Retirement: The subject all players think about but none like to talk about. It’s the specter that looms over practice courts and locker rooms, the shadow that grows darker as the years tick by and the injuries mount.

For many tennis players, the financial challenges of life after professional tennis can be an intimidating proposition. What to do with the next three decades? Where can you find a career that is interesting, challenging, and will earn you enough coin to live out your days in comfort?

We spoke with five retired American male tennis players who are trying to navigate those choppy waters. All are well-known in tennis circles, had successful careers on the court, and are now trying to adjust to life after professional tennis.

Chris Woodruff

Highest Career Ranking: 29
Last Professional Match: March 2002
Resides in: Knoxville, Tennessee

Career Highlights:

—Playing on 2000 Davis Cup Team in Zimbabwe. Won fifth and deciding tie against Wayne Black. “I was a last minute replacement for Pete (Sampras) and thrown into this crazy environment. But I came through. A great memory for me.”

—Winning Canadian Open in 1997 (ATP Masters Series event).

—Winning title in Newport, Rhode Island in 1999. “This was after my knee injury. Was important for me to claw my way back.”

Burnt out and slightly hobbled, Woodruff left the tour in 2002 with no real game plan in mind, other than reenrolling at the University of Tennessee. “I figured I would go back to school, get my degree, and see where that took me.”

He wouldn’t go far. Woodruff, who won the national singles championship at Tennessee in 1993, was immediately asked to be a volunteer assistant coach. He was then promoted to Associate Head Coach in 2006.

“It’s been ten years in the making, but it’s been nothing but a positive for me. I get to work with these top young players every day and teach them what I know: How to construct a point, how to get match tough, how to stay focused on the court.”

Woodruff was named National Assistant Coach of the Year in 2013 by the Intercollegiate Tennis Association. He is married with two sons and a daughter.

As for the future, Woodruff is focused strictly on the near term. “The season is about to pick up again, we have a good team (currently ranked No. 6 in the nation), and that’s all I’m focused on right now.”

Taylor Dent

Highest Career Ranking: 21
Last Professional Match: November 2010
Resides in: Newport Beach, California

Career Highlights:

—Winning first title in Newport in 2002. “My Dad and I (former Australian touring pro Phil Dent) became the first father and son to win a title on the tour.”

—Playing Andre Agassi on Centre Court at Wimbledon in 2000. Dent lost in four sets.

—Winning a five-setter at U.S. Open in 2009 against Ivan Navarro. “I pulled it out on the Grandstand, 11-9 in the fifth-set tiebreaker. It was a classic. Packed court. Great environment.”

When Dent retired in 2010, it wasn’t his much-maligned back that was giving him trouble. It was the time away from home.

“Once I became a father, my whole perspective changed. I still loved to compete, but being away from home for weeks at a time became a problem. I loved the tennis and the training and the tournaments, but the travel and the grind really wore me out.”

Dent knew he wanted to stay in tennis, and felt he had a lot to give back to the game. With the help of his father, well-known teaching pro Phil Dent, the Dent Tennis Academy was born. Located in Fountain Valley, California, the academy is focused on working with advanced kids of all ages.

“Being a tennis pro is a selfish life. It was all about me, me, me. My training, my diet, my practicing, my tournaments. Now, that’s all changed. Being a dad and a coach is totally different. Now, it’s about my kids or the player I’m working with. That different mindset took some getting used to. “

Dent is married and has two children. He has also done some television analysis for the Tennis Channel at the U.S. Open.

For now, Dent is happy with how his academy is progressing. He is also working with top American junior Jared Donaldson, who has been invited to train with Roger Federer in Dubai for several weeks in December. Dent will be traveling with him.

Jan-Michael Gambill

Highest Career Ranking: 14
Last Professional Match: September 2010
Resides in: Kailua-Kona, Hawaii

Career Highlights:

—Wins over three of the best players of all time: Pete Sampras, Roger Federer, and Andre Agassi. “Not many players get to say that.”

—Being widely acknowledged as one of the fittest guys on the tour.

—Reaching final of the Miami Masters in 2002.

Gambill wants to clarify one point: “I didn’t actually retire. I just stopped playing because of injuries.”

That is an important distinction for the 36-year-old American, who still feels the pangs of a tennis career unfinished.

“I still miss it. The competition, the training, even the travel. I look at Tommy Haas (just a year younger and currently ranked No. 12 in the world), at some of the guys playing doubles into their forties, and I wonder.”

