The Telecommuter

How I started working remotely and how you can too

Rohan Anthony Smith
6 min readJan 8, 2014

The Story
I had always dreamed about working from home. I visualised waking up at 8 a.m and pulling myself off to the kitchen for breakfast which I would consume, savouring every bite. Then I would hop off into the home-office in my underpants to start the daily duties. I could break and go to the mall if I became bored or take a day off in the middle of the week, then do a 16 hour shift to recover the time.
Well… right now I work from home and although it is not exactly what I had envisioned, I still manage to get most of the perks above but there are a whole lot of work and non-work related issues I had to face to get there and stay there.

Who am I? Where do I live?
I am a Caribbean national (Jamaican) and a programmer, I primarily make websites. For the past four months, I have been living in a small and quiet island in the southern Caribbean called Tobago. To give you a better idea, the places where I work are the places where people go for vacations and the three S’s, sun, sand and sea. I don't actually work on the beach, I am yet to find a place with both WIFI and a power source. However here in Tobago, I frequently do early morning 25 minute jogs from home to a beach on either side of the island.

How it started
I would frequently hear about programmers who would find opportunities to work online. To me, they were the very lucky and extremely talented few. I supposed that it took a lot of convincing to get an employer to allow you to work from home. Then one day at a tech meetup, a fellow web developer told me he was doing frequent work for a company in the U.S. That is when it became obvious that this was no more an imaginary possibility, I had actual proof that it was a feasible venture and normal people I knew were doing it.

Finding opportunities
The developer who was working online told me he had been telecommuting for a few months, he had built up a reputation on Elance and Odesk and was getting repeat work for what sounded like a reasonable rate. At first, at the mention of Odesk and Elance, I cringed because of memories of my earlier attempts. Being what I would like to consider a relatively proficient developer, the bidding system on these platforms forced me to undersell my value. Even when I did, I still lost out to competitors from countries where, I would suppose, could do a lot more per dollar earned than I could. My friend however had now exited these platforms with his new contacts and was making a reasonable earning. This then sparked my interest to go searching again.

Being a Drupal web developer, I decided to start searching the entire web for “Drupal Jobs”. I stumbled upon a network offered by the Drupal community that facilitated job listings, I was pleasantly surprised to see a “telecommuting allowed” filter. Then like a crazy person, I started sending out tens of applications. It however became wearisome writing custom emails for all applications. This lead me to create my template application which I would prefix with a two or three sentenced cover letter.
I landed a few short jobs and a couple interviews from this method. I soon expanded out into larger job boards where more “serious” and full-time positions would be available. This proved a more difficult task since many of these companies were used to their full time employees working on-site or at least in the same city. Some others were crippled by company policy regarding taxing and government association forcing them to hire locals. Each interview, turn-down and acceptance gave me a lot of experience and information on how to approach the remote work job market.

Choosing Your Employer
As enthusiastic as you may feel, you should be wary in choosing your future employer. Not every company that allows telecommute knows how to manage remote workers or how to create an environment that fosters remote worker productivity. This is a big disadvantage for both parties. The employer will not be able accurately track your progress and may measure you with the same metrics as their onsite employees. Lack of efficient online communication tools can make interaction very difficult and reduce productivity. Companies with little remote culture are also less confident in their remote worker’s capabilities and may terminate the agreement at the first sign of trouble (see Yahoo). Try and find companies which have a significant part of their team already online or who are comfortable with working remotely. This will greatly aid in the working experience.

Building Reputation
An extremely major aspect of landing a great telecommuting job is a great online reputation. I joined sites like Stackoverflow, Github and LinkedIn to create an online presence and a developer portfolio. These profiles won’t necessarily need to display you at codeguru level 100 but even a little online activity can speak volumes about your expertise and approach to work. I got a job with a company in New York after 1 month on Stackoverflow and 300 reputation points. Employers hiring remote workers may probably never get to interact with them in person, therefore it is critical that they can be convinced of the prospective employees abilities to adequately fill the advertised position.
Being a Caribbean based applicant has also given me a major advantage when applying for U.S. jobs. Apart from Canada, the Caribbean has the largest number of English speaking (as a first language), proficient employees in the same time zone as the United states. Many U.S. employers overlook that fact when outsourcing so I used it as an advantage to my favour. Find unique traits that will cause you to stand out from the crowd.

Maintaining Employer Confidence
Being an off-shore(I prefer the term near-shore) outsourced employee is considered a risky venture. The onus is on the employee to invalidate fears and impress on a daily basis. Always over deliver! Even if just for the first first few weeks, go beyond the call of duty. If it means working a few extra odd hours, you have to find ways of providing value to your employer greater than what an on-site employee would provide. As with any job there will come the day that you mess up a project or miss a deadline. Softening up your employer will improve your job security and their confidence early on in the relationship.

Moving on
After working for one U.S. company, you become much more attractive to other U.S. companies (in fact any other country in the world). The experience proves that you know how to work well with a U.S. based firm as a remote employee. If for whatever reason you decide to move on to a new employer, I suggest that you do the following.

  1. Do a job search while you are employed. The remote job market can be rough, I have literally applied to hundreds of companies over my job search period. Plus being currently employed is usually a big plus when applying for a new job.
  2. Have a killer resume. Ensure it outlines your best traits and stands out from the typical resume format so it will catch recruiter’s eyes. Here is a link to my resume and the source on github (latex) in case you want to use the template to create your own version. Having an updated LinkedIn profile is also invaluable because a lot of job boards allow LinkedIn profile submissions.
  3. Spread your search widely. The more applications you send out the higher the probability to get a positive response. This can get daunting, but working from home in your underwear doesn't come easy. You should however keep the quality of your applications high, ensure you have at least a two sentence cover letter. Fight the urge to just copy and paste after the 35th submission.
  4. Continually Improve your skills. Your skills are sometimes the most powerful indicators for prospective employers. Work on personal project or contribute to open source or non-profit project to keep on the cutting edge. You will be surprised how competitive you are when compared to the typical applicant.
  5. Finally, start a blog. Blogging is one means of expressing your prowess to an employer in a format and expressiveness that can beat any resume. Future employers can learn how you think and can observe skills that would be difficult to place on a resume.

Good luck with starting your journey into your next telecommuting job. Feel free to send me details as to how this post helped you land your dream job. Follow me on Twitter @frazras or my blog Third World Entrepreneurto get more tips and tricks for the telecommute lifestyle.

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Rohan Anthony Smith

Jamaican entrepreneur, remote #Drupal developer living on the beaches in Tobago. Currently focused on Amazon FBA, and coding #Flutter