Career lessons from Susan Boyle’s success

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I never watch American Idol, or other talent shows. I think I got my fill of them in the 1970s, watching year after year of the mind-numbing Miss American pageant. But there was too much hoop-la with Susan Boyle on Britain’s Got Talent, so I had to see what I was missing. I ended up watching her audition fifty times. Because every time I'm feeling slow or unmotivated or depressed, the clip cheers me up.

Last night she sang in the semi-finals, and what struck me most while watching her is how much we can learn about our own careers from watching Susan Boyle's. For example.

Everyone loves to be a shepherd of talent.

The act of finding a mentor is actually the act of showing someone you have talent and they can help you find it. It's very, very hard to land in the limelight on your own. So many studies of success — from Fortune 500 executives to startup entrepreneurs — all show that a key factor is finding people to help you navigate a system that requires many more skills than any one, single person could have.

If you ever wonder what you bring to someone who is mentoring you, look at the faces of the three judges when they realize (after four or five notes) that Susan is phenomenal. The joy on their faces is contagious. That's a big reason people like to watch that video clip: the moment when you see someone is very talented is so rewarding. It's a moment full of excitement and promise and you get to be a part of it because the person is asking you for help.

This is why mentoring is magical and electrifying to both sides. And seeing the moment on Britain's Got Talent reminds me that I should continuously seek out mentors and show them I perform well with the help they give me.

You can only shine if you set the bar high.

Susan sang a very hard song: I Dreamed a Dream, from Les Miserables. Not that I know anything about opera. But after watching the video of her at least 50 times, I got curious about how other people sing the song, I Dreamed a Dream. Then I started seeing all the places the song can trip up a singer.

If you watch the clip 50 times, you catch Simon Cowell saying, “That's a big song.” It's an important thing — that she picked a big song. Because if you want to be seen as someone doing something big, you have to pick something big to do.

Seth Godin writes about The Dip. It's the time when things look too hard. It's the time when you are trying to do something big, and it is not happening, because doing something big doesn't happen right away, it takes work. And it's very hard to do a lot of work if you don't know what will come of it.

Most people quit. That's Seth Godin's point: That you have to try something big, and you have to accept that anything big and huge requires you to have a dip — a point when you are wondering if it is worth it. And that's where most people quit. For the most part, you cannot do something big without going through this process.

I think I'm in a dip right now. With my company. I am lucky, because I have Ryan Healy reminding me that we're in the dip, doing something big, and we can't quit. And I'm lucky because I have been in the dip twice before — when I struggled to get on the professional beach volleyball tour, and when I was trying to finish my novel and still did not know that I would eventually get a publisher.

So this is what I know about the dip. There is no big win if you don't suffer through it. And the first part of the process is to pick a big song.

Settling for a day job does not destroy you.

We all love stories of early success. Child actors discovered in Mumbai, three-year-old girls whose singing makes you cry. In the tech industry, being a young founder is so legendary that founders have lied about how old they are. And in mathematics, it's always news if someone discovers something later than age 30 because it so seldom happens.

We love the stories of early, magical success. So when we find ourselves having to take a day job we don't love in order to do what we do love on the side — this is not the narrative we hope for in life.

But Susan Boyle is evidence that this narrative works as well. Huge talent can shine through at any age, and the world will respond. Susan Boyle did what so many people do who are not getting paid to do what they love. She kept singing, while she worked day jobs. She sang because she loved singing, and she got better and better and better.

A hallmark of talent is loving to practice. And Susan Boyle's story is the narrative of the hard work that talent takes. Our lives are first, and foremost, about getting up every day and practicing what we love. What you get paid for, what you get honored for, that is secondary. And success comes for those who work hard.

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  1. Sydney
    Sydney says:

    Between you and Seth Godin, I’ve been getting some very timely advice. Now that you’ve referenced the Dip, and I’m catching up on Seth’s posts, I must read it.

    I’d say moving from Tampa to Chicago is pretty huge. I want to be huge. Someday I will be. I’m at the dip. I’m totally excited and totally freaking out. I’m obsessed with researching the city and every angle for success or failure.

    Thanks for this post – great timing. And thank you for helping jumpstart my career. I owe you one.

  2. t
    t says:

    I think this might be the best post you’ve ever written. Particularly the first of the three points. Thanks.

  3. Joselle
    Joselle says:

    A big part of why the response to Susan Boyle has been so huge is that she is not conventionally attractive. She is not at all what a popular singer is supposed to look like. If she looked like Angelina Jolie, would people have been so blown away? Or would they have yawned and expected that someone so beautiful should also have a beautiful voice?

