⛰️ Trail & Error: One Leap Can Change Everything

Welcome back to Trail & Error, where we explore the journey of designing work and life on your own terms.

In this issue, I’m sharing the decision that reshaped my life—leaving the safety net of a traditional career not once, but twice.

If you’re questioning whether your work fits who you are and what you value, read on.

Taking the Leap

Most people don’t walk away from a career they’ve spent a decade building. And if they do, they rarely leave it twice.

But that’s exactly what I did.

When I left Pinterest, I had no clear plan—I just knew I wanted something deeper than another job title. So, I stepped back, leaned into parenting during COVID, and gave myself time to answer a question I’d been avoiding: ‘What kind of life do I really want?’

My family was, and still is, everything to me, but work was supposed to be fulfilling too.

I pictured this ideal life, one that felt almost out of reach:

• Work that felt meaningful and true to my values

• A flexible schedule that let me be there for my kids after school

• The freedom to be the parent and partner I wanted to be

• Enough income to keep growing my net worth without sacrificing my family time

Sound familiar?

In May 2021, I wrote in my journal: “I want to transform the lives of dual-working professionals… They think they don’t have enough money, but really, they’re stuck in an endless cycle of hustling, believing a fuller better life isn’t possible.” I knew I was on that same hamster wheel, despite just finishing my MBA.

But could I actually break away, make money doing what I love, and still support my family? That question lingered, and I put it on hold—avoiding it for another couple of years.

Eventually, I found my way into a full-time role leading marketing at Gitcoin, in the exciting, fast-moving world of blockchain & web3. It was chaotic, fun, and entirely different. But even though it scratched the surface, it wasn’t my path. Different industry, mostly the same old shit. Many headaches.

I kept at it.

My next move into fractional marketing roles opened up a new world. Suddenly, I had the freedom to choose my clients and to spend more time with my kids. I was even making more than I did full-time some months.

But I still wondered if there was room for what I truly wanted—to help people find freedom and fulfillment, as I was beginning to. To scratch that itch to help real people (vs. just businesses), I began coaching clients—one here, another there. I wondered if this could ever be more than a side passion. But it stayed there for the time being.

Then, just last week, I was in a group session recounting feedback from my oldest child’s school counselor. She praised his emotional maturity, his reslience—qualities I’d spent years modeling by choosing to be present and aligned with my values.

I realized then that every choice I’d made was paying off, and I couldn’t hold back the tears. In front of a Zoom room full of strangers, I felt this intense gratitude for every step I’d taken to align my life with what truly matters. This is why I left tech, why I chose this path. I’d finally created a life that felt true to me.

I mean, I’m still creating it, still striving, but the progress is happening. I can feel it.

This life we’re building, this work we’re doing on ourselves—it’s hard, so hard, most of the time. But then there are those moments of overwhelming gratitude, when we realize our choices are starting to pay off. It’s essential to hold onto those.

My work in this realm is still very much unfolding. It’s a total work in progress. And you’re participating in it in real-time with me. There’s zero guarantee of income, but there’s an endless sense of purpose. And I’m 100% here for it.

This journey isn’t just mine anymore. It’s ours. And I’m so grateful to be sharing it with you.

Thanks for reading Trail & Error. Our ranks are growing, with over 10 explorers joining in the past few days! If you enjoyed this issue, please share it. Together, we’ll help people build more resilient & fulfilling lives!