25 lessons I learned in my first 25 years as a New Yorker
“Missouri gave me roots, New York gave me wings”
August 21st is a bittersweet day for me.
Exactly 25 years ago today, I moved to New York City. I was 18, straight out of high school (and still acting straight), with big eyes, bigger dreams, and my first address: 44 Washington Square West, an NYU dorm.
Exactly 25 years ago today, my parents loaded up their Chevy Suburban with all my worldly possessions—plus a mini microwave and some recently acquired toiletries from Bed Bath & Beyond—and pulled away from the only house I’d ever known, in St. Louis, Missouri. (It’s still the house they live in today.)
Exactly 25 years ago today, I didn’t know a single person in this town: no cousins, no friends of the family, no emergency contacts. I didn’t have a cell phone, a computer, or a TV. The words 'social’ and ‘media’ hadn’t yet been conjoined and changed the world. My only entertainment was a CD player I brought with me, which played Dido’s No Angel on a loop. (“Here With Me” still makes me so nostalgic I get a little nauseous when I hear it.)
Exactly 25 years ago today, my mom made my bed in my dorm room for the first time. (Probably the only time, too.) I didn’t have a full-length mirror, so we walked to a hardware shop on Sixth Avenue to buy one. We got back and waited on West 4th Street for my dad to pick up the car from a garage—$27 per hour and still the most he has ever paid for parking in his life—to say our goodbyes.
And exactly 25 years ago today, my dad took this photo of me and my mom holding that mirror with his reflection in the glass, documenting the exact moment they drove off, and the rest of my life began:
This anniversary feels so surreal!
As I wrote in my inaugural Substack post, it continues to blow my mind that a quarter century has passed. I only lived in Missouri for 18 years, fewer than I’ve now logged in here. Yet, in my heart, I still identify as this small-town boy trying to make it in the Big Apple.
The more I’ve thought about this milestone, the more I’ve wondered: what have I learned?
I decided to make a list—not that I’d want you to think of it as an advice column. It’s like Oscar Wilde wrote in An Ideal Husband, “I always pass on good advice. It is the only thing to do with it. It is never of any use to oneself.”
The 25 things I learned during my first 25 years in New York:
When people honk at you in New York City, they’re not saying hi. Don’t wave back at them.
When you’re young, being super social is a luxury. When you’re older, being alone is a luxury. True enlightenment is realizing that both phases have value.
Walk fast. It’s a city!
Know who to fight with. Mark Twain, a fellow Missourian, put it best: “Never argue with an idiot. They will drag you down to their level and beat you with experience.”
Never say “nice to meet you” unless you’re absolutely, positively sure you’ve never met the person before. Maybe you only want to say that to a newborn baby. Why? If you have met someone and forgotten them, they will hate you forever. (I always say, “Great to see you,” just to be safe.)
A sense of humor is an essential quality in friends and lovers. Loyalty, kindness, generosity, punctuality, all that other stuff matters, too. But make sure the people closest to you can take a joke. Laughter is a salve.
Pay attention to who’s paying attention to you. Even the most important people in the world make time for the things and the people that they care about.
When in doubt, wear a navy blue suit. It will always feel absolutely incredible to find something you really love on sale. Use promo codes whenever possible. Saving money is sexy!
Be smart when you’re posting about other people online. Many years ago, I made a joke about an artist I’ve long admired on Instagram. Sadly, they didn’t find it funny at all, and they’re still pissed at me. The internet never forgets; always remember that.
Know your success metrics. Just don’t get so lost in the numbers that you forget to take in the bigger picture. (I need to remind myself of this constantly, by the way.)
When you are triggered (I know, I know, I hate that word too; it’s very… triggering?) by an email, a text, a WhatsApp, or a DM—do not respond immediately. Wait a minute. Take a beat. Digest. Ponder. Analyze. Strategize. Draft, re-read, proofread, ask AI to check your grammar. Then, and only then, press send.
“Happy to be here, easy to work with” has become my professional motto. As I told The Business of Fashion in 2019: “When I was an intern, I overheard a Vogue editor explain the reason she always booked a certain model was because she was, and this is a direct quote, ‘happy to be here, easy to work with.’ That clicked for me. Did I love waking up at 7am on a Saturday to unpack a bunch of trunks that had just come back from a shoot? Well, no. But I did it and I did it with a smile on my face, and the people I was working with were into that. Also, truth be told, coming from Missouri and suddenly being knee-high in couture dresses and diamond earrings wasn’t that hard to smile at.”
Why would you ever waste your money on buying an umbrella when fancy hotels have them for the taking right by the front door?
Vulnerability is sexy. Codependency is a turnoff. It’s OK to cry in public.
If someone is rude to a member of the service industry, like a server at a restaurant or an Uber driver, they’re probably a bad person. Tipping is karmatic—give what you can because generosity will come back to you.
Take the subway. It’s the fastest way to get around town, and it’s a true social equalizer. But bring hand sanitizer because it’s also gross.
The best week to be in New York as a New Yorker is between Christmas and New Year’s Eve, when the city is alight in holiday decorations and the locals have left town. This is my favorite time to see Broadway shows, go to museums, and eat at fancy restaurants, which are too crowded the rest of the year. (But avoid Rockefeller Center at all costs.)
Always check in on someone who’s going through a tough time. Yes, it can feel awkward to reach out when a friend has been dumped, received a bad review, lost a job, or been trolled online. But reach out. Don’t ask questions that require answers; don’t interrogate them. Find a way to say hi, check in, say that you’re thinking of them. It’ll go a long way.
When the time comes, you will be amazed at how many friends will be there to catch you when a bully tries to make you fall.
There is nothing healthy about a tan. Wear SPF!
Missouri taught me how to make small talk; New York taught me how to stop it. Read the news. Know what’s going on in the world. Be a culture vulture. Uninteresting, uninterested people are just the worst.
Cheap burgers can be delicious. Cheap sushi cannot. (Growing up in Missouri, the only raw fish I saw was on a hook at the Lake of the Ozarks, and I did not walk into a Japanese restaurant until I was a sophomore in college.)
This city is constantly changing—and you should be too. Stay nimble. I enrolled in journalism school at the precise moment digital media began disrupting the print publishing ecosystem. I never imagined I’d host a CNN show or work at YouTube, but both became professional chapters I cherish. I also never thought I’d work for an art gallery, but my longest, most loyal, most inspiring employer has been Larry Gagosian, an art dealer. Be up for anything.
To quote Dorothy Parker, "I hate writing, but I love having written."
Family comes in many forms. One of the things I’m most proud of is building a chosen family here—people I honestly cannot imagine living without. (Becoming a dad has been pretty awesome, too.)
Honestly, I’m pretty impressed with myself for moving here on August 21st, 2000.
Sure, there were moments when I wobbled, when I was intimidated or scared. I could have convinced myself to go to a local university, that I’d find a job in New York after graduation. But I’ll never forget the day my acceptance packet arrived in the mail, and my mom said to me, “You can do this.”
The TV show Felicity came out during my junior year of high school. Maybe that helped, too?
Missouri gave me roots; New York gave me wings. And I'm grateful for both.
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Derek C. Blasberg
#2, 3, and 12 are spot on. #9 and 11 are an interesting juxtaposition. Easily triggered people are usually not pleasant to be around.
Man, this made me a bit emotional. The picture with your dad in the mirror is priceless. Xx