How to be brave in your choice of career

Summertime is when all the music teachers and students disperse to various music camps, institutes, and conferences. The music teaching world is very local. The summer music world is location-independent.

We are in Claremont, Calif. right now, for the National Cello Institute, which is more international than national and my son has so many friends from Australia that he’s started talking with their accent.

As he plays his solo here, everyone assumes he wants to be a professional cellist. We all know that being a professional musician is a goal against long odds. And as Seth Godin wrote a whole book to explain (one of my favorites), the only things worth doing are things that are so hard you almost can’t stand the odds.

Because I’m a career coach, I think things like what if he loses a finger? What if he joins the Peace Corps? What if he just simply changes his mind? I want him to be ready.

Sometimes he tests me, “What if I want to stop playing cello?”

I know the correct answer, so I say it: “You can stop whenever you want. I only want you to play cello if that’s what you want to do. I love you no matter what you choose.”

I think he asks me that to make sure he has a choice. So I add explicit options and tell him that he could sell anything.

My older son says, “Mom, don’t tell him that. He’ll be a drug dealer.”

My husband says, “I know you think he’d be good at sales, but sometimes I wonder. The only thing I see him selling right now is himself.”

So I had an idea. I decided we’ll do a sales aptitude test so that both my son and I can relax a little bit about cello. He will still practice piano and cello four hours a day. He will still travel all over the country for lessons and performances. But all that will feel less risky because we will know he can fall back on sales.

I tell him, “We are taking a field trip to Staples in Los Angeles.”

“Dude! I love the Lakers.”

“No. The store. Staples is a store.”


“You are going to sell office supplies.”

He complains but then he stops complaining when he sees that I’m going to be paying a lot of attention to him and it will be like a performance.

We bring the cello into the store. It’s two hundred years old and it is very sensitive to changes in temperature so we never leave it in the car.

You know that experiment people did in school where kids carry around an egg as if it’s a baby in order to understand how much work it is to have a baby? That’s what I feel like we do with the cello. But it’s more like we have quadruplets.

We go to phone chargers. I tell my son he’s selling the Dual Device Rapid Car charger. He says he wants to sell one to me because he wants one for our car.

I tell him I’ll buy him one if he can make a sale to someone else. “Find someone looking at chargers and tell them why this one is great.”

People tell me that my son is a great cellist because he’s fearless. I can’t tell what that means in music, but I can see it here.

He walks up to a woman my age and he tells her she should buy the charger. “This will make your kids love you,” he says. “Also, my mom told me if I could get someone to buy one of these then she’d buy me one.”

The woman looks over at me.

I am dying. I am pretty much the worst sales person ever. Selling is about making a connection with people, which means you have to care about them. This is why sales is impossible for me but my son is incredible.

The woman bought the charger. Well, at least she put it in her shopping cart. I gave my son credit for that.

I told him his next mission is to sell a chair.

He says no.

I tell him he can pick any game he wants if he sells a chair.

I give him a choice of chairs. I tell him, “You do best selling when you sell something you like.”

He picks a pretty gross looking blue swivel, gives it a whirl and waits for someone to approach.

He learns another lesson in sales which is that it’s much harder to sell a product with no leads than if you have a sales funnel in place. He summarizes this lesson during a spin: “Mom, no one is buying chairs right now. I need something else.”

So we go to the pens. I hand him a 6-pack of pen style highlighters, saying, “Sell these and I’ll give you any game you want.”

He examines them and says, “I’ll buy these. Sold. Now you buy me a game.”

I like his spunk. I like that he sort of cheated because it’s something I would do. Cutting corners is a great career skill. It’s a sign of a winner.

I make him buy the pens. Then we pick out a game. And in the game aisle, someone approaches him.

“Is that your cello?”


“I used to play cello. How long have you been playing?” Dragging a cello with you is a great conversation starter—I recommend it if you feel shy at parties.

My son chats a bit more and then explains that I’m making him sell stuff to ensure he has a backup career if cello doesn’t work out.

The guy loves the story. He says, “I’ll buy something.”

Another sales lesson: people buy stuff because they like you.

My son says, “Can you buy these highlighters?”

The guy says sure, and without even asking me about how this affects our deal, my son picks out a second game. I buy it.

Later, I fish the empty game box out of the garbage and put it on my nightstand. It’ll be a great reminder that it’s fine for him to go after his cello dreams because he has a backup plan as well.

49 replies
  1. Eva
    Eva says:

    Great post, Penelope! And great idea with the back up plan. I think all parents should do something similar, although I believe it is easier to choose between cello and sells (especially when one loves cello), than between medicine and architecture (especially when one is great at art and at biology).
    Anyway, having choices is a good “problem” to have, so I just wish this to every teenager!

