Office Supplies for the Digital Nomad

It took me a while to get fully unpacked after two months abroad. I'm not known for "packing light" but in my defense, I brought along some key items that made workcationing possible. Here's my short list:

#1 most crucial Officelessness travel gizmo: Skyroam portable WiFi hotspot ($99.99). With 24-hour internet passes for just $8 each, you can connect most anywhere where there's cell coverage. I set up the AT&T Passport Plan on my phone, which gave me unlimited international texting and relatively affordable calling, but the data allowance was paltry (though there are lots of tips on conserving data and their international specialists are very helpful, too). I’m grandfathered into an unlimited data plan here at home, so I have no concept what amount of data checking email or social media or navigation apps uses (hint: a lot more than what the plan offers). Skyroam’s battery life is only about eight hours, but with a backup battery pack, you’re good to go, all day long.

Visiting multiple countries meant all different kinds of outlet situations. The BESTEK Portable International Travel Voltage Converter made things easy with plug adaptors and USB ports galore. One of my travel mates lamented its high-pitched whirr, but I wouldn't have noticed it, myself.

Having a separate checking and credit account for the trip was a good way to keep track of expenses on the road. Capital One Venture Credit Card has no foreign transaction fees and earns you points for travel expenses. The interest rate sucks, so as long as you pay it off in full, it's worth it. Capital One checking accounts also have no fee for international ATM withdrawals.

Three more things that made my trip easier and more comfortable: Merrell walking shoesBose Noise Cancelling Headphones and the Etekcity Luggage Scale.

Sartorial appeal: Limited. Complete comfort: Priceless

Sartorial appeal: Limited. Complete comfort: Priceless

These + Ambien = airplane ZZZ's

These + Ambien = airplane ZZZ's

Hanging luggage scale: Baggage overage fees are real

Hanging luggage scale: Baggage overage fees are real

What are your must-brings when you go abroad?

Travel ≠ Vacation

a little bit of this

a little bit of this

As glamorous as it may appear on Instagram, traveling requires constant effort – and the rigors of running a business don’t stop when you board that plane. Being jetlagged, exhausted or simply wanting to play the awestruck tourist means nothing to your clients, many of whom are working in an office and not particularly sensitive to the “plight” of the digital nomad.

... leads to a lot of this

... leads to a lot of this

I’m three weeks into my two-month Southeast Asian sojourn. Unlike last year, when I set up shop in a WiFi-enabled casita in Costa Rica for a month, this winter I’m making the rounds. With each stop on my itinerary, I’ve got ample baggage to juggle, multiple modes of transportation to negotiate and periods of uncertain internet coverage… followed by brand new scenery, cuisine and customs at which to marvel, and also foreign currencies, weather patterns and time zones to assimilate. 

This morning, I woke at 4am to catch a flight from Manila to Ho Chi Minh City, only to see a calendar alert for a meeting, and a missed call from an HR person of a business I’ve been courting for months. My time-difference related calendar snafu left me feeling disoriented and somewhat discouraged about my ability to world travel while working full time. I earn my living on doing what I say I’ll do to make my clients’ lives easier. It’s my job to work around their schedules, and me playing hard to get is not cute. I tried time zone apps like MirandaTimeBuddy and Klok, which should have helped me out, though Google Calendar takes it upon itself to make funky time zone adjustments, and to be honest, my general disorientation deserves most of the blame here.

Yep, travel takes you out of your both your time and comfort zones: showing you new things and challenging your ideas of the way things are, and who you are. This happens to me every day I’m on the road – and for that, I know I am #blessed. 

Business (Super) Casual

From nine years in a Catholic schoolgirl uniform to head-turning rock chick getups in high school and college, clothes always played a part in my experience in the world. One iteration for which I hold no fond memories: the obligatory early-career "business casual" phase: can't-miss office essentials that made me feel like I'd lost myself. With the goal of fitting in in a corporate setting to make my way in the world, donning pastel button-downs and black loafers seemed like a fair penance at the time, but getting dressed in the morning often felt more like a punishment than a pleasure. 

A decade after those fateful trips to Marshalls that lined my closets with employee-handbook approved garb, I don't work for anyone anymore, and so off to Dress for Success those garments go. Left to my own style devices, do I dress like Nancy Spungen or some fabulously eccentric baroness? Now and again, sure. I also like a nice Armani blazer as much as the next gal. But most days, I'm into athleisure, like the rest of the world. Yet another benefit of working for yourself to which I am grateful daily: dressing how I want when I want.

