In 2009, I quit my job to backpack around the States and South America, and started freelancing remotely to support myself (as a means to an end). That ended in 2012, when I went back to school.
In 2013-2014, I had an onsite position as a developer, but in 2014 I took a full-time remote position working as a developer for Tenable .
I wasn't sure what it'd be like working a full-time job remotely, but I loved it and was so much more productive.
In 2016, I started my own remote consulting firm, and I've been doing that ever since. I'm based in Boston, with most of my clients in New York or San Francisco.
I'm also working on a (personal) album of music that I'm hoping to release this fall!
I prefer not to work from home, as I get distracted easily. I also enjoy being able to turn off and separate home from work.
I'm part of a coworking space in Boston called Workbar. They have a number of locations around the city. One location is accessible via a secluded bike trail, so if the weather's nice I'll bike to work. Otherwise, I'll take the train to a downtown location.
I try to get my day started early. As much as I can, I devote Mondays to phone calls, errands, and other small tasks that tend to pile up during the week. For the rest of the week, I try to focus on deeper tasks like programming or writing.
On Fridays, I'll tend to work out of coffee shops around the city, just because I can.
I try to start my day with my most important personal task, which is writing. Otherwise, I find that consulting work or other tasks tend to box it out.
As much as possible, I try to combine similar tasks together. I use NotePlan (a markdown to-do editor) to track my tasks.
Yes, I am a member of a coworking space and use their facilities 4-5 days a week.
They have shared desks but plenty of external monitors, so I'll get in early, secure a prime seating location, and post up for the day.
Slack is big for remote work, though it can also be the bane of my existence. I tend to stay signed in via my browser to whatever Slack channel is relevant that day.
All my work is code, and I generally use whatever my clients prefer. That can include project management software like Trello, Github Issues, or a regular Google Spreadsheet, and either Github, Bitbucket or Gitlab.
I use NotePlan to track my tasks - although I don't use most of its features; I just like its markdown capabilities.
Every day gets the following layout:
I'll start by reviewing the previous day or week, and then set out the high-level goals I want to accomplish that day.
Then, I'll collect all the tasks I have to get done that day and mark them out by time:
These estimates are often wrong, but they give me a rough sense of what I can get accomplished. They also help me avoid wasting time on rabbit holes that don't push me towards my goal.
Read 36 answers from other remote workers
I love having the freedom to work where I want. I really enjoy being able to move around depending on the day and how I feel.
I like being able to choose the environment I work in. Too often, I've been forced to work in noisy crowded places with awful commutes that leave me frustrated and drained.
I like paying for a coworking space and having a say in how that space is run.
I enjoy the camaraderie of a shared working space. It's great to meet and mingle with people not in my industry (as well as people in my industry!) and learn new things.
However, I also liked my former at-home setup. I enjoy mechanical keyboards and blasting the keys at 100+ decibels, not having to worry about bothering others in an open-plan office.
I no longer have that setup (since I work from coworking spaces), but I am exploring ways to have a more dedicated desk.
I love not being distracted in person by the people I work with.
I really love the ability to be able to travel and work. My girlfriend and I enjoy hiking and camping, and we'll occasionally do longer trips that require us to leave on a Thursday evening.
Being able to just pull up to a coffee shop halfway through a trip, or work from a remote Airbnb, is one of the most wonderful things.
Also, the fact that I was able to move cities (from NYC to Boston) last year without so much as a hiccup in my work was amazing.
This is a hard question to answer.
I think if my goals were different - if I wanted to be more part of a team, if I wanted to move into management - I think working remotely would work against those goals.
But I am very happy doing what I do and my goal right now is to ensure I'm able to work this way for as long as I can.
I think that it can be helpful to work face to face for certain tasks. For instance, when doing deep design work, standing at a whiteboard together (or even at the same table) can be much faster than doing things in sync online. I think this can be solved with an occasional in-person meeting, though.
This may just be my computer, but video conferencing software often leaves me wanting. I look forward to better software in the future.
In 2009-2012, I backpacked and worked. Working out of coworking spaces was wonderful then, since it helped me network and meet people and also provided the essentials I needed, like quiet phone areas and fast internet.
In 2014-2016, I worked out of my apartment (that I lived in alone) in Brooklyn.
My first six months, I was siloed on a greenfield project by myself. I loved it - I routinely spent 12+ hours a day crafting my baby.
This inevitably came to an end. As I (reluctantly) started taking on managerial duties, it became harder to stay focused at home.
In 2016, I quit my job and my girlfriend moved in. I got a private office about 15 minutes away. That was really wonderful; I had a door that closed so I could be loud but also had a (small) community. The commute was also wonderful, biking through a park along the water with a view of the Manhattan skyline in the background.
I'm now living in Boston and working out of a shared coworking space, and I really enjoy the community here. I miss having a dedicated desk, but I think the community outweighs that.
Read 10 answers from other remote workers
At RemoteHabits we're always trying to improve our interviews, what question should we have asked Kevin Scott?
If you're in the Boston area and into AI or design, he's always looking for speakers for the AI & Design meetup.
Igor converted a part-time contract into a full-time remote software engineering job—learn how he did it and his tips for working remotely.
Andrew became a full-time freelance writer after experimenting with freelance marketplaces. After the first month, he was already earning more than his full-time job.
Keep your remote working skills sharp—get notified when the next interview goes live!