Defining the Essential Ingredients of a Post-Military Career
There are a few well-worn topics when it comes to military members talking over drinks in the Squadron Bar, around the flightline smoke pit, or in a 15-pax van on TDY. Besides a classic BCG session, there’s always talk of “what are ya gonna do when you get out?” This post provides a structured approach to defining your post-military career by focusing on three key questions:
- What are my interests?
- What am I qualified to do?
- What’s available to me?
From there, we apply personal constraints like geography, financial goals, and work-life balance to create a clear, actionable career path.
Part I: Three Key Questions
What Are Your Interests?
Strong performers in the military often engage in "job crafting"—modifying roles to align with their strengths and interests. If you found yourself drawn to mentoring, planning, or technical problem-solving, those interests can now take center stage in your civilian career. No one asked me to write Air Force Public Affairs articles when I was a Stan/Eval Chief, I just enjoyed sharing my squadron’s story. Now, in my post-military search, I can make marketing and writing a core aspect of my new job from Day 1.
Ask yourself: What aspects of my past military roles did I enjoy most? What strengths did I naturally lean into? Do I want these to define my next job, or should they remain personal passions?
If you were a senior leader responsible for hundreds of people, you might have a passion for leadership. However, maybe being a simulator instructor suits your desire for stability while you fulfill your leadership interests elsewhere—like running for the local school board or leading a community organization.
A love of learning may also take you far from the flightline towards a different career and that can be great too. Civilian careers allow you to integrate different passions into your work-life balance in ways the military rarely does.
What Are You Qualified to Do?
While interests are essential, they must be balanced against qualifications. You may love football, but that won’t land you in the NFL. Similarly, many veterans struggle to understand how their qualifications translate to the civilian job market.
Here’s where to focus:
- Understanding Civilian Qualifications: After leaving the service, there is no established career path that will push you to get your next qualification. Furthermore, there is no standard military labor market that treats all qualifications equally. While a PMP Cert (Project Management) may be a prerequisite for one sector, such as federal contracting, it may not mean more than the paper it is printed on in another, like tech.
- Industry-Specific Qualifications: For well-worn routes, there are tried and tested paths for folks to get their A&P mechanic certificate or their Airline Transport Pilot (ATP) certificate. The milblog Sitreps2Steercos outlines the veteran-to-Full-Time MBA pipeline in a very detailed way. A subject for another post – in my opinion, aviators should consider part-time MBAs with full career services. Leaving the job market for 2 years with defense contracting opportunities means forgoing between $300-$600k in lifetime earnings.
- Defense Contracting as an Exception: Unlike other industries, defense contracting highly values military experience. You have years of experience in a unique talent set that cannot be grown indigenously in the private sector labor market. Meanwhile, firms are competing with other firms for your talent as they compete for contracts.
- Don't Self-Eliminate: Many military members hesitate to apply for jobs where they don’t meet every listed qualification. Often, these job descriptions are written without full knowledge of true operational needs. Contractors will sometimes write wild requirements seeking their mythical 5,000-hour F-22 Weapons School graduate who has an Air Assault badge and speaks Farsi. If you meet the core skills, use resources like us or your network to get the real scoop and then apply with a referral.
As for timing, if you’re pursuing well-established pathways like the airlines, defense contracting, or an MBA, start preparing at least a year before you leave active duty. If you aren’t sure about what to do, short courses like Google Career Certificates or Coursera classes can help fill knowledge gaps and test your interests.
There’s also no harm in shoring up your fundamental skills. I was personally a bit embarrassed and humbled during my first MBA accounting course working on group projects. My lack of Excel knowledge could have been remedied with a quick course while on terminal leave. Who knew Excel could be used for financial modeling and not just names for the next day’s simulator schedule? Make sure you are confident you are able to execute at an industry baseline.
What Is Available To You?
OK - I’m interested. I’m qualified. Is the job available? While you can work on your qualifications, this third question is entirely dependent on the market, timing, and luck. My Air Force separation timeline just happened to coincide with the hiring of an initial cadre for a $21.1 billion Foreign Military Sales program. This sale was authorized six years prior to me getting out! Timing in the defense contracting world can be especially fraught – contract delays, government decisions, geopolitics, etc.
One of my favorite apocryphal quotes (often attributed to Yogi Berra or Niels Bohr) is: “Predictions are hard to make. Especially about the future.” Since timing is uncertain, the best move is to build maximum situational awareness. Here’s how:
- Follow us at Squadron Jobs to get an idea of what the defense contracting market looks like. Look at the locations, salary estimates, and types of programs that exist and how frequently the jobs turnover.
- Subscribe to industry news – I personally read The Merge to understand what’s going on in the defense market. Astute readers eventually see some cause and effect. For example, it’s no surprise that when Poland signed an LOA to buy 96 Apache helicopters in August, that we now see recruiters from 3 different companies trying to recruit for the contract right now.
- Join private communities like our closed aircrew LinkedIn group or places like The LAB for the Navy folk. The community wants to help you if you’re willing to put in the work.
- Attend industry events for your target industry, whether that’s Air Warfare Symposium for defense or affinity group pilot association meetings or the MBA Veterans Conference.
