So, how did you go from working for Disney to covering the NBA?

“So, I gotta ask…how does someone go from working for Disney for a long time to covering the NBA?”

That’s a really common question I get these days. This week there has been a lot of news that the NBA and Disney are in negotiations for the season to resume at Walt Disney World. That has brought a lot of attention to an article I wrote for Yahoo! Sports about why Walt Disney World makes the most sense as a single-site destination.

What made me comfortable writing that article is right there in the Editor’s note at the top of the piece: I spent nearly 20 years working for The Walt Disney Company. Most of that time was spent working at Walt Disney World in Central Florida. Outside of a year-and-a-half at Disneyland in California, I’ve been in Florida since I relocated from Massachusetts after college.

I started with Disney while still in college actually. In the late-summer/fall of 2000 I was a part of what was then called The Walt Disney World College Program. College students would leave school for a semester and be a part of what Disney then called “living, learning and earning” at Walt Disney World. My first job with Disney? I was a conductor on the Walt Disney World Railroad at Magic Kingdom.

For roughly five months, I lived with five other guys (all of whom became lifelong friends, along with a large circle of friends from working and living at Disney) in Disney-provided housing and worked on the train. I also took classes provided by Disney during this time. All these years later, I can still way it was one of the best periods of my life.

I went to Walt Disney World as a bit of a lost college kid. I had changed majors twice and wasn’t sure what it was I wanted to do. I really wanted to work in sports, but in these early internet days, I really didn’t know how to possibly make that happen. I figured my next passion was Disney, so why not go that route?

I stayed on as a seasonal Cast Member (Disney lingo for employee) while I finished up school in Massachusetts. Part of my role then was to act as a Campus Representative. I would hold information sessions and build buzz about the College Program and try to encourage my fellow students to apply. I also came back to Florida a couple of times to pick up shifts during breaks from school.

As college was wrapping up, my sights were set solely on working for Disney. I landed a post-grad internship with the company and headed back to Florida. This time the goal was to stay. I’ve written about this before, but my love of the 2002 Boston Celtics squad that made an unexpected run to the Eastern Conference Finals was directly related to this move. That team kept me connected to home when I moved away from Massachusetts.

Even as the Celtics run ended, my life started to solidify in the best ways. I met an amazing girl who was interning in the same department as me. In October, we’ll celebrate 15 years of marriage, so I’d say that worked out. We even got married at Walt Disney World at the Wedding Pavilion. We’re a Disney couple through and through.

Following my internship, I went full-time with Disney. My first full-time job was working as part of the Casting department (Disney lingo for hiring). If you called with employment questions for Walt Disney World, Disneyland (we answered their overflow calls) or maybe even ABC or ESPN from 2003-2004, you might have spoken to me!

From there, I went on to hold a number of different roles in backstage administrative areas. I was part of the Scheduling team (we built the Cast Members’ work schedules) at Disney’s Coronado Springs Resort, which is one of the rumored resorts to house NBA personnel.

I moved on to roles building workloads (how many Cast Members we need to run various operations and when we need them) for just about everywhere on property. I was part of the launch team for Disney’s Photopass group. That work actually put me in touch with folks in California for the first time.

In late-2006, my wife and I moved to California to begin working at Disneyland. Basketball winds itself in here again in a major way. The Celtics were horrible that 2006-2007 season. I spent the entire time actively rooting for ping pong balls in the 2007 NBA Draft Lottery. And I did all of that while living in Laker-land.

Little did I know a major present was coming for my birthday in the summer of 2007. Danny Ainge traded for Kevin Garnett and the Celtics were back. For the first time in ages, Celtics-Lakers was a real rivalry again. And living in Southern California, surrounded by Lakers fan, I was crowing every minute!

Alas, I didn’t get to see the 2008 NBA Finals play out while in enemy territory. Disney moved my wife and I back to Florida on the even of the 2008 NBA Playoffs starting. I enjoyed Banner 17 from the comfort of my couch in Central Florida. We were home. Shortly thereafter, our daughter was born in the middle of the Celtics run to the 2010 NBA Finals. Now, we’re a Disney family through and through.

It was around this time that I started to tinker with writing about basketball. I had a lot of thoughts and had no idea how to get them all out there. I started an absolutely terrible blog on BlogSpot. that thankfully no longer exists! And then I found the RealGM Forums.

