How did you get started with remote work?

Interview with Audrey, a military wife thriving as a marketing manager

I started looking into remote work options when I married my husband - who was an active-duty Army officer at the time.

I was moving from Louisville, KY to Colorado at the time with many more moves in our future, and I knew in order to really establish a career and advance within one position, I needed it to travel with me wherever the Army took us.

Luckily, the opportunities for remote work in marketing are pretty vast—and always growing.

Honestly, when I found a position with my current company Boldly it was not a difficult transition for me to leave office jobs behind.

I am a natural introvert, and I focus better in my own environment — so I found remote work very conducive to my preferred work style.

The company has a very inclusive culture, so even though I am working on my own, I never feel 'alone.'

I've been working remotely with Boldly for five years now, been promoted and genuinely enjoy what I'm doing — so it's literally a dream realized.

Marrying an active-duty army officer sent Audrey on the search for a remote work position—see how she has established her career while staying on the move.

Read full interview from Interview with Audrey, a military wife thriving as a marketing manager .

Interview with John, an international business writer sharing 15 years of insights

I was asked by a client to work remotely in 2002. My role was international business development and marketing. I’ve worked remotely since then except for occasional breaks totaling about two years. So altogether I’ve been working remotely 15 of the last 17 years.

For over a decade, John has worked as an international business writer. See his insights on the state of remote work, freelancing, and attracting clients who are the right fit.

Read full interview from Interview with John, an international business writer sharing 15 years of insights.

Interview with Tammy, founder and CEO of Workplaceless

I started working remotely for an edtech company in 2011. I was moving back to the US after several years in Spain, and I wasn’t sure where I wanted to live, so I focused on trying to find a job that would let me live anywhere.

Learn how this founder and CEO of a remote work resource and certification program handles the triumphs and trails of location independence.

Read full interview from Interview with Tammy, founder and CEO of Workplaceless.

Company Interview with Doug and Vivek, co-founders of remote tool, Pragli

I generally see two different reasons teams transition to remote:

• Talent retention: Someone needs to move away for a personal reason, but the company wants to retain them. This becomes a slippery slope to creating a remote policy for everyone.

• Talent acquisition: the company feels they are limited by their geography, so they begin building out teams remotely. A good example is Stripe.

I generally see three reasons teams start out remote:

• Founder lifestyle: The founder lives away from a talent hub or wants to be a digital nomad.

• Open source: Companies start as open-source projects with contributors all over the world. Examples: lots of crypto companies, Elastic

• Forward-looking: Some companies believe remote is inevitable, and want to lean into it by building a remote-first company

Doug has interviewed hundreds of remote teams as a co-founder of Pragli. Here's what he sees as common remote management patterns amongst those teams and organizations.

Read full interview from Company Interview with Doug and Vivek, co-founders of remote tool, Pragli.

Interview with Vernon, a freelance technical writer

A few years ago, 2012 I think, I began hearing about the freelance industry (well, it’s not quite an industry in the technical sense, it’s more a mode or collection of industries, but you know what I mean) and the possibilities thereof.

Now, being a creative, I was open to the idea of being a freelancer, but I hadn’t quite thought of it seriously. At the time I was still entrenched in the traditional (at least where I come from) world of the 9 to 5, a regular paycheck, J-O-B.

Last year I had been working at a high school as a system administrator before my contract ended. I was searching for my next job, doing interviews and sending out resumes, when I recalled that I created a profile on Upwork, an online freelance marketplace, some years before as a test of sorts.

I figured “Ok. In the meantime, until I get something else, why don’t I hustle online?” Almost simultaneously, I was exposed to technical writing and, it turns out, I wasn’t bad at it.

I also started exploring freelancing as a career choice and found, after running the numbers and doing the cost-benefit analysis, that this would be almost perfect for me.

Some would call me weird or crazy (I’m also a musician) but I don’t like large, constricting structures. I realized that I’m kind of an entrepreneur at heart and that, as a freelancer, I could maintain the kind of lifestyle that I wanted to live. My time and focus would, mostly, be mine to manage. The path of my career would be mostly under my control.

My progress and my earnings would not be dictated by the whims and decisions of a handful of middle managers or bureaucrats (in the case of working for the government) but by my sweat and effort and assessment of the industry landscape.

It’s risky, absolutely, but the risk is mitigated by knowledge. And you gain the knowledge you need through research, training, experience, and networking with those who’ve been doing it longer than you. But you also need tenacity. Your business, as a freelancer or entrepreneur or investor, will not become successful overnight. It’ll take time, and it’ll take consistent effort but, for those who choose this path, it’ll be totally worth it.

As for other things I've done, as I said, I've worked as a high school computer lab technician and system administrator. However, I've also been an information technology manager for a small company; an IT support agent; a technical support team leader; customer service and technical support trainer; and, most importantly, a musician (I had a band for eight years. Good times).

