So...You Want to Work in Pro Ball, Huh?

FUNdamental Skills
By Darren Fenster

Everyone has their own unique journey in the game. Some set out on a life path as a kid, and are able to follow it every step of the way. Others, like myself, set out on one road, only to get sidetracked and re-routed a handful of times on an incredible ride I never envisioned taking. For me, that road of happenstance brought me into the coaching ranks of professional baseball. My experiences in the game have been incredible, from the rewarding to the surreal.

A few years ago, when I was at a crossroads in my professional life, debating between continuing in the game and starting a new career path in the medical device sales field, countless people volunteered their time, offering their insight as to what working in professional baseball is really like. It was their collective experiences in the game that made me believe that there was still a place for me on a baseball field. And I’ve never been happier professionally since choosing that path.

Over the past seven-plus years, many have reached out to me both asking for insight as to what it is like to work in professional baseball, along with help getting into that side of the game, just as I did to others a short time ago. Here is my insight for all those inspired to find a position with a Major League club.

First, allow me to begin by offering some background as to how my career path took shape in the first place.

My playing career as a Minor Leaguer in the Royals system ended abruptly due to a knee injury, and I wasn’t prepared by any means to start a life after baseball, and had no plan B. So when I was released in the spring of 2006, I reached out to Fred Hill, the coach I played for at Rutgers, an ABCA hall of famer who has been like a second father to me, basically asking, “what do I do now?” He asked if I had any interest in coaching (I didn’t), because he thought I would make a good one if I got into it, and would create the Director of Operations position on his staff, specifically for me if I said the word. Well, without any other plans, I agreed, and by sheer good fortune, right place, right time, a position on a Big East Baseball program’s staff was created for me. Coach Hill saw something in me before I was ready to see it in myself. A huge break for me, which I didn’t realize at the time as I’ve since seen how incredibly hard it is to get a coaching position at any school, let alone one with a “big time” athletics department.

At the time, Division I programs could only have four “coaches” on the field, working with players, so, in the Director of Operations position, I was not allowed in uniform or on the field. That was actually a good thing because it enabled me to learn the complete inner workings of a college baseball program, and prepared me to step into an assistant coach/recruiting role when the opportunity presented itself a couple years later. In the meantime, I was able to get on the field, coaching experience, hooking on for one summer as an assistant in St. Cloud in the Northwoods League in 2007 when we won it all, and then the following summer in Orleans in the Cape Cod League.

After a few years on the coaching staff at Rutgers, and after testing the waters looking into a career in medical device sales, I began getting the itch to get back into professional baseball in a more baseball-centric position without having to recruit or worry about the countless off-the-field responsibilities of the college game. Having played for six years professionally myself, combined with the time I spent at RU, I felt like I had an incredibly strong resume that would make me a slam dunk hire for any professional team, well-equipped for a number of different areas in the game, that I would essentially be able to pick. My expectations were far off.

I spent the entire summer of 2011 discussing my desire to return to professional baseball with those who had positions with clubs that I already had relationships with. I went through the Baseball America team directory and highlighted every single name that I knew (or played with or against) and reached out with a call, text, or email. After three full months of conversations, when September rolled around, I got one, yes, just one, phone interview with the Rockies for an open hitting coach job. I didn’t get a second interview. Then I started considering internships in baseball operations, and was up for two: one with the Indians that had an amazing track record with some very big wigs in the game, and the other with the Mets working in baseball operations with a variety of departments. I was ready and willing to leave a full-time position, with benefits, and a mortgage to pay, just to get back into the pro game.