    I think Susan Boyle’s success is just as likely as Angelina Jolie’s. Meaning not very likely at all. Susan Boyle is just the flipside of nepotism and beauty (and yes, talent, too). And every once in a blue moon, we like to root for the underdog.

    I do think your guidelines are very sound and inspiring, though.

  4. Suzy
    Suzy says:

    My dip was deep enough that even after reading the book, I wasn’t convinced that it was a dip vs dead end. My non-profit start up has taken 3 years to become viable and cross our fingers sustainable. I fired myself after one year and now have a portfolio of jobs. The combination has actually brought more opportunities than if the start up had taken off right away.

  5. Mark W.
    Mark W. says:

    A quick note about Susan Boyle. She is getting all the attention right now. However, two years ago, the winner of Britain’s Got Talent (first one) was Paul Potts. He is a tenor who sang opera (“Nessun Dorma” from Puccini’s Turandot) for his first audition ( ) and later went on to win that season. He has an amazing story as told in the above video and his wikipedia entry. He also had an album released by Sony that same year.

    • Kate Davis
      Kate Davis says:

      I completely agree. When I heard the fuss about Susan Boyle I watched the video online and couldn’t help compare it to the Paul Potts video which I watch every now and again when I want some motivation.

  6. JR
    JR says:

    Susan Boyle sings quite well. Very well for an amateur. But not as well as any professional that I have heard sing “I Dream A Dream”. She couldn’t hit the low notes at all. But still, a great story. Is there any doubt that she already has won?

  7. Stuart Foster
    Stuart Foster says:

    I think dips only exist to make us stronger. If they aren’t there for that reason…I’m probably pretty screwed. I tend to have a lot of them because I think big and am sort of crazy. But I think in order to succeed big…you have to fail big first.

    • Chris Gammell
      Chris Gammell says:

      Hey Stuart,

      I think you’re right that Dips make us stronger. However, Penelope missed a key point in that book, namely that there are times where it’s BETTER to quit (a surprising point that Seth makes throughout the book). The most successful people stick it out when they know they have to and also quit right away when they know it’s not a dip (but instead a dead end…or worse, a cliff). Good luck with your future success (and as you say, very important failures)!


  8. Clare
    Clare says:

    Teaching is like mentoring. When your students finally get a point that has taken ages for them to absorb and understand… one of the biggest legal highs that you can ever get.

    Thanks for a great post.

  9. Kat Argonza
    Kat Argonza says:

    Just one thing, it’s actually not opera. It’s musical theatre, but not opera. Opera is a whole different technique of singing.

    Otherwise I agree with your post. We have much to learn from Susan Boyle.

  10. Alex @ Happiness in this World
    Alex @ Happiness in this World says:

    Wonderful, wonderful post. True success comes from work, work, work and not giving up and a little luck, and if no luck now, work, work, work, be excellent and still don’t give up and don’t give up until you die.

    A Buddhist mentor of mine once said, “In life you can only achieve a small fraction of your dreams. If you don’t dream big from the outset, I wonder what you will have lived for then.”

  11. Kathy | Virtual Impax
    Kathy | Virtual Impax says:

    I think we love the stories of early, magical success because these are often FAIRY TALES instead of based in reality.

    I used to love watching VH1’s series “behind the music” because week after week you’d learn how hard and long those musicians worked to achieve what appeared to those of us in the audience as “overnight success”.

    Susan Boyle is a prime example – she has such incredible talent and I think we all look at her and think – “Wow! Why is Paris Hilton famous at 17 and she wasn’t?”

    Unfortunately, we all know the answer… but we like rooting for the “underdog” in any case!

  12. NikiH
    NikiH says:

    Your posts can make me laugh and make me happy I’m not you. This one is a dose of reality that makes me think “oh yeah”. I gave up the thought of getting paid to do what I truly love because I worried I wouldn’t love it any more. I’m still practicing and doing what I love as a hobby and letting my day job pay the bills very well. I’ve heard people say this is selling out. But those people seem to have a very poor definition of selling out. Great post! Thanks

  13. Caitlin
    Caitlin says:

    Susan Boyle is amazing but I’m amazed that this made waves in America. I don’t even think the TV show itself is screened in the US, is it? It goes to show the power of the internet and YouTube.

