In the sixth grade, I received an envelope from professional snowboarder Danny Kass that would change my life.
I wrote to him for a school assignment with the goal of getting an autograph. In return, he sent me a hand-drawn cartoon that he signed, plus a new pair of snowboarding gloves from his company.
I couldn’t believe that one of my heroes would take the time to write back to me, but despite the small connection itself being awesome, dollar signs were quick to appear in my young entrepreneur mind.
What if I wrote to dozens or even hundreds of people and collected their signatures? Those things were worth money! I could be rich!
For the next year, I went on an absolute tear of writing to everyone I knew that was in any way famous. Athletes, actors, authors, business moguls, musicians, TV personalities, politicians, you name it. I collected dozens of signatures on baseball cards, posters, and printed out photos. Every trip to the mailbox felt like a chance to hit it big. What if Michael Jordan sent something back to me today? Paul McCartney?!
I was a genuine fan of some people that I wrote to, but more or less, I did it for the money. A few of my favorite signatures were framed and mounted on my bedroom wall, while the rest sat in boxes waiting to be sold.
Like many childhood hobbies, my attention to the autograph hustle eventually shifted to other things. I still have almost all of the autographs I received (a few were indeed sold), but for a long time, I stopped writing.
A decade or so later in 2016, I was on a road trip that passed through Pittsburgh, Pennsylvania where I stopped to visit the Andy Warhol Museum. After spending the day marveling at his artwork in the galleries, I decided to have a look in the archives, curious as to what kind of hidden treasures I might come across.
The archives were filled with Andy’s notes and sketches for planned artworks, as well as some random items that were taken from his studio. I thought most of it was plain and ordinary, but there was one item that caught my eye. A letter to Andy from a random fan.
He wrote purely for the sake of expressing his appreciation of Andy’s work and to let him know that he was excited to follow his career. He wasn’t seeking an autograph, or for Andy to check out a sample of his own work. He just wanted to say hello.
This letter was, to me, the most wonderful piece of art in the entire museum. It was simple, ordinary, humble, and didn’t ask for anything in return. It was beautiful. Human.
There was something magical too about seeing that this person’s letter had not only found its way to Andy’s desk, but that Andy had actually opened it, read it, and presumably enjoyed it well enough to have held on to it.
When I had been writing to famous people for their autographs as a kid, it often felt like I was just sending letters out into the void. I sometimes wasn’t sure if the address was correct, if my letter would get buried amongst piles of other letters, or if the person even bothered reading their fan mail at all. That letter on Andy’s desk sent me back to those frustrations and gave me hope. It reminded me that most of the time the letters do get read, and showed me that they are even appreciated.
And with that — I was inspired to write once again. Not for autographs this time, but for the sake of writing itself.
Since I came across that letter four years ago, I have written to many of my favorite authors, movie directors, podcast hosts, internet bloggers, and more.
Pretty much any time I catch myself thinking, “Wow. I would love to be able to talk with this person and ask them about X” or “Damn! I wish I could just thank this person for creating this thing” — I do.
I haven’t earned a dime from my letters, but what I have learned is this:
Thank yous are appreciated.
When I get a response from someone I write to, nine times out of ten it starts with a thank you. Wildly successful people often talk about it being “lonely at the top”. While their work might be reaching millions, they can feel entirely disconnected from the personal impact that they have on their fans’ lives.
A successful author can see their enormous amount of book sales, and an actor knows that they get paid as well as they do because of how many people watch their movies, but how many of those fans do they get to hear from personally? At the end of the day, famous people are still human, and it’s nice for them to receive a personal thank you.
You can get a look behind the scenes.
I once wrote to Daniel Quinn, author of the bestselling books Ishmael and The Story of B. In his response to my letter, he talked about how Ishmael took him over twelve years to write, during which he did nothing but write version after version. The printed version you can read today was his EIGHTH iteration of the story, the first version that was a novel, and the first in which the gorilla named Ishmael appeared. Pretty wild!
