I’ve written a lot of things over the course of my 46 years on this planet.
Funny things, sad things, smart things, and even a legendary thing.
Here’s a look back at the 46 most important things I’ve written in my life so far in (roughly) chronological order…
1. Something in Latin.
I took Latin in 1st through 4th grade and am sure I wrote something in Latin during that time.
I don’t remember any Latin, but I’m sure studying it an early age helped me develop the writing ability that’s served me well ever since.
2. An elementary school apology note.
I got in trouble for throwing clay at a teacher and was ordered to write an apology note, have my parents sign it, and bring it back the next day.
I knew my parents wouldn’t be thrilled with what I’d done, so I wrote an apology note for talking in class (a lesser crime) and got them to sign it.
Then as I walked to school the next day, I stopped at a friend’s house, cut off the part of the note that had my fake apology, and handed my teacher a fragment of paper with nothing but my Mom’s signature on it.
Somehow, I got away with it and got a fun story to tell the rest of my life.
3. A letter to my grandfather to pay a gambling debt.
As a little kid I lost a bet to my grandfather on a sporting event.
So, I taped the dime I lost to him on the back of a letter and sent it to him.
You’ve got to pay your debts…even to your grandfather.
4. Letters home from summer sleepaway camp.
I don’t remember what I wrote in those letters (probably, “Send more candy”), but I bet they were important to my parents who hadn’t seen me in weeks.
5. Articles for my high school newspaper.
This was the first time I was ever “published.”
6. My college essay.
I have no memory of what it was about, but whatever it was got me in to the University of Maryland’s journalism school so it must have been decent.
7. Freshman journalism class assignments.
At Maryland, any error in any paper for a journalism class got you an automatic F on the paper.
My first paper got an F because I put down the wrong date.
The second got an F because I had a typo.
It never happened again.
You quickly learn to be accurate or…you quickly get thrown out of the journalism school.
8. Articles for The Diamondback.
The University of Maryland’s daily campus newspaper probably reached about 30,000 people when I was there.
If high school was the first time I was published, this was the first time I was PUBLISHED.
9. An article about the first snowfall of the year.
Another journalism school rule was you had get a certain number of articles published each semester in order to remain in the school.
I was a bit of a procrastinator and waited too long to get going, so I needed to rush to get a bunch of articles published at the end of the semester.
That meant I had to take whatever assignments I could get.
And that meant when the school paper’s editor called me minutes after kickoff of the Super Bowl to go write a story about the first snowfall of the year, I had to bail on the game and go call the National Weather Service.
Worst Super Bowl ever.
10. A fake letter to record labels.
In college I spent all my money on CDs, but there was more music I wanted to buy than I had money to buy it.
So, I printed up fake letterhead for a fake local publication called “The Scene,” copied record label addresses from the backs of CDs I owned, and mailed letters out to the labels asking them to send me new music to review.
Sure enough, a bunch of them started sending me albums and headshots to include in my publication that didn’t exist.
11. Articles about Congress and the Supreme Court.
My senior year in college I landed a coveted internship with Capital News Service, where I covered Congress and the Supreme Court.
I wanted to become a political journalist after college.
These articles made me realize I didn’t.
12. My resume.
My resume coming out of college landed me my first job at a boutique entertainment PR agency and resumes I wrote every couple years after that helped me land a slew of other jobs.
13. A Game Show Network press release.
My first job was as an assistant answering phones at that PR agency.
One day they gave me a chance to write a press release about the Game Show Network’s new slate of shows.
Rather than write it as a standard, boring press release, I took a chance at adding some personality to it and they loved it.
I was promoted out of being an assistant a few weeks later and quickly turned into a writer who wrote materials for the whole agency.
14. Emails about my adventures in Hollywood.
When I first moved to Los Angeles I used to regularly send emails to friends and family back home about the surreal experiences I was having working in the entertainment industry.
Even just standing in line at a bagel shop next to Ed Begley Jr. was enough to inspire a fun email.
For a long time I was pretty bad at sending cards to people (sorry Mom and Dad!).