  14. Office Humorist
    Office Humorist says:

    Great post and ideas of what we can learn from Susan. I think she also (knowingly or unknowingly) taught us not to fear going after our dreams or worry about what others thought. Going before judges on a big program like that can be intimidating, but she believed in her voice and her dreams to say it was worth the risk of looking foolish.

  15. r.harney
    r.harney says:

    This is what you do best Penelope. Drawing work advice from popular experiences and cultural events.

    So damn smart.

  16. Miriam Salpeter, Keppie Careers
    Miriam Salpeter, Keppie Careers says:

    I resisted writing anything about Susan on my career advice blog when this story first broke. In my mind, Susan’s appearance was such a huge part of why her video went viral – the judge’s surprise that her voice was so amazing was magnified by the “unlikely” package delivering it.

    I wasn’t in the mood to write about appearance and how important it is for a job seeker…

    So, I was delighted to see what you’ve written. Especially the point about setting the bar high. What a terrific analogy – aiming high offers the opportunity to outperform. It also involves risk and weighing risks and rewards. It makes me think of Olympic gymnasts who attempt a “high point value” routine. If they “stick,” they’re golden. If not, they are out of luck and left to wonder if they made the right choice – possibly for the next 4 years or the rest of their lives. Careerists need to know when to take that risk and when to play it safe.

    Maybe I’ll be writing about Susan Boyle after all!

  17. Mark F.
    Mark F. says:

    “success comes from those who work hard” and “Huge talent can show through at any age”
    can I quote you!
    Words to live by!!!-
    P, I like your serious business side…
    P.S. Seth is sooo cool, he gets it!!!

  18. Susan Johnston
    Susan Johnston says:

    I was going to make the point about opera vs. musical theater, but I see that other commenters have beat me to it. :)

    I would add that the reason Susan Boyle knocked our socks off with “I Dreamed a Dream” is actually because she chose a song that fits her voice and allows her to connect emotionally. So many Idol candidates sing pop, R&B and other genres, and you have to admire her for taking the less conventional route of a musical theater ballad. (I know there’s a career lesson here. Maybe that you should be yourself and not the person you think the judges want? Or that you should dress for your body type and not a slave to trends?) Plus, I think she really connects with the song’s dramatic arc. That emotional connection makes for a much stronger performance than a lifetime of practice, though practice certainly doesn’t hurt, either.

    • Joselle
      Joselle says:

      She did write a novel. It’s very good. It just wasn’t written by Penelope Trunk.

      So, she’s published two books, that I know of. One, a novel. The other, Brazen Careerist.

  19. Pidge Meade
    Pidge Meade says:

    I loved this post. I have to admit, I was a little afraid to read it when I saw the headline, as I assumed you were going to say harsh things about Susan Boyle’s appearance. But I clicked through anyway, and I’m so glad I did. It’s you at your best — surprising, straightforward, personal and universal, from the heart, and creating value for others. Your thoughts on the Dip and the day job in particular hit home for me and gave me some new insights. Thanks very much.

  20. Randy
    Randy says:

    Sorry, but am I being stupid?

    What are the lessons from Susan Boyle…you segue to the value of mentoring but did she have a mentor? Isn’t one of her career success secrets that she portrayed herself as a nobody and then WOW’d everyone! Isn’t that exactly what the gal who is in Wicked said on Terry Gross?…that she used to go to auditions and introduce herself as a southern hick and then belt out a giant voice from her little body.

    Susan Boyle was singing in clubs for 20+ years… she entered MANY competitions and when she said “no one’s every given my a chance” is was a complete lie… so was “and I’ve never been kissed”.

    And of course when she admitted that wasn’t so everyone had no problem with it… her lesson the the same old as always… IT”S BETTER TO ASK FOR FORGIVENESS THAN PERMISSION!

  21. Kaneisha | The Dream Catcher
    Kaneisha | The Dream Catcher says:

    I still haven’t seen the Susan Boyle clip (I will watch it immediately after finishing this post), but thank you so much for the “permission” to have a day job while we pursue our dreams. As a Gen Y’er, I often feel torn between insisting that I absolutely do what I love–writing, creating things, etc.–and holding down day jobs where I learn and contribute a lot but am not necessarily in the epicenter of my dreams. I will continue to love to practice and I won’t let the dip bring me down. What a great post after a few days of being quiet. I wish I could meet up with you while you’re out here in LA, PT!