You’d be surprised what other little tidbits of behind-the-scenes information you can learn about by just asking. What is something you’ve always wondered about in your favorite book or movie? Would you want to know about your favorite artist’s creative process?
Why not ask?
Sometimes, you’ll forge a lasting connection.
Most letters will only have one back and forth, but hey, you never know when a single letter can turn into a regular penpal exchange.
I wrote to Mark Manson years before he wrote his bestselling books, The Subtle Art of Not Giving a F*ck, and Everything is F*cked. We exchanged a few emails, and eventually had a Skype call together where we talked about jobs, early life crises, and relationships. Back then, he was just happy to chat with an interested fan. I imagine that today he could sell a 1–on-1 Skype call like that for hundreds or thousands of dollars.
I still occasionally respond to Mark’s weekly newsletters, and he’ll usually shoot me back a quick response. I wouldn’t by any means call us friends, but maybe he’d remember me if we ever met at a book signing or something like that in person.
Connecting with people you admire is motivating.
It’s easy to feel like famous creatives live in a different world than us mere mortals. That they must have special gifts to do what they do or have an enormous amount of luck on their side. But when you begin connecting with famous people, you realize that they are just… people. Not much different than you.
This realization can be incredibly motivating. You’ll feel empowered to create more yourself once you realize that all of your creative heroes are just normal people too.
Put simply, it’s fun.
I often feel like my twelve-year-old self again when I get a response back from someone I wrote to. It’s a nice surprise to wake up to an email from someone I wrote to weeks prior, or to find a hand-written letter from an author in my stack of mail.
A couple of years ago, I wrote to Steve Hely of The Great Debates podcast, in order to thank him for creating the show and suggest a topic for a future episode. In return, he sent me an autographed copy of one of his books, shipped all the way down to Peru where I was living at the time, from his home in Los Angeles. My topic was discussed on a future episode of the show, too.
How cool is that?!
If you’re feeling inspired to start writing to famous people, here are some tips to get started:
Keep it short.
You want to make it as easy as possible for the person to respond. While you might have twenty things that you want to ask Brad Pitt, he probably doesn’t have time to read, nor answer all twenty. Don’t be overwhelming. By keeping your note simple and to the point, you’ll make it as easy as possible for the person to respond.
Be interesting.
No need to tell your whole life story (see above), but do include a sentence or two about yourself. Chances are this person is receiving fan mail from more people than just you, and so you want to stand out. Humanize yourself so that you’re not just another anonymous name above an address. One of my favorite ways to do this is by sharing something that I think we have in common.
Ask questions.
Make sure to give the person a reason to respond. Having a question to respond to makes it easy for them to know what to write back. Just be sure not to ask something too vague.
It might be hard (and overwhelming) for Stephen King to tell you about his entire writing process in a single letter, but you can instead get specific and say something like, “I often struggle with being able to finish the editing process of my writing. I always feel like there is more to add, or more I can take away. Any advice you have for knowing when a story is done? I can’t imagine how much more difficult that decision must be for full-length novels.”
Act normal.
Email A:
Hi Famous Person,
I finally found your email after searching for it all afternoon, I hope this is really you! Anyway, my name is Joe and I just wanted to say hi! I’ve read all your books, listened to every interview you’ve ever given, and even started following your dog on Instagram. Seriously, I’m your biggest fan.
…
Email B:
Hi Famous Person,
I just wanted to write to say thank you. Reading [Your Book] throughout the past month while I was traveling in Germany was such a treat. I love to read fiction set in countries that I’m visiting, and your descriptions of life in pre-unification Berlin made me feel almost as if I was traveling in time.
…
Put yourself in the shoes of the person you are writing to. Which of these email openers would you rather respond to?
It’s easy to express your appreciation of the person you’re writing to without coming across as crazy or stalkerish. Be normal and they’ll be normal with you.
Do you have a cool story about writing to someone famous? I’d love to hear about it in the comments below.
Thanks for reading. Write on.
