How I am Trying to Work Remotely

how i tried to work remotely

While relentlessly sifting through the endless sea of Facebook advertisements, game notifications, baby pictures and political YouTube videos, a curious advertisement for a program called Remote Year caught my attention.

Remote Year Work Remotely Advertisement

I learned that through this program I could travel and work remotely at the same time. They offer a structured, year long itinerary of destinations you work from for a month at a time while organizing all travel, accommodations, work space with internet, activities, and community events.

My curiosity instantly turned into a desire, arguably a lust. Confusion about exactly where I’m going in life probably compounded this substantially. The seed was planted; all I had to do was water it. How could I make this a reality? In other words, how could I ask my boss if I could pack up and live out of a backpack for an entire year, be in a completely different timezone, and maintain relationships with all of our clients virtually all while still being a valuable asset to the business and providing continued performance?

I figured it was time to put together a business case. Like any smart person nowadays, the first step in completely anything is to Google it: ‘how to make a business plan.’ Like 99% of all how to guides, they are vague, terribly written, and don’t contain an ounce of substance. Thus, I had to write my own from scratch.

Since I work at a large fortune 500 company, nothing happens without HR being involved in just about every decision. Therefore, I wrote my business plan in a manner where not only my boss (and upper management) would understand, but also HR.

I had an entire conversation over WebEx discussing my proposal with my manager using my business plan as a reference. I anticipated that a monumental amount of information like this would need to be reviewed (and I was right), so everything I mentioned during the WebEx was outlined in my business plan.

Because of the vague, terribly written, and lacking substance business plan articles on the internet, I figured I would post one that I actually wrote that I actually sent to my manager.

1. Introduction

I began with an overview of Remote Year. I wanted to paint a precise picture of the organization and everything it offered.

Remote Year brings together a community of 75 professionals to spend a year working, travelling, and exploring 12 cities around the globe. Spending one month in each city, the community will connect with local cultures and business ecosystems, forming lifelong, borderless personal and professional relationships along the way.

Remote Year coordinates all travel, accommodation, work space, and activity logistics so participants can focus on continued excellence in the workplace and simultaneously growing on a personal level.

The program provides the following:

  • All travel to each city on Remote Year
  • All accommodations during the entire year
  • Work space with excellent internet in each city
    • This is very important. Remote Year will be renting out corporate office spaces or co-working spaces in the city where I will have access to conference rooms and 24/7 internet access
  • Miscellaneous activities, such as community impact days, language classes, tours, and other community building events

Participants of the program will be able to travel whenever is necessary for work or leisure. They can also have family and friends visit at any time during the trip.

I followed the overview with a listing of the itinerary for the trip for them to reference and give an understanding the vast number of cities to be visited.


  1. Valencia, Spain (July 2016)
  2. Lisbon, Portugal (August 2016)
  3. Rabat, Morocco (September 2016)
  4. Sofia, Bulgaria (October 2016)
  5. Split, Croatia (November 2016)
  6. TBD (December 2016)
  7. Mexico City, Mexico (January 2017)
  8. Bogota, Colombia (February 2017)
  9. Medellin, Colombia (March 2017)
  10. Lima, Peru (April 2017)
  11. Cordoba, Argentina (May 2017)
  12. Buenos Aires, Argentina (June 2017)

2. Benefits to My Company

This is the bread and the butter, the meat and potatoes, the make and break section of the entire document. If this isn’t convincing, then nothing else matters. When it boils down to it the benefit to the company is the only thing that matters. If they have nothing to gain (and potentially a lot to lose) why would they take the risk? You can argue all day long that your company truly cares about what you personally have to gain from working for them. Bogus. They care about what you have to offer the company. Any danger to performance and results is an uphill battle. Thus, my job is to convince them that working remotely will benefit them more then not letting me work remotely.

The mobile work policy document states it is <company’s> prerogative to provide a mutually beneficial work arrangement that enhances employees motivation and engagement, improves job performance, and supports work/life balance.

