If there is one expression I hear most often upon describing what it is I do for a living, it would be "you're so lucky." I generally smile in agreement and suggest that, yes, it is a good life and I'm very happy to be partaking in it. Truth be told however, the term "lucky" always annoys me slightly, as it seems to suggest I've somehow won this role – that I could be working in a factory or in a cubicle or on a farm or any number of more strenuous and less enjoyable tasks had I not won the lottery on career day and picked "independent web developer" from the hat. In reality, on career day in high school I was informed I was best suited for the exciting career of airline steward. Even my guidance counselor struggled to provide suggestions on how best to prepare for my future role serving soda-pop and tiny bags of peanuts. Upon heading off to college, I chose to forgo that particular suggestion and instead opted to study journalism, having always had a great interest in writing. I also dabbled in history, computer science and a wildly brief stint as a filmmaker at an art school in Boston (I never actually showed up to that school - but that's a topic for another post).
By my junior year at the University of Delaware it was becoming increasingly clear that journalism wasn't going to be the correct path for me as writing loses a good deal of its pleasure when one is assigned what topics to write about and forced to be objective and ignore personal opinions on the topic at hand. I found most assignments ranged from boring to downright cruel. When asked to write a "sports" story, my fellow students rushed to various university sporting events to interview pitchers and describe the mundane details of a particular match, whereas I wrote a piece on two kids playing wall-ball off the back of a cinder-block dugout at a local little league game and compared their enthusiasm to the kids standing in the outfield of the actual game, being yelled at to "look alive." When we were assigned to go out and interview an elderly individual from our community, my peers rushed to the local senior home to find themselves an old person with no intention of returning again once they got their story. I instead wrote about a woman buried in a cemetery overgrown with tall grass along the major road in Newark, her tombstone pressed beneath a pathway students took to save time walking to and from campus. While my professors remarked on the creativity of my stories, my fellow students argued that I hadn't followed the assignment to the letter, and in truth they were correct and such antics would never have flown at the Times Herald Record, Kansas City Star, Sussex County Post or whatever other small-town newspaper I might have attempted to work at post-graduation. Then, during my senior year, a student was hit by a 7-Up delivery truck while riding their bicycle on campus and killed. My editor assigned me the story and provided me with some basic notes, which included the student's roommate's information as well as their mother's contact information. I explained that I couldn't possibly call the mother and ask for a quote for the school paper, that it was heartless and pointless and far too sad. It was at that moment that I knew mainstream journalism was not the path for me – the "if it bleeds it leads" mentality of modern journalism was far too cold for my taste, and I realized whatever career I might have had was over – that path, regardless of how far I'd walked upon it, no longer existed.
Thankfully along the way I had also picked up some skills in the newly created field of web design, mostly making hobby-websites for myself and the occasional band or local small business. Upon graduating with a degree in journalism my first job out of school was not for a newspaper, but rather making websites. This was not the "working from home on Maui till 2pm before going to the beach" job I'm so "lucky" to have today – quite the contrary. My first job was more along the lines of the film "Office Space", working in a windowless room at a company called IT-MIS (Information Technology Management Information Services). In fact, early on I was reprimanded for wearing shorts to work because it was against the company dress code – the irony of the moment being completely missed by my boss Joy who was sitting there wearing a skirt as she informed me of the violation. When I explained to my co-workers I was quiting to move out west with no job lined up, they looked upon me with an expression somewhere between confusion and genuine concern.
I never desired a career nor a job. I had no real interest to be an employee of any kind, although when I moved out west I hadn't really intended to be an entrepreneur either. Instead, I desired to be an artisan – someone who makes money from their skills via a variety of trades. Employees, or wage-slaves as they would have been known a century earlier until such a life became the accepted norm, survive on wages provided by an employer who at any moment can terminate their job. I felt that such a life inevitably led to unhappiness in one's career, stealing the freedom to decide how much to charge, what projects to take on and when the work should be done. A subtle fear permeates each moment as the employee has no true control over the success of the business beyond their tiny role, nor share in the profits of its success beyond occasionally building up the courage to ask for a small raise in salary, which could in-turn lead to their termination. I didn't simply choose to be a web developer, I chose to be a self-employed web developer, so that I could define my own wage, determine my own hours and seek-out my own projects. I could take-on pet-projects for causes I believed in at far reduced rates (or often at no rate at all), partner with various other designers and writers and creatives that best suited each particular project, and feel the direct result of my success via increased revenues.
The fact is most web developers do not work for themselves, and surely based on the quality of local business websites I've seen here, very few work from Maui. Nor must one be employed in a career that utilizes laptop computers and wireless internet to enjoy the freedoms I've described. It is not the career that matters – it's how one decides to develop and market their skills that determines the fashion of their employment. It is not "web development" that I sell, so much as the value of working with me.