But I’ve still likely sent hundreds of birthday, Valentine’s Day, and assorted other holiday cards to assorted people I love in my life.
16. Chat room conversations with pre-teens.
Don’t worry, this isn’t going to take a dark turn.
I worked as a content producer for a website that ran official celebrity websites for teen celebrities (think: Jonathan Taylor Thomas) and part of my job was to “host” chat rooms where kids would chat with each other about God knows what.
It was like I was a TRL host, but not on TV, not Carson Daly, and not interested in whatever was being talked about.
The internet was a simpler place back then.
Unfortunately, I’ve had to give a few.
Fortunately, I haven’t had to give many.
18. A fantasy football “Karma” article.
I’ve played fantasy football in the same league for about 20 years and years ago I used to write regular articles about our league…even when they were featured in a printed out newsletter because there was no league website!
One time, I wrote an article I vowed would unleash positive Karma and turn my season around…and it did.
19. The Timekiller.
My first blog.
I named it The Timekiller because I wrote it while I was at work staring at the clock, bored, and waiting for the chance to go home.
In a lot of ways, it’s how my “real” career began.
20. The Inside.com Daily Digest
I worked as the assistant film editor at a much-hyped (and quickly failed) online-only entertainment industry news publication.
Part of my job was to write a summary of each day’s film news with links to stories that had run in Variety, The Hollywood Reporter, and other industry publications.
But back then, those publications didn’t update their websites until midnight because they didn’t want to break the news until it came out in their print papers the next morning so I had to write my column every night from about midnight to 2 am.
In retrospect, it was a whole lot like what my newsletter has become today.
21. Resignation letters.
I’ve quit jobs for a lot of reasons over the years: To move, to take other jobs, to write screenplays, to become a consultant, and because I was bored with them.
Each resignation letter turned out to be a great thing.
22. Letters in birthday “albums.”
My family seems to like honoring notable birthdays for loved ones by having friends and family members write letters to the person and collecting them in an album.
I’ve written a few over the years and it gave me a great excuse to tell those people how I really feel about them.
(Well, at least the good parts of how I feel about them!)
23. The Crazy Eye Killaz videos.
I played on a recreation basketball team in a 6’2″-and-under league in a heavily Asian neighborhood where our team was pretty much the only one that wasn’t all-Asian.
Our team name was the Crazy Eye Killaz and for three consecutive years I spent countless hours cutting together elaborate highlight videos at the end of each season.
The year we won the championship I even included a custom song I paid a musician on the internet to record based on lyrics I wrote.
It was amazing and that video is possibly my greatest ever creation…even if there’s only about 15 people on the planet who will appreciate it.
A screenplay for a biopic about America’s first national sports icon, bare knuckle boxer John L. Sullivan.
It got me an agent who started to shop it around Hollywood until…Cinderella Man (a period boxing biopic starring Russell Crowe and directed by Ron Howard) flopped at the box office.
No one was interested in another period boxing biopic at that point.
25. Whip It Out Comedy
A comedy blog where I featured videos and MySpace blog posts (it was a simpler time) from comedians.
It wound up getting “acquired” and getting me a job running content and marketing at a comedy startup website.
Like so many things I’ve written, it was a side project that eventually transformed my career.
26. An email to Blerds.
When producing a standup comedy tour that went to Chicago, I looked online for some local comics to open the show.
That’s when I discovered Blerds, a group of about a dozen relatively unknown comedians and a young filmmaker.
I emailed them asking if they wanted to perform on our show, booked one of them, and it started a relationship that led to me ultimately manage/produce a bunch of projects with them.
Oh, and did I mention that “them” included comedians like Kumail Nanjiani, TJ Miller, and Kyle Kinane?
27. Connected Comedy blog posts.
My first real crack at consulting as a profession was powered by this blog in which I wrote daily posts featuring advice for comedians about how to grow their audience…while simultaneously trying to figure out how to grow my own.
28. 99 Places To Promote Your Comedy ebook.
This was the first product I ever sold online.
The realization I could sell an information product to people online blew my mind.
