(MONEY Magazine) – In the summer of 2001, Bob and Trisha Leseman were living happily in northern Italy, newlyweds on a romantic adventure courtesy of the U.S. Army's 173rd Airborne Brigade. It wasn't always easy for Trisha, 29, when her husband went away for weeks at a time to parachute from airplanes during training exercises, leaving her alone to care for their one-year-old son Alex. But when Bob came home, the family would take bike rides and ski trips or just stroll the cobblestone streets near their apartment. "It was a phenomenal experience," Bob recalls, "the high point of our Army career."

Bob had joined seven years earlier as a confused 20-year-old looking for discipline and direction, but he now realized the military was also a great career. He enjoyed ironclad job security, a salary that would reach $78,000 as he rose from private to captain, full medical benefits and a lucrative pension promising 50% of his salary after 20 years. Surprisingly, being a soldier didn't even seem like a particularly dangerous job. "I thought they were out there playing G.I. Joe," Trisha says. "It was like they were camping."

Then the Twin Towers fell. "That's when it hit me," Trisha says. "He could really go to war." Bob was not deployed to Afghanistan, but in November of 2003, eight months after the United States invaded Iraq, his battalion was sent over to help quell uprisings. His main job as head of a tactical operations team was to plan raids on the hotbeds of insurgency--Samarra, Mosul and Najaf--but he also often found himself on the ground with an M-4 rifle in his hand. "We had firefights right away in Samarra," he says, then suddenly stops himself with a glance at Trisha. Even today he still hasn't shared the details.

Military families develop various techniques for living through war, but even more difficult is keeping a marriage together during the long periods of separation. Bob was in Iraq for a year, returning only for two weeks, and he and Trisha never felt so far apart as when he missed the birth of their second child, Aidan, in March of 2004.

Most people don't have to endure the risks of a military life, but the crisis the Lesemans reached was not unlike what many families face when the demands of a career become too much to bear. When Bob finally came home to Olympia, Wash. in November 2004, he knew this war would not end soon. Within 18 months he would have to go back to Iraq.

In May, Bob told his superiors he was resigning. His battalion commander was shocked. Bob had recently been promoted and could have retired with his pension in just eight years. His bosses tried to talk him out of it, but Bob held firm. In September he landed a plum job in Woodbridge, Va. as business development manager for Med-Eng, a Canadian company that makes body armor and other explosion-protection devices.

Med-Eng offered a salary of $80,000, but now Bob and Trisha face a dizzying array of new questions on subjects ranging from housing to retirement. Suddenly, every decision in their life outside of Uncle Sam's protective embrace seems fraught with complications: Should they buy a house or rent? How are they going to pay for the advanced degrees they want? What will they do about retirement savings now that Bob doesn't have his Army pension?

"People asked me during job interviews, 'What's the biggest risk you ever took in your life?'" Bob says. "I always said, hands down, it was not jumping out of airplanes, not almost getting blown up in Iraq, but deciding to leave the Army."

When Bob was 20, still living with his parents in Waldorf, Md., he had almost no discipline. He managed to get an associate degree in engineering from a local community college but was having trouble juggling taking classes toward a B.S. at the University of Maryland and selling carpet for Sears. When his grades slipped and his parents cut back on subsidizing his education, Bob decided to fulfill his longstanding dream of joining the military.

Marine recruiters glanced at his high engineering test scores and suggested he become an aircraft mechanic. His father, a 20-year Navy veteran, encouraged him to work on a submarine. But when Bob went to Andrews Air Force Base and watched infantrymen drop out of the sky in parachutes, he instantly knew he wanted to be as proud and as tough as an Army Airborne Ranger.

After two years of toughening, he decided to go back to school on an ROTC scholarship. He was about to enroll at North Carolina State when recruiters from the University of Tampa called. It was a fateful moment: Tampa is where Bob met Trisha at a crew-team practice.

Trisha, studying to be a teacher, was instantly smitten. They dated through Bob's two years at Tampa, his assignment to Fort Benning, Ga. and his Ranger training. In the spring of 1999, when Bob was assigned to Italy, he proposed.

By then the undisciplined kid had grown into a methodical, organized soldier. As he moved up the ranks, making captain in 2001, Bob found he had a gift for creating detailed battle plans. This talent made him ideally suited to organizing family trips, even if his methods could sometimes drive Trisha a little crazy. Like when they went to Paris. "'Okay, the Louvre!'" Trisha says, imitating the character she calls Capt. Bob barking orders. "'You're stalling! Let's go! Now Versailles! Check!'" She laughs. "I was like, 'Can we at least go inside?'"

By the time he was summoned to Iraq in 2003, Bob was training with a light unit called the Stryker Brigade. During a raid in Tal Afar in September of 2004, an Army helicopter was shot down. When Bob and his troops tried to recover the aircraft, they were set upon by about 200 enemy fighters, which led to a bloody two-week offensive. The insurgents could not match the Army's firepower--"We tore the place up," Bob recalls--but such incidents made him realize how organized and well-armed the enemy was. The U.S., he could see, was going to be there for a while.