    • Hermione
      Hermione says:

      Just found your blog. You are very insightful. Two if your comments, “changing the ending changes the meaning” 2014, Hownto choose between two job offers, and “people buy things because they like you” so true

  2. sherry
    sherry says:

    This article was about you telling everyone how you are able to fly all over the country and possibly the world with your kids and do all kinds of things that most people probably can’t. Apparently you need people to understand that you’ve done well in your career and you have a lot of money. Some of your posts are mildly entertaining but here’s what I know about you and what I’ve learned from reading your posts over the last couple years. You are in an abusive relationship with an abusive man who has demonstrated abusive tendencies in front of your children and yet you have convinced yourself to stay in this marriage because divorce is bad for kids! Really you’re supposed to be talking about business stuff and every now and then you can clean little tidbits from what you say and there were a few morsels in this post. But for some reason you have a need to show everybody that you are Queen of the Universe and most of your posts really don’t stick or make a difference. Sorry to be so blunt but I’m pretty sure it’s not going to upset your day.

    • zsazsa
      zsazsa says:

      Why would you even write this? There’s a whooooole internet out there, if you don’t like Penelopes style, find somewhere else to wallow. Your words reveal more about you than it does about anything you’re trying to prove with writing.

    • Carol-Anne
      Carol-Anne says:

      The fact that you are able to “clean” tidbits from her posts is all I need to know about you.
      Thanks for coming out.

    • Sara Beth
      Sara Beth says:

      I think her husband got the rough deal. He sounds pretty awesome. He took in two kids, one special needs according to her though he seems not from many posts. If Penelope worked hard and has success good for her. Of course she brags. She admits she’s competitive. The whole blog is super competitive but it also has very moving parts. I ignore the bat crazy shit like the Sandberg rants.

    • khb
      khb says:

      ms sherry, are you out of your mind?
      What makes you think you know penelope so well that you come on her blog to type trash just because you have the internet?
      İf you have nothing useful to say, why dont you keep quiet or keep it moving?

  3. Stephen @ Thoughtful Growth
    Stephen @ Thoughtful Growth says:

    Thought-provoking as always, Penelope.

    As a member of a musical family, I understand so much of this post–hauling the instrument around (for me it was always a guitar), having siblings off at music camp during the summer. Though I’ll admit–my parents never let me sell stuff at Staples. I would’ve loved it.

  4. Jim Grey
    Jim Grey says:

    A 200-year-old cello?! Wow!

    A backup plan makes all kinds of sense when your first career choice has such a narrow path to success, and most people can’t make it.

    None of my kids was going to be brilliant at anything, so what I told them was that they needed to pick a direction that paid. My oldest son went into IT. My next son is studying medical lab science. My youngest thinks he wants to study mathematics. I did that and loved it. But I’m telling him to study computer science and minor in mathematics instead. Computer-science-related jobs are plentiful (where I live) and pay well.

  5. Mark W.
    Mark W. says:

    Great post. I loved the ending – “Later, I fish the empty game box out of the garbage and put it on my nightstand. It’ll be a great reminder that it’s fine for him to go after his cello dreams because he has a backup plan as well.” This post will be a great reminder for your son when he reads it sometime in the future regardless of the outcome of his career path. A good photo for this post would be that empty game box you fished out of the garbage.

  6. Chantell
    Chantell says:

    I read your posts, and I read this one twice.

    That’s saying a lot because the most useful skill I picked up in law school is how to skim. But I never skim your posts. I don’t have to discipline myself to read every sentence, because you make it easy and fun to do so.

    • Penelope Trunk
      Penelope Trunk says:

      I always feel so good when someone reads a post. Even when my brothers read and tell me it was stupid. I think, well, at least they are doing what brothers are supposed to do. But to say you read it twice — that makes my day. Thank you.


  7. Harriet May
    Harriet May says:

    Your ability to see your son’s talents, even when they’re exactly opposite to your own, is a superpower. My parents only saw how I wasn’t like them, which they found endlessly disappointing. My dad, who is dominating and charismatic, tried to make me good at math and finance. I can’t do math, but I can see that wallpaper in a foliage print would look great on our ceiling. And luckily I found a guy to marry who is willing to see what I see, so he lets me wallpaper the ceiling in our foyer. (Well, I don’t physically do the wallpapering… and actually once I’ve picked which one I want my fiance buys it and arranges the guy to come install it. We’re a great team.)

    When we go to visit my parents, my mom will get drunk and tell me I’m just like my dad and nothing like her, even though I inherited all her insecurities. And maybe her sense of humor too– my mom is really funny. Under-the-radar funny. But she doesn’t see that about herself, so I don’t think she can see where I get it from when I make her laugh.