  22. Erin Kennedy, CPRW
    Erin Kennedy, CPRW says:

    Hi Penelope,

    Loved this post for two reasons: Susan Boyle and the Dip. I never watch American Idol either, but after hearing so much about the Susan Boyle story, I decided to watch it on YouTube and was captivated. I have watched it so many times and each time I get teary-eyed. I love underdog stories.

    The Dip- love that. I love your honesty about your dips, too. I think that is what I am going through right now and your post hit the nail on the head. Stick with it to the end… not knowing where the end might be. Sure is fun along the way, though.

    Thanks again for this upbeat post.


  23. Brady
    Brady says:

    I love the wisdom that comes from this blog. I think you picked a poor example. While it is reality television, it is not reality, and the judges had heard Susan Boyle sing the same song many times in the semi-finals, before anything was ever aired.

    Les Miserables is a musical, which you confused with an opera and mispelled as Misearables.

    I have big dreams and am working on making them happen, one day at a time.

  24. Helen Romeo
    Helen Romeo says:

    Re: “Our lives are first, and foremost, about getting up every day and practicing what we love. What you get paid for, what you get honored for, that is secondary. And success comes for those who work hard”.
    Penelope, first of all, thanks. Because you gave me the inspiration to start a blog of my own. Then you linked to me, which gave me a leg up on readership. Unwittingly, you gave me a mentorship of sorts: reading your blog, picking up on your confidence, being inspired by your ups and downs. You see, folks, at this point I was down. Truly down. In the dip, as you put it, but maybe lower. I’d written a novel no-one seemed to want to read, staying up every night until past midnight after a day looking after the kids with no help. I was a stay-at-home mum with truckloads of ambition (but overwhelming frustration). I had no energy left to bother with a blog or give my love of writing an outlet, a means of honing my skill. No, I had no energy left. To bother with anything. I was about to give up.
    Now? one month later? I have a healthy readership ticking over, confidence, and am about to start editing a local magazine and bring it on-line. There are plans for something which could end up as a start-up in the future. I’ve made contacts, got my ‘mojo’ back! Little things, perhaps, to you major career bods out there, but I think Penelope would understand where I’m coming from. It’s no point thinking: “I’m almost 40, I’ve never achieved my potential, I wasn’t there at 23 so I can give up now!” No, you have to start somewhere, no matter what age and situation you have as your status-quo. And have the confidence to forge ahead no matter what. If you bow to the ‘dip’ then it’s just career suicide. Susan Boyle didn’t (and nor did one of our most successful entrepreneurs here in the UK, Duncan Bannatyne, who at thirty sat penniless on a beach and read about Alan Sugar in a newspaper he’d picked up off the sand. A couple of decades later he’s worth in the several millions of pounds). Ambition gives you lifeblood, but Confidence is indispensable, and, sometimes, even just one person who believes in you, be it from afar. Thanks, Penelope!

    • Helen Romeo
      Helen Romeo says:

      Sorry, meant Duncan Bannatyne is worth in the several HUNDREDS of millions of pounds – 320 million pounds to be precise in 2009, up 10m from the year before despite recession.

  25. Rowe
    Rowe says:

    Hi Penelope, this is a wonderful post. Very encouraging. I am a relatively new blogger and I often think I am such small fry in this big big blogosphere overflowing with so much talent.

  26. Remedy for Eczema
    Remedy for Eczema says:

    Thanks for the lessons, really fun reading them. The last performance of Susan didn’t impressed me much as she did in her first appearance. But she still brings it out to everyone.

  27. Chandlee Bryan
    Chandlee Bryan says:


    This post is on target on multiple levels–from mentoring and “picking a big song” to working “through the dips.” I’ll be sharing this with the Twitterverse as well as with my clients.

    One quick note on mentoring: Keith Ferrazzi has a new book out, “Who’s Got Your Back?” in which he talks about how we all need lifelines as well as mentors. Lifelines are peers who have similar interests or goals and who will support and challenge you as you move forward. Based on what I’ve read about Susan Boyle, it seems to me that she had great voice coaching, but not a wide enough support network outside her family to encourage her singing along. I wonder if she might have found the courage to share her voice earlier if she had a stronger support base among her peers.

    I personally have found lifelines to be as important as mentors in helping me achieve personal goals. It was a fellow classmate who inspired me to become a stronger student in college, and who taught me that it was okay to use my own learning style to digest course material. (I ended up making play-doh models to pass geology because I couldn’t see in 3-D.) I’m forever grateful to her.

    Again, many thanks for this valuable post.