Daylight Stealing Time

If you've ever worked in an office, chances are you've at least once helped yourself to more than your fair share of the seemingly endless resources onsite: ballpoint pens, sticky notes, legal pads, and the like. A victimless crime, assuredly. As a remote worker and business owner, I am guilty of the constant pilfering of one of my company's most valuable resources: Hours. I choose to use an additional 2–3 hours a day sleeping in, on the regular. Even with our recent hour backward shift – of which I am conscientious objector – I'm currently in a pattern of sleeping until almost 9am every day. This may make me the envy of some, but it's not without shame that I admit what feels like an excessive indulgence. 

When I worked a regular job, one of my least favorite aspects was the rush hour New York City subway commute from Williamsburg to Midtown, and the non-creative, sleepy, jostled and sometimes even violated state it would put me in, most days. As such, years after leaving the standard in-office schedule, not unlike a child allowed to eat ice cream for dinner, I continue to prioritize the pleasure of extra sleep more often than not. The only person this "hurts" is me, which makes it a hard habit to kick – patricularly considering one could argue that sleep is indeed good for you! I end up making up the hours when other people are winding down – evenings and weekends – which can cut into time I get to spend with the 9-to-5ers in my life and put a wrench into the cultivation of a normal work/life balance. My current game plan? I'm using the Sleep Cycle app to slowly shift my wake up time a bit earlier every week.

Placed on your mattress, the app uses your phone's microphone to measures your movements throughout the night and wakes you at a point in your sleep cycle where you are most likely to emerge ungroggy and ready to face the morning. It's pretty cool. What will I do with these morning hours? Breakfast, yoga, brisk walks... it's my time, I can use it however I want.

A Primary Residence of One's Own

My last foreseeable beach-houseguest just set sail on high speed ferry back to town, which leaves things feeling a little what's-nextish over here at Officelessness' floating HQ. When you work for yourself, remotely, the location question is an open-ended one. There's no commute to factor in, no colleagues to miss, no place with a wifi connection and a bedroom to rent off limits. You can go where the wind takes you, which might sound pretty nice, depending upon where you're at.

Pick a Portland...

Pick a Portland...

Any Portland.

Any Portland.

But then, there's that thing about roots. Community. Consistency. Popular wisdom suggests that someone my age should work toward owning a home. I love the Boston area for many reasons, but real estate is not what you'd call affordable, particularly for a single person in the first few years of running her own business. Anything semi-comfortably within reach hovers around 500 square feet. Sort of uninspiring to imagine my grown-up life of cooking fancy dinners on a stove overlooking my bed. I try to envision a life anywhere from Philly to Portland, Maine (or Oregon, really); Salem, Mass to Santa Barbara. Proximity to nature is important, as are things to do and good food. Decent weather is plus, but I'm hardy New England stock, so I'll take what comes. And of course, price is a factor, as are taxes, crime, solitude, proximity to people I know... It's near-impossible to narrow it down to that "perfect" place and put down roots. And so I flit from place to place, until I find a reason to stop. Is Residencelessness is the new Officelessness?

I'm Not on Your Vacation

[cue the tiny violin choir...] Yesterday, I spent the entire day indoors. It was a beautiful specimen of a Cape Cod day: birds chirping, waves crashing, sun warmly shining behind a pillow of puffy clouds. But there I was, slumped on a futon, shades drawn, concentration musak blaring, churning out a day-late assignment rife with moving parts/details that had I strayed for even an hour to go for a dip, I'd be left to backtrack over piles of papers and draw the work out all the more. By the time I hit send and emerged from my cave around sundown, I felt like a visitor to a new planet – eyes blinking, lungs hungrily filling with fresh air, positively parched in a way which only a mind-numbing beverage could quench. 

This is not ideal. My ideal day goes something like this: 

8am – wake up, make a nice breakfast, meditate, do the 7-minute workout, followed by 15–30 minutes of yoga.
9:30am–12noon – Sit in on one or two conference calls, sift through and send emails.
12noon–2pm or so – Focus intently (read: stay off Facebook) on work, completing and submitting assignments that are due. (I rarely work ahead, sigh). 
3–6pm – Head out to enjoy late-afternoon lazing on the beach/bike riding/running errands around town.
6–7pm – Catch up on the emails that came through during the afternoon, maybe send out invoices/pay bills/etc.
7–9pm – Dinner at home, on the beach or at a restaurant – this is when I tend to socialize – a key component to not becoming a very weird hermit.
9–11pm – Enrichment – reading, working on a crafty project, or, admittedly, catching up on TV shows I was too busy to watch first time around. 

