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Jorgensen attended the University of Wisconsin-Madison, where she swam and ran for the Badgers. She earned a master's degree in accounting, passed the CPA exam, and worked for Ernst & Young in Milwaukee as a tax accountant. Soon after graduating and beginning her new job, USA Triathlon, who was pursuing former college swimmers and runners, encouraged Jorgensen to enter the sport of triathlon. In 2010, she was selected as USA Triathlon's Rookie of the year following her silver medal at the World University Triathlon Championships in Spain.
In 2014, Jorgensen placed first in four consecutive World Triathlon Series races, something no other female had done in the history of the series. Her winning streak extended through 2015, with a total of 13 consecutive series wins by the end of the year. Her astonishing streak was finally ended in 2016 by Helen Jenkins in Gold Coast, Australia. By coincidence, Jenkins had been the last competitor to have beaten her before her streak, in Cape Town in 2014. In 2015, she joined ECS Triathlon, an elite club, based in Sartrouville, France.
At the 2016 Summer Olympics, Jorgensen won gold in triathlon. After winning the gold medal in Rio, Gwen entered the New York City Marathon and placed 14th with a time of 2:41:01.
Jorgensen announced via Twitter on January 19, 2017, that she and her husband were expecting a child. She gave birth to a boy, Stanley, on August 16, 2017 - almost two weeks after his due date.
In November 2017, Jorgensen announced that she was retiring from triathlon, and focusing on the marathon, with the goal of winning an Olympic gold in the discipline at Tokyo 2020. However, after suffering injuries and undergoing heel surgery during her marathon build-up, Jorgensen announced on December 4, 2019, that she will focus on qualifying in track, in either the 5,000m or 10,000m.
In October 2019, Jorgensen's mother and sister published Go, Gwen, Go: A Family’s Journey to Olympic Gold. In the book, they document Jorgensen's rise from a Milwaukee CPA to 2016 Olympic Champion and describe the family's experience raising an Olympian.
Jorgensen returned to the ITU World Triathlon Series in 2023