Working Remotely: How I asked my boss about it

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Ready, Prep, Go: How I asked my boss about working remotely Learning to let go: working remotely. Beach at Oaxaca

Working Remotely: How I asked my boss about it

I can tell you the day I decided to pursue working remotely: It was Saturday, November 24th, 2012, and I was in Oaxaca, Mexico, using up nearly all my vacation days to attend my sister’s wedding. Lounging on the beach drinking fresh-squeezed orange juice, I watched my son in the waves during a surfing lesson with a local guy named Jesus.

Wifi Signal on the Beach

As I was putting my iPhone into a  bag, I noticed that, defying all logic, the phone was picking up a wifi signal from the hotel, which was located 40 meters up the side of a cliff. I was on vacation, but I checked my work account anyway and saw something that would need to be taken care of when I got back. It was minor — a few questions that needed to be answered — but instead of waiting until I returned to Tokyo, I dealt with it right there in the sand. It felt good: I had crossed something off on my list, and my juice was still cold.

Reality of Remote Work

Most honest remote workers will tell you that this version of their life is both false and fantasy, and now I know they’re right. Most of my days have been spent indoors so far, with hammocks and cocktails few and far between. The moments of leisure and discovery are fantastic, but by no means constant. It’s a struggle.

That gloriously extended wifi signal I experienced? Some sort of Mexican miracle, apparently. But once I had my own small taste of the fantasy, I knew I needed more. My sister’s Oaxacan wedding was such an amazing trip for all of us that I felt compelled to see if we could somehow have more of that feeling in our lives — without going broke, of course.

Work on the road

There are many ways that working remotely can fit into travel. Some people decide to found their own company and/or blog and go into business for themselves. Others work freelance for one client or perhaps dozens of them. Still others try to do both. I felt confident that most of my job could be accomplished while traveling.

In fact, I was frequently working on the road already: once a year or so, a photo shoot or presentation sent me to a new place, and whether I was at a studio in Seattle, a hotel room in Washington D.C.  or a stretch of Costa Rican coastline, I often utilized the same techniques and technologies digital nomads use every day: Skype, password-protected documents, VPN, FTP, etc.

How I asked my boss about Working Remotely

I knew this, but I wasn’t sure how to get my boss to see things my way. He’s a smart and considerate guy, and I’m lucky to call him a friend. But this idea was completely new to everyone in my company, and to Japan in general. This is the land where it’s common for the office workers to eat lunch at their desks and head home around 8pm, midnight, or much later.

Staying late in the office is still considered by many as a sign of a hard worker, regardless of what that worker actually produces. These ideas are changing, but what I was proposing was a fairly alien concept to some of the decision makers. It took some planning and some patience, but in the end, I was able to convince them that I could still provide value no matter where I was. Below I go through the steps I took to get there, but before we get started, I’d like to mention perhaps the most important question you should ask first.

Why You?

Why would your company allow you to work remotely? This may sound obvious, but some people overlook it: how valuable does your company think you are? It doesn’t matter if YOU think you’re an asset to the company. It’s whether they consider you an asset. If they consider you replaceable, this it’s probably not going to work. You have to provide something that they can’t find in anyone else, or that would require too much work or risk for them to start looking for. I had that something — at least I did when I pitched this idea. In fact, I could very well end up being replaced, and that’s ok. More on that later.

How much of your job can be done remotely?

Come up with a percentage. What can and what can’t you do remotely? Empathize with your boss and coworkers: try to think of what problems might arise if you were absent. Pare up all of your responsibilities into three categories: what’s completely possible remotely, what’s completely impossible, and what’s “technically possible,” but would make more work for others. In my case, I figured 80% of my job could be done anywhere. I work at an ad agency, and most of my work is copywriting, editing and coming up with tag lines and other catch copy for new products. All of this can be is done on electronic documents: MS Word, Powerpoint, Excel, etc.

I often brought my work home with me already: whenever I left early to pick up my kids from school or stayed home with them when they had the flu, I made sure my coworkers knew that I was still reachable, and frequently worked late or over the weekend so they knew I could be depended on. After I decided to start planning a remote work strategy, I doubled my efforts from home. I wanted everyone to know that it didn’t matter where I was, I would finish their job on time.


My work also included lots of meetings. Some of them could be handled via Skype without much extra effort, while others were somewhat feasible to arrange, but would just be too much trouble for everyone and slow things down. Same with presentations to clients: Skype wouldn’t work — to participate I would need to be physically in the room — so that meant I couldn’t do presentations.

Considering these things, this is a rundown of the presentation I made to my company, with a few screenshots from the actual slides. This was a fairly slapdash presentation, so don’t expect anything fancy, and feel free to skip the parts you already know.

The purpose of the meeting

I started by simply explaining why I took them away from their busy schedules

Why I want to work remotely

I elaborated on how I would put this plan into action and why I thought it would work.

  • I detailed the 80% of my job that can be done anywhere, making sure they knew what I could do and what I couldn’t do.
  • I ran down the price differences between Tokyo and the places I planned to be traveling. Many of them knew this, but after decades in Tokyo, it’s easy to forget.
  • I told them that I wanted more family time. Some decision-makers in my company are old-school Japanese company men, from a time when being a family man meant working all the time to provide for them, but my direct boss is an involved father who I knew would empathize with this.
  • I touched on how I believe homeschooling & travel might be better than public school for raising global citizens. I didn’t spend much time on this one because it is pure personal opinion and an unfamiliar concept to them, but I emphasized that by homeschooling, I can teach my kids the conventional subjects in both languages, all while giving them more of what they don’t get enough of in school.