No matter how you work, keeping a schedule makes a huge difference. It's not always easy, like when peeps from all ends of the earth make their way through the Cape on their hard-earned August holidays, and the call to while away a day on the beach with them is louder than a seagull's squawk. When I take a full day off to play in the sand, I have to make up for it at some point, hence yesterday's lockdown. Life is about balance: being able to enjoy the moment one day and hunker down the next. 

Rover, Wanderer, Nomad, Vagabond... Call us what you will.

Today I had a Skype interview to potentially participate in Hacker Paradise, a floating coworking space, wherein you pack up your laptop and live and work with a group of other remote workers for two to twelve weeks in far-flung locales, working independently, and in tandem to create community and foster new ideas. They set up mini campuses everywhere from Costa Rica to Berlin where freelancers can work together, play together and learn together. The next trip is to Tokyo, followed by Taipei, then, who knows? 

Another pilot program in the same vein: Remote Year, which just kicked off its inaugural year on the road, each month bringing workers along for a once-in-a-lifetime experience of working around the world in a different locale every month. Their next year starts in February in South America (Montevideo, Uruguay) making its way through Europe and ending in Asia in Ho Chi Mihn City, Vietnam. 

More of a loner? NomadList and its Digital #Nomad Chat Community serve as a forum to communicate, troubleshoot and to get inspired for your next work/life destination. How fast is the WiFi in Phuket? Is Riga a safe place for women working solo? That kind of thing is calculated and searchable on NomadList. 

So with a group, on your own, for a fortnight or a year – if you can break away and make money doing it, life can be like a working vacation (my favorite kind). 

Stay Positive, Stay Productive

When I left my last full time job, just over eight years ago (WOW!), I assumed I'd soon enough be back in a full-time position somewhere, but it just never came to pass. I grew accustomed to hustling for different gigs, cobbling together a schedule of project work, replete with midweek downtime and working weekends. At first, grocery shopping or going for a hike on a Wednesday afternoon felt inherently wrong, like I was shirking responsibility or playing hookie or that I was some under-employed slacker. And working on a Sunday – the good Catholic school girl I am – well, that felt off, too. 

This way of working, on your own schedule, in your own environs, is gaining in popularity and acceptance in the world, but us digital nomads need to work on our own self-acceptance out here in the wilderness. One great you're-not-alone resource is Remotive – a newsletter created by an employee of Buffer, a 100% distributed team employer. 

Replete with weekly productivity tools like playlists that increase concentration to remote job listings, it's a must-read. 

That's it for Officelessness for this week – tomorrow is my birthday, and no matter what you do for work, you should take that one day each year to turn it all off, which is what I fully intend to do. As for the Saturday after, well, that's fair game. 

(In)voice Your Opinion

Among the many joys of being your own boss is setting your own rates. I work with many clients, in many different ways. Some are charged an hourly rate, while for others, I set a project fee which includes the discovery/research phase, along with two sets of revisions. On the rare occasion that I'm required to go onsite, I set a flat day rate, regardless of time spent working.

Just yesterday, a client requested my presence for an hourlong in-office meeting, which – by my calculation – warrants a full day's pay. When you factor in the travel time to and fro, the prep and the unwind, the meals on the go, and of course, the shifting of other work and life priorities to allot my full attention to one client on any given workday, it all adds up. If a client doesn't want to shell out for a full day, there's always the GoToMeeting conference call/Google Hangout route, which suits me just fine, and saves them money to boot – but I can't blame my clients for wanting a little face-to-face now and again. 

No matter how you charge, it's key to be upfront about rates beforehand so there aren't any surprises when you submit your invoice. That's where the handy dandy Budget Proposal comes in – but that's another topic for another day. 

#Rethink ––> Revolution

Here in its infancy, I'm beta testing Officelessness on the people I always turn to – one of which being my colleague and frequent collaborator Ben Spear, who suggested I watch this talk (see below) he attended in early 2012 with Sara Horowitz, founder of Freelancers Union. As a both community and viable way of working, the concept of "freelance" has made epic strides since even just a few years ago. We have access to healthcare (Thanks, Obama) – which gives us one less reason to stay tethered to a corporation; and an ever-increasing number of progress-enabling technologies like Squarespace, MOO and Wave that empower people to create professional consumer-facing personae to grow their own businesses. Hats off to Ms. Horowitz for pioneering with legislation designed to promote equality for independent workers to thrive in the world today.