How to make it in New York City

I took the kids to New York City for a week, and while Melissa was trying to figure out what to do with the kids for the day I was working, she came up with this idea that my seven-year-old son should do an internship with a stylist.

He wants to be a stylist. He talks about it all the time. And it’s hard for me because I’m so bad at dressing myself that he has actually reprimanded me: “Mom. That’s okay for the farm, but not for Boca Raton.”

So I thought we would just have this silly little day where a stylist shows my son a bit about her job. But really, I was blown away. The stylist Melissa contacted, LP Fashion Philosophy, is actually a girl/guy team: Erica Lavelanet and David Pena. And they set up a shoot with a photographer and makeup artists and model.

When we got there, I knew it was serious. The studio was in the trendiest part of Williamsburg and it was huge with hipster-grit and lots of natural light.

The spread of clothes and accessories was incredible. My son was in shock, and I don’t think I’ve ever seen him shy, but it happened. He could see that this was special.

The shyness ended quickly when David showed him how to sort through the clothes to pick a look. And how to get wrinkles out of the clothes you want to use.

They explained that the shoot would do three different looks. So my son went to work on the first two assignments, thinking in terms of punk and glamour, and he gave his selections to the model, Kate Welsh, to try. And he found he has a penchant for accessories.

At first I thought we were just doing this  in a pretend way. But soon I realized that each person was really top-notch, and they would use this for their portfolio. Watching my son manage the model made me realize that they were treating him seriously and that made him more serious about his own work.

The makeup artist, Rie, did three changes of makeup that took about 30 minutes each. Kate said, from the chair she sat in for a very long time, that this was much faster than normal.

Rie was unfazed when my son gave directions like, “I think gold eyes would be good,”  or “Let’s do blue and green lips to match the blue necklace and green belt.” She made it all look good.

We spent a lot of time waiting, between makeup changes, so while my son watched everyone in action, I asked about their careers. To my son, everything was so fun and easy.

But I wanted to stress to him how hard it is to make it in New York in fashion.

Erica and David launched their business when they were in college together, so they had a jump start when they got to the city, which is pretty much the theme of everyone in the room. Erica said that the amount they have to work to succeed is tremendous. You have to love working in this industry because it’s such incredibly hard work, is what she told me.

Spencer Kohn was the photographer.

He started doing this when he was fifteen, taking photos for his family’s low-budget magazine, then he got an apprenticeship with a fashion photographer in New York City, and since he was only sixteen, his dad had to sign a release so he could see naked women.

I looked at Spencer’s portfolio and I was blown away. He impresses me for his artistic ability, but also, he is so much younger than everyone in the room and still be able to function as the person in charge. And of course, he’s a great example of how you don’t need to go to college to get a great job. You need grit and determination and belief in yourself. In a city this competitive, good education doesn’t differentiate you enough.

At first my son sat back and watched as Spencer directed Kate and checked the results.

But then my son had some ideas of his own. And Spencer said, “Go ahead. Give it a try.”

And Kate listened.

Kate was so impressive because she was willing to take direction from a seven-year-old. He’d say, “Try this” and he’d do something, and then she would do it. The process reminded me of making jazz music, actually. They were working together to create something fun.

So many people would think they are too good for that kind of collaboration with a seven-year-old. But it was a team of people who were all early starters – they all appreciated that someone helped them so they could learn something they had no idea how to do, and so each person was willing to do what my son asked to give him the same experience.

Spencer said that usually he gave the model a lot of direction, but today he was mostly the camera guy, and he let my son play the role of creative director.

Then Spencer taught my son how to check to see how the photos are coming out.

Sometimes I had to cover my eyes. Where did he get the self-confidence to do this?

Sometimes he had to cover his own eyes. He never knew quite how the clothes he chose would look when they’re on, and at one point he said, “Oh no! Your belly button’s showing! Button your shirt! That’s not good for a little boy to see!”

Spencer showed my son how to go through the photos on the computer screen to make sure they got what they needed. And suddenly all those hours of unlimited screen time my kids have at home seemed really useful.

You might notice that by the end, my son had started wearing the clothes he pulled for Kate to wear.

So finally they asked him if he wanted to jump in front of the camera.

Guess what he said?

He was good, after about five minutes of practice. But then, proving that the best way to find out what you want to do is to try a lot and quit fast, he realized how much work the model does, and he took off his jacket and said, “I want to be a stylist. That’s what I really want to be.”

Then he sat back down in the chair behind Spencer and said, “You guys, I just love my job!”