    There’s a lot they still don’t (can’t, won’t) see, but I think my parents are beginning to see the vision I have for my life. It took me a long time to see it myself.

  8. Michael LaRocca
    Michael LaRocca says:

    Your son doesn’t have to play the cello as his career. I’ve been playing the piano for two years and I’ll never tire of it, but I couldn’t make a career of it even if I paid deaf people to listen.

    Playing the cello, and especially at his level, is its own reward. Seriously. If he can get paid to do it, even better, but if not, it doesn’t matter. Making music helps me stay sane.

    As for his career, meanwhile, I was almost 50 before I figured out what mine was. Don’t wait that long.

  9. Jonah Calinawan
    Jonah Calinawan says:

    I can’t say enough how much I love this post. The career and life lessons are clear, without philosophizing.:-) I really learned a lot from your courses. What a model to follow.

  10. Joel
    Joel says:

    Great post. I had a few chuckles at this as it reminded me of a few conversations I had with my mom when I was your son’s age.

    Thanks Penelope

  11. avant garde designer
    avant garde designer says:

    Your post reminds me of Frank Lloyd Wright. Yes, he was a good architect but his true brilliance was in how he sold himself. Even though there were many equally, if not more, talented designers in his day, he promoted himself as the greatest architect that ever lived. He believed this himself and he made the rest of the world believe it as well. He suffered many setbacks in his career, yet could always smooth-talk his way back.

    Creative thinking, moxie, and a vivacious drive…that’s what it takes. Your son will do well.

    • Penelope Trunk
      Penelope Trunk says:

      I didn’t know this about him. It makes sense, though.

      I always resist helping my son do social media. I tell myself he needs to live his life. I cannot help him with stuff like that because it will be too much of me being a Svengali or however you say it.

      But then I think, well, I’m not a musician and I can’t really help him in that regard, but I know how to self-promote (maybe that is all I know — it worries me, believe me) so maybe I should teach him that. Maybe we should do a cello YouTube channel together.

      Well. But wait. I can barely manage to write on this blog regularly so how would I do a YouTube channel for him as well??? I don’t know… your insight about Frank Loyd Wright gets me thinking, though.


  12. Mark L.
    Mark L. says:

    Thanks for the interesting and enlightening post. Have you had your son try playing cello for a crowd, in large, crowded, public areas, to enjoy their feedback and “sell” his skill? Also, has he tried to make any innovative YouTube Cello videos, to create a following? Thanks again for your blog posts.

    • Penelope Trunk
      Penelope Trunk says:

      Do you know what’s funny about that? My son played his cello across the street from the Art Institute in Chicago and he made $30 in fifteen minutes. And that became his standard for payment. As in:

      Me: If you weed the corn I’ll pay you $15
      Him: Why would I do that? I can make more money playing cello!

      So I think it actually gave him a skewed idea that cellists really rake in the dough.


      • Mark L.
        Mark L. says:

        As you travel to big cities, let your son perform in some of those open public spaces. Him, his cello and a crowd, with his personality, and he can earn a few buck s too, I think it will be a perfect learning and enjoyable experience.

        Why would you start the Youtube Channel for him? It is an idea for him to pursue if he wants and he can learn about how to start a channnel and make it successful, and ask for help or directional guidance from you, when needed. Again, as it grows, he can learn if, how, and how hard it may be for his channel to make money. But he is a showman, so it may be another good fit.

  13. Sarah
    Sarah says:

    I asked Andy what advice he would give your son for selling. He said not to worry about his ability to sell. It’s the ability to c0mmunicate with others. Reading books on how to talk to people (like zigzag ziglar,ect). Learning how to spot why an ad does what they do, how they worded it and how to read people. He also suggested a business degree because the pay goes up. Although he has been successful without one it was harder. Here’s the thing, when you watch an esfp you truly believe they like everyone. But if you can get them to “turn off” they only like a few people and view themselves as friendless frequently. When the seeds/food salesmen come around have him go out and watch them. If they are good your son will never see them “turn off”. Bad ones you see it the minute they turn around. Observing people and interacting is fun. You already know many of the social rules. Point them out to him. It won’t be a struggle for him to pick them up and use them well. Also, if there is a fund raiser he could do selling door to door or infront of a store that will teach quickly. There are scripts to learn with those. Great experience.

    • Penelope Trunk
      Penelope Trunk says:

      Such interesting advice! And it rings true to me. And the bottom line is that if someone is in the right job for them, they need very little training.

      You’re right about the seed salesmen. (It’s always men, of course.) They are selling a commodity so they get the farmer’s order by connecting with that farmer, over and over again.