Promises and Assurances

It was important to assure them that my integrity as an employee would not diminish with distance. I told them:

  • I will be DISCREET: I sometimes deal with confidential information. I showed them how I would meet all of the company’s privacy and non-disclosure protocols, and how if I needed to be pulled off sensitive projects for more boring work, I would respect their decision.
  • I will be LOYAL: This was NOT a vacation or a sabbatical, I explained. It is simply a new working style. I assured them that if they kept me on, I would continue to look after their interests and work just as hard…no, harder.
  • I will be VALUABLE: I told them that I will provide the company with even more value by doing this. This experiment was not just a about me — it would benefit them, as well.
  • I will be AVAILABLE: I haven’t left Japan permanently. In fact, my in-laws and many close friends are still here, and I will likely be coming back to Japan off and on for the rest of my working life. I also explained how things like Skype, Skype numbers Whatsapp and LINE keep me just as accessible as I was when I was in Japan.

My Itinerary

Here I showed them all the dates and places for my first six months, while in the next slide I presented information about the advanced WiFi networks found in all of my first three destinations: Taipei (Taiwan), Penang (Malaysia) and Bangkok/Chiang Mai (Thailand). I wanted them to have a sense of control (now they know where I will be and can easily contact me anytime), while also emphasizing that my decision was already made. This wasn’t some fuzzy future possibility. I had done my research and already booked our tickets.

Security, Confidentiality & Technology

I needed to assure them that I could work on confidential documents without anyone seeing them. If my boss did an image search of “digital nomad” or “remote worker,” it’s likely he’d see some dude on a beach at a cafe table, his laptop screen visible to everyone. I needed them to know that I would never work on company projects like that. I explained that:

  • I have paid extra for apartments with private, password-protected wifi and an office space, and I will also bring an Apple Airport Express so I can set up my own private network when needed.
  • I would sequester myself to a closed, quiet room while working or conducting meetings over Skype.
  • We will be staying at least two months in each location, and will travel to each new destination only on weekends so that I will be available to them on weekdays.
  • I will use VPN, pre-paid SIM cards and other technologies to keep me both available and secure in all the places we choose to travel. I explained how other apps and technologies will keep me connected and contributing: PDF readers, Skitch, Dropbox, DocScanner, Evernote, Fujitsu Scansnap, etc.

*I even added pictures of some of the places we’d booked, including our first apartment in Tainan.

My Proposal

Basically, I told them:

  • Cut my salary in half. That also means they wouldn’t pay my pension, health insurance or commuter card (don’t really need that last one any more anyway).
  • For that, I will work for them full-time for three consecutive days a week (Mon-Tues-Wed, Tues-Wed-Thu, etc)
  • I knew that they would be concerned about how this might affect company morale (“Why does JASON get to do this?”), and I wanted to address it. I simply told them that I’d like to be honest with everyone: if anyone complains, simply tell them about my dramatic pay cut. I was (and still am) fairly confident that this will be enough to squash any ill will. I like my coworkers — basically everyone — and I think they like me, so I didn’t want to leave on poor terms with anyone, or give my boss trouble by leaving him with resentful staff.
  • I proposed a trial period of 6 months: from September 1 to March 1 . We plan to come back to Japan (Osaka) for a visit at that time for my mother-in-law’s 70th birthday (shh! It’s a surprise). I told them that I would take the Shinkansen back to Tokyo for a review of my performance. If they felt that my plan didn’t work or they wanted to replace me, I would respect their decision and harbor no hard feelings. I would just be grateful that they let me try it in the first place. I would then do everything they asked to make a smooth transition to whomever they replaced me with.

Possible Replacements

I then offered up three capable writers that could step into my shoes. Long before this pitch, I had been searching for writers to help me with a growing number of projects. I needed writers who knew about cameras, could meet deadlines (as I mentioned here), and who also knew how to work in a Japanese company environment — not the most common skill set.

I presented three writers to the company, basically telling them that any of these guys could easily replace me, and if they wanted to, they could. I wanted to keep my job, but I also didn’t want them to feel that I was forcing the company to bend to my will. Two of them now work with us on a freelance basis, taking care of the 20% of the job I can’t do, as well as attending to many other projects that I might have been assigned.

The only advantage I have over them is experience, and the longer they stay, the less my experience could matter. I told them both that if the company ends up choosing them over me, I would be fine with it. And that’s not bullshit. My boss and my company have been very good to me over the years: compared to the usual Tokyo salaryman situation, I have been given much more freedom to be an involved father, so whatever decision they make A-OK with me.


I basically thanked them and asked for a decision soon, as I was leaving in about 2 months and would need to make other work arrangements if they said no. I also apologized for all the trouble and disruption this might have caused, because, well, that’s the Japanese thing to do, really, and having your main writer tell you he’s leaving town in two months is not the first thing these people wanted to hear on a busy Tuesday morning.

They ended up deciding to keep me on, but with one provision: instead of the 3-day-a-week model, I would need to be on call, as it would be hard to predict exactly when and how much I would be needed. If I didn’t know my boss so well, I might have hesitated, but I agreed to this because I knew he wouldn’t abuse this. Advertising doesn’t come in three consecutive day chunks. It’s an ebb-and-flow, feast-or-famine type business. Sometimes there is heaps of work — other times barely anything is happening.

If you have this kind of work or something you think might fit well with working remotely, how you you go about proposing it to the decision makers in your workplace? What have I left out?


  1. lena jenkins says

    You did a great job of prep work before taking off on this adventure. Proud of you, as always. mama