That day, everyone got photos to use in their portfolio. My son chose a photo as well, because maybe when he gets older he’ll want to make it in New York City.


82 replies
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  1. Joseph Fusco
    Joseph Fusco says:

    Great story. Please keep pushing the value of experiences, networks and internships. As a senior executive with almost thirty years of experience, I can say with absolute certainty these are the most important factors in success, and qualities in people we most want to hire, and who we see outperform their peers.

  2. heather
    heather says:

    what a fantastic post. Typo in the copy block under the 10th photo: “…and so each person was willing to what my son asked to give him the same experience.”

    • Penelope Trunk
      Penelope Trunk says:

      Thanks, got it.

      One day, when I offer up some dreamy-great internship for a seven-year-old who wants to be a writer, I hope he is a better copyeditor than I am!


  3. Shannon
    Shannon says:

    I would really like to see the rest of the photos from that day. Also your boy looks like a rock star.

  4. Dana
    Dana says:

    Just out of curiosity …

    Do you have any idea of how to make these types of opportunities available for kids/parents who don’t have the connections that you do? I’ve got a kid who wants to be a DJ, but being the 48-year old accountant that I am, I don’t have any connections to actual DJs,

    I just think this is such a great opportunity for kids – especially those like mine who are in high school, not at all on the college track, but with a passion for a profession.

    • Joe
      Joe says:

      1) Go to

      2) type in the name of your town and ‘dj’

      3) press the button with the word ‘search’ on it

      4) call one of the people listed

      5) Stop pretending that you’re helpless when the truth is that you really don’t want to do something.

      • Paul
        Paul says:

        Call one and keep calling till you’ve run out of numbers. A good rule in any field you want to break into is that out of 10 random contacts, 7 won’t give you the time of day and 2 will try to take advantage. And you never know which one is number 10 until you’ve taken your chances with the first 9.

      • Dana
        Dana says:

        Thanks for that amazing advice Joe, I’d have never considered that because I’m pretending to be helpless *rolls eyes*

        And Paul, I’ve called 12 DJs without success. I’ve not found my number 10 yet, but will keep trying.

        • Joe
          Joe says:

          I guess I don’t believe you. Local DJs are a dime a dozen. They play parties and bar mitzvah for dirt cheap.

          Here’s step 4a & 4b that will definitely work:

          4a) ask what their hourly rate is

          4b) ask them if they will teach your kid for it.

          And PLEASE don’t attempt to tell me that you can’t find one who will take your money.

          • Penelope Trunk
            Penelope Trunk says:

            I agree about paying their hourly rate. It’s worth it, and one hour of anyone’s hourly rate isn’t that bad.

            The other thing is that you need to ask for something specific. You can’t say “teach him how to be a DJ” but you can say “show him ow to put a song list together that will work” or something like that.


          • Dana
            Dana says:

            Joe, you and I are coming at this very differently. Yes, the DJs that I spoke with who were willing to let a kid stand next to them while they did what they do were more than happy to take my money, but I’m not looking for a high-priced babysitter – I’m looking for someone willing to be a pseudo mentor.

          • Joe
            Joe says:

            You’re protesting too much.

            4c) Call them, ask them “how much would you charge to per hour to mentor my son in his dream of being a DJ? And I don’t mean just babysitting him. I want a real mentor for him, and I’m willing to pay for it.”

            4d) write the checks.

        • Greg
          Greg says:

          Dana, there’s a DJ school in New York called Dubspot that has online classes.

          Joe, I think there are better ways of dealing with whatever you’re dealing with than taking it out on blog commenters.

        • Angie unduplicated
          Angie unduplicated says:

          You might try some out-of-town DJs, and make a day’s vacation out of it. Nashville, Austin?

    • Allison Williams
      Allison Williams says:

      It might also work to chat with your kid about what the first part they’d like to learn is, and put up a flyer on the local college music department and coffee shop bulletin boards – seeking DJ to teach young person to do first step. You’ll probably get more au courant people than the guys working bar mitzvahs.

    • Charlene
      Charlene says:

      Hi Dana, If your kid’s in high school I think you can encourage them to look for their own mentors. He/she can follow Penelope’s advice – find great DJ’s, get in touch, ask good questions. Ask friends for upcoming parties/events with DJ’s and see if you guys can sneak in for an hour or two.

