Searching for Purpose

Brendan Loudermilk
Nov 5 · 6 min read

This is the story of my unusual quest for a life with more meaning, why I reconstructed my life for greater happiness, and how I plan to do the same for my career.

The catalyst

I had only been cycling for a few months when my closest friend asked if I would join him on a bike tour over the Appalachian Mountains. It was the start of 2014 when he told me how he planned to ride from Nashville, TN to Asheville, NC in the coming month. Despite my clear lack of experience I didn’t think twice before signing on and a few weeks later found myself riding a fully-loaded bicycle out of Nashville in the middle of Winter.

Me (left) and Kevin (right) leaving our hosts in Nashville.

As it turned out, neither of us had put much thought into the details. Our daily plan could be summarized simply as “ride East until the sun sets, sleep wherever possible”. I still remember the moment on day one when my feet went numb and I asked myself: “what am I doing here?”

I ended up second guessing the trip repeatedly as we encountered new challenges each day: below-freezing camping, thousands of feet of climbing, miles of tedious farmland, and cities without bike lanes. In this unprepared state I was vulnerable, raw, and completely out of my element.

Not all was dark though. Our adventure also brought us countless rewards along the way: generous hosts, hidden hot springs, adrenaline-fuelled descents, serene campsites, live music, and much more. It also brought us closer together than ever before, as we shared this experiences and looked out for each other.

It was only by putting ourselves in uncomfortable situations that we created space for new and unexpected experiences to arise, like two sides of the same coin. If we had followed a rigid itinerary, I doubt it would have resulted in as many happy accidents.

Back to planet Earth

Eventually I flew back home with my bike in a box and the trip was over almost as soon as it started. I remember opening the door to my apartment, surprised to find all my stuff there waiting for me. I hadn’t thought of any material possessions on my trip other than what was attached to my bike, nor had I missed any of it. I had a similar feeling upon returning to work — almost like I was somewhere I didn’t belong.

Once the shock wore off and I found space for introspection, I asked myself a familiar question: “what am I doing here?”

I spent weeks reflecting on my experience. From the outside, I had the markers of what I felt at the time was success: partnership in a growing software business, an apartment in a hip neighborhood by the beach, a new car, and all the material possessions I desired. In a few short years I had ascended professionally, yet life as a whole was unfulfilling and I realized then that I was living with a constant emptiness.

I became aware of the fact that I was attempting to find fulfilment in material wealth. I was trying to create self-worth through validation of my external qualities. I was exhausting myself in a job that didn’t feel rewarding, while neglecting to nurture my personal life.

I believe my willingness to embark on that bike tour was my subconscious grasping desperately for a different life. I was coming to understand that the path I was on wasn’t taking me where I wanted to be. My way of living was broken, so I made the decision to change.

A life with purpose

Without knowing what I would do next, the best I could come up with was to start from scratch. I resigned from my job, sold or gave away my material possessions, and terminated my apartment lease. I reduced my material life to only what could fit in a backpack.

I ended up booking a one-way ticket to Thailand, living out of my backpack for a few years in a perpetually nomadic state. I traveled through Asia, rode my bike down the entire US Pacific Coast, and crossed the US by train. Later, I built a camper van and lived out of it for nearly two years.

No journey of self discovery is complete without growing a man bun (Banaue Rice Terraces, Philippines)

I went on more adventures than I can remember, each one characterized by putting myself in uncomfortable situations. I learned that leaving my comfort zone was the best way for me to grow. I experienced the joy of a life filled with experiences and relationships, not accolades and possessions. I minimized my workload so that I was working to live, not living to work.

In time my nomadic lifestyle slowed and I began to rebuild a more traditional lifestyle guided by new values. I fell in love, moved out of my van, and into a home with my partner. We still traveled, but maintained a home base which by this time, I was more than grateful to have.

A career with purpose

I spent my nomadic years freelancing as a software consultant for startups back in California. It was almost by accident that my business started to grow, as being stationary allowed me to commit to bigger and longer projects. Before long I was managing multiple clients, building a team, and working more than ever. Without meaning to, I had effectively come full circle professionally, back to the position I was in years before. The moment I realized this I stopped and asked myself “what am I doing here?”

I decided that it wasn’t entirely by accident that I got to this place. I was ready for my work to have a bigger impact, to work with others instead of alone. But I wasn’t interested in building a typical consulting business — I needed to find purpose professionally as I had personally. How could I apply my skills to work that really matters? How could I build a team of equal peers instead of a typical hierarchical organizational structure?

I set out in 2018 to answer these questions. I read dozens of books, investigated existing businesses, spoke with people who shared my values, and otherwise absorbed whatever information I could.

It turns out there are many parallel efforts to build better organizations, old and new. There are classic examples like worker cooperatives, with co-ownership and democratic governance. New movements like evolutionary organizations, with self-management and shared values at their core. Even legal structures like benefit corporations, which are accountable to people and the environment, not just profit for shareholders. There is a lot out there to draw from, which can be distilled into the right structure for any given situation.

There is also meaningful work to be done with software that can have a real impact. The climate crisis is a challenge to all people to apply their skills toward saving the environment. Countless social movements could use technology to move their causes forward. My assessment here isn’t original; there are already numerous examples of business that work every day to solve these problems.

Me and my partner participating in the Global Climate Strike (Nice, France)

Everything I’ve learned has me more optimistic than ever, that it’s possible to have a career that is both fulfilling and prosperous. I’m deeply motivated by the prospect of applying my skills toward projects with a positive social and environmental impact. I’m confident knowing there are blueprints for a better way to work with others.

I’m actively searching for collaborators who share my values. If you want to make a living making a difference, I’d love to hear from you. Just say hi: brendan@sinceresoftware.co

Enspiral Tales

Stories from a bold experiment - creating a collaborative network that helps people do meaningful work.

Brendan Loudermilk

Written by

Independent Software Craftsman

Enspiral Tales

Stories from a bold experiment - creating a collaborative network that helps people do meaningful work.

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