I’ve been working remotely for almost a year, about 70% of which I was in NYC, and the rest I have spent as a “slowmad” in SF, Hawaii, Mexico, and Singapore. Convos with @ossia, @ggallynn, et al made me realize there’s enough interest for a blogpost. What would you like to know?
Here are my takeaways. TL;DR: it wasn't all roses! I am settled into a long term lease now in NYC and it was a fun travel season while it lasted.
Table of Contents
- What is a "slowmad"?
- Some Context?
- Why So Much Travel?
- I'd like to know your biggest day to day challenges in finding good places to stay that also have reliable Internet & other amenities.
- What are some things you wish someone had told you your first month? What was the biggest challenge? What was easier than u thought it would be? What are the top things you need to do this successfully?
- Transition from Corporate Life: Anything different from in office and remote?
- How do you maintain focus?
- How do you resist the temptation to stay at home where the snacks are?
- I consider community/camaraderie an important aspect of work. Does it get lonely while working remotely? How do you deal with it?
- How far ahead do you plan travel? What do you do to find places? How big is your support network in places you go?
- Where did you feel most productive, where less and why? Why choose NYC as a base and not somewhere else?
- What inspirations did you get by working from different places?
What is a "slowmad"?
I think the idea of a "digital nomad" is very overrated. Travel isn't something to be glorified. It can be very disruptive and I don't get as much out of sightseeing as I could just browsing the wikipedia page of the thing (lame, I know). I like getting to know a place, traveling for a purpose, meeting people. Slow travel. I like the Slowmad idea.
Netlify is my first remote job. This was very gratifying as I got into webdev partially because of the optionality of being remote, and to go remote so soon was certainly an unexpected turn of events.
Of course, I had some reservations, because in theory getting some in-person mentorship in the early days is better. However my first job and anecdotal evidence indicated that this probably wasn't all it was cracked up to be anyway. So I went for it.
I interviewed and was hired entirely remotely - my first time meeting the founders or indeed any Netlify employees was after I was already hired. The interview process I have recounted in the Year One post, but probably the clincher was a mutually agreed take home project which I threw myself into for an entire weekend. We had a Slack channel open and I took it on myself to communicate every step of my process, including my roadblocks, and I believe that was a key part of what they liked. (I obviously agree with this decision)
I think having good documentation and erring on the side of overcommunication is very important for a remote job. Fill in the blanks on the arguments here, I'll probably agree with all of them.
Why So Much Travel?
Some of it was not by choice, much of it was. When I switched jobs my nonimmigrant status required me to return home to Singapore for the fastest way to get a new visa. My lease in Long Island City happened to be coming due, my ex-roommate was moving out, and winter was coming. So I simply let the lease expire, put my stuff in storage, and left for warmer climes with my two suitcases.
I didn't know it then, but I wouldn't see the rest of my stuff for another 7 months.
Once I had my visa, I mixed conference travel with slow-madding (this not an exhaustive account, I had a few weeks here and there in some halfway house or friend's place in NY):
- I spent January in SF for some conference and the Netlify All-hands.
- February was in Hawaii with JSConfHi and working out of a delightful coworking space.
- March was my only PTO to date for a Socorro dive trip (planned for over a year) with dive buddies and extended stay in Mexico, with stopovers in LA, SF, and Florida for speaking/work.
- April and May was my first time back in NYC (having entirely skipped out on cold season), but I knew I would be traveling again (including a brief trip to Bangalore) and didn't want to commit to a place so I found a dirt cheap, really crappy (the floor creaked when I walk around, and the roommate yelled at me if I didn't push my chair back in after a meal) sublet in Journal Square. During these two months I actively scouted and found my heart setting on my current place.
- June brought me back to Singapore for my big JSConfAsia talk (which Netlify did not support) and associated events, and then to Toronto and finally back to NY/NJ. I had more travel planned, but nothing that intense, so I decided to finally launch the roommate hunt and finally sign my first long term lease for a place since leaving SF 3 years ago.
What can I say? NY real estate has not been kind to me and isn't cheap for a single adult.
I'd like to know your biggest day to day challenges in finding good places to stay that also have reliable Internet & other amenities.
This is actually pretty easy! I always go for a Hostelling International hostel if one exists because I know they prioritize good internet, charging points, and a kitchen at affordable rates. Failing which I would recommend splitting up where you stay and where you work, for example getting a co-working space like Impact Hub. For me it is important that it is 24 hours as I am a night owl.
What are some things you wish someone had told you your first month? What was the biggest challenge? What was easier than u thought it would be? What are the top things you need to do this successfully?
It's not going to be cheap and living out of a suitcase isn't fun. My current apartment building, with a gym and living room and bbq pool deck, is $1750 a month. That's $58 a night. If you're not committing to a long term place you are going to be paying higher rates for shorter terms for worse living conditions. In NYC the best value for money is HI NY between \$70-90 a night depending on the night for bunk beds with no safety or privacy. You often can't cook so you'll be eating out more and that costs more of course.
This is self inflicted, as I chose not to go to cheap places for the most part, to do more speaking engagements and meet more people in places we wanted to focus on. There's another version of this that involves swinging through Thailand, Indonesia, or Columbia for next to nothing but none of these cheap countries coincide with work related things. I don't regard that kind of travel as appropriate for this job.
Find a coworking space. No, you won't do fine in a coffee shop or using the hostel wifi sitting in your bunk bed.
Leave the microphone at home. You won't have privacy to record jack shit.
