Beginning her career in 2005, she was regularly ranked among the top jockeys in North America in both earnings and total races won.

A native of New Jersey, she and her horse trainer husband, Joe Sharp, have homes in Louisville, Kentucky and New Orleans, Louisiana.

She continues to assist Sharp in training race horses, including 2017 Kentucky Derby contender Girvin.

[8] In early adolescence, Napravnik, along with her sister, went to work for trainers Lilith Boucher, Bruce Miller and Jack Fisher.

At 15, she decided to take a year off from employment in the horse industry to spend time with friends and to be an ordinary teen.

[9] Small had a good reputation for mentoring young riders and had helped several other women jockeys get started in their careers.

"[17] Sharp had Napravnik ride a horse for him at Penn National Race Course in 2009, and they began dating a few months later,[17] becoming engaged in 2011.

Napravnik was the exercise rider for the colt at Sharp's training stable, and commented, "I thought about putting out something on Twitter .

"[27] Of the couple's relationship, Sharp has stated, "Some guys might think being married to someone as famous as Rosie is a tough position, but I don't, I'm very proud of her.

[29][33] When a horse fell with her in a January 2007 race at Laurel Park, Napravnik suffered three compression fractures of her thoracic vertebrae and was out for several weeks to recuperate.

[29] In July, after recovering from the Laurel Park injuries, she had another fall that resulted in a major break to her wrist, subsequently repaired with a plate.

Initially, she faced some of the most significant problems in her career with intimidation by the male jockeys, but overcame the challenge by refusing to give ground.

[21] In July of that year, Napravnik fractured her arm again when the horse she was riding broke down on the track and fell.

[46] She received one minor injury in 2012: a non-displaced fracture of her toe, obtained when her horse hit the side of the starting gate at Saratoga.

[53] She then rode the filly Unlimited Budget to a 6th place finish in the 2013 Belmont, becoming the first woman to ride all three Triple Crown races in the same year.

[45] Napravnik also broke a record previously held by Donna Barton Brothers when she rode 45 winners at Churchill Downs' spring meet.

[60] She won the 2014 Lecomte Stakes and the Louisiana Derby[61] on the three-year-old colt Vicar's In Trouble, trained by Sharp while he was an assistant to Maker, and owned by Ken and Sarah Ramsey.

[2] With mounts on Vicar's In Trouble in the Derby,[65] Bayern in the 2014 Preakness Stakes,[66] and General a Rod in the Belmont,[67] for the second year in a row, she rode horses in all three Triple Crown races.

She was in contention for leading jockey at Churchill Downs' spring meet, in second place with 31 winners, including a single day where she won five races, setting yet another record for a woman rider.

But on June 15, the day after she had a major win on Tapiture,[54] she had another significant injury: a separation of her clavicle and left shoulder joint that occurred when a horse she was working in the morning broke its leg and fell.

[72] When asked if her retirement was "permanent", she replied, "It's indefinite—I mean, I'm not thinking about a comeback in 10 months, but I can't promise to stay off a horse forever.

[74] In spite of losing time due to injury and retiring with two months left in the year, Napravnik closed out 2014 seventh in the nation for earnings, bringing her lifetime total to $71,396,717.

After initially exercising the stable's race horses in the early months of her pregnancy, she moved over to ponying and other activities.

As of 2015[update], she and Sharp hoped to have two children fairly close together, and after that, Napravnik has not ruled out a return to race riding but has not made any firm decisions.

[76] She initially was uncomfortable finding herself viewed as a role model for girls, preferring to simply be noticed as a top jockey.

"[6] She does not ask for any breaks from male jockeys, and has explained that horse racing is a sport where women simply have to be just as good as men.

[1] But she also said in a 2011 interview, "a lot of young female riders are just girls who love horses, but they just don't have the strength and toughness, and they're not cut out to be jockeys.

"[39] In her early career, she simply tried to "blend in" with the male riders, but nonetheless encountered some owners and trainers who refused to hire a female jockey.

"[6] Napravnik has encountered harassment from male jockeys on the track when other riders would deliberately bump her or pen in her horse from all sides.

[13] Trainer Larry Jones, having witnessed other jockeys deliberately bumping into her on the track, commented, "Don't do Rosie that way, because she will run over you.