  • After this year of cultural immersion, I will have gained experiences that will allow me to bring a differentiated perspective and contribute more on project teams and initiatives. This comes not only from interacting with locals in each of the countries I would be living in, but from the individuals in the program as well. Over 50% of participants are IT professions who I would gather invaluable insight from.
  • Future employees deciding between multiple offers take perks and development programs very seriously. Offering a program like Remote Year to employees differentiates <company> and can help attract elite talent in a competitive work environment which will grow the foundation of future leaders in our business.
  • Losing top talent after spending time developing it sets back teams and companies. Employees my age constantly struggle with life choices and offering an innovative program where employees can fulfill that hunger for travel, while still progressing our careers will greatly help <company> with retention. Allowing employees to participate in programs like this could turn their relationship with <company> from a job to a career.
  • An international recognition of <company> as an innovative and flexible company. <company> will be one of the first companies in our industry allowing an employee to participate in a program of this nature. This will provide great exposure and showcase <company> as a leader in work flexibility.
  • I would gain insight into the way different companies handle remote work and how others use technology to improve their work environment. Many of these technologies could be introduced at <company> and GREATLY improve our performance.
  • Remote Year is receiving positive press from many news sources and I will have the opportunity to talk with many of them about Remote Year and <company> and how we are on the cutting edge of employee development, flexibility, and diversity. This would obviously need to be run through our PR department, but it’s certainly available!

Work Remotely Remote Year Recognition

  • Studies show that Millennials crave flexible work environments, and some even have expectations to work in a similar manner to freelancers. We are also growing up in a world where we have instant access to almost anything at the click of a button. Through my experience at Remote Year, <company> can learn to be agile and adapt to changing business requirements, use flexible and modern technologies to enhance <company’s> speed, and empower users to support themselves without having to reach out to IT as often. Implementing revolutionary ideas like these will give <company> a huge competitive advantage over other businesses that haven’t yet awakened to the opportunities brought about by the demands of the millennial workforce.

Millennium Work Remotely Survey

This is a trip filled with globally-minded citizens that are prioritizing experiences over material possessions. They have many community outreach events, trying to spread social good and touch the lives of many, all across the globe.

I finished breading up my butter by matching the points I came up with to points directly in my company’s mobile work policy document and attaching all documents pertaining to working remotely so no one had to hunt for them.

These benefits to <company> meet the objectives of the Mobile Work policy:

  • Drive results while improving individual and organizational performance
  • Promote consistency in <company’s> approach to flexibility
  • Foster an environment based on integrity, performance, respect for people, and innovation
  • Enhance colleague engagement and retention of talent
  • Meet <company’s> commitment to making <company> a great place to work

<<remote policy.doc>>

<<Mobile Work Guildelines.doc>>

3. Brainstorm

Like with any type of persuasive document, as soon as you state your point and your reasons for it, you need to follow it with responses to concerns you know will be addressed by the proposal. Thus, put yourself into your audience’s shoes and determine what the most important concerns they will raise to reject the proposal, and outline a counter to each concern. I came up with seven main categories of concerns:

  1. job responsibilities
  2. cost
  3. time zone challenges
  4. internet
  5. accountability
  6. returning home
  7. safety

4. Job Responsibilities

One of the biggest roadblocks I anticipated was how I could to perform my job responsibilities while working abroad. So, I broke down my job responsibilities at a high level and separated them into three categories: development work, documentation and meetings/calls. I also integrated my yearly goals in this part of the discussion to showcase that my goals for the year could be completed abroad.

Development work

Development work covers any programming, system modifications, access to any system/website/application I am responsible for. This can all be done remote because all I need is my computer and access to internet connection (see concerns below). Since I partially work remotely as it is, this would be an extension of my current situation.


This covers testing scripts, SOPs, and other forms of documentation. To create these documents I don’t even need an active internet connection. Like the development work, I only need an active internet connection.

