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Life as We know it

Observations of a Transitioning Officer - What It's Like: Looking back 5 years after getting out

  • krutch4u
  • Oct 21, 2022
  • 9 min read

Updated: Apr 16




It’s now been 5 ½ years since I donned the ol’ Army green one last time. We’ve been through 2 presidents, abandoned the Afghanistan mission, established Space Force, and armed Ukraine to repel the infamous Red Army, which seems to be working as of the date of this post. As time marches on I begin to feel older and older as I watch the faces of the men stay the same age. The technology is advancing into direct energy weapons, and electromagnetic weaponry (friggin’ lasers and stuff). Tactical drones are becoming the new hotness, and I’m still recalling training on M119A2 in my BDU’s (later ACU’s) and learning to hipshoot chart to chart as the M777’s were just coming out and the M198’s were all being recalled to retirement. Yep, I may not be the oldest fart, but I’m gettin’ there.


When I left the Army in 2017 (teaching at the United States Military Academy in West Point, NY) I had no idea whether I’d be successful as a civilian. Through a headhunter agency I earned an opportunity to work with a big corporate company in the greater San Diego area in a sales management position. After nearly 3 years I realized that despite the wonderful success and subsequent paycheck, working to make more money was not highly motivating for me.


I want to encourage you for a minute. Seriously, listen to this next phrase when thinking about getting out of the military. The infamous question of “what do you want to do when you get out?” took me 3 years to figure out after I actually left the Army, and I’m thankful for the opportunity to learn this lesson in one of the most beautiful vacation spots earning a really great living.


During my time in corporate I started looking for opportunities to sharpen my leadership skills that had been tucked away since my command time and mostly referenced during my teaching stint. Among many exercises that sometimes I charged for, other times I did pro-bono, I offered to look at my church’s organization and conduct an organizational leadership diagnostic – checking the pulse of the staff culture and cross-examining that with the company’s structure, vision, goals, etc (which yes, was a church, but is still a small privately owned non-profit).


I did my assessment for the church, was offered a job, declined it politely (as I’d done with past clients, not that I’m always being offered jobs, but it’s happened) and went back to my life. But I couldn’t shake the thoughts of possibility to get back into the leadership saddle and actually impact an organization. But a church? Come on bro. Not in a million years.


Big corporate was well and dandy. I made good money, had a comfortable life in the world’s best weather. What more could you ask for? There’s a general rule of transition out of military for officers that goes something like: You can pick a job that you love, one that makes tons of money, and is in a great location… but you can only pick 2 of those options (and it’s mostly true). I didn’t love what I did, but I made good money and loved the location. We crunched the numbers, made a plan for the future, and I took the leap. I left corporate and went into full time ministry (and yes, I had to eat my earlier words, it was a great running joke for almost an entire year). I’ll spare the preachy side of it all, but I cannot over-emphasize the importance of loving what I do now. For me, and this is completely just my application of the above 2/3rds rule, loving what I do was actually more important than making tons of money. It’s a valid thing you’ll have to reconcile at some point. What are your priorities?


Three Years Later – A reflection on the conversation that led to my change.


I remember him saying to me “I want you to do it [be the Executive Associate Pastor]”. Half-joking, I replied “Do you have any idea how much money I make? Pastor <first name>, you can’t afford me” as I chuckled.

His response? Immediately and almost dismissively he stated “oh, I’m not worried about the money part. God will take care of your heart about all the money stuff”.

I’ll admit, in that moment I was offended (Queue the dramatic notes played on an organ as I shriek back with a look of horror on my face and my covers my heart and I gasp as if to suggest I may faint)… A month later I called and accepted the job.


Before I blinked I'd left my cushy sales management job and now sat smack dab in the middle of being an Executive Pastor. Functionally, it was more like a “Chief of Staff” (COO in the corporate world. A lot like a Battalion Executive Officer and Operations Officer in the military “XO/S3, or X3”). They needed someone who could help make them successful within each of their ministries, organize the chaos and create structures and systems, and create a unity of effort; rowing in the same direction rather than in their own. Starting February 2020, I came in swinging. Implementing some small changes right away to get us more organized, streamlining reports, communication channels, etc. And, managing the struggles along the way with system changes, personal feelings, etc. About 1.5 months later, the world shut down because of COVID-19. Everything was derailed. But, it pushed people to change, to adapt; it revealed the need to get back to the basics. All the big flashy things were stripped away. Suddenly we were stuck at home. Suddenly we were alone. We had Disney +, Zoom, and Netflix’s Tiger King. But as we’d heard in church, those things would not satisfy what we truly needed as people. Over time the isolation changed people.


It was trying, especially for my first year in my new forever career. I was not excused from the chaos either. Both of my grandfathers (my mom’s stepdad and my stepdad’s father) passed away. My dad’s brother (my Uncle who helped raise me) passed away. I lost 3 military friends to suicide. My wife had worked at a hospital in the psych ward (which always kept me on edge) and finally graduated with her BSN and started working only to basically become yet another overworked nurse taking care of COVID patients. Both my kids (4th & 6th grade) did school online, which is pretty crummy, regardless of how great the program is (boys just aren’t meant to be cooped up indoors). And there are many other things too. I know my story is not unique or special. Others have faced infinitely harder times. I’m thankful for where I am and what I have, but things were just tough all around for folks.