  14. Lorna Wood
    Lorna Wood says:

    This is such a good article Penelope. I absolutely enjoy all of your work. I’m going to give this to my daughter to read. Getting your son to go out and sell is a great idea. Good experience and insight, but most of all exposure to choices. To actually put oneself into that position. Priceless.

    Really great.


  15. Honestly Laura
    Honestly Laura says:

    This is all at the opposite of being brave. Put all of it in and that’s being brave.
    Looking back I really wished I hadn’t had a plan B cause I settled and I felt and it took a long time to dig my way out. Don’t teach your kids about plan b until college when they choose a minor or certification. And even then…

  16. Mark W.
    Mark W. says:

    Also, there’s Marci Alboher’s book (One Person/Multiple Careers: A New Model for Work/Life Success) on “slash” careers to think about as you wrote in your post ( ) – “It’s clear that the age of job security is gone. And the best way to get security is to have multiple revenue streams, so that if one fails, you have a backup. In her book, Marci Alboher labels this the “slash” life — where you have more than one profession and a slash between them.” So your son could perform cello as well as teach it or do other related activities.

  17. Kristin Vandegriend
    Kristin Vandegriend says:

    As a career guidance counsellor, I am always trying to analyze my preschooler’s future occupational options so your article made me smile. The problem is that I don’t really have a sense of what occupations might be in demand in 15 years…the world changes so fast! But regardless, hopefully, she will have the skills and adaptability to find her way through.

  18. Sean Crawford
    Sean Crawford says:

    I can’t judge this post because I am a member of the older generation.

    Having said that, a good point is made by Honestly Laura. The army plans a lot. Do you know the army’s contingency plan for an assault that bogs down in no man’s land? There is none. The attack has to succeed.

    In Canada a successful comedian said in a CBC interview that all her young comedy friends who started out with something to fall back on, ended up falling back. She was the only one who lasted.

  19. mh
    mh says:

    I have a good friend who is a concert trombonist. He literally is in a sales job because he travels the world hustling for every performance. He barely makes ends meet.Chose not to have children but lives the music. But damn is he good at what he does.

  20. Tracy
    Tracy says:

    Entertaining & heartwarming.

    Your son is a born-salesman: he can intuitively work out how much people value things. In this case, 2 games was a small price to pay for a mother to pay to quell those fears of the future & get some peace-of-mind.

    • Penelope Trunk
      Penelope Trunk says:

      Yeah, I think this is really about my own peace of mind. It’s really about what I need, I guess. My son doesn’t think he has a plan B. He has played cello every day of his life since he was 4. He only wants to play cello. So the plan B is my own. And, really, no sane parent has ever been able to really plan their child’s life like that. People choose their own lives. And he is not choosing a plan B.


  21. Mariana
    Mariana says:

    Great post! I have an esfp husband so I wonder sometimes what the heck I would do if I had an esfp son! A lot of learning from you, thanks!
    Penelope, don’t worry about developing his sales skills, worry about those damn esfp annoying weaknesses! My husband makes a lot of money, but spends accordingly. Only after a major financial setback he started to stop to give all his money to people who said were in need (when they actually were not) or buying every new shiny gadget. Now we bought a little farm and he is happy to take care of it as his hobby and financial peace is finally setting in. For an Intj like me, financial meltdown was the best thing that could ever happened to our marriage!

  22. Mehul @ Search Results Media
    Mehul @ Search Results Media says:

    Nice article, having a second career option is the best thing and to identify a backup career is a tough thing. Doing what you love gives you most satisfaction but if you are not able to continue your passion than having second career option which you have selected makes you a winner. Thanks for sharing.

  23. Arise Johns
    Arise Johns says:

    You can choose your career as a Software developer working in an IT firm or you can pick marketing as your profession. The most important thing about picking the best career that you should know what you actually want? What are you actually trying to achieve? You should be aware of all the pros and cons of it and be brave while choosing the career.

  24. Helen
    Helen says:

    oh boy, this post fills me with worry. My son is an upright bassist, smack in the middle of his music degree (jazz). He wanted nothing else but music, and wouldn’t ever consider a plan b. He is very shy, except for when he is performing. Its like he is someone else when he is playing, he just blossoms then. I guess I get it now that I just wrote this about him.

  25. luis henrique
    luis henrique says:

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  26. BD
    BD says:

    Another great article Penelope! I absolutely enjoy every one of yours posts. I can promise you that as soon as I have children they will be reading some of your articles, including this one!

    Its so clever that you got your son to go out and sell! It is such a valuable experience that everyone should do this!

    Awesome. Please keep up!

  27. Maria
    Maria says:

    I have to admit that most of your blog posts are entertaining. Well, that was a great idea with a back up plan. It may be hard to choose what’s best for you but with the courage to take a stand in whatever your choices are, you’ll have a narrow path to success.

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