  28. David
    David says:

    Excellent column and sound advice for all the would be singers, writers and artists out there.

  29. PDX_Jeff
    PDX_Jeff says:

    Love this post because it is so, so true.

    Especially the last paragraph. Translated it is passion. Loving something so much you do it in any spare time you can find… that’s what makes you great.

  30. prklypr
    prklypr says:

    I listened to Susan Boyle and heard a lovely rendition of I Dreamed a Dream. You listened and heard something else enitrely. I love that. True success is all about “picking a big song.”

  31. Todd @ The Personal Finance Playbook
    Todd @ The Personal Finance Playbook says:

    I’ve been planning on blogging about Susan Boyle myself. Not on the exact same topic, of course, but maybe from a discrimination perspective – of corporate cultures. She’s a great example of how talent can exist in places that you don’t expect to find it. That’s the beauty of those shows (which I don’t watch, either).

  32. Pat Rocchi
    Pat Rocchi says:

    This is one of your loveliest, most thoughtful posts… a real inspiration to those of us who keep plugging away. Many thanks for the hope it conveys.

  33. Dale
    Dale says:

    Penny this is one of your best and I’ve been reading your stuff for a long time.
    The advice on handling a dip is something you could really go to town on as it is something many people face in a number of different ways.


  34. Connie Mettler
    Connie Mettler says:

    This is an excellent post, Penelope. The timing is right. I’m going to link to it on my blog at for all the artists who are trying to hang in there in these exceptional times.

    I haven’t read The Dip but am reading Tribes right now. Man, he is such a poor writer, I can’t believe he is such a big deal — the book reads like a series of Twitters. But, here’s to all the folks who can live through The Dip. It is hard when you really believe in yourself to take the job so you can support yourself and keep on going.

    Have you read Gladwell’s The Outliers? His thesis that you have to do something for 20,000 hours until you can truly be outstanding. There is something to that!

  35. Melissa
    Melissa says:

    This is the best motivational writing I have read in a long time. I have been reading your blog for about a month now. I usually read interior design blogs, so I don’t even know how I came across yours. But your blog is in my favs now and I read it often. I like your stratight forward approach. I think I am in the dip right now also and I just found a mentor who is setting me up for something big. I have alot of fear and think about quitting every day, but I want to make it, I want to try. I want my life to have a purpose. Thanks.

  36. Marie
    Marie says:

    Thank you for this blog post. Today is one of those “want to give up” days and your post reminded me that it’s ok to have a day job while working towards your dreams.

    Keep up the great work!

  37. @Sarahc28
    @Sarahc28 says:

    This was the best post I’ve read in a long long time. Thank you a million times. =)

  38. Balcony Bra
    Balcony Bra says:

    Most of the so called “talents” are made up. And that’s why it is so amazing when someone like Susan Boyle comes along.
    She is awesome.

  39. Nichole
    Nichole says:

    Just wanted to say that I have been following your posts for a while. I was recommended to you by Careerbuilder, while trying to figure out what to do with myself. You were recommended in blogs to be reading…and I have enjoyed pretty much every blog. Everything you write about is relevant, with all your trials and tribulations, your successes and even your personal life. You also put a lot of yourself in there which makes your blogs very easy to relate to.

    This post was very inspirational. I know of Susan Boyle, but have not watched her progress and only have heard snippets of her voice. I knew she had a great voice…but she has more than that. I am in a transitional state and I am still working on finding my way and this confirms that your never too old, never too anything to keep you from having dream and reaching it. Also, reinforces me the lesson of not judging a book by its cover.

    I look forward to your blogs and wish you much success in your endeavors.

  40. h
    h says:

    This is definitely one of my favorite posts!!

    Would you agree that in this current crisis, the “day job” something like “Mr Right Now” (and not Mr Right) considering that everyone’s trying to get into the few roles open?

  41. Tatyana
    Tatyana says:

    I like the post a lot


    Now we have another career lesson from Susan Boyle.

    She lost to Diversity with absolutely great performance because it was the same song. Everybody expected new great surprise. She played safe and gave improved but the same performance while her competitor gave great fresh new performance – new surprise – new step.

    I listened her “Cry me a river” and compared with other singers found in internet. On my opinion her version is one of the best. Why did she chose stay with the same song? I really expected what another surprise she will bring to the public. As many others did. Of course, now Susan will have her album…. but…

    Another Career lesson, do more steps, do next steps. Because somebody else do it. If you do not make next step you are moving backward.

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