Observations from the intersection of building things that matter, ultra-endurance, and the daily mechanics of a meaningful life.
I don't write to provide easy answers. I write to figure out what it actually means to live well. These notes are a documentation of the messy middle—exploring the constant tension between raw ambition and staying healthy. Between scaling a business and being fully present for your family. Between the noise of modern culture and the quiet clarity found on a long river.
Here, you will find raw, unhurried essays on entrepreneurship, psychology, fatherhood, the outdoors, and the ongoing practice of paying attention.
Why do we replace things so quickly?
A jacket gets a hole. Something gets old. Something stops feeling new.
So we replace it.
But what happens when we start applying that logic beyond the things we own?
Our attention. Our relationships. Our work. Ourselves.
Read MoreWhere is home?
After living in different countries, I’ve started to wonder whether home is less about a place and more about whether we’re actually present where we are.
Sometimes restlessness tells us to leave. Sometimes it tells us to arrive.
So where do you feel most at home?
This Field Note is the beginning of the thought, not the conclusion.
Read MoreWhat place does friendship have in a good life?
As we get older, friendships can quietly change or disappear. Work, children, ambition, relocation, fatigue and changing values all reshape who we spend our time with. But perhaps the more interesting question isn't why friendships disappear, but why some survive—and whether every friendship is meant to.
Read MoreEnough is a question we rarely stop to ask. How much money, work, ambition, activity, connection or achievement is enough—and how do we know when we've crossed the line from enough into too much? This week's Field Note explores the relationship between enough, attention, ambition, seasons and the good life.
Read MoreWhat owns our attention quietly shapes our lives. In this week's Field Note, Evan explores attention as the bridge between what we value and how we actually live—and asks what we're becoming by repeatedly noticing some things while overlooking others.
If death helps us ask “What matters?”, perhaps attention asks the harder question: “Does my life reflect it?”
Read MoreIn "No One Is Getting Out of Here Alive," Evan Sutter explores how confronting our mortality can serve as a powerful tool for living a more present and meaningful life.
Key takeaways from the essay include:
The Avoidance of Death: Modern Western culture actively avoids discussing death. This turns mortality into an abstraction, tricking us into assuming we have unlimited time and causing us to endlessly postpone what truly matters.
The Clarity of Mortality: Rather than being a morbid exercise, contemplating our own death acts as a clarifying lens. It strips away trivial anxieties, shifts our hierarchy of values, and brings the beauty of ordinary, everyday moments into sharp focus.
The Restlessness Trap: Acknowledging that life is short shouldn't trigger a frantic need to maximize every second by chasing thrills and abandoning responsibilities. True engagement requires patience, sacrifice, and doing boring work that matters.
Cultivating Range: Because we cannot know whether our lives will be tragically short or remarkably long, we must develop "range." This means balancing the discipline required to build for the future with the presence to stay awake and fully engaged in the mundane "middle" of our lives.
The Inspiration: Evan’s daughter turned three and asked “Why?” exactly 52 times on her birthday, highlighting how children naturally challenge the world while adults tend to blindly accept the status quo.
The Philosophy: Living a good life requires you to fiercely protect your time. To do this, you have to constantly ask "why" about the systems, tools, and routines that drain your energy.
The Business Connection: This exact mindset drove the creation of SwiftReporter. The founders asked why home inspectors tolerate outdated software and per-report fees, leading them to push 52 consecutive weeks of product updates to build a faster, fairer solution.
The #WHY52 Campaign: To celebrate both milestones—the 52 questions and the 52 updates—SwiftReporter is knocking $52 off their standard monthly plan. Using code WHY52, new users can lock in a $47/month rate for their first three months.
We live in a culture that equates activity with a life well lived. Travel, achievement, novelty and a full calendar have become shorthand for engagement, while stillness can look suspiciously like boredom. But what if boredom is sometimes something else—restlessness, discomfort, or an inability to sit with the season we're actually in?
Drawing on experiences from a monastery to fatherhood and building SwiftReporter, Evan Sutter explores the difference between being busy and being present. He considers why we so often reach for the next experience, project or achievement, and what might happen if, instead, we learned to recognise what the current season of our lives is asking of us.