Make all your meetings. This isn't something I wish someone had told me, it is just a rule I made for myself and largely stuck to. Remote travel is something you choose to take on on your own time. The company should by and large not care where you are but your end of that bargain is making all the meetings you are supposed to do regardless of timezone or what else you have going on (within reason). This demonstrates you are responsible enough to handle the travel aspect of the job. Nobody asked me to commit to this, but I do think this is important to uphold the implicit contract between you and your company.
Sticking to this rule regardless of timezone was probably my biggest challenge as I am a very flow-state driven person and can drive myself to many 3am nights working on a thing.
I don't think anything was easier than I thought it would be, but maybe because I didn't come at this with much prior expectations.
Transition from Corporate Life: Anything different from in office and remote?
What a tough question to answer! I have three transitions to discuss here: transition to remote, transition to a small company, and transition to a public facing job.
Remote: I think commuting every day, having lunches with your team every day, being able to see everyone leaving for the day, that is "normal" corporate life. Small talk, watercooler talk, body language, stocking up on office stuff, whiteboarding, all of that happens in a real office.
When you go remote you transition from that routine to something a lot more ephemeral. People have to announce that they're leaving for the day, if they even bother to do that. Most of the time if your coworkers have Slack on their phone they're in a perpetual state of "maybe always being around". (A subtle trick/reason why employers like having Slack, is the FOMO from missing chats and pings and thereby implicit longer availability hours).
We've loosely tried to do "virtual coffee chats" where I suggested adopting KnowYourTeam style get-to-know-you convos. It's nice and I work with great people but you can't help the awkwardness of a scheduled social conversation.
Startup: Another transition that has nothing to do with remote-ness is the "big company to small startup" transition. My prior job was at a large company of about ~2k devs, although I worked in a small unit of about 100, the culture was very much one of overwhelming structure and top down rule by fiat (with often Dilbert-level results which I am afraid I can't share for fear of libel). I went from that to being employee ~40 with constantly shifting management structure and a lot of self driven work with implicit trust that I will do my best in the best interests of the company. I have worked in a previous startup of this size so I knew how it was, so there wasn't much culture shock.
I guess what is important is we all seem to have a personal preference for the smaller company feel. It's less pay and more ownership. A pretty poor trade if you look at \$ per hour, but higher in terms of self actualization.
Public: One last transition I made in this job is the public nature of my job in particular. In my previous job I had to apply for clearance to speak in public, due to financial regulations, despite my content having nothing to do with the company whatsoever. I did my writing and speaking on nights and weekends in my own time. Now I am encouraged to write and speak on company time. I think this builds portable capital and assign a significant amount of nonmonetary value to this opportunity.
How do you maintain focus?
Coworking space is important, but also I constantly have earphones on me. I switch between Airpods, Apple Beats X, and my Bose QC 35's and that helps me tune out pretty much anything. Only restricting travel to weekends is also helpful so that it doesn't disrupt the work week.
How do you resist the temptation to stay at home where the snacks are?
Easy. I had no home.
I consider community/camaraderie an important aspect of work. Does it get lonely while working remotely? How do you deal with it?
I don't think I do this well. I was a lone ranger for much of my travel. Although I did actively participate in every local meetup at every location, beyond that I rarely came out of my shell. Hosteling International will organize team events and movie nights, I basically only took part in this while in SF because they seemed the most welcoming. This lack of established social group is one reason I keep coming back to NYC.
How far ahead do you plan travel? What do you do to find places? How big is your support network in places you go?
I plan travel between 2 weeks to a month out. I really like how Hosteling International caters to needs of remote workers so I typically check if there's an HI in that location first. I don't usually have any support network but all the places I go to speak English.
Where did you feel most productive, where less and why? Why choose NYC as a base and not somewhere else?
I felt most productive in Hawaii (explained below), and least in Mexico (explained below). NYC is my base because it was where I was hired and I have supported the NYC tech scene for a while now. I also have college and past work friends in NYC and in general love and know the city well. Even then I feel I have much to explore and grow with the Greatest City In the World™.
What inspirations did you get by working from different places?
I think Hawaii was my favorite non-home spot (I consider NY and SG home). I found a 24 hour coworking space that did wonders for my productivity, being able to work whenever I wanted, with great Hawaiian food and weather. I powered through my work and the first half of my Machine Learning course while there. I even got to speak at a local meetup and a local bootcamp and give some inspiration to fellow folks, or on another day also going for a great morning dive and be back at work in the afternoon. Hawaiians feel the dissociation from the mainland very strongly and all the techies want to leave to go to "tech hubs" (their term). I think thats true for junior talent, but I think Hawaii is a very good spot for remote workers if they can handle the occasional 7am meeting due to timezones. Traffic is a nightmare and the Honolulu Rail project is an embarrassment.
Mexico was a lot about partying and getting wasted. I didn't like it very much but it was cheap (\$15/night hostels!) and my friends were there.
I didn't spend long in LA, but I really liked JS.LA. In general I feel like the tech scene is really good in LA. Ben Horowitz is forever going on about how tech and entertainment have a lot of similarities, and you can feel it speaking with people there. A good mix of startups, agencies, ecommerce, social media, even Google has a big presence there now. Toronto is a nice runner up in this category.
Phew that was a long list and helped me work though a lot of reflections! I hope that answered some questions, I know my experience is going to be very different from others who've also traveled-and-worked so please know that you ought to shape your own remote work journey the way that fits best for you. I definitely don't feel like I've got it figured out but I've got a bunch of experience under my belt now.