New Players for a New Game: Remote IT Work and Global Possibilities


“Life is a puzzle, a riddle, a test, a mystery, a game—whatever challenge you wish to compare it to. Just remember, you're not the only participant; no one person holds all the answers, the pieces, or the cards. The trick to success in this life is to accumulate teammates and not opponents.” - Richelle E. Goodrich

Suppose life were viewed as a game and let’s think about that for a moment. We’re all involuntarily thrusted into existence with complex rules we don’t fully understand and predictable laws running the show. Just like a game, there are winners and losers. Life is basically the weirdest MMORPG we’ll ever play.

In this game, we’re all dealt different hands for better or worse. But ultimately, we are the authors of our story. History is full of examples of people from less than ideal backgrounds achieving success later in life. If it’s humanly possible for them, it’s humanly possible for us. But what is success?

Success is usually associated with economic prosperity. And if you’ve been reading the news lately, most of us aren’t very prosperous.

That definition of success won’t work. Instead of asking what success means, let’s imagine our ideal lives. Pretend you were just given $10,000,000 and don’t have to work anymore. Now imagine an ideal life where you are your best self. The partner you want, the social life you want, the friends you want, the home you want, hold nothing back. What do you see right now? Because whatever it is, it’s non-negotiable for your happiness.

Every individual chooses their own future. Whether through conscious choice or inaction, the choice to not make a choice is still a choice. We can swim towards something or let the tide carry us but if we don’t like where we’re carried, it’s on us. If the time will pass anyway, why not try to win the game and chase our happiest lives instead of letting life choose for us?

Beating the Game by not Playing the Game

“Whenever you find yourself on the side of the majority, it is time to pause and reflect.” - Mark Twain

The default road is to go to high school, college, work a career (or careers) for a few decades, and retire. This path is generally what most people aim for and what most parents preach to their kids. It’s also assumed you must stay in the same location nearly the entire time and people look forward to escaping the “9-5 office grind” and retiring so they can be “free”. But what if we want to be “free” now and avoid the rat race that is all too common in modern day work? Due to advances in technology and the rise of remote work, a sub-culture known as “The New Rich” are forging another path for people.

One of my favorite authors Tim Ferris defines the New Rich as those who abandon the deferred-life plan (waiting until retirement to truly “live”) and create luxury lifestyles in the present using the currency of the New Rich: Time and Mobility. Tim goes on to say that: “Life doesn’t have to be so damn hard. It really doesn’t. Most people, my past-self included, have spent too much time convincing themselves that life has to be hard, a resignation to 9-to-5 drudgery in exchange for (sometimes) relaxing weekends and the occasional keep-it-short-or-get-fired vacation.”

I’m with Tim, I don’t think most of our lives need to be spent on someone else’s terms. How can it be that all the people in the world need exactly 8 hours or more to accomplish their daily work? It isn’t. 9-5 is arbitrary. Starting today, let’s live life on our terms and break the traditional rules. If the default seems to be a 9-5 career that you just have to “deal with” while you watch your peers complain about stressful work environments, long-hours, stagnate wages, and other issues then what is it all for?

Let’s try to “beat the game” (obtain our ideal lives) without the $10,000,000. We can do this by not playing the game at all and reflecting on lifestyle design choices we can make. We won’t engage in corporate ladder climbing. We won’t trade 5/7th of our lives away doing something we dislike only to enjoy the weekend. We won’t slowly save up and hope retirement frees us to “truly live” at 65. Here’s the cold hard truth about retirement: it won’t be what you think. As Tim Ferris puts it: “Today’s traditional retirement could last 30 years and inflation lowers your purchasing power 2%+ every year”. Even $1,000,000 won’t be enough at retirement if you’re currently between 25-35 in 2019. Golden years? Try lower-middle class life from 65 onwards. But don’t worry, we don’t need to wait until our bones ache and our hair turns grey to start living. A new way of thinking about work and money can free us and expand our lifestyle options right here, right now.

