Observations of a Transitioning Officer: How to get out
- Josh McCaskill
- Oct 24, 2017
- 6 min read
Updated: Apr 16

So once you decide to take the plunge, where do you start? The most common question I got was, “well, what do you want to do when you get out?” It was infuriating in the sense that I know I have a lot to offer, I know there’s so much out there, but I have no idea where to even begin searching.
The problem is that you’re first asking the wrong questions. There are three primary questions you need to answer before you can even begin your trek into the unknown. These will help guide you much better so that eventually you can actually answer that stressful and scary question.
1. Where are you in the ‘getting out’ process?
This may seem like an easy question, but it actually has some complexity to it, depending on your life circumstances. Are you positive you want to leave? Just considering? On the fence? Are you single or married? With or without kids? Any special needs? Are they of school age? Have you talked to your family yet? Have you talked with others who are in the process or already out? Committed to getting out after Command/after some ADSO you’ve incurred? I recommend you heavily consider all of these things, especially the last one. I learned more about question 2 (soon to follow) as well as how much time I’d need to devote to the process by talking with those that have gone before. Hence, part of why I started this blog.
2. How do you want to transition?

School full time? Part time? Civil service? National Guard/Reserves? Full civilian? Use of private networks? JMO firms? Go the Lone Wolf route? This is also a complicated question, but it helps you to start narrowing your focus on what you want to do when you get out. Do you have full GI benefits? If so, you may be able to go to School full time to get your Masters. Do you want to go into civil service (police, FBI, etc)? What about the National Guard and Reserves? Those are good options to help work towards that golden pension everyone tries to convince you to stay for. It also could greatly offset the cost of health insurance that you’ve never had to worry about before with Tricare. Or do you want to divorce yourself completely from the military and start over? Depending on what you go into, the earning potential that enables your 401k package could greatly outweigh that of staying in the military all together. Are you sure you want to go corporate? Transportation? Entertainment? Healthcare? Manufacturing? Sales? How about non-profit? Soooo much to consider.
Are you going to utilize your “phone a friend” option? I say that quazi-jokingly. This is what I call the “Private Network”. Yes, it’s a pun. It seemed for a while before I took command that every Soldier getting out “knew a guy” that could hook them up with an awesome job. Turns out that was rarely the case (big surprise). I know I’m preaching to the choir so-to-speak, but it’s a real thing. More later on how I used my “private network” to actually get a really awesome interview opportunity.
Another option of how to transition is to utilize a recruiting company. There are TONS of them out there, all aimed at getting you a job of some kind. Each have their pros and cons. You can learn more about them by talking to buddies, or calling the agencies themselves. I swear Jim Lose has had me on speed dial for the last 10 years. All in all, this can be a great option. I’ll spare you from diving into it for now. I would encourage you to read my blog about JMOs entitled “JMOs-a combat multiplier”.
The last method for finding a job is what I call the “Lone Wolf” approach. This is invariably what a lot of people end up doing. This is, in my opinion, the hardest way. Submit your resume on indeed.com or Monster jobs, or whatnot. You look at the listing in your local paper, or call up companies to ask if they have positions available. You fill out online applications and such. You are out on the ocean of opportunity, alone and unafraid. You’ve opted not to jump on board a boat with others that carry oars, and you didn’t have the magic yacht on standby for when you went to sea. Instead you grabbed your oars, got in your boat, and rowed. Kudos on your independence by the way. Good luck sailing the uncertain seas of the job market. Obviously I highly recommend against this method. Why row alone when you can lean on the experience and assistance of others to help you navigate the unknown? Especially if the assistance is free to you.
3. Finally, the last but not least question of: when would you be making your transition?
Turns out many people who wish to transition still have some time before they even become eligible. For others, making a deliberate date on when to leave is one of the first steps. Word to the wise, the busier your current job is, the more time you’ll need (duh) to prep. My last assignment was TRADOC, teaching at West Point (poetic how my career started and finished there, eh?). So my schedule didn’t involve the care of Soldiers, property, maintenance, or preparation for deployment. I wasn’t involved in staff meetings, hail and farewells, motorpool Mondays, battalion runs/ruckmarches, and all the other time suckers that keep you from the 3,000 e-mails you haven’t looked at yet. I had a fairly predictable schedule for the most part, and knew at which points during the year I would be available to devote time towards transition. And you WILL need to devote time towards your transition (did you not read the part about prep and conference?)
Oh by the way did I mention that having kids in the military is free (so are vasectomies by the way). Kids cost a buttload from the moment they’re conceived (toys, diapers, crib, carseat, you get the idea). And that’s assuming the pregnancy and labor/delivery go totally smooth. If you need a specialist of any kind at any step along the way, the Army’s got your back. Think about these things before you put your date on the calendar.
Also, you’ll have to do extensive research for any path you choose. Want to go to the FBI? How does your time in service credit you towards that career? After all, you’re still in federal service. Determined that you want to make over $100,000 as you transition? Well my friend, you need the right marketable skills and background. I hate to break it to you, but you may not qualify. Want to use your GI? Does the school you want to go to provide a credible enough degree to warrant your time? Seriously. We check the box in the military, but there’s a big difference between a top 10 level MBA program and a top 1,000 level MBA program when you’re talking salary negotiations. That’s all to say, if you even need an MBA. You need to understand this stuff. Do you want to go into professional services? Transportation? Manufacturing? Finance? Non-Profit? What markets of what Industry? This crap takes soooo much effort. And it’s worth it.
If you’re feeling overwhelmed, take a breath. This blog, along with the endless amount of resources mentioned above, are here to help. If you are still really confused on what to do, one way is to read a book I’d recommend entitled: PCS to Corporate America (4th Ed). It’s by one of the founders of Cameron-Brooks, and it is a really good starting point to help you answer a lot of the questions you generated while reading this article. I've attached a link at the bottom of this article for reference. It'll take you to the Cameron-Brooks website. This is not an endorsement for the JMO program. Again, read my related article before you sign up for anything.
What I won’t get into during this blog are how to prep for an interview, what to wear, and all that jazz. The book more than covers it all. It is probably the best way to start that I could recommend (aside from reading this blog of course). I’m going to cut this one short as it’s already over the word quota I was aiming for. Ultimately, you need to realize the intersection upon which you’re standing. Most of your decisions up until this point have been “Y” type. You can go left or right, but generally you are still in the same direction. Getting out vs. staying in is a “T” type intersection in that whatever direction you choose to go, you are headed directly away from the other. It would be foolish to choose your decision simply based on the fact that know all the road ahead in one direction, but you know nothing of the other. If the military has taught you one thing about leadership, it’s that you should never base your decision on fear. Do the work, make a decision, own it, and win the day.
Cheers to future reads,
- Me
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