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 blogΒ (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. John Soares

    I remember listening to “Your So Vain” on the small radio in my room. Supposedly it was about Mick Jagger.

    I haven’t had quite the drama in my life as Ms. Simon did, but like everyone, I’ve had to face my fears. Early in my career I was very concerned that people wouldn’t like my writing. This was nearly paralyzing when I wrote my early pieces for bigger magazines with large circulations. I’d sit at my computer trying to get those first words out, and all I could think of was thousands of people looking at what I wrote and thinking it was boring or pedestrian.

    I’m still not entirely over that fear, but now I rarely worry about what people think.

    • Carol Tice

      Or it’s about Warren Beatty…or Cat Stevens…or maybe a woman. Or herself. Or each verse is about a different person. She’s created an enduring mystery about it — there’s a recent interview on just this topic where she throws out a few tantalizing possiblities but of course doesn’t really answer the question. The bottom line is we’ll probably never know…which is one of the things that makes the song great.

    • April Klimley

      John. Your frank comments are inspiring because I am sometimes afraid to write about the topics I know best and/or pitch those topics to editors.

      • Carol Tice

        Why, April? The topics you know are the easiest ones to get assigned, where you can tell the editor you have relevant experience and know who the good experts are to interview.

  2. Dee Dee

    What a fantastic article! I love Carly Simon. I remember being a little kid and hearing it on the radio and being fascinated by the lyrics. Who could be so vain to think that everything is about them?

    Then I got older and met lots of people who fit the description! πŸ™‚

    I love that idea of never letting yourself get in your own way, which takes some of us longer than others to remember. I’m just learning it, but like “You’re so Vain”, I’m about to turn 40 so maybe there’s magic in round numbers!

  3. Terr

    Thanks so much for this. You had me at “Carly Simon”. I’ve always wondered how a child of privilege could come across so earthy and in touch. Yes, she’s a product of her times; That’s The Way I Always Heard It Should Be was an anthem for so many (And the song cracks me up laughing). But if she was someone I admired from a distance before, she’s gained heroine status with me now.

    This was totally a post for me, and a great way to start my week. Like, I could go though the article points like a checklist. What is it about writers anyway, never thinking we’re good enough? But then, most talented artists in any medium rarely believe so, which is what makes them great.

    The bottom line of this post for me is, let go of the perfectionism, and just DO IT. Do what you were put on this earth to do. Carly was able to produce some of her best work during some of her darkest hours, probably because she had an innate belief that first being a lyricist, then a singer was her purpose in life. When you understand your purpose, you can focus on it, no matter what’s going on around you.

    P.S. You’re So Vain came out the year I was born, but I remember that song in my early childhood being played on the radio for YEARS after it first came out. And only Mick Jagger would be twisted enough to sing background on a song about him, so I think it’s about him πŸ˜‰

  4. Mark Hermann

    Great article, Carol! A nice reminder how hard “celebrities” had to work to overcome the very same adversities the rest of us face every day in order to become the persona we now know. And and it sounds like her priviledged upbringing was obviously not a slam dunk to the easy life.

    An interesting little side story your (and Carly’s) fans might like to know. While I was working as a producer/engineer out on the West coast, I was asked to work on a project with legendary producer, Richard Perry, who produced You’re So Vain, among many famous albums.

    On a break, he told me that the hit was actually somewhat an accident. The story goes that Carly’s Take two performance was stellar and that Carly and all the musicians felt it was THE take. But Richard felt there was still something missing that would make it a hit.

    Meanwhile, while the musicians were sitting around listening to playback, the drummer, Jim Gordon, did something different on the line, “I had some dreams there were clouds in my coffee…” before the chorus. He started playing this tom tom build up he didn’t do in the previous takes and Richard Perry ran in and said that was the thing he was waiting for.

    When he went to tell Carly, she was nowhere to be found. It turns out she was hiding in the studio office crying uncontrollably because she felt she gave the song her all and couldn’t possibly do anything better.

    Well, he persuaded her to do one more and the rest is history.

    Thought your readers might get a kick out of that one.

    Very inspiring article!



  5. Rob

    I think maybe this time you made an error of judgement. If what this article (found as a link on Carly Simon’s blog) is true, the author of the book is kind of a sleaze and his work probably shouldn’t be promoted:

    Following the author’s apparent disregard for citing sources, you could have written your blog without even mentioning his name or the title of his book.

    • Carol Tice

      Well, guess I could, but it was the book I read that led me to derive these lessons from Simon’s life, so it would be odd to pretend I got the concepts out of the air, I thought. I did fully disclose that there is controversy around some of the passages in the book.

      • Corey

        Great post! I also wrote an article that lists most of the errors in the book, but if you got the above from the book, then that’s awesome. Carly will be releasing her own memoir, I think this year, maybe next. So we’ll soon have the opportunity to read her life story from her perspective. Should be interesting.

        • Carol Tice

          I saw that on her blog, Corey – definitely interested to read!

  6. Christina

    I think you mean unauthorized biography, not autobiography, as it would be quite difficult for someone other than Simon to write her autobiography, or for an autobiography to be unauthorized πŸ˜‰

    • Carol Tice

      Oh snort! Can’t believe I put that. There actually is one book titled that, “Lemony Snicket, the unauthorized autobiography” – writer of the Series of Unfortunate Events books better known as Daniel Handler. Apologies on that.

  7. Pamela

    Great points in your blog post. I enjoyed it! Thanks.

  8. Caroline Leopold

    Bravo. I never thought I’d see freelance career and childhood trauma in the same article. That’s the kind of truth that inspires me. Overcoming one’s personal demons is often the touchstone of a successful career. To repair damage, one must be fearless and persistent. No, fearless isn’t correct. Willing to walk through fear is better. These happen to be mandatory skills for a professional writer.

    • Carol Tice

      I’d think that childhood trauma is really in every post about freelance writing! We all had some, right?

  9. Nancy Passow

    Carly Simon is a great example for overcoming your fears. I teach a Technical Communications course to college engineering, technology, and math students which includes teams making presentations in front of their classmates. Not that most of them know about Carly Simon as they’re too young, but I do use her as an example of overcoming your fears of speaking in public. (However, you can’t have an unauthorized autobiography, as that is written by the subject. You can have an unauthorized biography, as that is written by someone else about the subject.)

    • Carol Tice

      Yeah — already fixed it in the post!

  10. 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… ?

  11. 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 πŸ˜‰

  12. 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?

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