Squared Away changed my life.

In the course of those 20 years, I’d probably done just about every job you can imagine-and not one of them gave me a future.

Tiffany McCawley
Jun 5 · 9 min read

Trust me when I say, I don’t make that statement lightly. It’s made with an extraordinarily complicated legacy of loss and pain that is nearly impossible to put into words. Because no matter how much I try to make someone understand what it’s like to lose 2 of your 5 children, and then continue to get your ass out of bed every morning and raise the 3 that are still here while fighting for your marriage and what seems like your very existence, it’s damn near inconceivable to accurately describe what that journey is like.

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Five years ago, my life was probably pretty similar to most of the spouses and veterans that have become a part of the Squared Away family. I had 5 amazing kids, I’d been married to my kick-ass Marine for 20 years, I too, had served my country as a Marine and I had a resume that looked like a jigsaw puzzle put together by a blind man. In the course of those 20 years, I’d probably done just about every job you can imagine-and not one of them gave me a future.

Well, I guess I can’t drop that kind of a bombshell and not tell you what the hell happened.

5 years ago, our family was in the middle of yet another PCS. This one was a little, no A LOT, different than previous moves. It was our first in 5 years — an eternity for those of us who literally can’t claim to have lived anywhere longer than 2 years and 11 months — and our first with all 5 little people. We’d built and settled into a pretty big house, filled to the brim with STUFF. When we decided to take orders to Parris Island instead of retiring, we knew that we’d likely end up stuffed into a tiny base house that was less than ½ the size of the one we currently lived in, and we had some serious strategic planning/packing/prep to do. So for the very first time IN MY LIFE, I put my children on a plane to visit family in Texas. I hugged them, kissed them, snuggled them and inhaled their sweet kid scent in my garage in the predawn hours of June 7, 2015. I waved and cried as I watched their dad head to Raleigh to send them off to visit Nana & Grandpa and the rest of his family in Texas.

Just over a week later, 3 of them came home alive and 2 of them arrived in coffins.

On their 4th day in Texas, my babies went to visit family on their farm. They had a blast meeting the pigs, learning about all things pig breeding and explored the barn, the stalls, and the pasture.

And then they went on the Ranger. Without an adult, without seatbelts and without a shred of supervision or safety gear, a teenager driving SIX kids on a 4-seater that had one working seatbelt.

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I’ll spare you the details, because you’ll likely either throw up or be scarred for life if I tell you, but not too much later, my son Sammy was gone and his sister Mercy was fighting for her life, first pinned under 1100 lbs of vehicle and later on a lifeflight. Needless to say, she lost the fight.

I found out my son was dead while standing on the street in Swansboro and that my daughter hadn’t survived in front of a freaking airport in the pickup lane.

If anyone ever tells you that losing a child or children gets easier over time, they are full of shit. It doesn’t, it just slowly and painfully shifts into a weight that you either break under or you learn to carry.

And for a while, our family broke. Disintegrated into infinite little shards might even be a better term. To be honest, I’ll say we’re still broken, yet bit by bit, finding a way to glue those pieces back together. No, they’ll never fit again in the same way, but we’re fighting with everything we have to hold on to what we have remaining.

It was a little part of that gluing back together that led me to Squared Away.

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When my husband retired two years ago, he was at a point of complete physical, mental and spiritual exhaustion. Every plan, purpose and direction we had for our life had disintegrated three years previously and we were struggling. He knew that he needed a break from the military and therefore, working on base was not an option. So we made a new plan and took over a business that we loved-but due to circumstances that we never saw coming, we ended up with a pile of debt and not a lot of work.

SO-in a moment of desperation and determination that I needed to step up to give my husband some breathing room, I sent an email to Kelsey, our Director of Operations.

A little excerpt…

I’ll be honest. I don’t have a resume. Or a Linked In profile that can rock your socks off. I’m the kind of person that delights in interpersonal relationships and intentional communication. What I can tell you is that I’m incredibly organized, hard working, detail oriented and highly motivated.

There was a bunch of other stuff in that email, but that’s not what matters. What matters is that Kelsey took the time to read my email and despite my lack of a professional resume, reached back out to me and gave me a chance.

So I rose to her challenge to pull a resume together and was honestly kind of shocked by who I turned out to be professionally. The experience that I had amassed over the years in the management of military mom life, homeschooling, a mishmash of jobs, education and volunteering that made up my life actually meant something.