Not sure I realized it at the time, but the first $10 I made from the book changed the course of my life for years to come.
29. A vision statement for the potential of the Academy of Motion Picture Arts & Sciences social media future.
When I interviewed for the job of Managing Director of Digital Media and Marketing at The Academy, I had to submit an outline of my vision for what the Academy’s social presence could become.
It helped me get the job.
My vision included the phrase “sleeping giant,” but even I couldn’t have predicted I’d lead the Academy’s growth from 400k followers to more than 10 million in just a few years.
30. The Selfie follow-up tweet.
I was involved in the infamous Ellen Oscars selfie tweet that broke Twitter, but I can’t say that I wrote it.
But I did write the follow-up tweet we posted as soon as Twitter came back online that night.
31. The “Proposal” Proposal.
My first date with my eventual wife wasn’t a date – it was a business lunch.
At the end of our lunch (as I got ready to ask her out on an actual date), she whipped out a proposal to try to get me to buy an ad in Variety.
She didn’t make the sale.
Years later, I took her back to that same restaurant and gave her a proposal of my own – an engagement proposal, written in the form of a sales proposal.
I made the sale.
32. My wedding vows.
A case could be made this is the most important thing I’ve ever written.
Actually, it’s probably the second most important thing I’ve ever written since I also “consulted” on my wife’s wedding vows.
A daily newsletter in which I profiled a different creative person each day who was sharing their expertise with the world.
In retrospect, it’s clear this ultimately inspired me to do the same myself.
34. For The Interested.
The newsletter I’ve published every Sunday for the last 247 weeks in a row and that 10,000+ people read every week.
It’s the engine of my business.
It’s the engine of my learning.
It’s the most important business thing I do.
35. My Creative Mornings talk.
A few weeks after I left the Academy to go out on my own, Creative Mornings’ LA branch invited me to give a talk on the topic of “weird.”
I came up with a talk about why people should make more weird choices.
36. My two-minute writing tips article.
This article has been read by millions of people and led thousands of them to subscribe to my newsletter.
It’s quick, simple, useful, and the most-read article I’ve ever published.
37. Client proposals.
You can’t have a consulting business without clients and you can’t have clients without proposals.
38. My initial Newsletter Creators group posts.
A few years ago I had a hunch newsletters were going to become a big deal, so I launched a Facebook group for Newsletter Creators.
In the beginning there were only a handful of people in it, but I kept posting and it kept growing.
Now, there are more than 3,600 creators in the group and it’s become an incredible (and incredibly valuable) community.
39. My Newsletter Accelerator course.
The first “real” course I ever created.
A lot of work, a lot of value, a lot of payoff.
40. The Dad lessons poster.
For his 70th birthday, my brother and I collaborated to create a poster featuring the collective “wisdom” of my Dad.
41. The Dinner at Sheila’s menu poster.
For my Mom’s 70th birthday, we collaborated again and created a “menu” featuring her most classic dishes as if her kitchen was a restaurant.
It brought her Dinner at Sheila’s blog to life.
42. This Is How I Do It.
A decade ago I wasn’t comfortable blogging in my real name.
Now, hundreds of people pay to subscribe to a weekly newsletter in which I offer a behind-the-scenes look into exactly how I grow my audience and business.
That’s quite a transformation.
I love Twitter and find it the most valuable (and inspiring) of all the social platforms.
I’ve written thousands of tweets over the years (including at least five a day every day now) and somehow more than 13,000 people decided to follow me to see what I’ll write next.
I’m not sure if this counts as writing or not, but it’s my list so I’m going to allow it.
After all, curating is a big part of writing and music has been a big part of my writing process over the years.
I’ve spent endless hours listening to music and curating it into mixtapes, then burned CDs, and now Spotify playlists.
45. The Daily Graph
It’s only existed for three days, but my new daily newsletter feels like the start of an exciting new chapter in my journey.
46. My birthday blog posts.
It’s been 11 years since I started this tradition of writing a blog post on my birthday reflecting on an aspect of my life up to that point.
Hard to believe.
Here’s to a future filled with more adventures worth writing about.