Lifestyle design requires thinking about money in a new way: Absolute vs. Relative income. Tim writes: “Absolute income is measured using one holy and inalterable variable: the raw and almighty dollar. Jane Doe makes $100,000 per year and is thus twice as rich as John Doe, who makes $50,000 per year. Relative income uses two variables: the dollar and time, usually hours. The whole “per year” concept is arbitrary and makes it easy to trick yourself. Let’s look at the real trade. Jane Doe makes $100,000 per year, $2,000 for each of 50 weeks per year, and works 80 hours per week. Jane Doe thus makes $25 per hour. John Doe makes $50,000 per year, $1,000 for each of 50 weeks per year, but works 10 hours per week and hence makes $100 per hour. In relative income, John is four times richer.” Assuming we already make a decent living and because money inevitably has diminishing returns (Adding no more value to your life besides extra 0’s under your checking account), we should seek ways in which we become richer through time. This can mean re-arranging and negotiating work duties or shifting careers entirely.

As our options expand, so does the ability to live meaningful and fulfilled lives. Remember the new rich’s currency: Time and Mobility. We don’t need to retire to start living, we just need to reflect on designing the appropriate lifestyle for ourselves and figure out what the minimum annual income would be to acquire that lifestyle.

If you’re reading this blog, you probably work in IT or some kind of Technology field. Chances are you don’t want to be in an unhappy work situation most of your life. Whether your dream is escaping the 9-5 grind, real-life fantasy travel, long-term world exploration, or simply a dramatic career change…joining the subculture of the new rich can make that a reality.

Who are the new rich and how do they use time and mobility exactly? Tim has some great examples: 

  • It’s the employee who rearranges his schedule and negotiates a remote work agreement to achieve 90% of the results in a quarter of the time, which frees him to practice cross-country skiing and take road trips with his family two weeks per month.

  • It’s the business owner who eliminates the least profitable customers and projects, outsources all operations entirely, and travels the world collecting rare documents, all while working remotely on a website to showcase her own illustration work. 

  • It’s the employee working in data storage sales that realized most cold calls didn’t get to the intended person for one reason: gatekeepers. So they simply made all their calls from 8:00–8:30 A.M. and 6:00–6:30 P.M., for a total of one hour. Doing so, they were able to avoid secretaries and book more than twice as many meetings as the senior sales executives who called from 9–5. In other words, they got twice the results for 1/8th the time.

Remote IT work and Global Possibilities

“For all of the most important things, the timing always sucks. The stars will never align and the traffic lights of life will never all be green at the same time. The universe doesn't conspire against you, but it doesn't go out of its way to line up the pins either. Conditions are never perfect. "Someday" is a disease that will take your dreams to the grave with you." - Tim Ferris

If the new rich use Time and Mobility to design their ideal lifestyles, then as tech workers we are uniquely equipped to use our time and mobility to do the same. Consider what full-time remote work looks like for the New Rich. The freedom to go anywhere as long as there’s internet. Money can be worth much more in different parts of the world. This can enable you to live and travel on a discount compared to parking yourself in high cost-of-living locations like San Francisco and New York City.

Remember my “$10,000,000 is given to you, what is your ideal life” question I asked earlier? My ideal life is to travel the world, see and absorb as much as I can, meet fascinating people and have thought-provoking conversations with citizens from every walk of life. Maybe even try to change this world for the better in my own way. I considered this an unachievable dream for so long, I never once asked myself: “How can I begin to make it happen?”. After all, world travel sounds like something only the rich and retired get to do regularly.

As it turns out, there is a company called “Remote Year” that offers to pair a large group of remote workers together to travel the world and network with each other. For $2,000 USD a month, you and other remote workers will travel to a new country every month with planned country-specific events each weekend. The best part? That $2,000 covers room and board, shared office space, plane tickets, internet, and events on the weekends. If you’re anything like me who currently pays $1,000 a month rent in NYC, it doesn’t seem that expensive given the additional perks. By searching for a way to make this happen, I discovered my minimum annual income needed was $24,000 a year. Of course, this isn’t complete freedom. The program determines the countries we visit and the paid events but a compromise like this for your “near-ideal” life would be pretty cool, right?

I completely understand writing something like this is easy when I’m in such a privileged position. My interest in technology and computers at a young age turned out to be economically lucrative and I’m blessed to have job duties that can be performed remotely. But this isn’t to say that your situation can’t be pushed in a better direction with these ideas. Radical lifestyle changes often require much more work than I let on but we’re all capable of designing more fulfilling lives for ourselves. In aiming for our ideal lives, we give ourselves a sense of purpose and become masters of our faith. As remote work opportunities continue to increase around the globe, new worlds will open up for everyone. I hope this post has inspired you to attempt some lifestyle design changes and play a new game. A game where you live life on your terms and no one else’s.

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