One of my goals is to help service members successfully transition. Over the years, I have had a lot of conversations with our transitioning war fighters. Below you will find some of my thoughts on transitions based on these conversations. Please do recognize that there are a lot of conflicting views on this topic and that there is not necessarily a “right answer”, but I do hope that you find these thoughts helpful.

Q: Is there a right answer as to how to transition from the military to the private sector?

A: I do not believe that there is only one right answer but there are many different perspectives. It is a good idea to solicit varying opinions and thoughts.  One method is to do “50 Cups of Coffee”.  The concept is that you offer to buy an individual a cup of coffee and while you are having coffee you have a conversation with them about their experience. Basically, it is a low stress but highly interactive informational interview. Check out this article for more information: 


Q: What type of organization should I try to get a job with?

A: I personally believe that it is better for a Veteran to initially go to a Government Contractor’s job or to target a Fortune 500 military-friendly organization.  All things held equal, larger companies have established processes that you can follow.  Furthermore, assuming that they are “military-friendly” they will understand your background and in most cases be more patient with you. This will give you some time to figure out what you really want to do without it being a huge culture shock. Also, a larger company will have more opportunities for you to grow. If you find that the specific area that you are in is not a good fit, there may be more opportunities to transfer within the organization.


Q: Why not go to a smaller and more entrepreneurial company?

A:  Please do know that I believe in small startup companies and going the entrepreneurial route.  I just know that it can be quite a culture shock especially if you are not already familiar with how the “game is played”.  I do know several folks that have been quite successful in starting up companies or who have purchased franchises. But by and large, I just think that it is less of a culture shock to go to a big company with established policies and procedures. The irony is that a Veteran is actually well suited to go the entrepreneurial route.  You have a pension and medical benefits so you do have some form of income while you are developing your business.


Q: What is a military friendly company?

A:  In my mind, a military friendly company is more of an attitude of understanding what a veteran has done and is capable of doing.  A military friendly company will understand the language issue. A military friendly company will understand some of the nuances of the body language and not be so quick to judge.  A military friendly company will give the veteran a chance to “fit” in and provide the appropriate mentoring and coaching so that the veteran can be a productive part of the team.


Q:  How do you translate a team operator/fighter pilot/assault helicopter pilot/grunt into a private sector job?

A: Unless you really do have a job that is a direct correlation to the private sector (e.g. military pilot to airline pilot), I just would not try to do a direct correlation of your military skill set into the traditional private sector. It is really the attributes and the knowledge that transfers.  The key attributes are your ability to problem solve, make decisions, and lead remote teams. Now, it would be helpful to have a defined skill set as it is easier to sell but it is not a show stopper as you can acquire them as you go along. So you can fit in a lot of different areas…what is key is what is it that you enjoy doing (what would you do for free?) and how can you monetize it. So I would figure out what is it that you like to do that is productive and then work on figuring out how to make a living from it.


Q:  Why would I want to do something for free?

A:  While you do have to make sure that you take care of your responsibilities, it would also be good to find an activity that you enjoy doing.  There are very few things better than being paid for something that you would do free. I believe that you will be happier in the long run and live a more fulfilling life.


Q:  I found a job that would be perfect for me but I do not want to live where the job is located.  What should I do?

A: Sell yourself to the hiring manager and see if you can work virtually.  The truth is that most work these days are on a virtual basis. You may go into an office, but you will VTC/telecom with folks all over the world/country. For example, during one of my engagements, I was working with a particular senior level manager. Our session ended at 3 pm (EST).  He then would get on the phone with his teams and work around the globe. He started his teleconference with Germany (11 pm), then Brazil (4 pm), then Korea (8 am). While his example is a bit extreme, it is becoming more and more commonplace. 


Q: I see this job description, do you think that I am a good match for it?

A: One of the issues with any job description is figuring out what they really want. One way to do this is to set up informational interviews to better understand the role and the requirements. I am pretty sure that most all of us have taken on an assignment with a stated role only to find out that it was different than what was written.



Q: Why is it so hard to find a job?

A: Keep in mind that the prospective organization and you as the applicant have to agree on at least three issues. First off, there has to be a slot open for you to fill.  Back in the day, Companies use to hire in advance of needs.  So it was not uncommon for an organization to hire a person for a job that was 6 months out.  That is not necessarily true today.  Another issue is that you and the organization have to agree on the pay rate.  The third issue is that you and the organization have to fit culturally.  Cultural fit is in regards to work styles, ethics, life cycles, thought processes and so forth. It is a challenge to achieve agreement on the timing, pay, and cultural fit.


