Pickett grew up in Ward 6 of Washington D.C. As a freshman, he attended Spingarn High School but did not play for the basketball team.

Pickett played a postgraduate season at Massanutten Military Academy in Woodstock, Virginia to gain more interest from college programs.

On September 24, 2021, Pickett signed a two-way contract with the Pistons, splitting time with the Motor City Cruise of the NBA G League.

[16] On September 20, 2023, Pickett's rights were traded to the Grand Rapids Gold[17] and on October 13, he signed with the Denver Nuggets.

[20] On April 1, 2024, Pickett signed with the Atléticos de San Germán of the Baloncesto Superior Nacional.