• Loading stock data...
Sunday, August 31, 2025
The biggest names in sports media. All in one room. Get your ticket now!

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

Aug 6, 2025; Los Angeles, California, USA; Son Heung-min poses during an LAFC introductory press conference at BMO Stadium

Son Heung-Min Effect Will Hit Big for MLS and L.A.

With a record signing, the South Korean supernova has landed at LAFC.

4 of 10 Highest-Paid CFB Coaches Lose in Week 1

Alabama coach Kalen DeBoer was the biggest surprise of the Week 1 losers.
Ohio State Buckeyes wide receiver Jeremiah Smith (4) celebrates with offensive lineman Donovan Jackson (74) after a touchdown catch against Notre Dame Fighting Irish in the first quarter during the College Football Playoff National Championship at Mercedes-Benz Stadium in Atlanta on January 20, 2025.

The Most Expensive Roster Year in College Football History

The House settlement created revenue-sharing—and a big NIL loophole.
Rob Bonta

Users Sue Daily Fantasy Companies After California Calls Them Illegal

Underdog Sports and Boom Fantasy were separately sued.

Featured Today

‘You’re Going to Get Beat Up’: The Liberty’s All-Male Practice Squad

A select group suits up weekly to take on the defending champs.
August 24, 2025

The Honey Deuce Effect: How Tennis Perfected the Signature Cocktail

Sold every 1.5 seconds, they total more than $12 million in sales.
Dec 21, 2024; Austin, Texas, USA; Texas Longhorns quarterback Arch Manning (16) warms up as the Texas Longhorns prepare to play the Clemson Tigers in the first round of the College Football Playoffs at Darrell K Royal Texas Memorial Stadium.
August 23, 2025

Schools Are Hesitant to Allow PE Into Their Athletic Departments

Regardless of budget, schools don’t believe the risk is worth the reward.
Oct 2, 2024; Rosemont, IL, USA; Big Ten commissioner Tony Petitti speaks with the media during the 2024 Big Ten Women’s Basketball media day at Donald E. Stephens Convention Center.
August 22, 2025

‘Not Ready to Jump In’: Power 4 Commissioners Aren’t Sold on PE

Top leaders in college sports have yet to see a satisfactory proposal.
Aug 27, 2025; Los Angeles, California, USA; Los Angeles Dodgers starting pitcher Shohei Ohtani (17) flies out to left field in the eighth inning against the Cincinnati Reds at Dodger Stadium.

The Biggest Deferred Sports Contracts in Each Major Sports League

Shohei Ohtani will make $680 million after his contract ends.
August 11, 2025

NBA Christmas Schedule Leans on LeBron, Steph While Betting on Flagg

The Lakers, Warriors, and Rockets are all in action.
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.
Sponsored

Gareth Bale on MLS vs EPL, Retirement & Buying Cardiff City

Gareth Bale shares his post-soccer business playbook.
August 10, 2025

Bears CEO: Arlington Heights Only Local Location for New Stadium

The Bears currently play in Soldier Field in downtown Chicago.
August 8, 2025

Three Schools Sue Mountain West, Commish Over Withheld Funds

Boise State, Colorado State, and Utah State intensified the court battle.
Courtesy: Harlem Globetrotters
July 25, 2025

The Harlem Globetrotters Have Changed Hands Repeatedly, but Keep Making Money

The team is gearing up for its 100th season.
July 16, 2025

Judge Rules for NFL, Fanatics Against Small Apparel Seller

The lawsuit argued the NFL “aids and abets” Fanatics with its strategy.