Free agency is supposed to be a glorious time. If you had a halfway decent year and the general opinion is that you still have plenty to offer as a big league player, this could be your windfall, your golden parachute.

Jimmy Rollins, you are here. And I know a little bit about where "here" is located.

Jimmy Rollins stole more than 30 bases for the ninth time in his career in 2011. Howard Smith/US Presswire

For Rollins, a free agent who was offered arbitration Wednesday and has until Nov. 30 to accept, the challenge is how to weigh his options. Should the shortstop stay in Philadelphia, he has an opportunity to close out an entire career with one organization, an achievement that is next to impossible these days. Should he go, things will never be the same in Philadelphia. It would be the end of an era, and then it would come down to how the Philly public perceives his exit.

In between these two possibilities are the contract terms, the fine lines of what makes the deal. It can be years, money, incentives, bonuses. There will be some hair-splitting. So how does a player decide?

My first year of free agency came after the 2002 season. It was a tough year because I lost my father the last game of the season and I was coming off a year that marked the first time in my life that I sat on the bench for an extended period of time. I knew free agency was not going to be the final deal to push me into retirement. I was roughly the same age as Rollins is now.

I had a lot of priorities swirling in my head. I was playing for the team I loved as a kid, I was playing in the town of my alma mater, I had a house in the suburbs of Philadelphia, and my mother was less than a two-hour drive from the stadium.

There were not many reasons for me to leave. And because my season put me in a disadvantaged position that suggested I would be receiving utility outfielder offers, I didn't think one deal would blow any other deal out of the water.

Rollins probably will get at least one deal that will stand out from the rest should a team bet on him for the long term. The only problem would be if that deal comes from a team other than the Phillies.

So what should Rollins do? Does he leave the city that he has played for his entire career? Where he won a championship and an MVP award? Where he brought the swagger back to town? What will it take for him to go? More years? More money?

When some of the questions entered my mind in 2002, I called my mentor, former Phillies great Garry Maddox. He had built a wonderful life after the game. He owned his own business selling office furniture. He had stayed in Philadelphia after getting an MBA and was now developing the many relationships he made during his playing career. When I told him I was weighing options that would have me leaving Philadelphia, he was concerned.

His concern came from having the experience of transitioning from the game. He understood that the big picture was important and that any player who has had a long-standing tenure in one city could transfer those relationships into the next phase of his life. When you leave, you break up that continuity. You interrupt that love and connection with a city. As he pointed out, even the smallest break-up can hurt the future.

My issue with accepting the Philly offer as the "only and best" offer by default was that I saw myself as only a ballplayer at the moment, even with other options to lean on. So the most important factor in my free-agent deal was where would I get a shot to play every day. I did not want to be Marlon Byrd's valet, no matter how much I was excited to see him succeed. I thought I had more time on the clock as a starter, and I didn't want to hit the accelerate button to make it tick faster.

Maddox appreciated my will to bet on myself as a player and ultimately took me out on the town to ask Phillies fans for their opinions. He made the point very clearly that I would have post-career opportunities in Philadelphia like no other place, as soon as I was ready. I had a good time talking to fans, especially hearing Garry create hypothetical stories for people to put themselves into my shoes.

He did not bash my leaning toward an offer from Texas. But he thought it was a roll of the dice and I would have to accept that I may not have the same open door when I got back from Texas as I did that same night on the town. I accepted that possibility.

When I look at what Rollins is considering, I imagine it is much like what I was dealing with, but many times over. He may still get that lucrative deal from his home team, yet it may not be the best deal on the table for a variety of reasons personal to Jimmy. Then if he turns down a sweet hometown deal that later becomes public knowledge, he may lose political capital in the town he helped make a champion again.

I suppose I owe Jimmy a call in order to talk to him like Maddox talked to me. I would say some of the same things that Maddox said to me. I would let him know that I did go to Texas, I did get to play every day, and I got my swagger back in July of that year after hitting close to .400. That turned out to be an important year as I bought more time in the game and I went to the only postseason of my career. Although I wouldn't trade that experience for the world, I ended up coming back to Philadelphia the next season. And even though it wasn't a good statistical year, I felt like I was home again.

I will also repeat the clichè that money isn't everything. My contract with Texas had the worst incentives out of everything else I was offered, but I needed to regroup after losing my father and go far away from home. I needed to walk into spring training as the guy to beat out of a center field job. That trumped the paycheck for me, and Rollins needs to think about what trumps it for him.

Either way, he has to make the best choice for what is important in his life right now, even though the future will be his world very soon. Philadelphia certainly has the intangibles, so all things being equal, the Phillies have the edge. But it still will come down to questions that only Jimmy Rollins can answer. And in the end, that is everything.

Doug Glanville, who earned a degree in systems engineering from the University of Pennsylvania, played nine major league seasons with the Cubs, Phillies and Rangers. He serves on the board of Athletes Against Drugs and on the board of the MLB Players Alumni Association. His book, "The Game from Where I Stand," was released in May 2010. Click here to buy it in paperback on Amazon.com. Follow him on Twitter: @dougglanville