Timing is unpredictable, but by staying informed, you’ll be ready when the right opportunity arises.
Part II - Defining the Essential Ingredients
Now that we looked at the big picture mission scenario, we need to look at the constraints and risks of our operating environment. This list is not all inclusive, but rather a starting point for your own personal checklist that you can modify.
Financial
Your financial situation dictates flexibility. Retirees with pensions have different risk tolerance than those separating without one. Don’t overlook VA disability and GI Bill benefits as financial supplements. Determine whether financial security outweighs geographic preference or job satisfaction. Personally, I gave up a geographic preference to be in the US for financial reasons – a calculus that changed once my nest egg reached a target goal.
Geography
For many, location is dictated by family needs. Determine whether geography is an absolute requirement or a preference. If a job in Saudi Arabia isn’t an option even for $1M/year, it’s an essential constraint. Otherwise, consider ranking priorities to weigh financial opportunities against location.
Furthermore, approach the location consideration with an open mind and do some research by talking to those that have gone before. I’ve talked to many folks who weren’t keen on St. Louis, MO for jobs at Boeing, but are thriving there after finding the right communities in the region.
Work/Life Balance
After a grind in the military, the work/life balance requirement can mean a lot of things. For those considering the airlines or business development roles, I think this comes down to your amount of travel days versus days at home. I believe the desire for stability is a major factor in choosing defense contracting roles. Some contracting roles also have greater flexibility to take longer breaks of service, whether that is being on rotation flying abroad for a company, or a job that is hard to fill that you can go back to after a longer sabbatical. The market rewards this balance appropriately – you’ll need to be on the road to get started in the airline industry and no one ever made partner at a firm by just cruising…however, you should evaluate your actual total compensation by hours worked.
Mission
Do you want to be in the game still? You can keep your clearance, be embedded with active duty units, and fill your days as an instructor, mission planner, or support staff that gets overtime after 40 hours. There are even jobs where you can keep going TDY or deploy to the ship (not for me, but whatever floats your boat).
Working on foreign programs can bring a similar degree of satisfaction depending on the client (the upside might be work/life balance). You can also have high impact roles when it comes to managing programs to help the warfighter if that’s your thing. If this is not an essential ingredient, it’s also OK based on your service to go to the airlines or help companies make or invest in widgets. Again – is this a preference or is it “essential?”
Manager versus Individual Contributor (IC)
Contrary to the career escalator within the military, it’s perfectly normal to land an IC role and stay in it. The airlines and defense contracting are two paths where one can be an IC for 20 years earning a high salary.
If management is your calling, just realize that this might be a significant pay cut from a highly technical IC role. In this case, your labor market peers aren’t just other aircrew or maintainers with a high barrier to entry skillset – it’s a generalist role. Your competition includes everyone that got an undergrad business degree from Nowhere State University that has worked their way up to Vice President of [Your Airframe] after running the F-35 Blinker Fluid program.
While your technical skills will probably make you way better at the job, the market (and defense contractor corporate “ranks” AKA levels) won’t compensate you for it. Therefore, it is important to think about what kind of cog you want to be in the next system you join.
Benefits Package
Firms, particularly defense contracting companies, offer vastly different benefits. If you need strong healthcare and education benefits, look to large firms (the primes). If cash flow is your priority, smaller subcontractors may pay more with fewer benefits. I have seen folks switch both ways on the same program based on their individual family circumstances.
Temporary versus Long-Term
Lastly, in finding your first post-military role, you need to think about whether it is a temporary or long-term role. My friend went to an interview for a contracting job and expressed his interest in joining the company for the next 20 years if possible. The interviewers laughed a bit and were frank in saying that the whole enterprise would probably be sub-contracted out within a few years.
It is important to always be searching around the market regardless of how “long term” you think your position is based on everything from DOGE to business acquisitions to changes in local management culture. That being said, some firms are quite clear about the labor relationship being more transaction and others have more growth oriented cultures you can learn about from current employees.
Part III – Communicate Your Career Goals
Finally, the clearer you are about your post-military career goals, the easier it is for others to help. If you can say, “I need a $150K+ sim instructor or SME role in SC or NC near family,” you’ll get better referrals. Vague answers lead to vague results. They also make folks less likely to recommend because it could imply a certain degree of flakiness or lack of job planning.
If you don’t know what your ingredients are yet – that is totally fine. The way to tackle this problem is by doing “informational interviews” early. An informational interview is simply a 20–30-minute chat with someone in a profession you are potentially interested in. Do some research to use the time wisely and not ask easily searchable answers and these interactions will help build your personal post-military network.
This is an important step prior to getting out because you are simply learning more and don’t have any specific ask or request that may make the person feel uncomfortable.
Final Thoughts
By defining your interests, qualifications, and market availability—and applying your personal constraints—you can develop a clear, actionable career path. Your post-military career doesn’t have to be a mystery. Start early, stay informed, and be deliberate in your transition.
If you're looking for more insights, follow Squadron Jobs and aircrew are invited to join our private LinkedIn group to stay ahead in the defense contracting market. Good luck!