• Loading stock data...
Monday, March 9, 2026

The Decision

This post is part of the #YPSportsChat Blog Series! This series will give young professionals an inside look at the intricacies of the sports business world and advice on how to navigate it.


By: Jordan Leatherman, @JordanKay13

“This fall I’m going to take my talents to South Beach…”

In 2010 after seven years with the Cleveland Cavaliers, LeBron James announced he was taking his talents to Miami and free agency has never been the same.

Fortunately sports business professionals are always unrestricted free agents during their career (except for the occasional non-compete). However, that does not make the decision to change jobs or go back to school for an advanced degree any easier. So without further ado here are the five things to consider before 12:01 a.m., Jim Gray and ESPN not included.

1. Could this lead to a ring?

a. No, not an actual ring, although that is a possibility in some cases. What I mean is would this job or degree advance your career? What would be the next move at your current job? If you’ve tapped out of places to go in your current organization it might be time to consider options for growth.

2. Is this the dream team?

a. The idea of playing with the best is appealing, just ask Kevin Durant. Several teams, leagues and agencies are at the forefront of digital integration, fan engagement and corporate social responsibility. The opportunity to learn from the best is something that you will continue to capitalize throughout your career. Advanced degrees will also allow you to learn from people within the industry and provide great networking opportunities to use in the future.

3. Is your job done?

a. Remember the goals you set for yourself at the beginning of your job, what does that list look like now? Have you set the record for scoring or won three rings? If its close to being checked off it may be time to set yourself up for a new challenge, like bringing a championship to a city that has waited 52 years.

4. Call your agent.

a. I know you don’t have an actual agent, although that would be cool. What I mean is talk to your most trusted advisers a mentor within the industry, a professor from undergrad or even your peers. Layout your long-term goals you want to achieve. These people want the best for you and let them play devil’s advocate as you defend your choice.

5. Listen to the real MVP.

a. Finally after all of the above have been considered it really comes down to your gut. You know what you want to accomplish in your career, now its time to just do it. The decision isn’t going to be easy but as the clock nears midnight and the pro/con lists have been completed you have to ask yourself, why not? Just remember to be a professional because as you know the sports industry is small and burning bridges and jerseys are frowned upon.

If you feel like you are at a crossroad, I highly recommend Amy Jo Martin’s “Why Not Now?” podcast. Amy spent part of her career working in and around the sports industry and is now interviewing “why not’ers” about the moment they decided well why not. Her first few interviews include Mark Cuban, Troy Aikman and Julie Foudy.

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Dec 25, 2025; Kansas City, Missouri, USA; Kansas City Chiefs tight end Travis Kelce (87) reacts during the second half against the Denver Broncos at GEHA Field at Arrowhead Stadium. Mandatory Credit: Jay Biggerstaff-Imagn Images

Travis Kelce Return Delays Media Sweepstakes

The star tight end is expected to return to the Chiefs in 2026.
Oct 26, 2024; Charlotte, North Carolina, USA; Miami Heat guard Terry Rozier (2) drives the baseline against the Charlotte Hornets during the first quarter at Spectrum Center. Mandatory Credit: Nell Redmond-Imagn Images

Hornets Send Heat Second-Round Pick to Settle Rozier Issue

Rozier hasn’t played since his October arrest.

Live Nation Deal With DOJ Draws Pushback from Several States

The deal involving the Ticketmaster parent company draws widespread rebuke.

Featured Today

Alex Eala Has Become One of the Biggest Draws in Tennis

Eala will face Coco Gauff in the third round at Indian Wells.
Jun 9, 2021; Paris, France; The racket of Coco Gauff (USA) after she smashed it during her match against Barbora Krejcikova (CZE) on day 11 of the French Open at Stade Roland Garros
March 6, 2026

The ‘Rage Room’ Is the Hottest Place in Tennis

The idea came from a player podcast.
March 5, 2026

Mark DeRosa Is Still Baseball’s Swiss Army Knife

DeRosa is the sport’s utility player both on the field and off.
Nicole Silveira
March 3, 2026

The Tattoo Marking Membership in the Most Exclusive Club in Sports

For athletes, the Olympic rings tattoo is “about everything it took.”

Jameis Winston Says He’s Given Seven Figures to Florida State

Winston led Florida State football to its last national championship. 
Fernando Tatis
October 6, 2025

Arbitrator Says Tatis Jr. Must Pay Big League Advance Millions

Tatis has called the agreement a “predatory” loan.
NBA Cup
November 26, 2025

Luka Dončić Wants ‘Dangerous’ NBA Cup Court Designs Changed

Dončić first complained about the court designs two seasons ago.
Sponsored

From USWNT Star to NWSL Franchise Founder

Leslie Osborne, former USWNT midfielder, shares how athletes are moving from the pitch to the ownership table.
September 3, 2025

Ohio State–Texas Showdown Was Most-Watched Week 1 CFB Game Ever

Fox drew 16.62 million viewers on Saturday afternoon.
Oklahoma Sooners defensive back Woodi Washington (5) runs after a reception during the Armed Forces Bowl football game between the University of Oklahoma Sooners (OU) and the Navy Midshipmen at Amon G. Carter Stadium in Fort Worth, Texas, Friday, Dec. 27, 2024.
August 19, 2025

Oklahoma Selling Fans Tickets to Press Conferences

Press conference tickets for the Sooners’ season opener are already sold out.
August 11, 2025

NBA Christmas Slate Leans on LeBron, Steph; Bets on Flagg

The Lakers, Warriors, and Rockets are all in action.
August 10, 2025

Bears CEO: Arlington Heights Only Local Location for New Stadium

The Bears currently play in Soldier Field in downtown Chicago.