Former military pilot Chris Holladay never expected to be working in the financial services industry when he was in the cockpit of an F-14 Tomcat flying missions for the Navy. Even after his active service came to an end in 2000 and Holladay went to fly for United Airlines, becoming a financial advisor wasn’t part of the plan.

But after the airline industry laid off a chunk of workers in the wake of the September 11, 2001, terrorist attacks, Holladay found himself needing a new plan.

“I had to figure out what I wanted to do when I grew up, instead of flying airplanes,” Holladay, vice president of investments at Waterfront Advisory Group of Raymond James, said with a laugh.

Chris Holladay, former Navy pilot, now works as advisor.
Chris Holladay, former Navy pilot, now works as advisor.


Thinking back on conversations he’d had with some of his Navy peers about the stock market — admitting that at the time he really didn’t understand any of it — Holladay says he eventually realized how important it was and became fascinated by the impact it has on people’s lives.

Other advisors have followed a similar career path. For former Marine Rob Smith of Edward Jones, for instance, wealth management was the right choice for his post-service career. He says numbers and people are his two favorite things. And a “natural affinity” for the industry is what led former Coast Guard captain Jeff Farrar of Dynasty-affiliated firm Procyon Partners to become a planner.

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After having housing and medical costs paid by the military, members tend to rely too much on their branch of service to take care of them in retirement too.

Becoming advisors allowed these veterans to continue helping people — including their fellow service members — which is what they say drives them every day. Each of these planners works with a variety of investors, but included in each of their client bases are active and retired military personnel.

This is a group of people that can be underserviced and even preyed upon within wealth management.

Creating a financial plan for active and retired members of the military can present advisors with a host of complex challenges they may not face with other clients. Service members’ unique lifestyles require planning for variety of scenarios including constant movement, the transition back to civilian life and retirement.

Basic planning starts the same way as any other client, Farrar says. That includes figuring out where the client is at the moment, what their future goals are and what obstacles may show up along the way.

Some of the more complex planning needs for military clients have to do with their ever-changing lifestyles. A member of the military may find themselves changing locations and jobs every few years.

“Their life is not very static,” Farrar says. “So they need to have some flexibility. So if they can have some things in their life which don’t have to change like an advisor who’s looking out over their strategy that makes it easy. They might have to change their house, but they don’t have to change that relationship.”

A couple of mistakes military clients may make that advisors should be aware of and correct is their tendency to think in general terms and rely too much on their branch of service to take care of them.

“You know it gives them their pay, housing, medical and pension,” Farrar says. “They tend to rely heavily on it and so what I have to do is help them think about, if they’re going to go 20 years and retire, what life looks like after that when they have to take a little more care of themselves.”

This planning strategy comes into play a lot when clients are making the transition out of the military and back to civilian life. For however long a client serves they always know what they are doing and where they are going and there is always someone there telling them what to do. This change can be intimidating, so when possible Holladay says the best thing is to begin conversations about life after the military as early as possible.

“Most of the folks that I work with are pretty driven individuals,” Holladay says. “They’re very competent and they really can go out and do just about whatever they set their mind to.”

Amanda Schiavo

Amanda Schiavo is an associate editor for Financial Planning. Follow her on Twitter at @SchiavoAmanda.