But then Gambill catches himself. “First, I just don’t have the doubles-player mindset. It’s not natural for me. And the thought of playing Futures and Challengers and grinding out ranking points…it’s just not all that appealing right now.”

As he adjusted to life after professional tennis, Gambill dabbled in modeling, kept his game sharp with World TeamTennis, and even ran his own small tennis academy on the big island of Hawaii. But it wasn’t until he began coaching American Coco Vandeweghe in 2011 that he found a possible post-tour calling.

“We split a few months ago, and we’re still good friends. But I think we did some good things while we were together. It was a good experience for me, I really enjoyed it. The training, the traveling, the preparation for tournaments.”

“The women’s tour was a little different than what I was used to, especially off the court. I’d be open to coaching on either tour right now, but my preference would be the men’s.”

Gambill will be making his debut on the Champions Tour next February, joining Andy Roddick and Goran Ivanisevic in Delray Beach.

As for the future?

“There are a lot of possibilities out there for me right now,” Gambill said.

Which is just how he likes it.

Jeff Tarango

Highest Career Singles Ranking: 42
Highest Career Doubles Ranking: 10
Last Professional (Singles) Match: February 2002
Resides in: Manhattan Beach, California

Career Highlights:

—Qualifying for the 2000 United States Olympic Team in Sydney, Australia.

—Reaching the doubles final at Roland Garros in 1999 with partner Goran Ivanisevic. “Even though we lost, it was on the biggest stage.”

—Upsetting then-No. 10 Marcelo Rios in the second round of the 1996 U.S. Open on the Grandstand Court. “An electric atmosphere.”

With his street smarts and Stanford education, Tarango wasn’t just going to stick to tennis. After his retirement in 2003 (and again in 2009, after briefly sticking his toe back in the doubles water) Tarango drifted to the private sector, working at AON Corporation and then also in the real estate market in his home turf of Manhattan Beach, California.

“I’d grown tired of the constant travel. The living out of a suitcase. I loved the tournaments and the friends, but it got to be too much. And too tough on my family.”

While the private sector was rewarding in its own, unique way, neither job quite had the pull of tennis.

Around the same time, Tarango was offered the chance to do some television work, and with his gift for gab and astute analysis, he parlayed that into a regular gig, now commentating at the Grand Slams for both DirecTV and ESPN. “It’s ideal for me and my family. I’m away, but only a few times a year.”

Tarango also got involved in the politics and inner workings of professional tennis, both as a six-year member of the Davis Cup/Federation Cup Oversight Committee, and as a Vice-Chair of the Athletes Advisory Council for the United States Olympic Committee. “After 15 years on the tour, this was my chance to give back to the USTA.”

Finally, Tarango was a volunteer assistant coach with the USC men’s tennis team for two seasons, each resulting in a Trojan national championship. “That was a great experience. I enjoyed the team environment, and working with kids that age and that level. “

For now, Tarango is happy with his current routine: Being a father to his five kids, offering insight and analysis at the Grand Slams, and coaching a handful of talented kids locally.

Vince Spadea

Highest Career Ranking: 18
Last Professional Match: July 2010
Resides in: Beverly Hills, California

Career Highlights:

—Beating Andre Agassi in the fourth round of the Australian Open in 1999. “Definitely my biggest win.”

—Winning the ATP tournament in Scottsdale in 2004. “I’d made four other finals, but this was my first and only title.”

—Reaching the semifinals at Indian Wells in 2003 and Miami in 2004.

As his 17th year on the tour wore on, Spadea had very little desire to get ready for the 18th.

“It was getting tougher and tougher to keep the focus. At 36 years old, when it came to the diet and training, it was hard to keep the discipline I had before. I just felt it was time.”

Leaving the game and heading off to the unknown, Spadea didn’t just have a plan—he had multiple plans.

“I knew I wanted to try different things, and I knew I wanted to reach beyond just tennis. I relocated to Los Angeles and jumped into the entertainment space. I’ve been trying my hand at a bunch of different things.”

He opened a talent management company called 6 Star Ventures, with divisions that include model and acting management, film and television production, and music.

Spadea has also kept his hands in tennis, working in Southern California with some high-level juniors and high-school aged players. “Tennis has been good to me, and I always planned on giving back to the game.”

He has produced an instructional tennis DVD titled “Play Like a Pro,” and is also designing a line of tennis clothes called—you guessed it—the Vince Spadea Collection.

“Like I said, I wanted to reach beyond just tennis.”