Being a digital nomad is exciting, and in my case it all started with the itch of wanderlust. Unlike so many 20-somethings (see: Quarterlife crisis), I had not hit the panic-induced state where I question everything I’m doing. However, I was worried that if I ever did I wouldn’t be able to escape it.

I was afraid if I stopped moving I'd forget how to do it. @rgo_go #digitalnomad Click To Tweet

So I packed up my laptop and ran to the West Coast for two months to see if I could live and work wherever I wanted to.

How do you work remotely? Pack Hubstaff in your suitcase

Goodbyeeeee (for now)

What began as a run turned into the start of a great experiment. I learned how to work remotely and it was fantasmorphically great, even when it sucked. (I’m allergic to spider bites. That was not a fun lesson to learn.)

There’s this quote by the fantastic Seth Godin (whose website pops up first when you search Seth Marketing and third when you search Seth Bald) that goes “Instead of wondering when your next vacation is, maybe you should set up a life you don’t need to escape from.”

Instead of wondering when your next vacation is, maybe you should set up a life you don't need to escape from. Click To Tweet

This post is about how I did that.

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I have always loved working. Fulfilling work isn’t work at all, it’s how I make a difference in the world. I had an average of three jobs throughout college and still email some of my former employers occasionally to check in. My first job out of college was doing marketing for a local Oregon winery, which led to me becoming the Online Content Coordinator for 237 Marketing + Web. (If you ever need a sleek site built, look them up.)

How do you work remotely? Pack Hubstaff in your suitcase

This was the beginning of my career in remote work. I was living in McMinnville, OR and working from home and coffee shops on 3rd street for most of the week. When I moved back to the Philippines, my role transitioned into a completely remote one.

Once I was back in Manila (where the Internet sucks) I started doing more research into distributed teams and how to work remotely. I discovered that there were many burgeoning startups that are doing great things with 100% virtual teams.

There was one company in particular that caught my eye – Hubstaff. I liked them because I believed in their software and noticed their contributions to remote work in my research. At the time, they didn’t have a careers page yet so I reached out to Dave via email.

Email to Dave | How do you work remotely? Pack Hubstaff in your suitcase

After he replied, we got a Skype meeting set up to discuss their goals and what I could do for Hubstaff. Then I installed their timer and hit the ground running.

Email from Dave | How do you work remotely? Pack Hubstaff in your suitcase

P.S. The moral of this story is to go after the companies you like. I wouldn’t have gotten this job if I didn’t find them, like them and reach out. Even if there aren’t any openings on a company’s career page, sending an email and saying hello won’t hurt.

The great thing about remote work

Things got better from there on. I was working with a local wine retailer and an assessment agency when I joined Hubstaff, and all of these clients allowed me to work remotely after I proved that I could do it. The best thing about remote work is that everything comes down to your ability and output. The work you produce trumps the time you spend (or waste) in the office, and isn’t that what work is meant to be anyways?

This is what I love <3 about remote work.

Accountability – remote work and my Hubstaff timer keeps me accountable. I will always be working when I say I am, and the fact that I can work anytime means that I have no excuse not to finish something.

Productivity – I hate wasting time. I hate it almost as much as I hate the slow Internet in the Philippines, which causes even more wasted time by the way. Remote work means I’m more productive and I’m able to work on my best schedule.

Flexibility – this one is a no-brainer. Remote work is so flexible that I was able to take off to the West Coast for 2 months, eat all the raspberries, turkey and cherry tomatoes I could get a hold of, and continue to be productive and finish my work everyday.


My “office” in Spokane

Awesomeness – how cool is it to be able to work in PJs? I know a lot of people recommend changing into “work clothes” even if your desk is right beside your bed (and it’s a good suggestion), but I definitely have days when I work in the most insanely comfortable, ugliest, oldest clothes I have. Also, I can eat whenever and whatever I want. Cookies and ice cream for lunch at 3 p.m.? In a 7-year-old t-shirt with a hole in the side? No judgement here. I’m getting sh!t done.

It all started with a question

Can you do what you're doing from anywhere in the world? #digitalnomad Click To Tweet

Okay, so it started with two questions.

Am I stagnating?


