How did you get started with remote work?

Interview with Jacob, a site reliability engineer

In my previous role, I was travelling for the better part of three hours each day (when there weren't any train delays!).

After doing the long commute for a few years, I came to a crossroads. I wanted to take the next step in my professional development, but I also decided I wanted to spend less time on the train and more time with my wife.

I put together a list of qualities I wanted in my next position as well as the maximum amount of time I wanted to spend commuting.

With this list, I started looking around and talking to recruiters and colleagues about available local positions. However, nothing really got close to the goals I had set.

To be fair, I didn't live near any capital cities or sexy tech/startup locations, so most of my searches ended up at small boutique web shops which would lack much of the professional development I was looking for.

One night, as I was scrolling through an online job board, the location filter of "Remote" triggered a lightbulb moment.

Working remotely wasn't something I had previously done in a full-time capacity. Sure, my existing role occasionally allowed me to work from home. However, it was never a well-defined thing, but rather a perk unique to myself and another colleague due to the distance we travelled.

After that night's epiphany, I began searching more and more for remote work.

As luck would have it, I was following someone on Twitter that had become a recent alumni of Envato who, despite going off to his own startup, was spruiking the available roles and how great the whole environment was.

I ended up checking out the jobs page and politely DM'd him some further questions about a role. He then put in a note to the recruitment team to have a chat with me and the rest is history!

Jacob is a Site Reliability Engineer who believes in asynchronous communication and bullet journaling - learn how he maximizes his daily "deep work" time.

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Interview with Mark, a programmer building bespoke business applications

I had my first remote job while still in college. The office was a hefty drive from campus and I could rarely afford the time to make the commute. Thankfully, my employer already believed in the merits of remote working.

In my time there, I learned a lot about the tools and attitude necessary to successfully carry out remote work. My employer believed in the power of results and trust in his employees.

Ultimately, I think my employer's attitude really seeded a lot of my habits and philosophy about remote work today.

For example, he always insisted on video chats so we could actually see each other, and now that tendency is drilled into me. It became so second nature that one time during a video chat, my girlfriend accidentally walked into view with only a towel on! Needless to say, I am now much more cognizant of my surroundings.

For Mark, avoiding distractions and sticking to regular hours are perhaps the hardest parts of being a freelancer - learn his secrets to achieving a good workflow.

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Interview with Rosemary, a digital content marketing manager reveals must-see freelance tips

Many years ago, I went to a conference in London to learn about the opportunities that were rapidly emerging online. From that, I took my first steps to learn online skills, which started with social media.

I got my first opportunities for teaching and training businesses in the world of social media marketing after focusing on my own online presence to showcase skills and know-how.

My career then moved from teaching to managing social media accounts and content creation for chosen businesses.

I was hired by my clients so that they would be able to do online promotion but save a lot of time and headache by being able to focus on the offline side of their business.

Remote work crept in because the better a job you did for business, there was less and less need to meet in person, such that now even doing different online work types, I rarely meet a client offline more than once.

I have clients I have never met in person, and I work for these clients on an ongoing basis.

Also, this realization along the way awakened my interest in project management and freelance tools that make so much possible remotely, so I focused on being more of a remote worker.

In the last four years, I had a "Joe Kennedy moment" when the shoeshine boy was giving him business advise. For me, it was about how to run social media accounts for business as it were. It became very apparent to me that I would alter my online offers to focus more on online digital content creation for local businesses.

Rosemary, a digital content marketing manager shares the freelance lessons she has learned over the years—see her tips & exceptional entrepreneurial wisdom.

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Interview with John, a full-stack web developer who works remotely

I was a freshly graduated young man and I had a choice to make, I could go work a regular 9 to 5 job or go into freelancing which was something I had learned about a few months before graduating as I was planning for the future.

What really made me decide to go into freelancing was that my dad has worked a regular 9 to ... random exit times sometimes as late as 12 AM and he missed out on a lot with his family, I know he missed out on a lot of us growing up because he had to work to provide for us.

There's also the fact that to me it seems like not everyone appreciates what you do in a regular job.

Recognizing this and not wanting this to be my norm, I definitely don't want to miss out on my kids life when I have my own, I went into freelancing, super scared if it would work or not but 3 years later here we are!

I think the most important thing was I was reasonable with my pricing.

I was just recently graduated and starting out in the professional space so I started by charging $10/hour or sometimes even $8/hr depending on the job.

I see a ton of new freelancer make the mistake of charging $15 or more from the jump without 0 reputation to back up that value. You can't expect to be paid what you want without having a way of proving that value in some way.

If you didn't work at a company before or have an impressive portfolio you won't get any clients at $15 or more per hour. Reputation first, then up your prices.

The second thing I did that I think was super important with clients was I delivered days before the deadline, this made the client happy, likelier to work with me in the future and they left a good review praising this which is a good motivator for future clients as it shows I'm a dedicated worker.