In "Walden", Henry David Thoreau tells the story of a local Indian who learns an important lesson on making money:
“Not long since, a strolling Indian went to sell baskets at the house of a well-known lawyer in my neighborhood. "Do you wish to buy any baskets?" he asked. "No, we do not want any," was the reply. "What!" exclaimed the Indian as he went out the gate, "do you mean to starve us?" Having seen his industrious white neighbors so well off—that the lawyer had only to weave arguments, and, by some magic, wealth and standing followed—he had said to himself: I will go into business; I will weave baskets; it is a thing which I can do. Thinking that when he had made the baskets he would have done his part, and then it would be the white man's to buy them. He had not discovered that it was necessary for him to make it worth the other's while to buy them, or at least make him think that it was so, or to make something else which it would be worth his while to buy.”
Thoreau illustrates how simply having a skill or taking on a job does not guarantee success nor financial reward. It is not enough to simply "do" something, you have to convince others of its value. There are many web developers out there who are better programmers than myself, and certainly many who are less expensive if "price" is guiding a purchase decision. I studied how to sell my skills just as much as I studied how to program – I learned how to network as much as I learned how to code – and discovered (sometimes painfully) how to manage the finances of a business as much as how to work with the software of my trade. Because I worked for myself I could take risks otherwise not afforded wage-earners, taking on projects for little profit in the hopes of the attention they would bring or the skills I might learn, or the people I might be introduced to. Because I was not simply "doing the work", I could be out front, shaking the hands and meeting the contacts required to grow my reputation over time. I could also focus more on quality of life and the free-time that I desired over profit potential. As Thoreau puts it:
“Instead of studying how to make it worth men's while to buy my baskets, I studied rather how to avoid the necessity of selling them.”
As I grew the number of clients who turned to me for web development and increased the cost for which I could charge them, I opted not to grow the business and hire more employees as many of my entrepreneurial colleagues did – but rather focused on efficiencies and techniques to allow me to earn more with less effort and in less time. My goal was not to create a web development empire, but to carve out a lifestyle that reflected my initial intentions – to live more like an artisan than an employee and perform the work when and how I desired. In my evenings I experimented with other business models, studied my earnings to see what improvements could be made, read books on finance and philosophy, read blogs on programming and design, and networked and talked with as many folks as I could to constantly expand my skills and optimize the time I applied to work. The things I disliked I'd outsource and the tasks I was particularly good at or enjoyed I specialized in. As time went on, the lines between work and pleasure, career and hobby, job and lifestyle vanished until all were one. I could spend weeks at a time back east visiting family and friends, seemingly on vacation while still putting in the work required to serve my clients. I could live for months at a time in Europe while still landing new projects. I could find insights in the philosophy of writers like Thoreau and apply those not only to my personal life but also my trade, for they were now one in the same.
I'm not sure how one would explain to their boss they've decided to stop coming into the office and instead will be working from an ohana in Maui – I didn't need to. I suggest to those that ask that they explore the potential of becoming a consultant for their current employer, looking at how to take what they do and create efficiencies that might allow them to do it for multiple employers. I recommend testing the waters, experimenting with business models, researching the finite costs required, playing with the numbers to see how profits might be gained by increasing their customers from five to ten, to twenty or more. When I started offering web hosting at around $25/month, I had three customers. I now have 45+ clients who pay me anywhere from $75-$225/month for that service. I didn't stumble into this, I planned for it and worked to make it a reality.
Life, as I have said so many times on this blog, is a game. It should be fun. The adventure should be filled with laughter and curiosity, not frustration and boredom. You are not working towards something – there is no finish line nor reward for those who succeed beyond the satisfaction of enjoying the experience of success itself. Fear of failure holds so many back from even trying, and that is beyond foolish for the only difference between a successful person and a failure is that successful people fail all the time. "Fail harder" as the expression goes. I'm not suggesting you take a leap of faith, but rather, walk proudly in the direction of your dreams. For if you do something you love and erase the lines of work and play, of career and passion – you will discover success comes not from increased revenue or a life on Maui (although those will come too), but from waking up in the morning excited for a new day that is yours to define. Then you too can be one of the "lucky" ones.
"A master in the art of living draws no sharp distinction between his work and his play; his labor and his leisure; his mind and his body; his education and his recreation. He hardly knows which is which. He simply pursues his vision of excellence through whatever he is doing, and leaves others to determine whether he is working or playing."
- Lawrence Pearsall Jacks, "Education through Recreation"