I had used RealGM as a site for a long time, but hadn’t hit the forums. Once I did, I found my people. Passionate basketball fans, who welcomed discussion and embraced debate (attack the post, not the poster!). The Trades and Transactions and Celtics forums became my homes. These were people who didn’t just like the same parts of basketball I liked, but they loved it like I did.

After thousands of posts, I got up the courage to ask about writing for the main site. They said yes, and the rest was history. Well, sort of.

I wrote for RealGM for a while. Was part of a group that tried to site an independent basketball site, which failed spectacularly. I made a ton of friends in the media and with teams, mostly because I understood the salary cap and CBA. Those friendships led to other opportunities, including here at CelticsBlog (shoutout to Kevin O’Connor for recommending me to Jeff Clark!) and at Yahoo! Sports.

Eventually, this little side job started to take over more and more of my life. It became very much a second full-time job. I would get up each day around 5:30 AM to get ready for the day. We’d get our daughter off to school and I’d head into my office at Walt Disney World. I’d be there until 5:00 or 6:00 PM. Then it was home to cover games. If the Orlando Magic played, I’d duck out of work early to get to the Amway Center in time to start my second job. Most nights, I’d fall into bed around 1:30 AM. In-season, I was sort of a walking zombie.

In the offseason, it didn’t get a whole lot better. I used a couple of weeks of vacation time each year to attend NBA Summer League in Orlando (I miss you Orlando Summer League!) and then Las Vegas. The rest of my vacation time was largely used to take days off around the trade deadline, draft and NCAA Tournament.

About a year or so ago, it was time to either cut back on basketball or make it my job. During the 2018-2019 season, I pushed harder than I had ever pushed on the basketball side. I wrote hundreds of articles for CelticsBlog, Yahoo! Sports, RealGM and occasionally one-offs elsewhere. By the time the 2019 offseason got here, I felt like I was in a place where I could make basketball the job.

But I hesitated. Why? Concerns for taking care of my family. Nearly 20 years of working for Disney had put me in a good place with the company. After my wife and daughter had already sacrificed so much for me to chase this dream, I couldn’t ask them to give up even more. We talked it through and decided to give it one more year. If I couldn’t do basketball full-time by the end of the 2019-20 season, I’d dial it back considerably. I was going to refocus on my Disney career, which I had let stagnate to chase the basketball dream.

The other reason I hesitated? Fear. I love Disney. I loved working for Disney. You tell people you work for Disney and you inevitably get a smile. They ask what you do as a polite segue to a million questions about the parks and resorts. That never got old for me. I was afraid to leave. Without Disney, who was I as a professional? Fear is a pretty strong binding agent.

In late-January into early-February, the pull of covering the NBA was too strong. As much as I love Disney, I love basketball more. I was finally in a place to have enough steady freelance and part-time work to make the leap. My wife had gotten promoted, which eased the financial concerns. It was now or never.

For three glorious weeks, it was awesome. I was getting a full night’s sleep in the middle of the basketball season. I was writing and watching more hoops than ever. I wore basketball shorts and t-shirts every day unless there was a Magic home game!

Then, COVID-19 had different plans. The season shut down. I was furloughed from my two steadiest employers. I was lost. I wrote about the feeling for CelticsBlog.

After it was clear it wasn’t going to be a couple of weeks of a pause, we started hearing about ideas to save the basketball season. Islands, cruise ships, single-sites. None of them caught with me. I just kept going back to the place I left just a couple of months earlier. Why not Walt Disney World? Now, it looks like that is going to happen. My worlds have come together in the oddest Venn Diagram possible.

Back to the question: So, how did I go from working for Disney to covering the NBA? Through a lot of hard work and a lot of sacrifice. Not just by myself, but by my family and friends. I’ve missed birthdays, weddings and funerals. I’ve missed phone calls and texts. I’ve been a pretty horrible husband, father, son, brother and friend at times. They all say they understand, but I can never pay them back fully.

Working for Disney led me here. Working for Disney gave me the courage to approach a total stranger, introduce myself and start a conversation. Working for Disney made me appreciate the small wonders and details that make things special. Working for Disney made me fully appreciate that hard work is a good thing. Sure, you aim to “work smarter, not harder”, but sometimes it takes putting your head down and powering through.

Most of all, working for Disney made me realize that if you have a dream, you should chase it. Not at the expense of everything, but those who support you will encourage you. It sounds corny and cheesy, but Walt Disney World is a place where dreams come true. That happened to me multiple times. And I have faith that when the NBA comes back, it’ll happen for me again.