After retirement, Jackson began writing football-related commentary for the New York Times and various online publications, frequently drawing upon his experiences as a player.

[2] After going unselected in the 2002 NFL draft, Jackson was signed as an undrafted free agent by the San Francisco 49ers on the recommendation of former 49ers coach Bill Walsh, whose son was the athletic director at Menlo College.

During Jackson's 2004 season with the Broncos he emerged as an option at receiver, catching 8 passes for 73 yards, and also recorded 7 special teams tackles.

His writing about the NFL has appeared in Slate,[10] Deadspin,[11] The Daily Beast,[12] The New York Times[13] The Wall Street Journal,[14] BuzzFeed,[15] and Defector.

According to Jackson, the Browns' players were already beaten down because Mangini didn't treat them with respect, unlike Broncos coach Mike Shanahan.

[19] In a piece written for Defector published on February 21, 2024, Jackson admitted to using human growth hormone to recover from an injury after leaving the Broncos.

[20] Jackson has called on the NFL to remove cannabis from its list of banned substances,[21] citing the pain-relieving capabilities of the drug as well as its neuroprotective properties.