Sam Brown

The challenges of working remotely

I get asked about this a lot. How does it work? Do I enjoy it? Am I more or less productive? I have had many conversations about working remotely over the years. I felt compelled to write some thoughts and tell you a little about how it works for me. In doing so hopefully expelling some myths and answering some oft asked questions.

Working from home is something I have been doing for the past 6 years. The majority of that time I was self-employed working with clients from all around the world (Fun fact: I had 2 local UK clients in 5 years). This last year and a half I have been working for foursquare based in New York City. I make regular trips to our New York headquarters but 90% of my time is spent in my home office just outside Edinburgh Scotland.

Home Office Photo

Get dedicated and be flexible

Working from home is a constantly evolving challenge and is not easy. Distractions come in all shapes and forms, you will get everything from noisy neighbours and home renovations to personally having to deal with deliveries and the chores of running an office, just on a slightly smaller scale.

Funnily, the first distraction everyone thinks will hit you hardest is sitting around watching TV in your pyjamas. While that may be true when you have a day off from work that certainly isn’t true of someone working from home. Getting showered and dressed are pivotal moments in the day, as is having a proper sensible working environment which I will touch on later. Getting out of the home office for short walks and lunch breaks also helps break up the monotony.

Being flexible to your client or employers needs is key. Be sure to let them know exactly what to expect from your situation, what hours you will be working and what hours you will not. Replying to emails and communication outside of your normal office hours is tempting and is likely to lead to you being expected to reply at those times always. Do not fall down that rabbit hole. My normal office hours are from around 10am-7pm.

Home Office Photo

Using Time Zone’s to your advantage

Surprisingly this is one of my favourite reasons to work remotely. The New York office is 5 hours behind me, this means that when I start work in the morning nobody else is online. I usually have a mountain of emails and things to work on for half the day before anyone comes online.

We then get half the day online together to talk, discuss and move forward with projects before I then go offline. The second half of the day in New York – that I am offline – often leads to even more work for the next day. Turning what sounds like an awful 5 hours time difference into an amazingly productive work feedback cycle.

Office Setup

More important than you at first realise is a proper working environment, a desk and office setup that is only used for working is ideal. Having somewhere that is solely used for working will help you focus on just that and not having you think about other things. I try not to use my home office outside of my office hours, using my iPad on the sofa in the evening to actually “surf the internet”, read and see all those funny cat pictures you have posted to Twitter is something I relish.

Home Office Photo

Communication tools

Having great communication skills and good personal relationships with the people you are working with is going to play a big role in how successful you are at working remotely. Email, Instant Messaging, Campfire, Video Chats, you have to always be ready and prepared at a moments notice. We use email as our main communication medium backed up by video meetings and discussions. Instant messaging to quickly grab some information or chat with someone and Campfire as an additional group/team chat tool.

One year of remote meetings

Believe me, I have tried every single form of video communication tool over the course, nothing is perfect, nothing is full-proof and I am continually striving to find the best solution to this.

Below is a short video of around 150 screenshots from stand ups, 1 on 1’s, product reviews, team meetings, white-boarding sessions with Dens and Mayor Mike Bloomberg visits that I have taken over the past year of working at foursquare.

View the video on Vimeo

Fancy working alongside these fine folks at foursquare? We are hiring!

Working remotely is both a pleasurable and productive way to work but do realise it absolutely has some downfalls. It is lonely. It is challenging. It is something I am constantly striving to improve at. I would love to answer any questions or hear others peoples experiences, please do leave a comment.

Post a link to this on Twitter ↩


Phunky 1 December 2011, 14:09 #1

Awesome insight into your life at Foursquare, do they take on many remote workers? I’d love to work from someone like that but sadly can’t relocate at this time.

I’ve had the pleasure of working in three timezones for the last 18 months US, UK & TW and the overlap is awesome when everyone can communicate correctly, but it only takes one person in the loop to slow things down ten fold.

I think our best experience has been with out QA process being in TW which meant we would develop here in the UK and then go home, at which point TW would start waking up and QA while we slept. This allowed for really agile and rapid development cycles – when it worked :D

Craig 1 December 2011, 14:26 #2

Great tips. foursquare is definitely on my list as one of my dream jobs.

Jerome 1 December 2011, 15:47 #3

I’ve been working from home for the past 4 years as a freelancer and then got hired full-time at Flowtown which also allowed me to stay home.

I agree, it is challenging. For me, the worst part is the loneliness. I don’t have much trouble staying focused. Then when I’m not lonely, with friends, I sometimes feel bad to stop working while every body is still working in the company’s time zone.

I was glad to read about the time zone advantage as I’ve also experienced it. In the morning when nobody is around, you’ve got all the meetings-free time in the world to just get your things done. Nobody seems to get used to it either, so they wake up with work already done and they’re usually happy about it :)

I find that I am more productive when working from home. At the office, I get knocked out of my zone every hour or less.