    • Diane
      Diane says:

      Hi! Forget Google and cold-calling. The way to meet a DJ is to go on Facebook (and LinkedIn – and any other large-ish social networks you may belong to) and post that you’re looking for a DJ to mentor your son. If you have a decent network that also includes acquaintances across a variety of age groups, odds are someone will know at least one DJ and they will introduce you.

      Anytime I am looking for anything (very minor exaggeration here), I turn to my network and it always delivers. :-)

    • Jen
      Jen says:

      Hey Dana!

      Does your son know what kind of DJing he wants to do? For example, is he interested in radio? Does he want to do parties and weddings? Is he thinking about being the “noises and loops” guy in a rock band? If he’s focusing on a specific area, it might help narrow your search.

      If he wants to be a radio DJ, most local stations will have internships at the community colleges or universities, and you may be able to connect him with those stations through the intern coordinator. You can also try calling the midday or latenight jocks (they may have more time because they’re less in-demand) to ask if you can book a tour and take it from there.

      If he’s thinking about being an event DJ, he can start by throwing parties, making playlists, and seeing if people dance. Go to a few community events where someone is MCing and playing music — get some business cards and maybe you’ll find your good number 10 in that crowd.

      And if he wants to be a more experimental DJ, like in a band or other musical enterprise, try the want ads at local music stores, record stores, and craigslist. (Disclaimer: I’m a musician.) I think there are plenty of people who understand the basics of DJing (play good songs, don’t be an ass on the mic) who would be willing to show him the entry-level stuff, and through that you might find a connection with someone who can mentor him further.

      Hope that’s helpful!

    • Kayla
      Kayla says:


      I would suggest reaching out to the radio station at whatever college is closest to you. You might deal with an asshole or two, but you might also get in touch with someone like me. I was a radio DJ all throughout college, and I would have loved to show an interested kid the ropes, free of charge. Good luck!

  5. Cheri Sundra--Guerrilla Historian
    Cheri Sundra--Guerrilla Historian says:

    What a wonderful experience for your son! I think many parents are too quick to tell children what they can’t do….and more often than not, project their own fears and insecurities upon them. It takes an enlightened person to encourage the gifts possessed by others. Clearly, this was an impressive group of individuals!

  6. Mark
    Mark says:

    Would have loved to read the article, but had a hard time with it. The WordPress theme you are using has in the meta tags of the html, a property thus: user-scalable=no which does not allow me to increase the text size to something I can read.

      • Mark
        Mark says:

        Okay, got it. Using an ipad the pinch/zoom does not work as on other sites but can use three finger taps to make it zoom. Good article btw!

    • Lisa
      Lisa says:

      Mark, I noticed the same thing. If you subscribe to the blog you can enlarge the text in your email rather than reading it directly from here.

      The blue and green lipstick, interesting combination I think I actually like it especially with the green belt.

  7. Emily
    Emily says:

    What a fantastic and inspiring story. The next time you and your kids pass through NYC, I’d love to have your son go through my closet with me, he’s got a great eye!

  8. CL
    CL says:

    If my parents had really believed in self-directed learning, I would never have to had taken Ramit’s Dream Job. It’s an excellent product for lost 20 somethings who don’t know what they want to do. But you nip that problem right in the bud and teach your kid to try new things. To echo tdodge, Bravo!

  9. Jennifer
    Jennifer says:

    Now *that* is homeschooling at its best.

    I’d love to hear how his experience is reflected or incorporated back on the farm. How will you keep him from losing the momentum he gained in the city?

  10. Kathy Donchak
    Kathy Donchak says:

    Wow, that is what education should be! Great experiences and having the ability at such a young age to try something new. Having that kind of support from a parent is a gift. He is lucky to have you.

  11. Deena
    Deena says:

    I’m in love. What an AMAZING opportunity for him and what amazing people to do that, to truly listen and be a part of who he becomes. Great job mom, he’s got your city genes.

  12. Kelly Exeter
    Kelly Exeter says:

    I wish I had something more interesting to add than ‘this is so cool’ … but it IS cool and I am so thrilled your son got this wonderful opportunity.

  13. Paul
    Paul says:

    How to make it in NYC often involves having some experiences there before you’re old enough to really know what it’s about. That’s why natives often do so well there – besides a socioethnic makeup that embraces education and competitiveness.

    NY has a singleminded energy, an insistence upon itself, that you have to give in to fully – learn to crave, really – or it will tear you up so badly you’re really not much good for anything. In NY or outside it.