Meanwhile, Trisha was missing Bob beyond measure--particularly during life-changing events like Aidan's birth, which Bob had to learn about by e-mail. He was so angry about being far away that he didn't even tell anyone the good news. "I started to wonder if I really wanted to do this for the rest of my life," he says. During his two-week trip home in July of 2004, Bob was leaning toward retiring, but upon his return to Iraq, his battalion commander pulled him aside and said, "We're going to give you a command."

The promotion was a tremendous milestone, forcing Bob to reconsider. Also, he couldn't ignore the military's economic incentives, including a $1,500 monthly housing allowance. Meanwhile, his commander and peers peppered him with the same questions he'd already been asking himself: What will you do? Your last job was selling carpet! "All I knew is that I didn't want to be in the Army anymore." At the age of 32, he says, "I'd just lost my lust for being cold, wet, hungry, tired and away from my family."

After giving his notice in May, Bob threw himself into job hunting with the same methodical zeal he had used to plan attacks. He was about to accept an offer from Home Depot for a supervisory position when he decided to contact the military recruiting firm Bradley-Morris, which told him about Med-Eng. The position required a move to Northern Virginia but paid $80,000 and would let him use his military experience to sell Army and Marine procurement officers on Med-Eng's devices. He grabbed it.

In early September, as Bob reached his final days in the Army, the Lesemans felt some trepidation. Bob found that he had very little patience with his sons, especially when they started to scream. The children were also confused. Aidan treated him like a stranger, and Alex went right to Mom whenever he needed anything. "This has been a stressful time for all of us," says Trisha.

Financially, the family got a break when they sold their house in Olympia for $240,000, a profit of $49,000 after closing costs. After spending about $10,000 to move and buy suits for Bob, they paid off loans on their two cars, leaving Trisha's $18,000 student loan at 5% interest as their only debt.

But by the time they moved to the Washington, D.C. area, they were faced with a vexing series of questions: Should they have saved part of that profit for a down payment on a house? Does it even make sense to buy a house for upwards of $400,000? Both Bob and Trisha want to pursue master's degrees, but can they afford it? With only $18,000 saved for retirement, they know they're behind.

The Advice

Financial planner Sandra Diamond of West Financial Services in McLean, Va. offered to help the Lesemans. Diamond has experience with such transitions--her husband is a Navy commander who left active duty in 1996 to become a reservist. Here is what she suggests.

• PUT OFF BUYING A HOUSE The Lesemans were on the verge of buying a $425,000 house in Fredericksburg, Va., financing even the 20% down payment, but decided against it at the last minute. A wise move, Diamond says. Their $2,700 mortgage payment would have been a full $1,000 more than the $1,695 a month they pay to rent a three-bedroom townhouse.

• BUILD A CASH CUSHION The biggest shock when a family leaves the military is the discovery of how many freebies they took for granted, says Diamond. "It's very hard to budget at first because you don't realize all those expenses are there until you actually have to start paying them." To cushion the blow of unexpected charges, the Lesemans should build up their savings to $13,000, or about three months' living expenses.

• SEND TRISHA TO SCHOOL Bob and Trisha would eventually like to own a home, but right now a top priority is graduate school. One of Bob's biggest concerns about leaving the military is losing job security, and he wants to stay competitive by getting his M.B.A. at an elite university like Georgetown. Trisha also wants to get a master's degree so she can teach. Who should go to school first?

Tuition for Bob at a top business school would cost $60,000 to $80,000, only about $7,000 of which would be covered by the G.I. Bill. Because Trisha's education would be much cheaper--$2,000 to $4,000 a year part time--she should enroll first and then get a teaching job to help pay for Bob's schooling.

• MAINTAIN A HABIT OF SAVING Right now the Lesemans have only $18,000 in a retirement plan, and they are saving just $50 a month in 529 plans for Alex and Aidan. A hundred dollars a month won't make much of a dent in either their retirement or college needs, but Diamond wants to keep them in the habit of saving and suggests they invest in a Roth IRA instead of 529s. That will give them the flexibility to tap the account for either retirement or college. (You can make penalty-free withdrawals from a Roth for college, though you'll owe taxes on the earnings if you're below retirement age.)

Ideally, graduate degrees for Trisha and Bob will result in an income spike that will let them save more. "It's more important to invest in our education than to put all that money toward retirement and find out five years from now that our careers have stalled," says Bob.

In the meantime, Capt. Bob is trying to adjust. He wakes up at 5 a.m. wondering how to pass the time before work. And he's restless around the house. "It's literally a physical challenge for him to sit still for a few minutes, just to sit on the floor and play with the boys," says Trisha. "We're still so new at this."

In a few years Bob could try to make his sons understand why he had to be away for so long by telling war stories, but he's not that kind of guy. "I don't consider myself a hero or anything like that," he says. Someday, when they're running down the soccer field and look over to see their dad cheering them on, Alex and Aidan might disagree.

The Bottom Line

Except for a student loan, the Lesemans are debt-free. But they need a larger emergency fund and more retirement savings.