"I work from home" — a phrase I have uttered hundreds of times and is often met with instant amazement, envy, or jokes about pants. My goal for this book is to teach you the hacks I have learned in my career to help you land your dream job. If you feel stuck in the job market and you don't want to relocate, this is the book for you.
Chapter 1: The Road to Remote
So you have made up your mind, you want to work from home.
- The first step to attaining this goal is to make it a priority.
The suggestions and advice in this book come from my life experiences. Not all of my experiences will apply to you but I hope that we might find, together, at least a single thread of universal truth. In order to know, I think it makes sense to briefly review the anatomy of my life from childhood until now.
I'm currently 32 years old, but I started working with computers at a young age. As an elementary schooler, I had a bright childhood friend named Brian Brennan who although younger than I, was my first mentor regarding computers. At age 9 we played lots of video games, original playstation and Nintendo 64, as well as countless hours of computer games on his Gateway computer.
At one point Brian learned how to make the computer work for him instead of other the other way around. Together we started learning HTML and Javascript. I didn't have the Internet on my family computer at the time, but my parents did have a WebTV so I started building HTML web pages for things I enjoyed and used the WebTV to upload my pages Geocities.
Flash forward to age 13, I finally had dial-up. Now we didn't pay for dial-up, in fact my parents didn't know I was "connected" as we used to call it, but I was. I had the "setup" credentials for our regional phone company — I was living the dream of free Internet!
I covertly routed speaker wire from our pantry closet to the computer room. Yes, I learned early on that in a pinch speaker wire can work as telephone wire, although I don't recommend it. This was one of many hacks I stumbled on. Hacks, the combination of science, trial & error, and creativity, are a common theme through out my life.
I spent my highschool career building HTML pages instead of powerpoints slides for school projects. At home I built my own computers out of parts, as so many of us did back then and gamed all night during LAN parties where we traded "warez" and "pr0n". I was 15 when we got an A-DSL connection (125kbps down / 15kbps up) and I started hosting my websites from my house on a Windows server hiding in my bedroom closet — later this server was reborn running FreeBSD 3.
Most of my highschool education was spent figuring out how to get out of class and either into the computer lab or the library with friends. We basically met as an informal computer and tech club. For more details about this era, checkout my long time friend Charles Hooper's blog post titled "How I hacked my high school".
When I was going to community college for Computer Science, I worked two part time jobs — I worked for my parents and separately at a large retail chain in the electronics department, where I slung "HDTVs". I was working 40 hours a week, doing 4 courses a semester, and I didn't have time for anything.
I started hosting my parent's small family business website which I coded by hand and I mostly resented my mall job. I hated how cruel companies were and how they actively shit on their employees. I spent my lunch breaks in Borders reading computer and business books and dreaming of my perfect job.
In between Calculus and selling TVs, I also found time to build the best damn real estate search engine a local agency in South Eastern Connecticut could buy. I was taken advantage of; I worked at least 500 hours on that site which was commissioned for under $500. I did however learn a lot about business and tech. I was brave and dumb and took on more then I could chew but it was successful. Hands down it was the best solution on the market at the time, this was long before Zillow existed.
While working in the retail store, I met George, an IT guy working for my region's pharmaceutical company. George referred me to a job making $18/hr migrating Windows 2000 computers to Windows XP. I accepted the contracting job thinking I was on the top of the world, I finally had a "real" computer job.
I did awesome work but what I didn't know was this world is cruel to contractors. They don't get sick time, they don't get vacation, and they certainly don't get respect. Contractors are fed lies and false promises and they are the first to get cut. Managers treat contractors like physical resources. It's honestly sick.
From there I moved to a technical call center helpdesk, also as a contractor, of a contractor, of a contractor of the DoD. If you follow the money, I was making $17/hr but at the top of the pyramid they were billing me out at $55/hr. After some time I managed to move onsite and successfully cut out one of the contractor layers.
I still lacked negotiation skills and confidence so my increase was only a dollar, bringing me to $18/hr as a desktop support tech. I fixed computer problems whether it was hardware or software and I was fast and could basically solve anything handed to me. I quickly transitoned to a desktop support engineer role where I learned how to package and push software to small fleets of computers. A couple years later I transitioned to the Unix server team.
Each step was a very big promotion as far as responsibility (I was one of two employees who designed and operated a multi million dollar Hitachi SAN) but my salary didn't increase proportionally. People were coming "off the street" for the same or lower position and making more then double I was. At the time I was working my ass off for $32k a year and hardly had enough for what my family needed. I was watching people get hired for the same job for $65k a year ... After being let down for so long, this was the tipping point, this is where I started to shift my thinking.
The only way to move up is to move out.
I felt stuck. I worked for both the big industries for my region and they both failed me. I knew I did not want to relocate but I also didn't want to work for companies with obscene priorities and worse culture.
I started moonlighting on side projects. I had so many flops and failures, to many to count. Finally I launched an idea with traction called LinkPeek. During the code development phase of building LinkPeek I became active in the open source community for the framework I was using called Pyramid.
I was networking, even though I didn't know what it was called at the time. I taught myself some tricks to career development and ended up meeting a hiring manager who appreciated my skill and was willing to take a chance with me working remote. I flew across the country to Santa Monica and had a bit of culture shock but I landed the position!
This victory would be the first of 4 remote positions I have held since finally taking the leap to "work from home".
Tune in to the next chapter where I describe how I positioned myself to win the interview.