What Being Deployed for Christmas Taught Me That Will Last a Lifetime

In this heartfelt episode of Commander’s Intent, Derek Oaks and Rob reflect on choosing gratitude even during holiday separation—whether caused by military service, demanding careers, leadership responsibilities, or life circumstances beyond your control. Drawing from years of deployments, missed Christmases, and time spent far from family, they share powerful stories about perspective, service, and finding meaning when you’re missing the people who matter most. 

Transcript

Have you ever frozen in the key moment of making a critical decision, whether it's in business or in life, it can cost you everything. Commander's intent will teach and inspire you how to lead with clarity, courage, and purpose. So here's your host, retired Air Force Colonel Fighter Pilot, and your leadership mentor, Derek Oaks.

Good day everyone. I'm Derek Oaks and welcome back to another episode of Commander's Intent. I'm here with my good friend Rob, and we're gonna talk a little about how much we love the holidays and some of the challenges we've had over the years and how gratitude is a choice even when you're missing out on what matters to you most.

Gratitude is still a choice and it's in the eyes of the beholder, and it's something that each of us, I think can get better at and each of us can benefit from. Holidays are an awesome time of the year. It gives you a chance to pause, to reflect on what matters to you. It gives you a chance to think about your [00:01:00] family, the blessings you've had, the opportunities you've had, and if it's an end of the year holiday, Christmas, new Year's, or Hanukkah, you're looking back on the entire last year going, what did I do?

What do I have to be grateful for, and what can I give thanks for? And it's a time to recommit. It's time to reconnect. It's a time to. Take a break. I'm not very good at taking breaks. My wife really doesn't like going on vacation with me because I'm not a great vacationer. I'm always thinking, what am I supposed to be doing right now?

Christmas is a little different. I'm able to just take a pause and there's work to be done at Christmas time, and it's about setting up the tree and taking down the tree and cleaning up dishes and wrapping presents and all those things. They're able to fill my mind and fill my activities enough to where I, I detach myself from my work a little bit, and so I appreciate that.

Holidays can also be very stressful. If you're not with your family, if you can't catch a break, if you're working on Christmas, if you're separated for other reasons, for family conflict or whatever it [00:02:00] is, it can be a stressful time. It can be a time where you're focusing on your dissatisfaction. You're focusing on the frustration with everyone from the government to the enemy.

You're fighting to an ex-spouse or whatever it is, and you can focus on the shortcomings of your life, and it can. Actually be an unpleasant time for you. I have friends, I have family. I see it in the papers all the time of individuals who experience those kind of things. How many have spent time away from family at Christmas time?

You know how many have spent time away during your most important holidays or when everyone else is taking a break? You're not taking a break. And what was your experience? What did it feel like? Hey, thanks. I'm with you. I love Christmas. I love the holidays. Although I will say that over my career I found more and more my wife and I had a difficult time in the holidays because there was always so much stress.

So you know, whether I was at home or away, [00:03:00] there's always a lot of stress because there's a lot of things that come up during the holidays, whether it's finding the right gifts, going to the holiday parties, all the kids always had things going on, so it was always jam packed with a ton of stressful events and situations.

But I will say it was particularly challenging when I had to do it from a remote distance, and I did it a number of times, both in the military being deployed overseas in Iraq, Afghanistan, Africa, you name it. I did it multiple times there. And then also when I retired from the Air Force and flew for private jets, I was gone for a handful of the holidays there as well.

And I will say. It was different, but created its own unique challenges. And so that's always, I think, a hard thing. And my kids and I, we used to joke that, how do you know you're a military kid? Well, there's two answers. It's you've A, been grounded via Skype and B celebrated Christmas via Skype. And my kids have done both.

And you know that I'll never forget one particular [00:04:00] year I was deployed to Cutter for a year and was gone over the holidays, my Thanksgiving, Christmas. We celebrated Christmas. My kids, I got to at least Skype with them and they put a camera up so I could watch an open presents. So I at least got to be part of it.

