Remote Worker Interview: A.J. O’Connell

When A.J. O’Connell became a newspaper reporter after graduating from college, she thought she might be a journalist forever. That didn’t turn out to be the case — the hours were long, the pay was terrible, and more and more newspapers were closing down. So when A.J. became a parent, she needed to figure out another way to provide for her family. The answer was remote work — she went freelance, working remotely from a farmhouse in rural Connecticut, writing marketing copy for technology clients.

Tell me about your career trajectory. Did you always want to be a remote worker? If not, how did you go from being traditionally employed to what you do now.

I began my career as a journalist and ended up teaching journalism at a local community college, but unexpectedly found myself working as a remote content writer less than a month after my son was born. It was a happy accident. We were moving away from the college where I worked as an adjunct, and I needed to figure out how to make money while taking care of a baby.  A friend contacted me, looking for students who might be able to write for him, so I sent him some suggestions and asked for an assignment myself.

That was five years ago. I’ve been working more or less steadily as a freelance content writer for tech companies ever since.

What made you decide to work remotely, instead of renting an office space?

We have a big old farmhouse, so there’s room for an office. It also made sense for one of us to work from home, since our child is small. He goes to preschool, but having me work in a home office ensures that one of us is home for him no matter what.

Also, we have a lot of animals: a dog, two cats and a flock of chickens. Our neighbors have a horse and goats. A lot can happen when you’ve got a bunch of animals, so it’s helpful to be home during the day if a bear shows up (this has happened) or a pony escapes (this has also happened.)

Why do you like remote work?

When I worked in a newsroom, I lived, technically, 20 minutes from my job. But I lived in one of the most congested areas of my state. Sometimes it took me two hours to get to work in the morning. I love that it now takes, technically, me two minutes to get from my bed to my office.

I say “technically” because my commute often involves getting my child ready for preschool, feeding our barn cats, and taking care of our flock of chickens.

Remote work is really the best way for me to have a job and manage our menagerie. Plus I get to spend time with my son when he’s not in school.

What are the challenges?

One of the challenges that surprised me most about working from home is the isolation. As someone who once had to do her best work seated under a noisy police scanner while local news blared from a television and my colleagues chattered, I always assumed that I’d love working in a quiet place, by myself, with nothing to distract me. I do love it, but I miss coworkers sometimes. I live in a rural area, so I don’t see people who aren’t members of my family unless I make myself go out and see people.

Another challenge: time management can be hard when you work from home. I have to set firm boundaries so I’m not working during family time, for example.

How do you structure the day to make it work? What is a typical day in the life look like for you?

I try to use my best brain for the hardest work, so unless I have a rush of unexpected clarity during the day, I do most of my client writing in the morning. That’s when I’m well-rested and can focus. I take out the projects that intimidate me most then: super-technical pieces, new clients, or pieces that I’m on a tight deadline for.

In the early afternoon, I work on things that are less difficult. Sometimes that means working on easier writing projects, sometimes that’s research, interviews, or returning emails. And sometimes I can’t focus at all, so this is when I run errands, walk the dog, or take care of the chickens.

In the late afternoon, I handle my prospecting.

Sometimes, if I have a lot of writing or research to do, I will wait until the family is asleep and work at the bedroom desk. I usually focus on the projects that interest me most then.

This is an ideal day. Often it gets jumbled up, because that’s life. Clients work in different time zones, kids get sick, and deadlines change. But this structure is what I strive for.

What does your workspace look like?

I have an office. It’s located right off the playroom, because that seemed like a good idea when I was pregnant and we bought this place. Let me tell you something: it was not a good idea. Not only does my proximity to the playroom mean that I’ve done most of my afternoon prospecting to the sweet, sweet sounds of Dinosaur Train, it also means that even when my child is being watched by my husband, I’m stepping out to find lost shoes, answer questions, and say “No, sweetie. Don’t play the accordion right now. Mommy is working.”

My office is also the island of confiscated toys. Seriously. I’ve got two tubes of glitter glue on my desk right now. I think there’s a kazoo in here? It’s a mess.

Because the office-off-the-playroom was such a bad idea, I have a second office upstairs in the bedroom, which I use when I’m working on a tight deadline, a big project, or am doing phone interviews.

How do you manage projects with your clients from a distance?

In many cases, that depends on the client. Many of my clients have systems in place when I come to them. Many use tools like Trello or Slack for project management. Sometimes they use Microsoft Office to keep track of projects. In those cases, I simply go with their systems.

For myself, however, I use Airtable’s content management tool to manage projects, deadlines and the prices of each. I also have a physical Kanban board and a giant calendar on my wall so I can see all my projects and their deadlines from my desk. I use Wave to send invoices if clients don’t already have an invoicing system in place.

Have you ever gotten resistance from clients who don’t understand your remote work lifestyle? How did you handle this?

I did lose one job recently because a client originally wanted a remote worker and then changed its requirements, but for the most part, clients are okay with me being remote.

I think that’s because they know what they’re getting when they hire me: they know I’m going to be working remotely, and they have a good grasp on the fact that, outside of scheduled meetings, I’m free to work at whatever time of day works for me. I try to keep lines of communication open with clients, so they know how far along their work is and when it will be submitted. I think that helps.

I get the most pushback about being remote when I’m talking to potential clients. Often prospects think I’m a good fit for them, and then ask if I could possibly travel. I also find that recruiters tend to ask me to travel. I don’t dislike working on site, but it’s not possible for me right now, so I’m usually just firm and polite with those prospects.

Where do you see your business in five years?

Although I am always open to the idea of going full-time for the perfect job, I’d like to still be freelance and remote in five years. My dream is to be exclusively ghostwriting books at that point. As much as I like the instant gratification of a finished blog post, a long project, like a book, means I get to focus on one topic for a long period of time.

What is your advice for current remote workers?

If I could tell all remote workers to do one thing, it would be to get good systems in place. For example, know when you’re most productive and work at those times. Have a good system for tracking your income, or the projects you are working on in a day. Systems are my life line — on days when I’m distracted or just not tracking well, I use my systems to keep me on track. If you’re starting out, it may take a while to find systems that work well for you, but that’s okay. Try one thing, stick with it for a bit, and then, if it doesn’t work, try another system. And keep doing that until you find a system that helps you to be productive.

One more piece of advice: if you’re not productive one day, don’t beat yourself up. Remember: when you were working in an office, you didn’t have a stellar day every day. Not every day is going to be a winner when you’re remote, either.

Oh, and don’t put your office right next to the playroom.


Photo by Markus Spiske on Unsplash