So as the fall of 2011 was progressing, and while going thru the long interview process for those internships, I was preparing for another year at Rutgers. During instructional league in mid-October, I followed up with the Red Sox assistant General Manager at the time, Mike Hazen (now running the Diamondbacks), who I played against when he was at Princeton, and he said there was a possibility of something opening up in a few weeks, but nothing for sure. For the next month and a half, crickets. Figured nothing was open after all, or they filled it with someone else. Then, during Winter Meetings in December, he called me out of the blue to ask if I was still interested in the hitting coach job, as the A-ball job had opened, and later that day I did a phone interview with the Farm Director. A week later I was up at Fenway for a face to face, and the following week they offered me the job. Literally six months-worth of banging doors down with next to no opportunities, and then just like that, within a quick two weeks, I had the job. That transition has been thenbest move of my professional life. Simply getting my foot in the door was also the hardest transition of my professional life.

Having just completed my seventh season with the Red Sox, I can unequivocally say that working in professional baseball is awesome. I absolutely love it, and honestly can’t really see myself doing anything else outside of the game. But rest assure, it is not an easy lifestyle on a number of different fronts. My days are spent teaching the game I love. I have a passion for what I do, and a purpose to my days that go far beyond the field. While much of the world is inside, making a living doing something they may not enjoy, I’m outside throwing BP and hitting ground balls. I’ve been a part of, and have had an impact on, one of the most storied franchises in all of professional sports. I’ve worked in the cage with a future hall-of-famer. I have a World Series ring…with my name on it.


But for as rewarding as a career can be to work in professional baseball at the highest levels of the game, there are many challenges that come with doing something that we love.

In Player Development, you will work from one extreme to the other. Yes, our days are spent on the field, making our players better; nights spent competing under the lights. But being a coach in professional baseball means sacrificing any sense of a work-life balance. Days are long, often times arriving at the ballpark before noon for a 7:00 p.m. game and staying as late as midnight or later. Our schedule is one of the extremes, pretty much working just about every day from mid-February thru Labor Day before enjoying an off-season with little to no responsibility. The fall and winter provide me with a ton of flexibility to branch out and do a handful of other things in the game that has literally taken me all over the world and have given me life experiences that most could only dream.

There is a culture and camaraderie in our organization that is very much a family atmosphere full of like-minded people who truly have a passion for the game and helping those in it. I have built relationships with both colleagues and players that I hold as dear as I do my own relatives and people I grew up with. Sustaining a “normal” family life, however, is a huge challenge. I am not married, and don’t have any kids, so it’s very easy for me to up and go where I want when I want, or to go wherever the Red Sox tell me to go. Some guys will go weeks and months without seeing their wives or kids and are able to make it work.

And lastly, there is a big misconception when it comes to compensation in professional baseball. Put simply, you’re either in the Big Leagues, or you’re not. Unless you are a Major League manager or a long-tenured guy on a Major League staff, you will not get rich working in professional baseball. It is in many senses a labor of love. The majority of those working in the game are doing it for the love first, the money, second. But, if you’re financially responsible, you’ll be able to pay your bills, and will have opportunities to make money in the off-season if you find your way in as a coach.

Scouting, both amateur and professional, and baseball operations are other departments that every Major League club employs, and while I don’t have personal experience in either, much of the same premise applies as does in Player Development. No job in baseball is a traditional 9-5, and few will be able to sustain a career in the game without a genuine love for the game.

A life in the game requires many sacrifices. Sacrifices that many don’t want to give up or can’t give up. But those sacrifices come from a place of passion. And that passion is a bond we all share, and one that keeps us enthusiastically coming to work day after day, year after year. We all take a great sense of pride in being a part of something that is so much bigger than any single one of us.

Darren Fenster is a contributor to the USA Baseball Sport Development Blog, and is currently the Manager of the Portland Sea Dogs, the Double-A affiliate of the Boston Red Sox. A former player in the Kansas City Royals minor league system, Fenster joined the Red Sox organization in 2012 after filling various roles on the Rutgers University Baseball staff, where he was a two-time All-American for the Scarlet Knights. Fenster is also Founder and CEO of Coaching Your Kids, LLC, and can be found on Twitter @CoachYourKids.