Could I work remotely from anywhere in the world?

I was starting to wonder about my next steps. One of the most important goals for my career and personal life is to never stop learning. When you stop learning, you stop growing. I was terrified of that.

I decided to do two things;

  1. I reached out to each of my clients and asked if there were additional responsibilities that I could start to handle.
  2. I began planning an extended working trip to see if I could be productive and useful from anywhere in the world.

My 2-month digital nomad experiment

Spoiler alert: It was a success.

How do you work remotely? Pack Hubstaff in your suitcase

My life has been split between countries for as long as I can remember. Growing up, I spent my school years in California and summers in the Philippines. I’ve lived in Oregon, Beijing and am hoping to add New Zealand to that list. As it turns out, wanderlust and professional careers can be symbiotic thanks to remote work.

I left on September 1st, 2015. All in all, my trip took me through;

  • Spokane, WA
  • Walterville, OR
  • Beaverton, OR
  • McMinnville, OR
  • Seattle, WA
  • Newcastle, WA
  • Redwood City, CA
  • San Francisco, CA

In that order.

How do you work remotely? Pack Hubstaff in your suitcase

The view from an awesome hike in Oregon

I learned to feed a mule (his name is Gus), visited my old roommate and her dog Dante, harvested honey, went camping, hiked all over Oregon and Washington, ate entirely way too much, attended 3 beer festivals, tasted wine in 7 tasting rooms and somehow ended up with 14 bottles of Oregon wine. I’m not complaining.

My fridge always has more wine than food. *Not all of these are from Oregon.

I would recommend a two month West Coast trip to anyone who wants to see how beautiful the world is. In addition to my new found love for dungeness crab, I also discovered something else that surprised me about how I worked.

My Hubstaff time sheets, reports and activity levels revealed that I was even more productive on my trip than I was in my home office. I believe this is thanks to faster Internet.

How Hubstaff has helped me evaluate and succeed

Different companies measure remote worker productivity in different ways. Some companies look at number of projects completed, others look at how many hours were logged. I monitored myself using a medley of tools from Hubstaff. My overall analysis of whether I could work remotely came down to what the Hubstaff reports told me.

Here’s what my weekly report summary looked like while I was in Seattle;

Seattle time reports from Hubstaff | How do you work remotely? Pack Hubstaff in your suitcase

For these two clients, this is what a productive week’s time reports look like. I was able to spend 3 to 4 hours on them each day and get a lot of work done while I was at it. Here’s what my activity levels look like from the Tuesday of that week.

October 6 activity levels | How do you work remotely? Pack Hubstaff in your suitcase

As you can see, all my activity levels are in the green, showing that I was doing quite a bit while I was tracking that time. I aim for Hubstaff activity levels above 80%, but much of my time was 90% and above.

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These reports show that I spent more time productively for these clients than I normally do. I used that information and compared it with my working patterns in the Philippines and discovered that I am the most productive when I work in chunks of an hour or two, followed by a non-work activity like kayaking (Oregon), playing mini golf (California) or trying out a floating pod (Washington).

Other tools I use

Aside from Hubstaff, I used a lot of other awesome tools while I traveled. Here are a few that you may find useful if you’re going to work on-the-road anytime soon.


This is a great project management tool that uses virtual kanban boards to organize your tasks. I used it for my marketing projects and have different boards for each of my clients. Each card has one actionable item to do, and allows you to attach files, describe the project, have discussions, and add due dates.


Skype allows you to call and message your teammates (or friends and family) in other countries for free. All you need is an Internet connection. This was incredibly useful for having meetings with colleagues, sending quick messages and sharing screens to explain work that has to be done.


I use for my own blog, and for many of my clients’ blogs. It’s a content management system (CMS) that’s incredibly intuitive and is always getting better. It’s amazing for creating websites or blogs that need a lot of functionality like a shopping cart.


I see this as a mix of social media meets blogging. I used Medium as a content platform to blog about my trip. I aimed for at least one blog post a week while I was traveling.

