Background:

Almost exactly one year ago I lost a job that had changed my life. I was working for a company out of Texas, and I was spending half of my time managing the company’s office in Costa Rica.

I had spent a few years living in Dallas, but had moved back to Florida to work remotely from my house. I would spend two weeks at home, and two weeks in San José, Costa Rica every month.

When I would tell people that I traveled to Costa Rica every month they would be so envious and tell me how lucky I was. I would try to explain to them that it wasn’t like they imagined or had heard, not in the city where I lived and worked. The mountains, the volcanoes, the rainforests, the resorts…yes, all wonderful, but San José is another world from the Costa Rica you hear about. It’s gritty and bustling during the day, and dark and dangerous at night. Even so, I looked forward to my trip there every month.

In 3+ years I made over 50 trips to Costa Rica. I didn’t speak much Spanish (and still don’t), but I met a lot of wonderful people, made lasting friendships and learned a lot about myself. Travel has a way of making those sorts of things happen.

Full Circle:

Unfortunately, about 1 year ago the ownership of the company I worked for decided to close down the operation in Costa Rica. I had felt for awhile that from a business standpoint it was coming to an end, so I wasn’t at all surprised by the closure. The worst part was that several fine people were left without a job, in a very tough Costa Rican job market. I was also out of work, but in the United States there are is high demand for what we do.

New Opportunities:

The work I do is computer design work in the construction industry, so I decided that because I wanted to be able to continue traveling at a semi regular pace, that I would seek out remote work. I teamed up with two of the best designers from the Costa Rica team, and now we do contract work from wherever we are.

The obvious downside to this arrangement vs. the old one is that my travel expenses are no longer reimbursed by a company, but the freedom I have now is amazing.

Just this year (thanks mainly to miles and points) I have traveled and worked from Hawaii, Hong Kong, New York, London, Brussels, Scotland, Austria, Iceland, and Costa Rica a couple times.

Later this month myself and one of my friends, who also works with me, will be spending a couple weeks in Bali, and next month I’ll be in Hawaii again for a week working from paradise.

Lessons Learned:

I can basically make my own hours, but I’m more comfortable working the same hours that the Texas based company I do most of my work for is working. Since it’s my business I feel that it’s important to be available during work hours and respond to phone calls and emails in a timely manner. Because of this, no one that I work with is even aware that I’m halfway around the world…unless I tell them of course!

Lesson Learned #1:

Time zones matter!
Hong Kong is 13 hours ahead of Texas. That means that the regular 8am-5pm work day in the CST time zone of the U.S. is 9pm-6am in Hong Kong. I was in New Zealand last year, and it was 16 hours ahead there. That is very difficult to get used to, especially on a short trip, and makes it tougher to manage your sightseeing and sleeping time.

Hawaii, for me, is the ideal place to work from because the “Texas Time” work day in Honolulu is from 3am-12 noon. I was able to spend the afternoon at the beach or pool, or do some hiking, get a solid 6 or 7 hours of sleep, and then get up and work from 3am.

It does depend on if you’re a morning person or a night owl, but either way, if you have set work hours, you have to get used to doing things on a different schedule from normal.

Lesson Learned #2:

Build a weekend into all of your destinations!
If you’re working remotely from one place for a long period of time, it should get easier to adjust to the time zones, but it can be a struggle. Short stops in each place are much tougher. There have been times I was so tired I didn’t want to leave my hotel room after working odd hours on a weekday.

This is why I always try to have at least one weekend at all of my stops. That way if I’ll only be there for a few days, at least I know I will have a day or two free from working crazy hours to see the things I came there to see.

This is obviously even more important when the things you want to see are long distances from where you’re staying. When you have set hours that you need to work like I do, doing things like driving the Ring Road in Iceland have to be done on the weekends.

Lesson Learned #3:

T-Mobile has been invaluable. I’m not well versed in the international plans from other carriers, I’m just saying that I am extremely happy with my cell phone service. I have to communicate a lot for my job, which means a lot of phone calls, texts and emails.

T-Mobile has an international plan that includes texting, $0.20 per minute calling and slow internet, but they also offer a premium international plan that includes free calls, free texting and faster internet speeds. I buy the 1 month plan for $50 and for me it is money well spent. As I mentioned earlier, most people I work with have no idea I’m in Hong Kong or London when they’re talking to me, and that’s important. I’m sure there are other similar or better plans out there, but I’ve been a long time T-Mobile customer, and I’m happy with what they provide.

The Item I Won’t Travel Without:

The work I do is very detail oriented and I need to have a lot of windows open on my computer, at any given time, so when I’m at my house I use a 3 monitor setup to do my work. My 15.6” laptop screen acts as the first monitor, with a HD 27” monitor as the second, and a 32” TV as the third.

That setup is obviously not something I can travel with, so for awhile I just worked from my laptop when I was away, but that was a struggle.

My life was literally changed one day a few months ago when I realized there was such a thing as a portable monitor. I just had never been aware of that, but after some research I settled on a 15.6” screen and my life hasn’t been the same since.

I can’t overstate what a difference it makes to be able to work off of two monitors. It slips into my laptop bag and takes up almost no extra room. The resolution is excellent, and it has made me much more productive remotely. I would highly recommend anyone that needs to work remotely to take a look at these. Time will tell if this particular model holds up over time and distance, but so far I feel like I got a bargain for $170!

The Wrap Up:

Working remotely from around the world has been unbelievable, and something I never dreamed I would be doing at this point in my life.

My previous job that required me to spend half my time in Costa Rica set me up for this in many ways. It set in motion a series of events that allows me to continue working with two of my favorite people, and it built my confidence to get out into the world and not wait for tomorrow.

With each trip it gets easier to manage working while traveling, and figuring everything out as I go has been a big part of the adventure. I just need to ramp up my miles and points earning so that I can continue to do this for a long time to come.