It All Started With a Facebook Post
One Facebook post turned into a career I had only dreamed of.
As a Military Spouse, how many applications have you sent out?
The working relationship between Michelle (our CEO) and I started with a Facebook post; Michelle was looking for a Virtual Assistant. I had previously applied to about 25 positions and had excellent credentials. At the time, I was volunteering with the National Military Family Association, had completed my Bachelor’s Degree in Business Finance, and was looking for a position I could take with me since military spouse life is full of unknowns. My then 4-month-old was home with me, and my other child was in part-day preschool a couple of days each week.
On the day of our interview, I put my babe down for a nap and set my preschooler up with plenty of snacks and an iPad. I locked my bedroom door and mentally prepared for the interview (I repeated to myself, “you got this”). Michelle called me on a Tuesday afternoon; I had my headset on and a pen/paper readily available. I was shocked to hear her excited to speak with me; I was thinking, “someone wants me and values me!” Michelle offered me the position while we were on that call. Contracts were excitedly signed, and we got to work.
For the next six months, I worked 1:1 with Michelle on work she’d delegate to me. She worked me hard, and, in my mind, failure was not an option. I respected the work she was putting in, and the harder she pushed me, the more I felt a need to prove myself to her. I would work from every area of my house, outside, while on walks with my kids, from the preschool parking lot while my babe slept (waiting to pick up my preschooler), and late at night to catch up before the next day.
The Day I Learned About Boundaries
I will never forget the time I was working on a task for a client and had emailed it back to Michelle (for her review) at 12:38 pm EST. It was the first time I learned about boundaries. She was kind and encouraged me to only work within my “working hours,” letting me know I didn’t have to work late at night. I found this the best time to work. I’m a night owl and, when my kiddos were home with me, my brain could concentrate better at night. Going forward, I would work late at night and save my emails as drafts, ready to be sent out the next morning at the start of my workday (scheduled emails are now my saving grace).
The next step of our working relationship was Michelle explaining that she and Shane were working on something. She told me it was a business secret that we needed to keep internally but to know that it’s going to be something big. At the time, it was still Michelle and me working together (she was sending me delegated tasks) around August 2017.
Squared Away’s Launch Day
On Veterans Day is 2017, Squared Away officially launched. It was Michelle, and I supporting a more extensive client as the client’s go-to assistant for their team. Michelle was the point person, and Kelsey handled any overflow/delegated work. We weren’t sure where Squared Away would go, but with Michelle’s knowledge and our dedication, amazing things began to happen; Squared Away had CLIENTS.
First Client Jitters; Imposter Syndrome?
At the beginning of 2018, I started working with my first client. She was NYC-based, and I admired her lifestyle/career. Something you may not know about me is when I was in college and studying Business; I always imagined I would graduate and “do big shit.” To me, “big shit” meant living in a city, working my ass off, fully supporting myself, getting my MBA from a top school, and being able to afford a pair of Louboutins.
When I got on my first call with my first client, I was back in my bedroom with my preschooler in school and my babe down for a nap. She was about 8 minutes late, running on NYC time. Those whole 8 minutes, every second, I watched the clock creep along. I was anxious and nervous, self-doubt started to set in, and I began wondering if this was too good to be true? Sure enough, she called me. I popped my headset in and tried to be confident and sure of myself, woman. We spoke for a bit, discussing military spouse life, her NYC career, and some of the similarities we shared. She was a real gem and someone I will forever remember as being the first high level professional to take time to work WITH me. We built a trusting relationship and worked together over the next year.
New Teammates: Excited or Nervous?
Once I began working with my first client in early 2018, Michelle started looking for additional teammates to add to Squared Away. We added them one at a time; they would see job posts on the Savvy Spouse Facebook page and email Michelle their resume for screening. No training, we just jumped right in and learned on the fly. We now refer to our original crew as the OG’s. We still work with a few members of our “OG crew.” Throughout 2018, we gradually added teammates and clients. At the time, we were adding about two clients per month and one assistant per month. We thought this was growth. In December 2018, we had seven teammates.
2019: Growth and Finding My Spark Again
I knew 2019 would be a year of growth; I didn’t realize how much. I had fully taken on the Director of Operations role at Squared Away, we were scaling immensely, and our team has grown in ways we never expected. Being on the front lines in these seasons of growth has not been easy. There have been times where I was so overwhelmed with work; I didn’t know how I’d dig out of it, I cried, I, at times, had unrealistic expectations for my spouse and children, I wasn’t always easy to be around, either.
Amongst all of this difficulty, I have grown in ways I didn’t expect; I am more confident than ever before, and my boundaries are stronger. I am better at being “all there” and deliberate with my time, and I have heard I’m a better wife and mom since I began working again. I don’t think I’ve figured it all out; lifelong learning is a concept I believe in.
How Do You Make It All Work?
Timeblocking
Getting to this spot, I had to learn to schedule a time for my spouse/kids (time blocking) and I’ve found ways to actually step away from work and let my brain reset (hiding email and other apps in your phone on Saturday’s so you take one real offline day each week). I’ve learned to appreciate what’s in front of me (this is thanks to military spouse life, enjoy the moments you do have, not the ones you’re going to miss).
Outsourcing is another piece of the puzzle.
- Grocery pickup was the first thing I ever outsourced (outside of childcare). I raved about it so much that my friends would jokingly tell me that I was becoming a grocery pickup spokesperson.
- Next came meal prep — some weeks, I need to mix it up and still cook a healthy dinner. Meal boxes like HelloFresh and Blue Apron have been huge helpers in this department.
- Cleaning is the other principal stress area of my life. I felt I was giving so much of my little free time to clean our home until recently, where I learned about the magic that is a cleaning person. Her work has allowed me to cook a healthy dinner then go outside with my kids after dinner (other nights, it’s meant a low-stress shower).
I now have a Saturday and minimal stress on the weekends. I cannot tell you how relieved I am to have this help. I am grateful for these individuals, their businesses, and their services.
Give Yourself Some Grace
This year, I have learned to have more grace for myself and my family, and I have stopped trying to separate work and home during the workweek. For the last 1.5 years, I had tried to keep my family and work lives separate, out of fear that I wouldn’t know where to draw the line. When I finally relinquished control and let myself have the two cohabitate at times, I found great relief. Life is messy, and the more I accept it’s quirks and blurred lines, the easier it is to accomplish things.
Overall, in 2019, I’ve found a greater appreciation for the life I have; Squared Away and our fantastic team is a large part of that. To our teammates reading this, I genuinely care about every one of you. There is also a huge sense of pride having been in the trenches with Michelle when Squared Away began and seeing the brand our team has collectively worked towards.
From 7 Assistants in December 2018 to Now
Squared Away currently, proudly, stands at almost 50 military spouses, who are remote, Chief Executive Assistants. We work hard, collaborate, lean on each other on the tough days, and celebrate each other on the great days. On the hard days, I remember my why; my kids, my husband, and the team that’s relying on us to make it happen/keep it going.
Our CEO, Michelle, and I have worked together almost daily for the last 2.5 years (starting in July 2017), and this was the first time we met — October 13, 2019. Michelle has been based out of Hawaii for the last 2.5 years while I have been in North Carolina. We are both USMC spouses. Remote work does work; be ready to over-communicate.
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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Ready to get Squared Away? Email Michelle@gosquaredaway.com.
