A Day in the Life as a Chief Executive Assistant with Squared Away

Christine Swearingen
SquaredAway
Published in
5 min readSep 4, 2019

Wondering what it’s like to work from home as a mom and military spouse? Come, take a peek at a day in my life as a chief executive assistant with Squared Away.

JBER, AK Sunrise

The alarm goes off. It’s a quiet morning. The air is cool blowing through the window. It’s 4:45 am in Alaska and it’s time to get up for work. I start each day this way. Bright and early.

By 5:00 am, I’m downstairs, usually on the couch. On my computer, coffee in hand, checking in with the Squared Away group chat. I’m so proud to be a part of this tribe of incredible, supportive women. I look forward to working every day. I start my morning with emails. Clicking through, reading, responding, scheduling. I check in with my client to see if there’s anything urgent she needs. She works in New York City and starts her days early.

My dog, Cooper, wakes up and comes downstairs. I take a break to let him outside and feed him. He curls up beside me on the couch while I continue to work. This is another perk of remote work for me; being a stay at home dog mom.

My husband heads out the door to workout for PT at 6 am. I kiss him goodbye and I’m back to work, starting in on my bigger projects for the day. Researching travel companies, updating the company website, and monitoring the social media pages. Although they’re not huge projects, they make a huge difference for my client. These are all tasks I’ve lifted from her load so she can focus on the more important aspects of her business that only she can do.

Around 8 am my 11 month old daughter wakes up. I log off to go upstairs. I feed her, cuddle her, and we read a morning story. I can’t imagine a better way to start my mornings than starting them slow with her. There isn’t any hurry to get her ready for daycare. There isn’t a scrambling out the door. There isn’t time with my daughter I’ll ever have to miss out on for work. I change her diaper and dress her for the day.

Meanwhile, my husband is home again, preparing for the rest of his work day and making breakfast. I briefly check my email and we sit down to eat breakfast as a family. Our mornings together are when I’m most thankful for Squared Away. Of course we still have crazy mornings here and there, but the flexibility makes them few and far between.

When my husband goes to work, I play with my daughter for a bit. We practice pointing to our eyes, nose, ears, and mouth. We sing songs together. I love being the one to teach her these things and watching her learn. Once she’s occupied I pick back up on my projects and get ready for a phone call with my client. The call lasts about an hour as we go through the priorities for the next week. Our calls are always productive and fly by quickly.

When I’m off the phone, it’s naptime for the baby. I take her upstairs and rock her to sleep. While she’s sleeping I get myself ready for the day, throw in some laundry, and clean up the kitchen. Working from home gives me the ability to keep up with my home while being productive at work. I check my email again to see if my client needs me. I fire off a few emails and coordinate a meeting for her.

By now it’s lunch time, my husband is home and my daughter is awake. We eat lunch as a family and talk about our morning. My husband reminds me of some work I have to do for the FRG (Family Readiness Group). I volunteer as a leader for the Troop FRG. I’m thankful that the flexibility of my job with SA allows me to serve others in this way.

After lunch I finish up my work for the day while my daughter plays on the floor nearby. Soon it’s 1 pm and my work day is complete. I work under the east coast time zone so my days start early, but they end early, too. The rest of my day is mine.

We aren’t expected to work outside of our hours. In fact, Squared Away encourages us to spend our offline time with our families. Being a team of military spouses, we all know how valuable that time is. Afternoons, evenings, and weekends are still ours. The rest of my day will consist of a walk with my baby, taking her to the park, housework, heading to the grocery store, and family time. I treasure my free afternoons with my baby girl. It makes the early mornings and the occasional morning juggle of working from home with a baby extremely worth it.

Life as a military spouse and working mom is always changing; for me, working outside of the home adds too much stress. I love being able to work remotely with Squared Away. It’s rewarding to watch a company grow and know I was a part of that process. Each day is a little different. Some are easier. Some are more difficult. But every single day is worth it. The #squaredawaylife is one I wouldn’t trade for the world! Being able to contribute to my family, raise my daughter, be there for my husband’s events at work, volunteer, and have the flexibility to take care of all that is on my plate, is priceless.

Squared Away is comprised of military spouses who are your trusted assistants. We help CEOs, VCs, executives, and startup teams get their time back. US-based. #SquaredAwayLife #ChiefExecutiveAssistant

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