The 250 Square Foot View

In February 2005 I started at my first post-college job at Petry Media Corporation in Manhattan. The sole perk of this position, besides being gainfully employed, was the company softball team.

An athletic guy who played sports all his life, I thought I’d automatically be given a spot on the team. (What an entitled millennial I was!)

Instead, the manager and starting pitcher for the team, Marty, explained that the team was highly competitive, dating back to the 1970s, and that if I wanted a spot on the team I’d have to try out for it.

When the season started a few months later, I was given an opportunity to get into a game and show Marty that I could play. I barely passed my audition, managing four infield singles and solid defense in the field. But Marty was impressed with my speed and glove, so I had earned my spot.

After that tryout, I started on Petry’s team for 11 consecutive seasons until I recently moved from the New York area to just outside of Washington D.C.

Now, I find myself, at 34, trying out again, this time for the local softball league. There’s no such thing as a résumé or references when it comes to joining a softball league. I can regale the head of the league with stories about how I once hit four home runs in a game (leaving out the part where I committed seven errors at shortstop in the same game), or how I hold virtually every team record for the Petry Pilots (again, including most errors in a single game), or how my lifetime batting average is around .450.

But none of that matters. I’m starting from scratch. I’m just some not-that-young guy who is looking to keep the last of his competitive fire alive, meet some good people and make some friends in the process, and maybe have some fun and win some games, too.

After asking too many questions for the league commissioner, he eventually informed me that there would be an open tryout on March 12 at noon at the local field for “free agents” (i.e. prospective players without a team) like myself, and that I had the opportunity to showcase my talent (if I had any) to any of the team captains and coaches who chose to attend the tryout. If they liked what they saw they could select me from the free agent pool and add me to their rosters.

I hadn’t had to try out for a team since 2005* so I didn’t really know what to make of the situation. I had to put my feelings of entitlement and indignation aside and focus on showing these guys what I had to offer to their teams. (I also had to get used to the fact that despite my improved play at shortstop—that seven-error game was years ago, so lay off!—there was no guaranteed I’d get to play my favorite position.)

*I’ve interviewed for many jobs since 2005, which were all effectively tryouts to some degree. But sports feels a little different.

And so I went out and gave it my best without being too flashy. My defense was solid, though I didn’t get much of a chance to show off my arm. My hitting was passable for not having hit a softball since last August. All in all I gave them enough to judge me as a guy who could add value to most softball teams.

During the warm-ups, the scrimmage game that followed, and after we ended the official tryout, several coaches approached me to ask me what night I was interested in playing on (each league was assigned a night, much like the Petry Pilots had all their games on Tuesdays since, I think, the beginning of time), as well as what position I was interested in playing (and which other positions besides shortstop I would be open to). They also told me about their own teams, trying to put their own best feet forward. “We won our league last year,” or “We’re a fun group of guys,” or “Do you like burgers and beer? We’re partially sponsored by a local pub.”

I played tennis in college but had walked onto the team without being recruited by any schools, and so this feeling of someone actively pursuing me based on my athletic ability was new. None of them offered me a sports car or illicit cash in an envelope, but they were certainly jockeying with each other for the best possible players for their roster. And by the time I left I had given my contact info to four different team captains. (When I left I said, “Okay, well that’s enough speed dating for me!” No one laughed.)

Though a full-time position as shortstop is not guaranteed on any of their teams—just like I had on Marty’s team, I’d have to earn my position—I ultimately decided to play for Frank, a retired military guy I met during warmups who reminded me a lot of Marty, my former coach.

Frank has a first-place caliber team who lost a few guys during the off-season and is looking to reload his roster. He brought one of his teammates to the tryout, who hit a couple of home runs during batting practice, so it was clear they had at least one guy who could swing the bat.

The first game will be in a few weeks, and that’s really when my tryout begins. Will I be able to secure playing time on Frank’s team throughout the season, and prove him right in selecting me for his roster? (I use “select” loosely as he group emailed me and four other guys after the tryout about joining his team.)

Maybe Frank’s team will be a bust, or maybe I’ll play 11 seasons for him. Either way it’s a fresh start in a new place, and I’m thrilled for the opportunity to be playing competitive softball again.

I should only hope the tennis team tryout I have next week goes so well…