John works remotely while using the latest web development technologies, learn how he works by reading his interview.

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Interview with Mike, a software engineer who works remotely at GitHub

I never intended to work remotely. I'd left my last office job and received an offer from my new, dream organisation that had no offices in the UK. As a result I decided it was worth accepting anyway and just rolling with the whole remote working thing.

Despite thinking I'd miss the social aspect of work, I loved my increased productivity and flexibility, got my socialising done with friends outside of work and chatted with coworkers during the day online (instead of in person).

Mike got started with remote work after getting an offer from his dream organisation. Learn how he works remotely while working on open source projects and publishing books.

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Interview with Adam, a UX engineer building his own consulting company

I was approached via cold email regarding my posts on Hacker News.

They saw the answers I had posted and saw the links to my GitHub/portfolio in my profile and that intrigued them.

We exchanged information and I provided my rate and that's how I began to work with that company on a contract basis. Because of that, the transition was seamless!

Learn how Adam started working remotely from a cold-email on Hacker News, to how he's using a local co-working space to grow his business.

Read full interview from Interview with Adam, a UX engineer building his own consulting company.

Interview with Nikita, an entrepreneur building a website to learn anything

I started with working remotely quite naturally. The only real 'job' I had was university in that I had to actually physically go there and be present at times.

However I was always working on some personal ideas I had in form of various projects. I discovered GitHub a few years ago and fell in love with how easy it was to share projects I made there. It didn't have to be code and I could write something in a README file and git push and it was online for the whole world to see. I started sharing my notes on GitHub, first as normal files then, in form of mind maps and later it grew into an actual website with code that I helped work on in a team.

Working remotely in that sense was completely natural since Learn Anything is an open source project, there is not one single place I have to be to make any changes to it and improve it. I just need an internet connection and a laptop.

Nikita is an entrepreneur working on his startup while optimizing his productivity—learn how he organizes his life and work to maximize happiness

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Interview with Scott about working remotely for 20 years

I got started working remotely in 1998. I had been working in New York City for the first few years of my career. I was eager to make some decisions about my professional life before getting married.

My wife and I had explored myriad housing options in New York and on Long Island but nothing seemed to fit. Restless, I was beginning to see a job change as an avenue to a geographic change.

I had a good job in a big city, yet my heart was telling me that it was not my path.

You might think me naive for doing so, but I told my boss the truth. I told him I was about to be married, and Amy and I were looking to live outside of the New York City area. To that end, my goal was really to inform him that I was going to be looking at other jobs: either transfers internal to the bank or finding another company. I had no other angle. No other goal.

He considered what I said carefully. After just a few beats, he asked “How would you like to work from home?” Mind you, this was in 1998, and working remotely was not as popular as it is now.

Making the switch was seamless, though. The company put an ISDN line into my new apartment in Massachusetts. Several years later when we wanted to move farther away, they were totally cool with it, as long as I could get to New York City when they needed me. Fast forward 20 years, and I’ve been working remotely the whole time.

Scott is a designer and developer that's been working remotely since 1998, read his interview to learn how he's been successful

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Interview with Sarah about working remotely from an RV

I got my first remote job when I was working at my first job out of college. I worked as a marketing coordinator for a law firm and the firm was in some financial trouble. I wasn't sure about the future of my employment and half the firm split off to form a new one. I was really good friends with one of the lawyers splitting off and agreed to help them with their marketing as a freelancer.

Soon, the tensions at my firm reached a head and turned in my notice for not receiving a paycheck one pay period. I called up my lawyer friend and told him what happened and we came to an agreement for me to work for his new firm part-time. The caveat was that because I was quitting my job with no full-time prospects, I had to make the hard decision to move back in with my parents so I would have to work remotely as they lived 3 hours away.

My lawyer friend agreed to allow me to work remotely part-time, which allowed me to pursue other passions during the other half of my day. I worked for that firm remotely for 2 years before I found another full-time position which forced me back into commuting and living in an apartment.

I remember how blessed I felt that my lawyer friend had put so much trust in me to work remotely, and I didn't take it lightly. I created a routine for myself and got up every morning as if I had to commute and it allowed me to really create my ideal work environment. I remember feeling more productive, self-reliant, and excited about work than ever before.

Sarah is a digital marketing manager who travels the United States with her partner and two dogs while working remotely in her RV.

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Interview with Alexandra, a freelance fashion designer building her own brand

I graduated a few years ago and I started working for some high end fashion brands for a while but after I decided that I would like to focus more on my own brand and find something remote since I was also traveling a lot back then.

I started looking for remote jobs, which wasn’t so easy at the beginning because I had to build up a profile and a more commercial portfolio for my clients on Upwork.

Once I built up my profile and I gained more experience, I started realizing that a freelance job is way more interesting, better paid (maybe just in my case as a fashion designer) and allows me to move, not like a permanent job.

Alexandra is a freelance fashion designer who works remotely while traveling and building her own brand.

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