a coaching practice dedicated to guiding leaders through the tricky stuff of building products and high-performing teams.

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Note: This one's a bit more personal. Less takeaway, more reflection. Felt right to share it anyway.

A year ago this month, I left Slack.

I left for all the reasons I knew I eventually would, reasons clear to me even before I joined. It happened a little sooner than I expected, but the timing felt right despite the uncertainty ahead. I learned. I grew. I worked alongside some of the smartest, kindest people I've ever known. It was a career highlight in a very fortunate, very lucky run.

And still, I found myself longing for a third vision quest in eight years — with short stints between each.

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The first came after I left Betterment. I needed to clear my head, so my wife (then my girlfriend) dropped me off in Italy like a parent at summer camp. We spent a long weekend in Milan, then she waved arrivederci, and I traveled solo throughout northern Italy for ten days. I never planned more than a day ahead. My next meal, bed, and destination were all perpetual questions.

I roamed around speaking little to no Italian (read: none), hunting for off-season cooking classes. The idea came from an episode of Salt Fat Acid Heat — the one where they make focaccia in Liguria. That became the mission: learn to make focaccia, my favorite bread, in Liguria, among olive trees.

I had never traveled alone before. It's a different experience. Beyond always choosing where to eat yourself. You get a lot of time with your thoughts. And the bad part? You get a lot of time with your thoughts.

Solitude strips away the distractions that usually buffer you from yourself. Without meetings to attend or colleagues to impress, I found myself face-to-face with uncomfortable questions I'd been avoiding: Was I building something meaningful or just climbing a ladder? Was I creating things that mattered to me, or just things that looked good on paper?

In between meals, I listened to an audio book about the science of sleep, wondering if I could learn to rest better — to value stillness as much as momentum. The irony wasn't lost on me: even in my escape, I was trying to optimize something.

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The second quest came after I helped Casper IPO. I hadn't done that journey before, and I wanted to.

I've always loved cooking. Some of my earliest memories are playing on a blanket in my grandmother's kitchen while my mom and grandma walked around me. After college, I cooked Thursday night dinners for my grandmother. I cooked for friends. For people I loved. I even worked as a recipe tester on the side for the Washington Post food section. The best part? This twenty-nothing year old could expense groceries. Hello, Whole Foods. If the dish was great, I was great. If it flopped, it was a bad recipe. Cooking from a script forces you out of your comfort zone.

Unlike my day-to-day work, cooking was fleeting. You created, consumed, and moved on. Even failures vanished with the plates. You worked with your hands, not just keyboard taps. That impermanence was exactly what I needed after years of building digital products designed to last, scale, and define me professionally.

Heading into my final year at Casper, I started making a lot of bread (pre-pandemic, I was ahead of the curve). One of my close friends, a professional chef, caught the same bug. We took a class, swore allegiance to the metric system, and started experimenting. We made a ton of bread.

I was ready for a break from tech — not just a vacation, but a fundamental shift in how I experienced work. Digital products exist in abstraction; bread is tangible, immediate. So I enrolled in the French Culinary Institute's 8-week bread intensive: forty to sixty loaves a day, kitchen whites, standing all day.

After years of conference rooms and Slack threads, I craved the immediacy of physical work — of going home with flour-dusted shoes and muscles aching from honest labor. I wasn't just tired of my job; I was tired of living exclusively in my head.

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Day one was scheduled for April 1, 2020.

So it never happened.

Around that time, I also found out I was going to be a dad. And suddenly, walking away from tech and a steady paycheck felt reckless. The pandemic redefined risk overnight, transforming my career break into something that suddenly felt reckless.

What's strange about interrupted dreams is how quickly they can feel like they belonged to someone else entirely. Within weeks, my culinary school plans became a luxury from another lifetime, fading behind pandemic anxiety and the immediacy of preparing for fatherhood.

During the pandemic on the side, I started a company with friends — a Zoom-based cook-along project called Kitchen Rodeo. We raised over $175k for folks hardest hit by the pandemic. It was the best of times during the worst of times. I met incredible chefs. I was once on a Zoom call with Daniel Boulud, who was wearing two separate AirPods — because he was on another call at the same time. He was kind. I was reminded: people are human.

And somehow, I ended up creating the culinary school I had always wanted to attend. I learned. I practiced a new craft. I was woefully out of my league. And I loved it.

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I reunited with friends and former colleagues at Slack just as I welcomed my second daughter. Being present as a dad was my top priority. That proved hard to achieve at a startup. And then I left — a year ago this month.

To do what? I wasn't sure. But I was anxious for a change. I wanted to feel the vertigo of incompetence again — that precipice where growth actually happens. That's always been the pattern: every four or five years, I shift. I mix things up. It's how I keep growing. Each role I've held (engineer, designer, product manager, executive) has added layers to my understanding while calcifying assumptions that eventually needed breaking.

