If you've never won a race, you don't know how to cherry pick. Every metro area has tons of little charity 5ks that are won in 19, 20, 21 minutes. Go find one.
I'm old and WELL past my prime, but I still occasionally win road races overall just because there are so many lame ones around these days.
Yup. I won my first race this summer, a small charity 5k in a little over 20 minutes. Last year someone ran 16:00 so I wasn’t expecting anything but nobody showed up this year. Second place was a 12 year old so I wouldn’t say it was my proudest running moment but it was fun to win something anyway.