There were other times when I wasn't in a situation where I could do that, and so I think those challenges that you're talking about of how do you connect, how do you remain grateful even when you're in a situation where, yes, I would've much rather been home celebrating with my family. Now I have the time to reflect on that.

In fact, this year, since I retired last February this year, the very first year, I've gone in the lead up to the holidays and the holidays themselves without having to worry about going to work or coming home from work or juggling all of this. And I will say there is kind of a nice, peaceful, more relaxed atmosphere than I've ever had, I think in the last 20, 25 years.

But as you said, there are things that I think we gained and learned from being gone and deployed. [00:05:00] That hopefully we can pass a along to some other folks that may be struggling with some of their own stresses and difficulties, and with the holidays not being exactly what they want. Yeah. My experience is probably not unlike yours.

I spent a year away in Korea. We had four little kids. I think our oldest was eight or nine, and our youngest was one. And here I left to Korea and I missed Thanksgiving. I missed Christmas, I missed anniversary. I missed every single birthday except one. That was challenging. And my wife is at home, like I said, still with a baby in diapers, taking kids to sports and piano lessons and swimming and everything else.

And I felt detached from being a part of the family and very difficult for me and doing it for a year was challenging. I come home and my youngest is now two, and she was a little tentative around me and that was hard to stomach 'cause I'm like, I'm her dad and I should be there. I had hard feelings, not towards [00:06:00] anyone in general, but feelings of frustration that I, I wanna be her father and I wanna be with her.

I really miss being a part of the family, and I, I think it's a very common thing for somebody who travels a lot. And we see this a lot in military families, that there's a reintegration process when you come back home and your spouse has been doing that by myself for the last two months, four months, a year.

Mm-hmm. And now you're stepping in, you're messing up my plan. And so you have to be aware of that. And so then you don't wanna be a conflict. And it ends up being a conflict sometimes because you don't really know how to integrate, you don't know how they've been doing it, and they've been managing life by themselves.

That makes it harder going away knowing you're gonna come back to that. It was a challenge. And yet, I never wanna say I'm glad I was away from my family 'cause I wasn't. I never was, but I'm so grateful for what I learned. Those settings. But you know, my year in Korea, you've got a bunch of Class B bachelors where they're living or, and they're [00:07:00] living on their own, their families are elsewhere and they're trying to enjoy themselves.

They're trying to grow professionally, and they're trying to. Help each other for all the mental emotional things that you don't realize. You're helping all the people around you with. You may be struggling, but there's a good chance the person next to you is struggling even more. We had our Christmas parties, we had events.

We were always focused on the mission I my time in Korea, it was a six day a week work week. Just because you're there, what else are you gonna do? And so we worked almost every single week. It was a six day a week, at least a five and a half day work week, and we were just constantly busy. I remember going home for a short break about a two week break, and I love being with my family and I love being, but I'm thinking about, I'm falling behind in my work there, and I felt guilty about thinking that.

Fast forward a number of years and I missed a number of holidays and vacations and but Christmas, I only missed four. One was the. The career year, and then I missed three other Christmas [00:08:00] three outta six in a row, 2006, 2008, and 2010 I spent in Afghanistan and with my squadron. And those were challenging, but they were also some of the greatest experience in my life because of the camaraderie and the closeness and you just looked out for each other.

Everybody just felt. We're here by ourselves, we're missing our family, we're missing Christmas. We wanna be there with them. So we're gonna make the best of it. And lemme give you one experience that's really stuck with me. One was flying in northeast Afghanistan, south of Bagram. And I'm looking out to my wing and I are flying over this area.

We're just doing sensor scans. We don't have a specific assignment 'cause everybody's bented down. We're just making sure that there's gonna be out doing something stupid and and hurting coalition forces. And I remember flying over just huts. And they're covered in snow and they're cold. They don't have any electricity, they don't have indoor plumbing.

They don't have any of the comforts of life. And I think back to millennia ago, [00:09:00] and even though in Bethlehem they may not have had snow, it was exactly the same. You're they're delivering a baby without warm water, without running water, without a way to clean it all up. And the stable was probably not that much dirtier than the actual house, right?

