Alumni who left the Military after your first five, do you regret your decision?

This is a very reddit like question, but I really am curious about the benefits of leaving and vice versa.

I remember you at Duke.

What a lineup with you, Jason Williams, and Dunleavy, Jr.

The decision to stay or go is very personal and often flavored by your experiences during those 5 years. The rear view mirror of regret is then flavored by how life went AFTER you made the choice to depart and is the classic dilemma of the road not taken and FOMO. Did the assumptions you made about the alternate choice pan out?

I would say in my own case, I made faulty assumptions about the private sector that did not play out as anticipated. It could be the game -- or more likely it could be the player. Much of my experience is related to the small-business direction I selected coming out of the military. I recognized the error of my ways quite early, but could not return because of larger force reduction initiatives at the time. In all fairness, there were people in my life tried to point out the benefits of remaining in the AF. In retrospect, I was not listening because the grass appeared to be far far greener in the civilian sector.

In the end, we make big kid choices that have rewards as well as consequences. We get one chance at this game, and the rear windshield is far more clear than the front windshield on the rocketship we fly during our limited time here.

For some, they were never a fit for the discipline and process orientation required from a military lifestyle and I have to think there is no remorse for separating after 5 years of service for those in that category.

For others who enjoy the camaraderie, common goals, common struggle, order and discipline, clear growth plan, achievement mindset, etc... it is often something that cannot be found in other professions. Often, as a ~27 year old human, you don't fully know yourself as well as you do as a ~40 year old human. Perspective shapes what you value and if you are able to learn this about yourself sooner, you will often make better longer ranging decisions that align with your true values.

Everything I wrote above only answers part of your question -- and again, the answers vary SO WIDELY based on each individual's circumstances and background. As for reasons to stay or go, one reason to stay would be resume builder. Military officers are asked to do far more than civilian counterparts at a much earlier age. The longer one is in the military system, the more responsibility they are asked to take on. There are some examples within structured corporate managerial training programs within the civilian sector, but it is not the norm.

An example that hit me the other day was seeing a job posting ($400K/year role) that asked two key filtering questions:
1) What is/was the largest team you have led or managed?
2) What is/was the largest budget you have been responsible for?

Within the civilian sector, large teams and large budget are possible, but not as plentiful as a mid-to-senior military officer. If you consider a 20 year military officer who is an O5 or O6, they would likely run a 200+ person organization if not into the thousands. Their budget would be in the 10's to 100's of millions of dollars. With a high degree of certainty, the person who stayed in the military longer would have better resume bullets in these areas than the grad who got out as a Junior Military Officer and went the typical civilian manager path. Yes, there are other criteria for a role like this, but I point out these two criteria as one example of why someone may opt to stay in the military to build a resume in anticipation of a second career outside of the military.

I don't regret getting out, five and dive. Some people transition over to reserves but it was time to make a clean break. There are sectors that are specialized, it the longer you stay in the hard it can be to break in. I think there are people who are expecting those $400K jobs right out. That's not typically going to happen. While you will deal with large budgets and extra bodies, once you get out you'll also be competing with people who have been in an industry or a sector for years.

Now, I don't think transitioning is especially easy. There is a degree of satisfaction you get serving that you may not have in your first opportunity out. I also think people rarely stay in the first leap for long.

For academy grads (at least in my CGA experience) once you get out it's easy to feel disconnected. I don't know what's going on with many classmates. The service, surprisingly, continues on just fine without you (and me). But I'll also tell you, it's fun to watch your classmates advance. And it's not bad on the outside. Many times, it can be much better.

Back to that service thing.... when I got out I went to a PR firm, spent time on a DHS contract. I hated it. I felt like I was trying to justify our contract's existence instead of working for the taxpayer (although this agency was fee-funded). There was also a division between the feds and the contractors (similar to the division between uniformed military and civilian employees). In less than a year I went from the PR firm to a regulator in the private sector regulator. It felt more like service and as a staff member I was part of the team instead of a hired hand. After about three years I left for a federal job and I've been there for almost five years. I get the satisfaction of serving, being part of a smart team, and enjoying the work.

The military years were interesting, and I value what I experienced and learned, but it's now a chapter in my life. I've been out of the military now longer than I was in (including academy time). In comparing my experiences with other past CG coworkers, I think coming from an academy makes that chapter feel more important. A significant part of your growing happened in uniform, from freshman year of college until you separate or retire. It's not just a job after college, but an extension of it and a bigger part of your early adult life.

So, stay in for life? Great. Leave after five years (five and dive)? That's great too. Do what's best for you, and eventually your family (and having kids can change your priorities pretty quick).

shiner said:

The decision to stay or go is very personal and often flavored by your experiences during those 5 years. The rear view mirror of regret is then flavored by how life went AFTER you made the choice to depart and is the classic dilemma of the road not taken and FOMO. Did the assumptions you made about the alternate choice pan out?

I would say in my own case, I made faulty assumptions about the private sector that did not play out as anticipated. It could be the game -- or more likely it could be the player. Much of my experience is related to the small-business direction I selected coming out of the military. I recognized the error of my ways quite early, but could not return because of larger force reduction initiatives at the time. In all fairness, there were people in my life tried to point out the benefits of remaining in the AF. In retrospect, I was not listening because the grass appeared to be far far greener in the civilian sector.

In the end, we make big kid choices that have rewards as well as consequences. We get one chance at this game, and the rear windshield is far more clear than the front windshield on the rocketship we fly during our limited time here.