Because not every season is meant to be exciting. Some are meant for planting, some for harvesting, and some simply for staying long enough to see what grows.
Read MoreThis post explores the fundamental difference between simply measuring success and actually building a good life. Drawing from his diverse experiences across startups, river expeditions, and fatherhood, Evan Sutter argues that while ambition is a powerful tool, it should never consume the person doing the building. The essay highlights the importance of moving with life's natural rhythms, recognizing how our past "failures" compound to shape our foundations, and prioritizing long-term health and relationships over pure financial accumulation. Ultimately, it serves as a gateway to his broader ecosystem, guiding leaders and builders toward his podcast, 1-on-1 conversations, and the free download of his field guide, 42 Notes from a Life of Trying Things.
Read MoreWe spend so much of life searching for certainty—the right job, the perfect business, the ideal routine—that we forget life was never designed to stand still. In this Field Note, Evan reflects on the balancing act of building meaningful work while navigating family, creativity, health, and uncertainty. Through stories from startups, keynote stages, removal trucks, and friendships spanning decades, he explores why resilience isn't about having the perfect plan, but about staying adaptable enough to keep moving when life changes the rules. Perhaps the good life isn't found in certainty at all, but in learning to negotiate each season with curiosity, range, and playfulness.
Read MoreI used to think getting better meant going harder. Now I'm increasingly interested in what happens when we build enough range into our lives that one difficult season doesn't consume everything else. From a 54-kilometre trail run to building SwiftReporter, this Field Note explores balance, resilience, ambition, and what it might mean to grow old well.
Read MoreAt twenty-five, success looks like a flash car and a public display of wealth. At forty-two, it becomes clear that money in isolation tells us nothing about a person's health, presence, or genuine joy. True success isn't an external image to be seen, but an internal balance to be felt—an ongoing practice of stepping off the high-stress treadmill to protect what actually matters.
Read MoreFor decades, we have inherited a corporate narrative that equates ambition with burnout, and success with extraction. We measure our businesses entirely by quarterly financial outputs, completely ignoring the structural health of the machine generating those numbers.
Read MoreWe spend our childhoods questioning everything and our adulthoods defending everything. From how we define success to how we measure our days, most of the rules we live by are not actually ours—we simply inherited them. An exploration into the danger of borrowed stories, and why building a good life requires us to finally audit our assumptions.
Read MoreWe have become experts at measuring success—revenue, equity, and scale—but somewhere along the way, we stopped measuring the quality of our lives. In this Field Note, we explore the paradox of the modern operator: spending our healthiest years sacrificing time and relationships to chase things we hope will eventually buy them back. Ambition isn't the enemy, and building things matters. But the ultimate metric isn't the size of what you build; it's whether you are becoming someone you’d actually enjoy sharing the journey with.
Read MoreThis essay dismantles the idea that a non-linear career path is a series of mistakes. Drawing on a seemingly scattered background—from living in a Buddhist monastery and launching social enterprises in Bogota and Brazil, to paddling the Hunter River and building a tech startup—the piece reframes past "failures" and detours as essential Research and Development. It challenges builders and operators to stop regretting the chapters that didn't go according to plan and instead reclassify them as the exact raw data needed to construct their current iteration of success.
Read MoreA practical look at the unglamorous reality of building startups, creative projects, and a life of genuine aliveness—and why the most important work happens before anyone is watching.
Read MoreProgress doesn't always look like progress. A reflection on building businesses, parenting, personal growth and the invisible work required before success appears.
Read MoreA 470km paddle down the Hunter River taught me an unexpected lesson about business, fatherhood and life. The most dangerous phrase isn't "What if I fail?" It's "I should be further ahead by now." Here's why comparing reality to an imaginary timeline creates unnecessary frustration—and how learning to work with reality instead of expectations might be one of the most valuable skills we can develop.
Read MoreThis article explores what the river taught me about patience, adaptation, fatherhood, business, wellbeing, and the often-overlooked value of taking steady steps towards our goals rather than constantly chasing faster results.
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