Because everything's perpetually dusty. The way things were fabricated then, and I, I felt not bad, but I had compassion for the people that were living in that house. And it made me think of the birth of Christ a very important day in my life. And then another time, the last time I was there by Wingman and I Nestle flagged, we flew together quite a bit.

And we did patrol over an outpost over Christmas morning and then also over New Year's, and we were just there to wake up. We kind of flew over and let them know that we were there. You have these soldiers. I was living in a nice, comfortable hoot for the most part, and the chow hall food wasn't great, but it was food and it was worn, and yet we go out to these little outposts and you've got.[00:10:00] 

A platoon, a company of soldiers, and they're in the middle of nowhere and they've got just about nothing, and they're definitely not getting a warm shower. And just to be able to say, Hey, I got you. I'm there for you. Merry Christmas. I felt honored to do that, and I was grateful that I gotta be able to do that.

I was missing my family, I'm missing my kids, missing my wife, but I was so grateful that I got to. Be there for them. 'cause these guys are all missing their families, missing their kids, and they're living in a little crap hole of cardboard box, right? Practically some kind of a hut in the middle of nowhere and they're in harm's way.

I was grateful that I was able to do that as I grew to be a professional and to think about what the professional of arms was. And as I grew as an adult, to understand what I needed to be grateful for. And the first was 1995. I was a brand new first lieutenant. I had been at my first assignment for six months.

I think I was barely qualified in my airframe. I had just gotten qualified, but every [00:11:00] year my unit had a money drive, a clothes drive, a mattress drive. They would collect all year round fights and games and toys and money and you name it. And they would load it into the back of the C one 30, about a week before Christmas.

We loaded it up in the back of the C one 30 and it filled the back of the C one 30. Other than the people sitting along the web seating on the outsides. The entire C one 30 was filled with this menagerie of things, I mean overflowing, and we flew down to Honduras. And I don't know the whole story of how my unit started this.

I do have some ideas that it began with some of the 1980s drug anti-drug stuff that they were doing in and out of Honduras. But somehow they got involved with an orphanage in Honduras. Every year they would fly down. Now this will give you sense some of the politics of the region. We had to throw two parties.

The first party that we threw, we gave about a third of the toys, gang bikes. We threw the parties for the [00:12:00] Honduran Air Force base that we would land at, and the base commander and all of the kids and everybody would come out and we would throw this party and give him candies and cookies and toys and games.

Was great, but all that was basically to grease the skids so we could load the rest of the stuff from the C one 30 up into trucks and we would truck up into the mountains and there was this orphanage up in the mountains full of 50 or 60 kids all there with nothing like you're talking about. I mean, they had nothing.

And we'd pull up with these trucks and they're offloading supplies and mattresses and everything else, but we also offloaded all the toys and bikes. And I got to be part of that. I got to be there and give donuts and cookies to all the kids around the this pavilion that we were sitting in. And then one of the guys dressed up as Santa.

And the kids would come up and they could pick one presence and. One little kid I remember, he was probably four or five years old, not very big. I remember him going up to Shabb and he picked a skateboard that was bigger than he was, and he's loving this [00:13:00] skateboard back to his spot. Biggest grin on his face.

Now, he probably had powdered donut sugar around his mouth as well. I didn't miss Christmas that year, but it was my first Christmas. I spent away from my family because I couldn't go back home to my parents' house. Because of our mission requirements. I had to be at my duty station in Florida, and so I spent a Christmas there with some friends that I had made.

It was my very first that I spent away from my mom and dad, and so it was an interesting one for me, but it made me realize that I could grumble and complain about the fact that I couldn't go home and spend it with my family, or I could realize that I had a pretty good. That these kids that were down this orphanage who the only joy they got every year was this Santa Claus C 30 that comes in and brings 'em all their stuff.