For some, they were never a fit for the discipline and process orientation required from a military lifestyle and I have to think there is no remorse for separating after 5 years of service for those in that category.

For others who enjoy the camaraderie, common goals, common struggle, order and discipline, clear growth plan, achievement mindset, etc... it is often something that cannot be found in other professions. Often, as a ~27 year old human, you don't fully know yourself as well as you do as a ~40 year old human. Perspective shapes what you value and if you are able to learn this about yourself sooner, you will often make better longer ranging decisions that align with your true values.

Everything I wrote above only answers part of your question -- and again, the answers vary SO WIDELY based on each individual's circumstances and background. As for reasons to stay or go, one reason to stay would be resume builder. Military officers are asked to do far more than civilian counterparts at a much earlier age. The longer one is in the military system, the more responsibility they are asked to take on. There are some examples within structured corporate managerial training programs within the civilian sector, but it is not the norm.

An example that hit me the other day was seeing a job posting ($400K/year role) that asked two key filtering questions:
1) What is/was the largest team you have led or managed?
2) What is/was the largest budget you have been responsible for?

Within the civilian sector, large teams and large budget are possible, but not as plentiful as a mid-to-senior military officer. If you consider a 20 year military officer who is an O5 or O6, they would likely run a 200+ person organization if not into the thousands. Their budget would be in the 10's to 100's of millions of dollars. With a high degree of certainty, the person who stayed in the military longer would have better resume bullets in these areas than the grad who got out as a Junior Military Officer and went the typical civilian manager path. Yes, there are other criteria for a role like this, but I point out these two criteria as one example of why someone may opt to stay in the military to build a resume in anticipation of a second career outside of the military.

Click to expand...

This reply was beautiful, thank you.

I did 5 years. I never had really set a timeline for myself when I graduated USNA and honestly thought I would do more than 5 years. Well after several years constantly deployed and being told I was going right back and my B Billet (Shore Tour) was being delayed a year, I knew it was time to drop my papers. I was not mentally or emotionally ready to go back after a really tough tour. I knew it was the right time as I was exhausted in every aspect. I did consider the reserves, but during that time it was nearly a guarantee to be activated and go right back, so I passed and took the risk that I could possibly be activated from the IRR (it was happening during this time).

I really had no idea what I wanted to do. I had started down the federal law enforcement path and they can take a long time. So in the meantime I went to DC and worked as a Defense Contractor for the USMC. I kept moving along in the Federal Law Enforcement hiring process, then it would be halted. Then it was completely revamped, then it was paused, then frozen... it happened for years. In the meantime I explored some local law enforcement options and even law school... but, I passed on all them. During this time I was thriving in my job and there were parts I really enjoyed. I worked daily with and for Marines, traveled to units and did some cool things. After a decade or so I decided it was time for a change of scenery. I wanted to do something different and move. I did move and found a wonderful company. I work for a very large company now, Fortune 50ish, etc. I was terrified I would just be a number at this large company and lost in the system. I have never had better leadership, transparency or investment in me as an employee and a human. My work life balance is also so much better. Alot is demanded of me, but that is what I signed up for. I did initially take a few steps back career wise to make this move, but it has paid off in every way. The work is fulfilling and we have a very strong company culture which really helps. I still led more people in the USMC than I do today, but my sphere of influence, relationships with vendors, driving the roadmap for the company and many other things are much larger. Making decisions in the middle of combat... I will never touch that level of split second complexity and responsibility that I did while in the middle of Iraq and Afghanistan, but the ability to take in massive amounts of data, develop courses of action, risks, and many other things has served me well in my decision making process today. Overall I make alot more complex decisions on a daily basis today than I did in the USMC (except when out doing an op).

I tell my friends the same thing that are getting out. What are your must haves in a job? Is it location, pay, benefits, work from home, flexibility, vacation time, a certain type of job, culture. Once you narrow those things down that will drive alot of what comes next. Also fully understand what your military pay is and how it would change in the civilian world. Not paying state tax, BAH is tax free, how much is health insurance in the offer, 401k benefits, are all things to consider. I have had friends who said they were only going to live in one spot... well that means you have what is available in that town or a WFH position. I have a few friends that could care less what they did as long as they made X. Living in large cities can often drive higher pay, but cost of living is not cheap. The further you live from said city, sure it gets cheaper, but that means less time at home. All factors you may need to consider in your job and family. If you have a family then these things get even more complex with school districts. Finding fulfillment in your job can be tough. I always tell my friends any job is what you make of it. They will give you a position description and its up to you what you do with it. Sometimes a job will provide fulfillment and others will not. In that case, finding something outside of work with volunteering, vets groups, etc. can be a huge help. Do I believe the grass is greener since I got out? No, I think it's a different shade. It ultimately comes down to what shade of grass is best for you (and your family if you have one).

It’s a tough one. I’ve seen people who say they are getting out when their ADSO is done... for thirty plus years.
I’ve also seen some who were “career” in the basic course but then left as soon as their commitment was up.
Some who leave don’t look back.
Some leave and continue serving in the Reserves or Guard.
Some even return to active duty.
Much depends on your assignments. One guy in particular who I know and have mentioned before said he was getting out as soon as his flight school commitment was up. He said the same thing as a senior captain... but then they gave him a cool job so he stayed in just for that, but then he was getting out. Then he was given another cool job... and now he has pinned on his second star.
Leaving can be tough. You really kind of live in a bubble when you’re in the military. It’s a different society. That’s why many who leave will be drawn to professions where there are fellow veterans.