If the first quest was about solitude, and the second about skill, this one … might be about alignment. Or maybe humility. I don't know yet. Maybe that's the point. The third quest didn't start with a passport or a classroom. It started with stillness.

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I took most of the summer off. The city is great in the summer — doubly so with young kids. I bought a Burley Honey Bee bike trailer and loaded the kids up for adventures to the park and splash pads. No Sunday Scaries. It felt good to be exactly where my feet were. If my daughter wanted me to color with her at camp drop-off, the answer was easy: of course.

I played a lot of tennis. Much like cooking, it's a comfort from my earliest memories. I hadn't played much since labrum surgery after rediscovering tennis in my late 30s while playing like I was 16. The kitchen and the court: two places I felt most at home.

I tried not to think about work. I wanted to cleanse my palate completely, creating enough distance to feel a genuine longing for something specific rather than just the habit of busyness. I hoped some dormant passion would surface in the stillness, announcing itself with absolute clarity. Instead, I found myself in an unfamiliar state: contentedly purposeless, yet nagged by the suspicion I should be striving toward something.

I was driving without a map, hoping a sign might find me.

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I caught up with friends, some in tech, most not. Whether they meant to or not, many were processing similar questions. What's next? Where is all this going? I jokingly called it a mid-life crisis. It wasn't. I'm unbelievably fortunate to be in this position, and I know that. But it was mid-life, and that's humbling.

And maybe, just maybe, I was tired of doing the same thing I'd been doing since I was a teenager, or at least something adjacent to it. That wouldn't be crazy, right?

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After Labor Day, I started to feel anxious. Not the productive kind of anxiety that propels you forward, but the stagnant kind that makes you question your worth when you're not visibly producing something. Not sure why then. Maybe it was the run-up to the end of the year. Or the back-to-school energy in the air. But I felt a pull — to do again.

One thing you learn if you're lucky enough to coach people: most of them already know what they want. They're just trying to get comfortable with the decision they've already made.

For me, I realized the constants in all my favorite chapters have been two things: connection and building. They go hand in hand. It's more fun to build with people you care about. So whatever's next, it has to include both.

I started telling friends I was "building the business of Frank." That might be overstating it. Yes, I told them that exactly, but with a wry smile rather than confident bellowing.

"What's that?" they ask. "I'm not sure. I think I want to spend half my time coaching people and half my time writing code."

That was what I wanted, despite prefacing it with I think. If I'm being honest, I probably knew that back in early summer.

With the explosion of AI tools, the creative landscape had fundamentally shifted. Suddenly, the gap between imagination and execution was narrowing daily. A solo builder could now experiment, iterate, and launch ideas that would have required teams just months earlier.

For someone who'd spent years managing increasingly large teams and complex processes, this felt liberating. A return to direct creation, amplified by new capabilities. The prospect of building something meaningful with minimal organizational friction was more than intriguing. It was magnetic.

I started small. Updated my website. Offered free coaching calls, which gradually evolved into paid client relationships as word spread. Leaned into my community. Each day, I wrote code and became a student again. I was busy learning.

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September began with two questions:

Would I enjoy spending my days coaching? I'd always guided others on the side, but never as my primary focus. Could I make it an interesting business?

By December, I had my answer to the first question: yes. It wasn't novelty. It was purpose. Working with someone one-on-one, watching them clear hurdles they once thought impossible. There's magic in that moment.

When someone chooses you — I want to get better, and I want you to help me — it creates a different energy than managing direct reports. They're all in. And so am I. That's the reward.

It took me five months before I updated LinkedIn. Five months of helping others navigate their careers while hesitating to publicly acknowledge the shift in my own. I told myself I was just being cautious, testing the waters before committing. But something deeper was at work. For years, my identity had been tied to well-recognized companies and established roles. To step away from that framework meant facing questions I'd been avoiding: Who am I without those institutional affiliations? What if people don't value what I offer when it's just me, without the backing of a recognized brand?

In college, my roommates were musicians who regularly performed publicly. I'd watch them put their creations out there, completely exposed to praise or indifference. I admired that courage. The willingness to be seen creating something personal, something that might fail.

Updating my LinkedIn felt like my own small version of that vulnerability. It was publicly claiming an identity outside the safety of established roles and recognized companies. It meant saying: this is me now, without the institutional armor I've always worn.

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I wrote this because I needed to write it. Because I needed to hear it. Anniversaries are a natural time for reflection. I was on a podcast recently, and the host said their company thinks of a job search as a hero's journey. I liked that idea.

Looking for a job or figuring out your next chapter isn't time out of your life. It's a part of your life. A chapter worthy of the same attention and dignity as any title or job. It's a journey worth exploring.

So did the third quest end?

Not exactly. But I stopped wandering off-course, looking for someone else's map. I stopped searching for answers that weren't mine to find.

And that feels like progress.

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