And so I, I gained a lot of respect for all the good things that the United States military does. Not just in the defense of freedom, but in promoting some of the values that we as Americans have. That's the first big story. And the second [00:14:00] was a lot like yours being deployed down range. It was much later in my career, I was a colonel by this point.

I was in command of a forward headquarters in Qatar, and I had six to 700 people that were there temporarily with me and managing how we handled the holidays over there was a whole different ball of wax. I had done it myself with my unit before I had been down range. I had missed lots of Christmases, but this one was different because we weren't flying missions.

We were a, a fully support unit forward, but not directly in the line of fire. We were in Cutter, but we were supporting everything going on in the CENTCOM region. And we still had a mission to do every single day, but I've got six or 700 people who are missing their families at Christmas and trying to manage of their expectations, their needs, their wants.

And so we held Christmas parties and I tried to be a leader that would get out and see everybody, and I had a phenomenal First Sergeant and a phenomenal command sergeant Major. These two senior enlisted guys [00:15:00] knew how to take care of the troops. They knew what they needed. I watched them as they led us through the holidays and I gained just a phenomenal appreciation for the hearts and the spirits of those people who understand that yes, they don't wanna be there, they don't wanna be giving up time away from their family, but understand that serving the greater good sometimes means that's what we have to do.

The term that comes to my mind in all of that is embrace the suck. Yep. If you have a choice of where you wanna be, it's with your family and it's doing things with your family. But if you don't, because you've made other choices, like joining the military, embracing where you are, and finding the good in it, and finding o other individuals that need your help, it's easy to get down.

You go to those locations and you're watching your kids open presence, like you said, and you're not there and you can't hug your wife, and it's easy to focus on what you don't have. Well, like I said, at the very [00:16:00] beginning. Finding points of gratitude is a choice, and it can determine whether you gain from the challenges or you're just enduring them.

I'll never say I don't wanna be with my family. I'm glad to be away from my family, but I was glad to serve and I was glad to be with some of the greatest people on the planet jointly enduring the challenge of separation from those we love. That's one of those things where the bonds that were forged and created through those embracing the suck as a team, not only were we doing the nation's bidding and the nation's work.

In embracing the suck of being together on the holidays, it actually made us all tighter and we became a family and we did things like a family. Even though all of us came from different backgrounds, I, it was phenomenal. Now, before we go though, a lot of stuff we talk about in your book, confident Leader and Leadership and Management, one of the questions that always came up to me, and it was a difficult one for me as a commander, I commanded four different holiday seasons where I was a commander at different levels, and the big question became.

What do I do as a commander to help them celebrate the holidays? [00:17:00] And I had a fair number of people who thought the right way for me to do that was to go down range with them in Africa or Afghanistan or Iraq and go spend the holidays with them to bolster up their morale to rally the troops. And I struggled with that because yes, there is that aspect of it.

I think that the people that work for you need to know that you appreciate the sacrifices that you're making for them, whether they're working on the holiday, whether it's a truck driver or a first responder, like my dad was as a fireman who always had to spend Christmas and Christmas Eve at the fire station.

The people need to know that you appreciate them, and yet I always was cognizant of the fact that when I as a boss would go visit my troops down range, because I wasn't there to be part of a mission, I really just was kind of in their way. I didn't want to intrude on the things that they already had, and so I went back and forth and so I'll lay that out there for some of the listeners to think about for their own selves.

If you're a boss, if you're a manager, [00:18:00] how do you celebrate? I actually, I thought about this about two years ago. My daughter is an operating room nurse at a hospital, and she had to work on Christmas Eve and New Year's Eve because she was one of the newer people, and I asked her, I said, Hey. So they have a big food spread that they put out outside the operating room so that everybody's celebrating a holiday and they can go by and eat cookies and whatever.

It's just like, no, the hospital doesn't have that kind of money. Why would they do that? And I thought, wow, that's really strange, because those were things that I took for granted in the military that we always tried to make sure that we took extra better care of the people that were working on the holidays because we were aware of just the stressfulness.

