Nancy Sinatra: I was too shy to pursue a big career

Nancy Sinatra was “too nervous and shy” to fully take advantage of all the opportunities afforded to her as a younger lady. 

The 80-year-old singer and actress — not to mention daughter of one of the 20th centuries great entertainers Frank Sinatra — admitted that she felt the younger Nancy didn’t make the most of all the opportunities which came her way.

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“If I could go back in time I would probably take more jobs that were offered me along the way,” Sinatra said.

“I was nervous and shy and I didn’t take advantage of opportunities that I had. And that’s very sad. They say that what you regret at the end of your life is not what you did, but what you didn’t do. And there’s a lot of stuff I didn’t do.

“I was offered a TV series where I would have been a mom with a 14-year-old child. And I said something real smart alec, like I’m too young to have a 14-year-old child. No, thank you. 

“In actuality, I was not too young but for some reason I had hurt feelings that they would offer me something like that. But I should have done it. I should have taken it.” 

Start Walkin' 1965-1976 is now available to stream on the service of your choice! https://t.co/uML1EVrHVV

— Nancy Sinatra (@NancySinatra) February 5, 2021

Sinatra, whose singing career spanned decades including a brief stint on screen, has released a collection of her hit singles from 1965 to 1976.

Talking to Jane Graham for the Big Issue’s Letter To My Younger Self, she didn’t hold back when it came to giving the 16-year-old Nancy some life advice.

Sinatra said despite lacking confidence, she believed some things happened for a reason and she hoped she had succeeded in her goal in contributing something to women.

“I was OK with a certain amount of success but I didn’t feel confident enough to really pursue a big career. I don’t know why. I think I was just too shy. Maybe it wasn’t the career for me,” she said.

“I’ve always been interested in anthropology. If I’d stayed in school, I might have gotten into that. But I also believe in destiny. And I don’t know, I think I was brought here to the planet to contribute something to women. And I hope I’ve done that.” 

"Sinatra 100: An All-Star GRAMMY Concert"

Nancy Sinatra performs during "Sinatra 100: An All-Star GRAMMY Concert" celebrating the late Frank Sinatra's 100th birthday at the Encore Theater at Wynn Las Vegas on December 2, 2015 in Las Vegas, Nevada. (Photo by Isaac Brekken/Getty Images)

Sinatra spoke about her “manufactured” image as a young woman – which later became iconic – and how many didn’t understand it until later on. 

“My look came from London, with hair and makeup from New York,” she explained. “It evolved thanks to Mary Quant and a friend of mine named Amy Green.”

“She took me to a salon called Kenneth in New York and I met a lady who coloured my hair blonde. And I loved it, that new persona. I was grateful for it because I had been floundering. It was playful and a little sexy,” Sinatra went on.

“It was courageous for me to step out like that. I remember in Los Angeles when I was first wearing miniskirts, I would get smart alec comments like, are you going to play tennis today? 

“People in LA didn’t understand the fashion trend – it took people like Jean Shrimpton coming to America to really nail it.”

Read more about Nancy’s musical family, her “innocent” twenties and wishing she could have one last conversation with her mother in this week’s Big Issue, available through The Big Issue app now.

Start Walkin’ 1965-1976 by Nancy Sinatra is released on Light in the Attic on March 26