May 30

Post-Military Career Risks: Are You Ready?

Choosing the right path for your post-military career is a balancing act between many factors, including, but not limited to, your: interests, talents, financial needs, aversion to risk, family considerations, and the level of effort you are willing to put forward. Many veterans go back to school to pursue another dream job and some start their own sdvosb.

All of these factors came into play for Lisa Wolford, a Marine Corps veteran, when she decided to launch her own small business in 1997. I asked Lisa, from her vantage point as President and CEO of Constellation West,  to share some of the most important lessons she has learned along the way:Lisa Wolford's Headshot - Red Suit

VSB:   While risk was an inevitable part of work while on active duty, many veterans may be uncertain about taking the risk to start their own company in civilian life. What made you decide to take that leap?

Wolford: When I started my firm, I worked 100% billing directly to customers for my technical expertise.  At the time, 19 years ago, I was an architect for Client/Server technology.  I was also a single mother of two children and understood the need to plan ahead. I knew I needed to save before starting the company and would need to save even more, in order to have a backup plan for a rainy day. I think veterans who are interested in starting their own business need to assess their comfort level with risk and overestimate what they will need in startup funds.  Timing and understanding the business environment, which includes technical acumen, are essential to determining when and where to position yourself in business.

Sometimes it is necessary to create your own opportunity.  A basic question you must answer is, “how much risk can you tolerate?”  A veteran, particularly with a family, should do the necessary planning to ensure that the family’s needs will be covered, either through a military pension, if the veteran has one, through savings, or through a spouse’s employment.

The level and type of stress you will experience from owning and managing a business is different from being an employee.  The time it takes to become profitable may be years.  If you are honest with yourself, and the ones closest to you who may be affected by your desire to start and run a business, you will be better prepared mentally and emotionally to survive unknown challenges in the early years of doing business.  An honest risk assessment related to finances is an important activity you can undertake prior to finalizing your commitment.

There are franchise opportunities that are open to veterans that can be quite successful, but may require some upfront investment. Some veterans choose to start a company as a part time endeavor which is a fine way to start out.  Not everyone is going to have the same solution or strategy; individual goals and family situations will usually inform the approach to risk.

The bottomline that made me decide to take the leap was that I had the technical and business capability appropriate to the business environment. To make a better life for my family for the long term, I decided the time was right to go out on my own.

VSB: You describe Constellation West employees as individuals with the following characteristics: Constant learners, committed, loyal, hard-working, adaptable, principled, problem-solvers, integrity, passionate about mission success and more. This is a good description of many military leaders preparing to leave active duty. As they compete with each other, and with their civilian counterparts for a great job in the private sector, how can transitioning service members further distinguish themselves to help them stand out from their competition?

Wolford: I want our veterans to remember that they are very special breed.  If they don’t get an offer from a firm that they would have liked to join, maybe that was a huge favor to them.  There are firms that will welcome a veteran and be excited to have them on their team.  In my firm,  about 42% of my employees are veterans.  We understand the value that they bring to the table.

Veterans should also understand that leadership in private industry can be different that in the military. In all cases, you must adapt and make yourself relevant.  Whether you’re an E-1 or O-10, you must adapt your skill set to remain relevant in a rapidly changing business environment.  Skills learned 2 years ago, let alone 20 years ago, may not suffice in today’s market.

Become a constant learner.  Whether you get advanced degrees, technical certifications, or just-in-time training, you further distinguish yourself by providing meaningful solutions that can be implemented in a timely and cost-appropriate manner.  Keep your knowledge up to date with the audience (prospective employers, co-workers, teammates) and be able to communicate important and key elements to decision makers.  You distinguish yourself by being relevant.

Whether you’re an E-1 or O-10, you must adapt your skill set to remain relevant in a rapidly changing business environment.

VSB: Leaving behind a team and structure so integral to military service can be among the greatest challenges in adapting to the civilian workplace. What advice would you give to help military leaders in transition reframe their thinking about how teams form and operate in the private sector?

Wolford: One of the best skills I have honed is to leverage the strengths of others.  That means I have to listen, observe, ask questions, and challenge people.  The best solution does not always come from the first or loudest to speak.  I leverage the strength of those individuals or companies who can fill gaps in my understanding of technology, business, and the customer.

As a transitioning military leader, the approach you used in military may, or may not, work in the private sector.  Leave your rank at the door.  You do not need your military rank on your business card.  What you need is information that will allow you to assist someone else in meeting his or her need.  He, or she, will be looking for someone who listens, understands and can present a feasible solution, both technically and fiscally.

You do not need your military rank on your business card.  What you need is information that will allow you to assist someone else in meeting his or her need.

Finally, remember your potential employer, teammate, and customers have choices; they want to work with someone they like or with whom they can get along. Know what your customer needs and, if you can, meet that need; if you cannot meet that need, do not enter into a relationship or contract when you are in a weak position.  Know what you cannot change; have the courage to change the things you can; and the wisdom to know the difference. Leverage your strengths and the strengths of others.

VSB: Any other advice you’d like to share?

Wolford: Sometimes you need to reinvent yourself; that often starts with attitude, a good support system that can deliver effective feedback, and the ability to change your thinking.  Leverage the strengths of others, along with your own strengths, to make a meaningful and positive difference in the business environment and in the lives of others.  Get some informal mentors – you can have more than one; and never stop learning.


Lisa Wolford is President and CEO of Constellation West, founding the company in 1997. As a service-disabled, veteran-owned, woman-owned, small business, her company is focused on delivering top cyber security, agile development, and IT systems solutions to help federal agencies tackle their toughest challenges.


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