5 Years Later

Michelle Penczak
Published in
4 min readAug 7, 2020


August 10, 2015 was a day that literally laid the framework for what would later become Squared Away.

I was in Hilton Head, South Carolina. I had arrived the previous evening to spend a few days at the beach with my in-laws and baby niece. My brother and sister in law were in transit to a new Marine Corps duty station from Germany to Japan, and my husband, Sean, had just deployed to Spain a few weeks earlier.

We were also three months pregnant with our first little boy, Sawyer.

I intended to relax with my family and work with my team & clients throughout the week. Remote work at it’s finest. However, that would not be the case.

Late Sunday night, I couldn’t log into my work-issued laptop, which was extremely odd. I messaged Zirtual and let them know I was locked out — thinking it would be resolved in the morning. When I awoke, I had no response and still couldn’t log in. My team and I started messaging each other to figure out what was happening since we were due to begin working.

Then we received Maren’s email.

I was in shock. My 13 team members were in shock. We were scared for our futures, and we were hurt by the team we trusted. I had had a management team call with Collin on Friday — there was 0 warning to any of us.

After taking a moment to absorb what I had just read, I called my clients. Daniel Houghton was my first call. We had been working together for almost two years, and when I let him know what happened, I started crying. I was sad for everyone involved, and I loved working with him. He told me, “don’t worry, I’m not going anywhere, and I’m going to keep working with you. This is going to be fine, and you’re going to be better than you were with Zirtual.” His words touched a nerve, and I had my motivation to kick ass and take names.

I told every person on my team to reach out to their clients and see if they would be interested in working with them. Then, to make it happen.

Most of us were locked out of our Zirtual-issued computers, so I had to make a trip to Best Buy to purchase a new, decently working one so that I could do work. My clients kept confirming they were sticking with me throughout the day, which motivated me to push on.

My team and I kept motivating and supporting each other throughout the week. There was no ‘real’ vacation for me. My family was supportive and just as shocked as I was.

When Sean called me from deployment, I burst into tears. I was emotionally exhausted from experience. After everything I had put into Zirtual for two years, I felt betrayed. I busted my ass to become a manager and then had no warning when the rug was pulled out from under myself and 400 other people.

Then, like a phoenix, rising from the ashes, were the bones of the house that would become Squared Away — just two years later.

During that time, I built my own independent contractor support with clients from the East to West coasts, including Canada. We also welcomed our sweet Sawyer in January of 2016 and moved six timezones with the Marine Corps from North Carolina to Hawaii.

It hasn’t been easy. My journey has been riddled with complications and challenges, deployments, tests in my marriage, health complications with Sawyer, and complicated pregnancy with Jameson in 2019.

I’m incredibly blessed to have two healthy boys and a loving husband, but the flowers that line my path were watered with lots of tears along the way. Building Squared Away has taken an immense amount of my time and energy — and there is a lot of guilt that goes with that. I hope that my boys see everything I’ve put in and done the same in their own careers someday.

Now, on the anniversary of that emotional August day, I feel at peace and blessed.

Squared Away has over 120 military spouses that love working with our almost 200 clients and us. The men and women who are part of our family inspire me to bust my ass for them and our mission each and every day. We even have another Zirtual alum, Yesenia Camacho, as our Director of Client Connections.

Zirtual taught me a lot, and I’m forever grateful for the relationships and skills I built while working with them. I learned that the most critical job of a CEO is communicating with your team and comforting them that their job isn’t going anywhere.

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

Drop by our social media and say hi👋 Instagram, Twitter & Facebook.

If you’re ready to get Squared Away, visit us at GoSquaredAway.com or grab some time for a call.