  14. Patricia Rossi
    Patricia Rossi says:

    Loved this post.
    We take our cubs to work with us every chance we get.
    Communicating with people young, more mature, and in-between is the best education in the world. When I was shooting a segment at Fox they let cubs run the camera. When I shoot a special for Autism in our community last Friday for USF/CARD, cub read the interview questions to me as we drove and listened as I practiced. He also hung out in the control room the entire time, which he really enjoyed. Thank you Penelope for a wonderful article, going to share with my family.
    My best,

  15. Mark W.
    Mark W. says:

    Great story and a shout out to Melissa for coming up and carrying through with this idea. Education and fun are really shown to be a great combination here in this post.

  16. Mary Robinson
    Mary Robinson says:

    This is awesome, Penelope. My mom used to tell me I should be more “well rounded”, but I stayed very “pointy”, and it worked for me. When my youngest son was totally into gaming and programming I let him run with it. Now it’s a fabulous career for him. These special jobs require special focus and when a kid just knows what they want, the best thing a parent can do it help them to make it happen.

    • Tom, Internship USA
      Tom, Internship USA says:

      Totally agree with you, Mary.

      And even when the child THINKS they know what they want, putting them into that actual immersive situation such as Penelope did will do 2 things for that person: either confirm that yes, this is indeed the direction they want their life to go in or instead act as a very useful wake-up-call to realize ‘Hey, you know what? This is a lot harder / less fun than I’d thought. I think I need to keep looking.’

      We set up university / college students with internships, often working with international students.

      Even as an adult it can be eye-opening to experience what you had only studied academically now in a real-world setting. Get the (work) experience as soon as possible and find out what’s it all about.

  17. Annabel Candy, Get In the Hot Spot
    Annabel Candy, Get In the Hot Spot says:

    Great idea to get someone on board by paying them. My 14 year old has to do a week internship this year. It seems very young but a friend says it gives them a chance to what the jobs really like as opposed to their idea of it and to see that they have to do grunt work too.

    There doesn’t seem to be any grunt work for these stylist though I bet they put plenty in to get where they are.

    Looks like you pulled out of the work you had planned to hang out with them too :)

    • Penelope Trunk
      Penelope Trunk says:

      It’s a good question. By age 3 he was demanding to go shopping to pick his own clothes. And then by age 4 he started cutting his own clothes to make them fit differently. And then he wanted to dress me.

      And I kept going up wrong paths – art, acting, clothing design, etc.

      Something that really helped me understand him was his Myers Briggs personality type: ESFP. They are frequently in the fashion and design industry and they love to buy things and they are obsessed with appearance. That’s when I realized that it’s how he’s born.

      I’m a huge fan of using Myers Briggs to help steer kids to what they will be great at doing. And, to be honest, it’s Melissa who had this idea. I think I was still incredulous over the idea of being a stylist. It’s so outside my own frame of reference.


  18. Ann Stanley
    Ann Stanley says:

    I loved this. ‘Try a lot and quit fast’ – true true true. I stayed too long (four years) in a job I didn’t like once and I’ll never do it again. If I’d known my Myer-Briggs profile then (INFP) I wouldn’t have gone near the job (Office Admin) in the first place and I would have gone into my present job (teaching) sooner. But then I wouldn’t have learnt the important lesson about staying too long.
    I’d never thought about giving my kids this kind of valuable experience before. As a parent who relies on conventional schooling I have lost some of my imagination.
    Very inspiring.

  19. Melissa
    Melissa says:

    This is just really amazing. I wish I had those sorts of opportunities as a kid. Also I’m always super impressed by Melissa’s abilities and your posts about her. I must admit that her life seems pretty fascinating – and I wish I had the skills she seems to have in making connections and networking. I’m not sure I have the personality for it. But I do so love it when you write about her.

  20. Lynn Lawrence
    Lynn Lawrence says:

    ooo omg Penelope,

    Good + Easy = The stratosphere in which the gifted soar. I cannot wait wait wait for our phone call, which Melissa has scheduled.


  21. Sheila
    Sheila says:

    I love this. So much. What an amazing opportunity and memory your son will carry with him. Now *that’s* education!!!

  22. Melissa
    Melissa says:

    This post brought little tears of joy to my eyes. As a designer, I fully appreciate what a stylist does. It’s a very specific skill and absolutely essential to making a great fashion image.

    “Try a lot and quit fast” is good advice for work and child-rearing. I can’t wait to try a whole bunch of things with my extremely artistic and precise 7 year old sister.

  23. MichelleMarie
    MichelleMarie says:

    Okay. I never leave comments but I just want to say that this is too cool/cute!!!