Meetings/calls (maintaining communication)

Maintaining communication covers in person meetings, WeBex meetings, and phone calls. In person meetings can easily be replaced with a WeBex call or video conference call. Phone calls and WebEx meetings will obviously stay the same. Internet plays apart here, but the biggest considerations are cell phone service/carriers and time zone concerns. <company> already has a global cell phone plan, so I can already use my cell phone in over 200 countries.
In fact, I stayed monitored emails and phone calls while in Beijing and in Thailand. I actually made a phone call while standing on the Great Wall of China. 99% of my work would be done in either an apartment they provide or in a 24/7 rented work space with WiFi. This means I would always be available in the event of some critical system issue. Free services like Google Voice would allow me to make phone calls for free while also having the option to purchase local SIM cards.

5. Cost

My company is huge on cost. They hate spending an extra dime if they don’t need to.

There is no cost to <company> in allowing me to participate in Remote Year. All costs associated with the program would be paid by me. In addition, all related costs like travel back to the states or additional cell phone charges would also be paid by me. <company> might even save money because office space would increase and my desk could be used by someone else.

6. Time Zones

Time zones were a big concern until I performed a time zone comparison against the East Coast using World Time Buddy (I live on the West Coast working East Coast hours). The document I provided in my plan juxtaposed all of the locations on the itinerary so my boss could visually see time zone overlap.

Work Remotely Timezone Comparisons to East Coast

When I work would be a matter of discussion. It would depend on what meetings are scheduled for the day and what other work needs to be completed. At a bare minimum, 8-5 in any location has at least 3-4 hours of overlap. Time zone considerations are only needed for the first half of the year because of the European time zone differences. For the other half, I would be in Central America which is pretty much on EST time. I would obviously be very flexible to when I needed to be online even if it was 8 or 9pm my time.

7. Internet

Given that internet is the lifeblood of remote work, there is always an excellent internet connection and there are always backup options in case of disaster. I Skype’d with the Remote Year recruiter while she was in Buenos Aires and the connection was sublime.

8. Accountability

I have the option to work from home on a regular basis and even when I’m in the office, my boss and a majority of my clients are on the East Coast. Thus, I already have a level of accountability established through my performance, which speaks for itself.

I’m not sure we need to implement any new system of accountability. We could always increase the frequency of our 1:1 discussions or I could put together documents outlining weekly/monthly goals.

9. Returning Home

If for whatever reason my presence is required back in the US (failed virtual collaboration, required person team meeting, emergency, etc.) I will return to the US.

10. Safety

Remote Year prioritizes safety of all participants when selecting cities, work spaces and accommodations. They also subscribe to International SOS, the market leader in security and emergency response. They are also in constant contact with local emergency contacts and local embassies.

11. Personal Benefits

I threw together a quick list of personal benefits of participating in the program. While these are far less important than the prior sections, I think they are still a nice touch to show what it is about the program that really interested me.

  1. I would receive a ~20k raise without <company> having to pay me an extra dime.
  2. The average age of participants of the program is 30. This is far different than my current work environment. Being with 74 other people of my own age with the same ideals about remote work will greatly improve my performance to a level I doubt I even knew I was capable of.
  3. Global professional networking
  4. Learning a new language (Spanish)
  5. Challenging myself in a new environment
  6. Building confidence and leadership skills
  7. Understanding local businesses and global industries
  8. Becoming a better communicator
  9. Challenging myself to meet and exceed business expectations in a diverse and unique environment

12. Final Thoughts

As a conclusion of sorts, I thought it would be great to finish with a quote directly from my company’s remote work documents.

Managers should make every effort to enable mobile work by challenging their own assumptions about how results can be delivered. However, if managers believe that results cannot be achieved through mobile work for a given role/colleague, they have the authority to require on-site work. When in doubt, managers should err on the side of flexibility. In the event that a manager believes business needs cannot be met through a mobile work arrangement, the manager should consult with his or her manager before making a final decision.


Thoughts about what I could have potentially done better or how you would have structured a business plan to work remotely? Leave me a comment!

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