We spent the next two years rebuilding our systems from the ground up – focusing on things that mattered the most and balancing that with things people needed right away. There have been a lot of leadership skirmishes and sometimes battles, but overall I still believe with all my heart that leadership is leadership regardless of the industry. There are differences in application and approach, but the principles and lessons learned in the military still have just as much relevancy outside of it. The biggest difference in leadership I’ve come to learn in my first year is that position matters very little by comparison to relationship.


In the military, you can apply positional authority (also referred to as positional authority). This means, you do it because I’m the boss and I said so. It requires no relationship to be established. This works incredibly effective if the only thing that matters is mission accomplishment. Think of General Patton. Not exactly the kind of guy you want babysitting your kids on a Friday night, but definitely the guy you want to be next to in a tank fight. Violating positional authority lands you in hot water in the form of mission failure or getting kicked out. You can’t sabotage the authority without causing risk to yourself. And, you’re taught that the mission is bigger than anyone. Everyone can be replaced. Which is ugly, but true. So ultimately, it can* work as a strict means towards success. Recommended? No. Just offering this as a comparative point.


In the corporate world you fall somewhere in between. If you want to keep your job you have to do what your boss tells you. But as a boss, if you want to be the “most” successful you need relationship too. “Because I’m the boss” may get the immediate job done. But often the risk for disobedience is less personal. You may even be able to get away with outright lying or sabotaging the effort. And if all else fails, you can just go find another job. So as a leader, the balance is critical. You need to dance this dance to get the most productivity and ensure employee satisfaction (translating to low-turnover, reduced stress, etc). Everyone here is somewhat replaceable, but with a direct economic hit to the company and employee workloads, so it’s in the best interest of the leader to balance both sides accordingly more-so than the military allow for.


Now in church, the pendulum is much farther over towards relationship as a means to accomplish the mission. Referred to as “relational authority”, it means “I do it because I like/respect you, not because you are the boss”. Unless you attend a very dogmatic church, “grace” is a heavily used ingredient when dealing with most situations. “Because the boss said so” is less immediately understood to be the law until the culture reinforces it as such. Until then, there’s a significant amount of follow-up, encouragement, assistance, “grace” that is applied. One of my favorite authors and leading guru’s on leadership (secular or biblical) states that “people’s willingness to change is directly impacted by how much influence you have over them”. I believe it is truer in a church than in any other industry. Losing someone on staff has massive impacts as most run incredibly lean. There are big churches/staffs out there, but it’s more the exception than the norm. Every person on a church staff can feel like family. Replacing family members is a slow and laborious process. Each member adds their own ingredients to the overall culture, and you have to be precise when measuring what flavor of work environment you are trying to create/shape.


Personally, I’ve had to learn to slow down and really listen to people’s concerns, consider what I’m asking them to give up in order to change, and learn (hardest part) to encourage/motivate/guide accordingly when they say “yes” with their words, and “no thanks” with their immediate next action. Dr. John Maxwell states that “the start of change means the death of whatever was there before…. When considering change people will first consider what they are giving up, and what they have to gain from this change.”


No organization is perfect. No leader is perfect. Mistakes have been and will be made. But there has to be an understanding that the mission of the organization (church in our case) is bigger than any of us. You matter to your organization. But that doesn’t mean that you are the focus. We’re here for a purpose. It’s not to work here so we feel good about ourselves, although that’s not a bad thing. Our purpose is to advance the organization’s goals. For ministry, that means if I need to preach on Sunday I’ll preach. Teach a bible study class in Kid’s ministry? Done. If I need to set up chairs, pick up trash, clean a toilet, done. Pay me what I need to survive and then just tell me what you want me to do. I serve at the pleasure of the church. This is a calling, not a job.


Sounds a lot more like military life when you approach it this way, huh? Funny enough, people who have the mindset of growing their organization are often the people who get put in positions of greater authority and responsibility. Those who think that time/experience = rank/privilege often leave feeling frustrated and resentful once we start to focus on the mission.


So to close this out, what’s it like being out now that I’ve been out for more than half as long as I was in? Honestly, I still miss the Army every day. But it helps I’m doing something I feel is bigger than me. I love what I do now, and the people I get to do it with. I could make more in the corporate world sure, but I couldn’t do what I do if I did. So, I’ll say that it’s actually pretty great, once you find your niche. So find your niche. I started with a higher paying career doing something I wasn't passionate about becuase I'd never been a civilian in my adult life before. But once that fear/concern subsided and I found my stride, I began looking for something I actually could identify with and feel good about. For me, it was the church. But it doesn't have to be that for you. It's okay to want to make money, or live near family, or do something impactful that brings you joy. It's okay to not have all that at once. Figure out the answer to this question and you'll find that you're in the right spot: "What's the thing that I can't not do?" For me, now that I've tasted what being in ministry is like: helping people win with what matters, I don't think I'll ever be able to do anything else. This is what I wan to do for the rest of my life. What is that thing for you? It took me 3 years to figure it out. So there's no rush for you to get it right the first time. Transition well, work hard, and position yourself for what matters as you learn it.


Cheers to future reads.

 
 
 

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Josh McCaskill -
Middle-aged, energetic, and not sure what he wants to be when he grows up
Former Army Officer stud turned Corporate regular guy.

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