Great post.

Sam Brown 2 December 2011, 12:04 #4

Worth noting, we are hiring across the company but out of both our New York Headquarters and San Francisco office. We don’t intentionally hire remote employees, a few have moved out of the offices but naturally we would prefer our teams to be together in the office.

Andy 3 December 2011, 12:45 #5

Excellent summary Sam. Although I’ve been working in an office environment in the past few months, until six months ago I’d freelanced from home for five or so years full time, and loved the experience. The points you make are absolutely the same I would regarding a home office environment regardless of where your clients are.

I agree, discipline is key, but luckily I never particularly struggled with that and felt that the flexibility in working hours allowed fantastic productivity (although my quieter period was in the evenings). It also allowed me to go for a swim in the afternoons which kept fitness on the agenda and something I really enjoyed to split up the day.

I internationally-remote worked on a couple of projects a number of years ago, but always found timezones troublesome, partially due to the unreliablity of the technology – but it seems things have moved on by your experiences, and I’d definitely enjoy that challenge again someday.

Nice insight to your cross-continent setup.

Dan Eden 6 December 2011, 11:00 #6

Great post Sam. I’ve worked with a few people across the pond, and I absolutely love the time difference. It’s really great – I get up, like you said, to a bunch of emails and whatnot, work through them during the day, chat with the client a little in the evening and then they check over my work and send more emails while I sleep. It means I don’t get bogged down sending emails back and forth with minor changes.

For me, it’s usually been an 8-hour difference since they’ve been on the west coast – I suspect communication is easier with a smaller difference!

By the way, what’s the clock app on your iPhone? It’s gorgeous ;)

Graham 6 December 2011, 23:25 #7

So what websites, apps, programs do you recommend to make it all easier?

Onder Vincent Koc 6 December 2011, 23:55 #8

Hey, Firstly GREAT POST!

I have worked 2-3 years freelance and remotley and recentley after moving i have really taken into thought of a proper home office ethos and enviroment. Allot of people here will be asking how you like to do things, i noticed the ipad and moleskine.

Hope things are well, and thanks for the insight! :D

Miranda @boucksy 6 December 2011, 23:56 #9

You hit the nail directly on the head. Having worked remotely for nearly three years, I always get asked how it feels to work in my pajamas and cue my own hours. It’s challenging to say the least…lonely, a word that couldn’t be a better fit. No one realizes how often they have simple conversations just by sitting in a normal office environment improves their working morale until they’ve come to work remotely and realize they haven’t opened their mouth to say a single word in close to four hours.

bravo, man.

Radu 7 December 2011, 02:11 #10

Great post, Sam, I guess this proves once again that doing great design is unrelated to your / your clients physical location.

I’m currently working with a startup on a 9hrs timezone difference (UK / Alaska, USA) and I must say It’s great! Even better when I’m working from Romania (11hrs). I find it very productive to open Basecamp in the morning and find all the tasks / feedback I need.


mariam ayyash 7 December 2011, 05:27 #11

lifting and inspiring, i have a question tho, how do u manage multiple clients at a time? how do u tell a new client off because u dont have the time? and something else, what are the legal steps u need to take to make ur work legit… finally, how do u convince the other party, especially those overseas, that u are who u claim to be? what kind of remote marketing someone like myself need to do?

Tomaz Zaman 7 December 2011, 09:14 #12

Great article, could not agree more. I was working from home for a couple of years as well, until we got children – after that I decided to move to town because the distractions became to big – in a positive way, but still :) One more benefit of having the office out of your house is the ability to hire people when you get too much work to do on your own, which happens eventually.

I use to find new clients (when in need) and it works out fine for me – although I’m usually the most expensive provider, I don’t have problems getting the work because I’m an expert in a particular niche (CMS) and my portfolio – and certificates – prove it.

Which brings me to my last point: Be an expert, take exams, focus on a niche. Don’t be a jack of all trades, even if you’re flying solo. I outsource design and html/css all the time and I’m fine with that. It allows me to focus on things I’m really good at.

Aria 8 December 2011, 13:24 #13

I’ve been working remotely at home since I first started my career.

For me, the real challenge was, and is, inspiration. Especially for a job that needs you to be “on” most of the time. Some brains — like mine — sometimes need a reasonable amount of human interaction to get “on”, and that’s much harder to get when you are working at home. And for me, social networks almost have an adverse effect in that situation.

Anyway, I learned that the sense of being in the outdoors is — at least for me — a real inspiration trigger. So I developed a new trick! I cheat my brain by putting on my jeans, which I’m not very comfortable in, just to make it feel like I’m not at home. And it works wonders!

P.S: I’ve never over-used that trick, cause I think doing that will kill the effect.

Commenting has closed for this article. Feel free to me.

Sam Brown co-founded Iterate, and was previously VP of Design at Foursquare. Based in NYC.