And for a broken-hearted mom who has lived with an intense feeling of failure for the past five years, I needed a freaking bright spot.

Michelle and Kelsey gave me that bright spot. For. the. love. They gave me a glaring spotlight. They gave me a chance, they believed in me and they sent me on a path that I could never have expected.

This is where Jordan, client matching guru, took the wheel. Man, does that woman have a gift for matching. For my first few weeks, I spent my time helping with delegated tasks and picking up some work from other assistants. When Jordan reached out and asked me if I would be interested in working with Doug, the owner of a Solar Energy Development Company, I VERY nervously jumped at the chance. It certainly wasn’t what I’d expected to be doing, as I had assumed with my writing background, I’d likely end up somewhere in the world of writing/editing and proofreading. But it was my organizational, process and construction experience that stood out to her. Many thanks to my beloved Dad and the USMC for honing that skill.

From my very first conversation with Doug, I knew Jordan had hit the nail on the head. We blew through the initial 15 hour block in four days and Doug asked me how many hours I could give him per month. So I went from thinking I’d work a few hours a week to working 25 hours a week and absorbing a firehose worth of information pretty much every single day.

And I loved it.

About two months in our journey, Doug asked me if I wanted to become the third ever NextGrid full-time employee. Needless to say, I was not only speechless, I was blown away. I now have a fantastic job with an amazing company, with a boss that I can’t put into words how much I respect and admire. Co-workers who are kind and thoughtful, and best of all- for the first time in five years, I don’t feel like a failure anymore.

Let’s be real, even though I rationally know that what happened to my children was not my fault, as a mom I don’t know that I’ll ever reconcile feeling that somehow, someway — I should have done better and they would still be alive.

But I don’t have to live in that narrow little definition of something I had no control over. What I can do is choose to find a new way forward. Show my husband, my children, and all those that know and watch our story that even when the worst things in the world happen, it’s still possible to live life with meaning, purpose and joy.

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Trust me when I say that I know my shoes are pretty different from those the rest of the Squared Away family has walked in. Yet, each of us has had a unique and often difficult journey walking alongside our spouses as they serve our country. We sacrifice much, often living with uncertainty, fear and constant unknowns. Every. single. day, we’re at the mercy of an organization that is mission focused, not people focused. Because that’s the way it has to be to protect our country, our freedom and the world at large. While we know that and we’re ok with it, it doesn’t make things any easier when life is constantly shifting sand.

The gratitude that I feel for Michelle, Shane and Kelsey for having a vision and never letting it go is immense and powerful. Squared Away isn’t just a family, it’s a powerful and unique tribe, an incredible place where visionaries come alongside one another to build futures.

6 months after the accident that changed our lives forever, my sister and one of our childhood friends had a vision too.

A vision for a foundation that would bring awareness to the dangers of operating UTV’s and ATV’s without proper safety gear, training and supervision. And when I became involved, I knew that our vision also had to include providing grants to help other grieving families meet their needs when the world as they know it implodes and they are forced to face a lifetime of grief. We were exceptionally blessed by the outpouring of support after Sam and Mercy ran ahead to Heaven and our heart’s desire is to be able to serve other families as we were served.

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With Sam and Mercy and the devastation of losing them at the forefront of our collective minds, we started our G3 grant program, . Our goal with this program is to allow families to apply for a one-time grant that can be designated for needs following the death of their child(ren), to include counseling services, grief retreats, a family retreat to reconnect, and camp scholarships for surviving children. This list is not comprehensive or restrictive, as we will consider each application on a case by case basis. It is our honor to serve other families walking in grief and give them hopeand help in whatever form they need.

Please visit both our and to learn more about our organization, our past events, our goals and our mission. If you’d like to donate to assist us in achieving our goals, we’d be humbled and thankful to partner with you. The SaMercy Fund is a 501 (c) (3) organization and your donations are fully tax-deductible.

This article is in honor of Sam and Mercy McCawley. Sammy would have been 10 years old today. As of this year, he’s been with Jesus as long as he was with us, and we live holding tight to the hope we have in our reunion as a family in Heaven.

If you’d like to know more about our family and our journey, please visit my blog at either or .

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If you’re ready to get Squared Away, visit us at or for a call.

SquaredAway

Military Spouse Chief Executive Assistants For Your Team.

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