Google Drive

I could not do what I do without my Gmail and Google Drive account. I keep all my files in the cloud, share documents and spreadsheets with my colleagues and generally keep it as my virtual filing cabinet. For example, when I’m working on something new, I can set up a Google Doc, add my thoughts, then share it with my brilliant colleagues. They can then make edits or add comments/suggestions (depending on what type of permissions I set). It’s an excellent collaboration tool for distributed teams.


Viber provides free calls, texts and photo sharing with anyone who has a Viber account. It’s free to sign up and use, and was vital to communication since I didn’t get a mobile phone plan while I was there. Instead, I would find some WiFi and message/call friends via Viber.


I see Uber as a safer, more convenient version of a taxi. You request rides and an Uber driver will pick you up from wherever you are, then you pay securely with a credit card linked to your Uber account. On-call ride sharing is great for the environment, affordable and so, so convenient when you’re in a place without your own car.


Airbnb is awesome for finding a place to stay. It’s a platform that connects people looking to rent out their house/apartment or a room to visitors looking to stay in the area. I plan to use it to rent out my apartment while I travel to make some passive income, as well as to find nice places to stay within my budget in the areas I want to visit.

Next journeys

I’m going to New Zealand in 2016 for 2 to 3 months. A friend from college and I have always wanted to go and make our way there, plus I want to go cave diving. If you’re interested in visiting, New Zealand offers some working holiday visas or you could go through WOOF.

In 2017, I plan to return to Oregon to visit The Best Dog in The World (Dante) and eat all the turkey I can. After that I’d like to check out Estonia, which is making some waves lately with their new digital-nomad-friendly e-residency program.

But for now, I’m happy where I am, knowing that I have the tools that I need to pick up and go whenever I want. Whereas before I was afraid of stagnating, now I value the stillness.

Besides, maybe when Telstra comes to the Philippines our Internet won’t be so awful. *fingers crossed* I’m working with 1 mbps speeds here, so we need all the help we can get.

Oh, and I bought a plant! That takes location-committment, right? I’m growing my own Kale (we’ll see).

There is going to be kale in there soon. Maybe. Hopefully.

Travel tips

For those of you who are about to embark on a journey in remote work (or if you’re already on that road), here are a few things I would suggest.

Preparing for your trip

  • Want to get great airline deals? You can set up a few alerts at sites like TripAdvisor or airfarewatchdog.
  • Have a game plan for getting to the airport to your hotel/destination all ready before you get on that plane.
  • If you’re going to a country with a different currency, purchase some cash at your bank. It’s less expensive than doing it at the airport.
  • Check out the weather patterns for the place you’re going to visit. For example, don’t come to the tropics during monsoon season.
  • Make sure you’ll have WiFi wherever you go (for those who want to work while they travel).
  • Photocopy your passport, plane ticket and drivers license. Photocopy all your important traveling documents and give your mom a copy.
  • Shameless plug: Install Hubstaff and track your hours and productivity before you go and during your trip, so you can see how travel affects your work.

In the airport and in the air

  • Be nice to everyone, but especially the airport staff. I try to pack light, I really do, but I’ve had more overweight baggage fees waived than I can remember.
  • Be selective when it comes to your carry-on items. When I fly, I stick to my laptop bag of awesomeness and a small roller bag of food, toiletries for the plane and a spare change of clothes.
  • Don’t put your passport or any other small, forgettable items in the seat pocket in front of you.
  • Hydrate.

The airport in Taipei has massage chairs!

When you land

  • Get a mobile plan. The one thing I missed on my trip was having access to mobile data and being able to tether my data in a pinch. The West Coast was great about having WiFi everywhere, though, so it wasn’t a huge setback in this case.
  • Establish a location where you can do some work. In each place I stayed at during my trip, I went out and found a coffee shop or library with WiFi nearby that I could turn to in a pinch.
  • Have you seen these awesome belt fanny packs that don’t look like fanny packs? I’d totally use them to store cash while out exploring.
  • Explore and enjoy.

Your turn

Are you a digital nomad? Do you work remotely? How did you begin on your journey and what inspiration have you encountered so far? Hope to hear from you in the comments below. More travel tips always appreciated.

Learn more about the pros and cons of working while travelling. Check out this article from our friends at Always Wanderlust.

Discover more ways you can make money while you travel. Check out That Travel Blog by Dave Weatherall.