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Osborne had her first season as an apprentice in 2020 and rode her first Classic four years later St Leger-winning jockey Saffie Osborne says the "fear of failure" has left her after she became the first woman to win a British Classic.
The 24-year-old said that despite wanting to achieve "so much more", her victory at Doncaster on Saturday means she will always be able to look back and think her career was "worth it".
Osborne said the sport can be "very lonely", she estimates she drives 65,000 miles a year, often alone, and she has suffered some serious falls, breaking numerous bones. But she told BBC Sport that winning one of British Flat racing's five Classics had been a dream since she was five.
She has now fulfilled it. While racing is a sport where men and women compete against one another, opportunities have not been equal.
Only six female jockeys have had rides in British Classics in 250 years, totalling 12 rides, according to the National Horseracing Museum.
They are Gay Kelleway (The Oaks, 1986; The Oaks, 1987), Alex Greaves (The Derby, 1996; 1,000 Guineas, 1996), Hayley Turner (The Derby, 2012) Josephine Gordon (1,000 Guineas, 2017), Hollie Doyle (The Oaks, 2021; St Leg er, 2021; The Oaks, 2022) and Saffie Osborne (2,000 Guineas, 2024; 1,000 Guineas, 2026; St Leger, 2026).
"It has been a male-dominated sport for an extremely long time, and I suppose it's becoming less and less of a conversation, which is quite nice," she said. "When people talk about the firsts of what women have done, I think to have my own one is quite special.
"I think it's also quite poignant because there's so few left of first things for women to do in this sport." 'I did it because I loved it', St Leger winner Osborne On Saturday's groundbreaking win, she added: "That sort of fear of failure has sort of disappeared.
However much more I want to achieve, and I want to achieve so much more, it's kind of like I can always look back on my career and know that it was all worth it.
Osborne's ride on Highwayman in the St Leger was her first for trainer Joseph O'Brien, and only came about because of an injury to regular jockey Dylan Browne McMonagle.
She acknowledged that the success of a jockey is dependent on "being chosen", but is adamant that her gender isn't a factor in the opportunities she gets. "I don't feel like in my position now that I'm ever looked at any differently be cause I'm a woman," she said.
"Any jockey, when you're starting out, it takes years to gain respect and be looked at as a person that people would want to use. And I don't think my gender at this point would have had anything to do with it.
"Hopefully Saturday will open more doors. But when it comes to me as a female jockey, I don't think I'm viewed any differently within the industry."
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