The Carly Simon Guide to Overcoming Your Freelance Fears and Achieving Superstardom

Carol Tice

Carly Simon

Carly Simon with her Working Girl Oscar in 1989.

Do you sometimes worry that you don’t have what it takes to make it as a writer?

That everyone will laugh at you and you’ll be humiliated?

Feel like you can’t get your personal life drama to stop long enough to write?

If you answered “yes” to any of those questions, take a page from the book of legendary singer/songwriter Carly Simon, who is the subject of a recently published unauthorized autobiography, More Room in a Broken Heart: The True Adventures of Carly Simon. While I gather the book may not be entirely accurate, it gets the basics straight.

You might think of Simon as tall, beautiful, and naturally gifted — I always did — but that wasn’t always how she saw herself. She was paralyzed with stage fright for much of her career. She was shy and stammered as a child. Not exactly an obvious formula for an award-winning singer.

She also had quite a few low points in her career, including one nightmare concert where she was so stressed she reportedly started menstruating onstage and then collapsed! It doesn’t get a lot more embarrassing than that.

Her determination to keep going no matter what life threw her way allowed her to create an award-winning career that included an Oscar for writing a song for the movie Working Girl, in 1988. Some of her songs still represent an era for many of us — for me, when I hear You’re So Vain, I’m transported back to that 1972 Girl Scout beach-cabin trip I took, during which it seemed to play hourly on our scratchy transistor radio.

How did Simon rise above the mess of her life to craft memorable songs? Here is a guide derived from the points I took away from her story:

1. Don’t let your childhood trauma block you. Simon’s childhood was privileged in one way, as the family had a summer compound in Connecticut and her father was one of the founders of publishing powerhouse Simon & Schuster. But her father was eventually forced out of the company and rendered frail by heart attacks, and the family’s fortunes declined. At the same time, her parents’ marriage was unstable and for a prolonged period before her father’s early death, her mother seemed to be carrying on an affair with one of the children’s attractive male tutors, the book relates. Simon came out of all this massively insecure, but committed herself to moving forward with her songwriting dreams despite it all.

2. Keep evolving. Most people probably don’t remember this, but Simon’s first singing gig was as part of a folksy duo with her sister Lucy. They sang a kids’ lullabye on Hootenanny, dressed in goofy matching outfits. Shortly after this brief brush with fame, her sister decided touring and performing wasn’t for her and moved on to motherhood and family life. This could have been Simon’s cue to hang it up also, but instead she began networking in the music community and looking for opportunity as a solo act. Later in her career, she was offered opportunities to move into new areas, scoring theatrical movies and even writing an opera. She could have run from these big leaps into new areas, but took them on and excelled.

3. Get out of your comfort zone. Terrified of flying, Simon had to get on an airplane to play her first big solo gig, which was at the famed Troubador on Sunset Boulevard in Los Angeles. She brought a friend for moral support and took tranquilizers, but she got her butt there. She opened for Cat Stevens. The rest is history.

4. Make connections. From early on, Simon realized that connecting with other famous songwriters could help her career. She set her sights on having Mick Jagger sing backup on You’re So Vain, for instance, and didn’t stop until she got him. Her celebrity friends helped her at many stages of her career, introducing her to new record-label execs and managers when she needed a fresh start — a situation she found herself in time and again, after albums stiffed or didn’t do well when she couldn’t tour.

5. Rise above your personal-life dramas. Simon fell hard for songwriter James Taylor. When they married, he was a heroin addict, and struggled with addiction throughout their marriage. Living with an addict and two small children might suck up all of an ordinary person’s mental energy, but Simon somehow continued to write, producing some of her best albums during this period. After divorcing Taylor, she married Jim Hart, who came out as gay toward the end of their relationship. Simon was not exactly lucky in love! Despite not having the stable base of a loving, functional marriage, she kept on writing and confronting her performing fears. In more recent years, she has also survived a battle with breast cancer and moved on to new creative projects.

6. Seek help when you need it. Simon saw a therapist for many, many years as she strove to overcome her performance fears and deal with her painful marriage breakups. Without professional help, it’s unlikely Simon would have become the famed writer and performer she did.

7. Get over the embarrassment. Although Simon is a famously private person, clearly at some point she learned to deal with it. She’s still around (and looking fabulous!) and making music. Her personal blog (before it was removed during her website redesign) provided a frank account of many of the dark times in her life, and shared the good times with fans, too.

Carly Simon photo: Flickr-Alan Light


  1. Diane Schultz

    Thanks for pointing out that her connections started out a lot higher than most of ours; that kept it real, while pointing out the general that we do need to make connections, and that we too can fail and fail and need to keep starting over (same paragraph you wrote above). I did track down that You’re So Vain is supposedly revealed by Carly herself in a remake of the same song to be about someone named David (rollingstone mag: ) which sends you to a (supposedly) reversed (and forward, first) version of the song, located at: which appears to be a UK mag called The Sun. I wish Carly would just be straightforward about it. The fact that it fits any number of men would still exist, regardless. The fact that it is her version of a real person has been well-known, but has tainted the images of men other than the one she meant. Still, it may be her record producer at the time, but must be (from the song) someone she was intimately involved with…but who else can/did fly their jet up to Nova Scotia?

  2. Ali

    When I started blogging I was scared of making mistakes… really scared. I thought people would laugh at me and I’ll end up embarrassed. But when I started, I was always depressed as there were only a few returning readers and subscribers.

    Then I read somewhere that it’s good to have few readers in the beginning as a few people will see you stumbling.

    Today I read making mistakes is better than not trying at all… thank God I did try. I made countless mistakes but I’ve learned a lot from these slipups.

    Now, I won’t mind winning an Oscar for my writing 😉

  3. Susan B. Bentley

    Great post Carol, your headlines always grab me! I had a big discussion with a fellow creative yesterday about evolving; that we can dare to dream and take our business in different directions and shouldn’t feel restricted to just one job title or one area of work.

    • Carol Tice

      Thanks Susan —

      I liked your linked post there — would have Retweeted it but I don’t see a button… ?

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