Q: I am a year out from transitioning, why won’t a company hire me now or even talk to me?

A: Again, back in the day it was not uncommon for companies to hire a few months out.  But nowadays, most companies like to have a slot open and then hire into the open slot. So it is possible for you to submit your resume a few days early or a few days late.  So timing really is everything.


Q:  In the job description, they keep mentioning about needing a specialized degree like biochemistry or some other scientific field.  Is this a show stopper?

A:  You cannot be everything to everybody so it will be incumbent for you to demonstrate that you can do the job.  Where you may run into an issue is that the technical background requirement is more of a cultural issue in how the organization thinks and operates. It is like placing an Aviator in an Infantry unit. Neither is right or wrong, but they do bring different perspectives to the team and it may or may not be a good fit.  One firm I worked for wanted everyone (to include the accountants) to have an engineering background. Not so much that they would be engineering a product but because of the way that they approached problem-solving. It was more of a cultural issue.


Q:  They keep mentioning this technical degree requirement but I do not have this particular degree.  What should I do to overcome this issue if I just do not have this particular technical degree?

A: If they keep mentioning the technical degree and you do not have this particular degree you may be able to demonstrate to them that you have the technical attributes and the mindset as noted by your experience. Keep in mind that Human Resources (HR) will screen applicants out based on that criteria so you will have to network with the hiring manager. This means that you have to find the hiring manager (or team) and connect with them so that you can get past the gatekeepers.



Q:  What are your thoughts on salary and the job requirements?

A: I would compare & contrast the salary versus the requirements.  Companies will list a “thousand and one” job requirements but the “truth” is often found in the salary range that they list. For example, an organization may want a Financial Analyst. Keep in mind that a fully developed Financial Analyst that is working on Wall Street or for a Fortune 500 Company can easily make upwards to $175,000 a year. On the other hand, a Financial Analyst can also be employed at the same organization and may make $15/hour. While they both have the same title, the expectations are very different.  The same analogy can be made with the General Manager title.  A GM can make $30k to $40k a year with one organization or can make greater than $250k at another organization. Again, the job title and description can be almost identical but the truth is really held in the salary range as to what the expectations are.  


Q: This Company is listing all of these job requirements, is it possible for one individual to be able to do all of these activities?

A: Well there is such a thing as a “purple squirrel”.  This means that the person really does not exist.  I have seen job descriptions that required a licensed physician who was a Master Black Belt and had a CPA.  In my personal opinion, this is a sign that the company really does not know that they want and it may be better to pass on them.  After all, if they cannot articulate their needs how are you going to be able to meet their needs? The reality is that the company does have to realize that one person just cannot hold all of the resident knowledge on the theory and application of every single aspect of a work effort…therefore, the company does have to make sure that you are properly resourced (of course, you have to make sure of that as well). So you do have to know yourself and your skill sets (however, don’t be afraid to stretch). This is also where it is helpful to have some knowledge as to what specifically they are referencing so that you can match your experience set to the appropriate scenario.



Q:  What do you think about starting a business and going the entrepreneurial route?

A:  Personally, I like entrepreneurs.  I just know that it is not for everyone. If you do decide to go the entrepreneurial route (and I do encourage it), just make sure that your family is in agreement. Family situations do matter as there is definitely an income drop on the startup. 


Q:  Are there any safe jobs?

A: If you believe that having a corporate job is safe, it really is not. Companies hire and fire every day; they buy and sell assets (Divisions) every day.  Early in my corporate career, I was most responsible for re-engineering organizations.  Based on my experience, you are always at risk. In fact, your division can be doing great but a weakness in another part of the Company can cause your Division to be sold. One of the differences between being “fired” in the military versus the private sector is that there is no loss of income in the military…you are transferred. In the private sector, there is an immediate loss of income. So you still have to plan for that contingency (keep your skill sets high and your debts low).  Again there are no right or wrong answers in these scenarios. What is key is knowing what your definition of success is and living under your terms.


Q:  Are there any robot-proof jobs?  All I want to do is find a job that is safe so that I can retire in a few years.

A: NPR has been running a show on the robot-proof job ( so that might be a good resource to look at.  But in my mind, there is no real security.  I believe that it is best to keep your skill sets high (through continuous learning) and your debts low. If you do that, you should be good to go.



Q: What are some big picture thoughts that I should keep in mind?

A: Just realize that it is a journey and not a destination. Life will be different but you do have a lot to say as to what type of life you wish to have.