We've been there, we've done had. And I thought to my daughter, I said, I get it. The hospital may not have money to do that, but I will guarantee you that the hospital's CEO has enough money to throw out 500 to a thousand dollars worth of spread for the folks in the hospital to celebrate the holidays. So I'll leave those [00:19:00] thoughts with the listeners to think about for themselves to ponder how you think it's best to help your people as they try to embrace the suck in whatever job they're doing.

That's a great point because as you were speaking. I thought of the different things that I did as a commander and we would do as a group. We never went to the Air Force and said, Hey, can we have some money so we can throw a party for our folks? You reach into your own pocket and you bought your own stuff to give and to share.

Not because I'm exceptionally altruistic in giving. That's just the way you did it. Everybody just naturally did that. You don't look for the organization to do that. The organization's got a mission. The organization doesn't exist to pat you on the back. The people in the organization are gonna be the ones that make difference.

The hospital may not have the money. May not have the bottom line, but you're right, that has a few extra shekels and he could have passed the plate for his leadership team and said, Hey, let's do a spread for the hospital staff. And it didn't have to be, it would be a nice gesture. That is a decision as a [00:20:00] leader that demonstrates empathy that says, Hey, I know you drew the short straw and you're doing what you don't wanna be doing right now on a holiday, other than the fact that you may be getting time and a half.

I also recognize that time and a half does not substitute for time with the family. Hey, that actually brings me to another one that a friend of mine brought up years ago that I never thought about, but I actually knew a guy that got out of the military because of this. And so over the holidays, a lot of times we as leaders are commanders try to think about our people and we say, oh, there's Jimmy, or there's Steve and they've got kids at home, so I wanna make sure they get off work early or that, Hey, I don't want them to be deployed because they have family.

The guy said nine times out of 10 drew the short straw. And I'm sure you've heard this in your units. Hey, that guy Jason, he's single. So send him overseas 'cause nobody's gonna miss him at Christmas. Well guess what? My buddy brought it to my attention 'cause he was the single guy in the unit and he was like, yeah man, you guys have got me scheduled every Christmas to be deployed over Christmas.

Be very [00:21:00] aware of the inequality that we're building into it now. I love families. I think families are great. It made me step back and think about the way I approached families and folks with families that worked for me, and I made it my, my mission at that point to not treat them differently just because they were single, because the holidays are just as hard for them and they have families.

It maybe their mother and dad or their brother and sister, but remember they're out there. So try to be aware of your own bias that you automatically put into. How you schedule and how you decide who works and who doesn't. That's a great point. 'cause everybody has a family. Everybody has a collection of close ones, and if they don't for some reason, every once in a while you find the one-off individual that has just made it through life on their own.

They keep getting scheduled as a single guy. They keep getting thrown into those jobs. When everybody's gathering, everybody's showing love, and they're off in the middle of nowhere. And they're not participating, so you have to give them the same opportunities. Those were [00:22:00] just my kind of two lessons that I got as a commander of how do I help people celebrate the holidays, and how do I make sure I don't totally hose over one set because I've got a bias implicit myself.

Everybody celebrates the holidays a little bit differently. Everybody has different sets of beliefs. Everybody has different people that they're missing. I think though a true sign of an empathetic leader is somebody who looks for. What matters to somebody else and how do I improve on their lives? And as you do, if you're separated from your family for whatever reason, you are gonna find as you're focused on other people and focus not on what you're missing.

You're gonna find joy and pleasure in what it is you're doing because you're helping somebody else find that joy. You're helping somebody else enjoy an otherwise not pleasant time in their lives. It's easy to focus on the chromi in our lives. But it's so much better to focus and find those points of gratitude, and it can.

It'll determine whether or not you're just [00:23:00] enduring something or you're growing and enjoying something Very Christmas and happy Holidays to everybody out there. We'll go back in the next episode to talking more specifically about how confident leaders make better decisions and you can get better results from those better decisions.

Subscribe to Commander's Intent, follow us, and keep getting, becoming better decision makers with us. Thank you.

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