The Side We Don’t See: Squared Away’s CEO on Marriage, Motherhood and Mental Health
The end of February is an odd time to do a reflection on the previous year. However, this is around the time in 2020 that COVID started to rear its ugly head, and Squared Away started to prepare for worst-case scenarios.
A year ago today, Sean and I had our last date. He took me flying around Maui and Lanai with a pit stop on Molokai so I could take a bathroom break at the airport fire station. Not even kidding.
This time a year ago is when everything felt normal to us. When the idea of COVID was something foreign and unimaginable, it’s wild what can happen in 365 days.
This last year was wonderful for Squared Away but extremely challenging for my family.
I thought being a CEO meant to be transparent about the company and take care of your people, but I believe it also means showing them that you’re human and have the same struggles and challenges.
We moved in July from Oahu, the only home my two boys have known, to San Diego. Military kids are extremely resilient, but moves are difficult, and it’s tough to explain to them.
It also took a massive toll on my marriage.
Most people don’t know that Sean and I separated for two months in the fall of 2020. During a pandemic, with two kids and being a CEO, it sounds pretty impossible. I’ve never experienced a lower point while having to be a rock for a team.
They kept me going when the tears felt like they wouldn’t stop. Whether or not they knew it, they motivated me when I needed it the most.
I get messages from team members regularly telling me how thankful they are for the opportunities they’ve been afforded, thanks to Squared Away. Tiffany McCawley with NextGrid and Katherine Robinson with Gennev — they are the reason we do what we do and focus even more during tough times. We are so proud of all you have accomplished since starting with Squared Away in 2020!
My marriage wasn’t the only challenge. My now 5 year old son, Sawyer, has also had a really tough year. We’re approaching a 2nd ear surgery, a 3rd new preschool, and a potential health diagnosis we didn’t see coming. My mama heart is breaking for him.
How do I relay to my 5 year old not to give up and things will get better unless I walk that walk myself?
He asks me all the time why he’s different and other kids don’t have to have the same experiences. My best answer is that God chose him to teach others how to be strong when things are hard.
As of this morning, my marriage is in a much better place. We hit a low that neither of us thought we ever would, but it’s better now than ever. A lot of hard work and perseverance went into it on both sides. The biggest lesson — don’t give up on who and what you love the most.
Looking back, I’m super thankful for a good therapist (if you don’t have one, get one, it’s the best thing you can do for yourself); friends that support me through thick and thin; and a team that I can be open and honest with.
I’m sharing this with you all now for a few reasons:
- To let you know that if you are a CEO, be human and vulnerable with your team. Don’t live on a pedestal.
- To my Squared Away family — thank you for being there for me when you didn’t realize you were.
The past few months have been really hard on me and my family but you have all made every single day worth it.
❤ -Michelle
