Inspiring Work From Home Story: Alaina Leary

By Cailey Lindberg

Massachusetts native Alaina Leary is a veritable powerhouse in the publishing industry, with bylines in The New York Times, The Washington Post, The Boston Globe Magazine, The Boston Globe, Teen Vogue, Cosmopolitan, Healthline, Seventeen, Allure, Marie Claire, Bustle, and more at only 26. Leary is one of the inspiring women who has managed to go completely remote in her career and is living life (and her art) on her own terms.

While Leary gets her regular income through her editing and social media work, her real passion is spreading awareness for people who suffer from disabilities through her articles. Born with Ehlers-Danlos syndrome, she struggled in a series of office jobs before deciding to go 100 percent remote two years ago. Her story is an inspiration for anyone who may not fit into a traditional corporate office and is proof that a woman can be successful beyond the cubicle. By sharing her story, Leary has given hope to an entire generation of disabled millennials, that they can be successful on their own terms.

So tell me a little about your journey, how did you transfer into a successful career working from home?
I’ve worked office jobs before, but I’ve always performed best when those jobs offered the flexibility of working from home. Before I started working from home full-time, I already had experience freelancing and working remote part-time, contract, and internship roles. I decided to start working from home full-time in 2017 because I could no longer manage my Ehlers-Danlos syndrome while doing my best work. Since then, I’ve worked completely from my home office- with occasional travel and the ability to do things like attend an in-person meeting (if we were having one locally), go out to interview someone, attend a work-related conference, go cover an event, etc.

What are the benefits for you personally and professionally in a remote position?
I have a disability called Ehlers-Danlos syndrome that makes it challenging to work in an office setting. EDS causes chronic pain, fatigue/exhaustion, and brain fog. There are days when I can do a lot of work, but I can’t walk to the train station, stand on a packed train full of people, get off, and walk to the office. Working from home, I can work in my pajamas if that’s most comfortable (which is a serious blessing on high pain days). On my worst symptom days, there have been times I’ve worked most of the day from bed- sending out emails, editing stories, and scheduling social media posts. EDS is so variable; I might feel completely fine for weeks, and I can have a massive wall of symptoms hit me out of nowhere- because of that, I’ve totally mastered time management.

Working from home allows me to really put my health first. When I worked in an office, I spent about 90-95 percent of my total energy on just going to the office and staying in the office – being alert, being “on,” as you need to be to make small talk and navigate office politics- and going home. I couldn’t do things after work even though I was getting out at 4:30. I couldn’t attend plays, couldn’t see my friends, couldn’t enjoy my life. I was living to work. Now that I work from home, I go out and do things multiple days during the week, and I still have enough energy to make plans most weekends. I have the energy to take longer trips; I went to Bermuda last year, and this year I’m traveling to Aruba and San Francisco. That’s because I can make the surrounding days next to those trips “recovery days,” where I’m spending most of my day relaxing and storing up energy, something I’d never be able to do in an office.

Also, the benefit of being able to have a flexible schedule is incredible. I can make doctor’s appointments, I can sleep in/stay up late, I can work the hours I’m most productive. I can work two 12-hour days and then take a full day off midweek if I want to.

What does a typical day working from home look like for you?
I’ll be a cliche and say there’s not really a “typical day,” but a lot of my routine tasks are the same. As an editor for Equally Wed, I’m in charge of our digital and social media. I’ll be making sure there’s no LGBTQ+ news we need to cover that day, going through our weddings/engagement/family submissions, editing submissions, working with freelancers I have commissioned, working on branded content campaigns- I recently did an exciting one with Bed Bath & Beyond- scheduling our Facebook/Instagram/Twitter/Pinterest posts, and fielding PR pitches. I also have a few ongoing roles; I write and do social media for Healthline, I work on social media and short story contests for We Need Diverse Books, and I work on web and social media for Womenade Boston.

Sometimes I’ll be working on one-off freelance projects as well. I just recently published in Quartz and TalkPoverty, and I’ve done two sensitivity reads for full-length manuscripts this year. I also worked on a series of 2019 Best Blog awards for Healthline, a few stories for HelloGiggles, and a few stories for Bustle, including a timely piece interviewing Jason Reynolds and Brendan Kiely. With timely stories like that, my typical day can become totally skewed; there have been times I’ve elected to work a little bit on a Sunday or after my “normal day” might end so that I can get in a draft that’s tied to a news or pop culture hook.

What are the benefits of working from home as opposed to a nine-to-five office schedule in your opinion?
I feel like I said a lot of this above, but it’s truly the ability to cater your work environment to you. My home office is quiet, but I have space where I can get up and have a 15-minute dance party if I have a sudden burst of energy (and I often do because I’m really excited about my work). I can eat meals whenever I want, which is huge for me because I’m on a specific meal plan to help me manage my EDS.

I was always told it’s not good etiquette to eat seafood in an office, and seafood is my primary source of protein. It made heating up meals in common areas awkward because I still brought in salmon and tuna regularly. I also eat small meals and snacks during the day instead of three larger meals; that I can just eat whatever foods I want whenever I want, has made a huge impact on how I feel. It’s so difficult to transport food to an office that I used to end up eating the same three or four frozen meals a lot or spending a ton of money on buying food near the office.