    Reminds me of when I was 7, and all I wanted to be was a fashion designer. I’d spend hours sketching clothing designs. Everything would inspire me.

    And my mom took all these sketches, made sure I signed them, and kept them. She’d gravely say that we would send them to Calvin Klein, and I’d nod in a business-like fashion. That really did seem like the next logical step.

    We never did send them, but sometimes I wonder what would’ve happened if we did. Probably nothing, and yet? Who knows.

    Even though I never ended up being a fashion designer, it stays as a warm memory of my mom taking me seriously, believing in me.

  24. Tom, Internship USA
    Tom, Internship USA says:

    Hi Penelope,

    nice post!

    I see a RESOUNDING chorus of very positive reactions.

    I attribute this not only to the general ‘cuteness’ of a 7 year old proving input and direction to a group of adults. (And it is cute)

    But something more fundamental is going on here with all these readers. It’s like a collective nodding of heads, a satisfaction at seeing an affirming event like this take place for a little kid. A sense that this is ‘the right way’ to help someone identify their passion, this is how to facilitate someone finding out what they want to do as a career or with their life.

    And I think maybe it resonates, because we’ve all experienced / witnessed poor career guidance at work; and even winced seeing adult friends or acquaintances not get this right, or take far too long to get it right or just give up because they never got it right at all.

    I work within an organization which charges a fee to set up fully immersive internships for university / college students across a broad range of industries, often (but not only) working with international students. The results immediately bolster their Resumes and rapidly increase their employability. (Right now we have a New York Hedge Fund talking to us to source Finance or Business-related students who might be interested in interning with them –- can you imagine the massive benefit an experience like that is going to give to a new graduate’s biography??!!)

    But it’s not only about raising the job prospects.

    Even for an adult, a 19 or 22 year old, it can be eye-opening to experience what they had only studied academically until now and finally see it put into real-world action.

    We are big believers in clocking up that experience ASAP. That’s when you really find out what it’s all about.

    Like your son just did.

    (Except in his case, he’s already getting a taste of it at the age of 7, he’s already ahead of the curve. Now I’m starting to wonder if there’s demand for mini, one day internships for kids. Now wouldn’t that be great?…)

  25. Molly M
    Molly M says:

    What a great experience for your son Penelope! Good mom!

    The following line really struck me: “watching my son manage the model made me realize that they were treating him seriously and that made him more serious about his own work.” I thought about how similar this is to way really great companies manage their talent. Conversely, some companies create a culture of micromanagement & distrust, ensuring an employee will only be working hard enough to avoid termination.

  26. Becky Castle Miller
    Becky Castle Miller says:

    When I was a homeschooled high schooler, I was able to volunteer as a writer for my local newspaper. They created a one-page teen section on the back of the Sunday comics and staffed it with area high schoolers. We had regular editorial meetings with the supervising writer and learned how to receive direction, propose story ideas, research and write stories, and work with photographers.

    A couple of the different reporters who led the section over the years also let me shadow them at work (I got to sit in on the REAL editorial budget meeting with the staff writers and the editor-in-chief of the paper, tag along to interview a source, and watch the reporter fact-check her own stories). It was an amazing education, and I had a massive portfolio before I even went to college. I was able to get a scholarship position on my university’s paper because of that high school experience, and then I got my first job out of college because of the university paper experience.

    I probably could have bypassed university entirely and just gotten a job at a newspaper right out of high school based on my experience, but my parents expected me to go to college.

    Internships for kids are AWESOME.

  27. Julianna
    Julianna says:

    Funny, I’m on my way to my kids’ school auction in Brooklyn tonight and there is a whole category of internships for kids K-5th grade, from one-day things to 4 weeks things. There must be 50 positions offered

    • Penelope Trunk
      Penelope Trunk says:

      That is totally interesting to me. Now I’m thinking, so many people could charge $100 to give a really young kid an internship. It’s totally worth it to the parents and it’s fun for everyone involved. I wonder if that would be something that could grow into something big…


  28. Joselle
    Joselle says:

    This is so awesome! I read this while holding my 3 week old daughter and it was so inspiring as a new parent. I want her to have confidence and experiences like this. i honestly don’t care about school for her. I was a classically “good” student and it did nothing spectacular for my career. I wish I’d been braver.

  29. me
    me says:

    Standing ovation for Lynn & David and all the rest who provided such an outstanding experience for a young boy. Truly inspiring story. Thank you.

    It takes a village, indeed ….

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