Apart from being a musician, all of these jobs were 9 to 5's with regular salaries. Being a musician, that kind of life can feel “soul-sucking,” but I had my band and my music. That allowed me to survive spiritually, while the jobs gave me a steady income that allowed me to survive physiologically.

Transitioning to remote work was risky, but I believed in it. Still, do. That’s why I’m still doing it. My income is not where I would like it to be, but it has been growing steadily as I get better at it. Plus, the market is, by definition, worldwide.

Yes, I’m competing with people from all over the world, but there’s more than enough to go around in my estimation.

Vernon is a freelance software technical writer that uses lists to organize his hectic freelance schedule—see how he maximizes his time throughout the workday.

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Interview with Danielle, an author who found the benefits of coworking

I was in an online grad program at Syracuse University, which allowed me to complete courses and attend live classes virtually, so I was able to stay in warm Atlanta year round.

I was also new to ATL and wanted to meet people, so I searched for remote work and co-working groups on the app Meetup. I found a great group called ATL Ladies Work Remote and have been in love ever since!

I enjoy asking questions and learning from others, so when I joined the group, I asked plenty of questions of people about what they do and how they best co-work. Based on some suggestions, it was easy to try out new ways of trying to get work done.

Most importantly, the women in my group have become friends of mine. We spend time together outside of working hours, and I have been able to see first hand how they balance their routine and how successful they are at it.

Many of them travel and work, which is a goal of mine, so I’m always asking questions and learning more about how they do it!

Danielle's remote work journey led her to become an author—see how coworking with other remote workers and digital tools have helped her to fulfill her passion.

Read full interview from Interview with Danielle, an author who found the benefits of coworking.

Interview with Lauren, a content marketing team lead and hybrid remote worker

As a content writer, much of my work can be done remotely. I live in Chicago and especially during the winter, there are days where leaving the house is out of the question. After having to make a few miserable commutes in my career, I focused on finding a job that allows me the flexibility to work remotely at least twice a week.

When I came to G2, they promoted their WFH policy proudly as a perk and I was sure to ask around with people I knew who worked there to ensure the policy was as flexible as they claimed. And it is!

I think anyone looking to work remotely part-time or full-time should have those conversations upfront to ensure they’re getting what they want.

For Lauren, remote work was a non-negotiable arrangement—see how she manages a hybrid remote work situation and her tips for those on the remote job search.

Read full interview from Interview with Lauren, a content marketing team lead and hybrid remote worker.

Interview with Alyssa, a copywriter and content strategist

I took a remote paid marketing internship for a music technology company.

Alyssa has found her rhythm as a freelancer and founder of the blog, Freelancing Flow—see her tips for keeping it all running smoothly.

Read full interview from Interview with Alyssa, a copywriter and content strategist .

Interview with Laurent, an introverted remote worker & engineer

I started working remotely 11 years ago. At the time, I didn’t really think it was possible to be hired to work remotely.

I thought this was only a privilege you could get after having worked for some time for the same employer.

So I was quite happy and considered myself lucky to find that opportunity. It was for a Bay Area-based company, that was one of the few competitors we had at my first company. One of my previous co-workers worked there, and our specialized background made us really attractive to them. So we got hired as remote employees.

After that, I really wanted to be able to keep working remotely. I didn’t want to work from an office full time anymore. Not wasting time commuting, being able to live wherever I wanted to, being able to spend more time with my kids, the possibility to travel more were the biggest reasons why I wanted to keep working remotely.

I was still skeptical of being able to find remote positions, but I knew I wanted to try every time.

As such, I was taking a lot of effort to apply to places where my background was really relevant, and where I knew the skills they were looking for was hard to find.

This was giving me more confidence when selling myself in the interview process.

As time went by, I also found more and more places that were open to remote hires. So now, I’m not worried at all about finding a remote position if needed. However, I’m not looking right now 😉.

In this interview, this VP of engineering shares his strategies for managing family time and organizing meetings as an introvert.

Read full interview from Interview with Laurent, an introverted remote worker & engineer.

Interview with Kati, a co-founder shares her tips for juggling multiple side hustles

​Without giving away my age, I started working for myself from home before the internet was popular, and before everyone had a computer in their home. I was an early adopter of technology and saved up to buy a PC so I could create contracts for my in-home daycare.

As a side hustle, I began creating contracts and intake forms for other daycares, which lead to some desktop publishing for local businesses. At the time, most remote work opportunities were envelope stuffing or court record research. And there were lots of scams that I, unfortunately, bought into.

I was frustrated and wanted to make more money, so I created my own niche.

Since then, I have always had a remote side hustle. Eventually, I was able to work remotely at least part of the time in my corporate jobs.

Recently, I left the corporate world to pursue my own adventures remotely.

Kati has made a career at using the internet and gig economy to her advantage—see how she successfully manages multiple side hustles and a business.

Read full interview from Interview with Kati, a co-founder shares her tips for juggling multiple side hustles.