The craftsman's journey

One of my coffee table books (at least when I had one) was Apprenticeship Patterns: Guidance for the Aspiring Software Craftsman. I wouldn’t call it your traditional coffee table book filled with picturesque landscapes or abstract art. The book got its coveted spot on the table not because of cosmetic reasons, but for its value as a pattern-language compendium for navigating the path to craftsmanship. It lays out how to learn from the best, draw your own map, follow the long road, and embrace the idea that skill has no final state. Viewing my career as the cultivation of craftsmanship, rather than a strict ladder to ascend, gives me perspective I return to for grounding.

Unfortunately, the software craftsman’s mindset doesn’t always marry well with the contemporary Silicon Valley ecosystem. That incongruity can leave you disillusioned, jaded, and questioning whether your work really has the depth it was originally sold as having. It’s easier than you think to turn into a robot, bracketed in by man-made constructs of what you can and can’t achieve.

I’ve jumped around, been a part of companies of various sizes, and watched coworkers come and go. While each subsequent move was arguably progress on paper, I still itched for an environment where the momentum was tangible, and the consequences of my decisions (good or bad) were critical to the business.

Then came Natural. Shortly after learning about the company, I spoke with Kahlil. I thought I knew exactly what to expect from a conversation with the CEO/Co-founder. I’ve had enough intro calls to recognize the choreography: a few pleasantries, then a quick tour through my résumé, followed by some calibrated questions about role and fit—the kind of conversation that feels more like a song and dance than anything.

My conversation with Kahlil didn’t follow the pattern. He asked about what actually drives me. How I define success. And, more pointedly, how would I know if I had succeeded a year from now based on that definition?

I found myself puzzled, pausing more than I expected. I opted to reach for answers that felt candid rather than what would be considered conventionally impressive. Kahlil’s genuine curiosity forced me to sharpen focus on my career progression values, not just the outputs. I think for most, this unexpected pivot would have been uncomfortable. For me, the discomfort was the draw. Kahlil put me in an introspective state, and I thought more deeply about how I’d shape my career in my own chosen mold.

After my initial chat with Walt, I knew this wasn’t going to be an opportunity I would let slip away. Walt is a true operator. He bridges product, engineering, and business effortlessly, breaking down complexity while clearly articulating the “why” behind the work and the value it drives. Lots of people in the Valley say, “We’re the right ones to build this” or “If not us, who else?”. When I spoke to Walt, I actually believed it.

Coming to San Francisco for a 5-day work trial was a no-brainer. I knew by just saying “yes”, I would have a deeply enriching experience regardless of outcome. To say that the trial was all-encompassing is an understatement. I was given a project that was fundamental to Natural’s product infrastructure, and I was afforded the latitude to explore it in every direction I deemed appropriate. While in San Francisco, I felt the warmth of the team on both a personal and professional level. I was pushed to think deeply and defend my decisions, but the conversations always felt grounded in shared ownership of the outcome, not ego. The experience only reinforced my belief that this was the team to execute something this big.

I’ll leave you with one story from the end of my work trial. During my debrief with Eric, we took a (very) slow walk down Pine Street (mind you he’s on crutches). He asked me what I would want out of the experience if I joined Natural. I took a long pause as my mind drifted back to my coffee table book. I told him I wanted to be the best at what I do: go deep into a problem, own the domain, be the expert, go down “the long road”. He told me that if that’s what I truly wanted, I could do that at Natural. He was pragmatic in telling me that it wouldn’t be easy, but the rewards of my labor would be deeply fulfilling. For me, that was the spark that sealed the deal; I felt emboldened by Eric’s passion and spirit.

On my flight back to New York, I collated what I had experienced during the past 5 days. Working with Kahlil, Walt, Eric, and the rest of the engineering team gave me a breath of fresh air and a new perspective on what it means to build from the ground up—the way a craftsman would: grounded in first principles, attentive to invisible details, and building infrastructure meant to endure.

Beyond that, the common thread that ties the team together is the intentionality behind decisions and the laser focus on doing things distinctively our way. Pedigree, credentials, and caliber can take you quite far (and we have those too), but without a cohesive ethos, the top of the mountain will always seem distant. I genuinely believe we have that here at Natural, and it touches every corner of our work. The brand, the product, all the way down to the nitty-gritty details, frankly anything with the Natural name attached to it. It sounds ethereal, but it is truly one of those “you can only feel it when you’re here” sentiments.

When I left New York 3 weeks after my work trial with two suitcases and goodbyes that were a little too quick, that uniquely human sense of self-doubt didn’t creep in. Big life changes often invite other people’s biases and perceptions to shape our thinking and cloud our convictions. Why would someone leave a comfortable job and a familiar environment for an unproven entity? What’s often forgotten is that the people around you have already constructed their version of your perfect path. It makes sense though; from the outside, decisions that appear nonlinear can seem irrational. But more often than not, it’s those very decisions that lead to the most outsized outcomes. Now, as part of the team, I feel even more certain that trusting that instinct was the right decision.

It might seem like the canonical journey from apprentice to craftsman doesn’t make much sense at a company like ours, but I disagree. Yes, we’re in the early innings, delivering at a relentless pace that requires everyone’s best work. In truth, a place like Natural embraces someone who takes pride in precision and constantly sharpens their skills. Natural embraces the craftsman.

At my core, I don’t believe the true professional has a terminal state. The journeyman always plays the infinite game. And for the first time in a long time, I feel like I’m exactly where that game should be played.

If you resonate with this, join us at /careers.