Turning 30 was the day I realized everything I ever thought in my twenties was total horse shit. My grandma always told me that “if you don’t make it by forty, you’ll never make it.” She said it as a throw-away line, something to give me a decade buffer to do what I’d set out to do, but what the fuck did I set out to do? I was confused still and had to figure it out, and figure it out fast. Forty was around the bend. Well, as a 36-year-old man, here’s what I’ve learned thus far…

My grandma was wrong, but her theory was decent. Actually it was my alcoholic grandfather who I never met that said that line, which my grandma kept in the family after his passing. I think what she meant was if you’re still lost by 40, you’ve laid some pretty heavy groundwork that’s beginning to solidify into concrete and it’s time to fix that shit up ASAP. When I was age 30, I was still living in Los Angeles. And I didn’t move there to become a famous movie star writer actor producer photographer filmmaker. No, I moved there because I was damn lost without a clue or where to tread next. I had exhausted Brooklyn as a raging coke head and needed somewhere warm to rest my soul. 

At Age 30 I Made the Biggest Financial Fuckup of my Life

In fact, at age 30 was the year of my biggest financial blunder of my life. Maybe I made it cause turning 30 felt like the pressure of time was weighing on my back and I had to do something fast. So, I took all my money I had earned as a freelance publicist–around fifty thousand dollars–and invested all of it (in addition to another buncha thousands of credit card debt) into a midnight vaudeville festival. 

Why did I do that? 

Cause when I asked myself if I was supposed to be an entertainment publicist, my answer was OF COURSE NOT. I’m supposed to have a publicist of my own! I should be the one with a publicist. Not the other way around! I’m not supposed to be a successful PR agent! How silly of life to offer me that! Ugh! Fuckin moron I was.

Life Should Be Clearer by Now, Right?

Turning 30, I thought a clear path must be somewhere in the making. Now I realize a clear path is totally unnecessary nor is it needed…

But at the time I busied myself so much trying to figure out what I was supposed to be, that I arrived at the conclusion I was supposed to be a theatre producer. That was the identity I created in my head for myself and I was determined to force it into a weird-shaped hole. Sure I was only a few years sober trying to pull three decades of my life together, rebuild relationships that I’d torn down my entire existence and enjoy a lucrative lifestyle as a PR dude free to travel the world, but I had to tear all that down immediately before it was  too late! My grandma said so! And she’s never wrong! But was she? She mighta been wrong all along…

Becoming 30 Years Old – Wisdom Nugget #1

That was one of the lessons I learned somewhere around 30: Everyone is just a goddam person with ideas about life that are generally not correct. But I didn’t know that back then, I thought I had to listen to people with it all figured out. Nobody ever has shit figured out. 

But I told all my clients that I was no longer interested in furthering their stupid career; that from here on out I would build my own career as a theater tycoon. I’d start off doing what I originally started doing when I turned 20: producing theatre. I thought that was my compass. Whatever I was originally doing in my twenties is probably what I should still be doing. I was producing theatre back then, so I thought to myself that I would get back in the game with a midnight vaudeville festival, and I’d do it in Hollywood. 

So I got a theatre and came up with a concept and rented airplanes to advertise the festival all over Los Angeles, skywriting in the sky: “Carpe Noctis.”

The plan was to sell 1,000 tickets at $75. Only problem was I ended up spending close to $90,000 promoting it. I spent so much on promoting the festival that I went broke. I rented a cinderella carriage with white horses to parade around downtown LA giving out blank invites cause I thought it was clever, I threw popup parties on the beach in Santa Monica cause I thought it was cool, I wild-posted flyers that said “what the fuck is carpe noctis” all over LA cause I wanted to be seen, and I even guerrilla projected our logo onto the tallest building in Hollywood until the LAPD helicopters showed up cause I wanted to be obscene. 

That made the papers. 

We were in LA Weekly the next day, but only because I emailed one of the editors and told him “the producer of this new festival almost got thrown in jail last night trying to promote his festival”…

…that producer being me of course.

Anyway, that part of it worked. Everyone knew who we were. Tickets were selling, but even if we sold out I would lose fifteen grand. And to think at one point I was good at math.

Turning 30 Made me Rush to Bad Decisions

girl blowing birthday candles

Even though the math couldn’t possibly work, in my head I was playing the long game. It’s okay, I thought, this will pave the path to the second and third festival. I’ll make the money back on those.

Then I was notified by my General Manager that I hired that I would not be able to provide alcohol with the tickets; that it was illegal. Of course it’s illegal dammit, but that’s how we charge so much for each ticket!

So I had to drop the price from $75 to $45, but then nobody ended up buying the fuckin tickets soon as I announced that alcohol would no longer be permitted.

Then I dropped the ticket price from $45 to $15.

Good news? I sold 1,000 tickets. Bad news? It was at $15.

Let’s do the math… $90,000 – $15,000 = me fucked.

Good news is everyone in town knew about me, right? No. Wrong. I had to beg my parents to bail me out of $30,000 of debt or else I would have to declare bankruptcy.

I was Backtracking at Age 30

After that debacle I declared to myself: well, now I’m 31 and I’m worse off than I was when I was 20.

But what about the fact that I was no longer strung out on drugs and the fact that I was now talking to my family and had built a few relationships in LA? None of that mattered in my head. That shit wasn’t important. But actually that was the only shit that I shoulda been payin attention to. None of my real progress was being accounted for cause I was too blind to see it. I was desperate to appear to the world that I had “made it” at 30, or was at least well on my way.

That’s why I decided to break the Guinness World Record for Longest Road Trip in One Country.

If I couldn’t be a theatre producer, I’d be a famous travel writer. That was the original goal when I was a kid anyway. Maybe that was my mistake. I went back to doing what I was doing in my twenties, but maybe I shoulda went way back to when I was a teenager. I used to write shitty poetry when I was fourteen and I’d always loved the beatniks, so I dedicated an entire year of my life to breaking the record for longest road trip and spending every dime I earned as a social media manager for this interior design company on funding this crazy trip up and down the U.S. That was the job I got to make back all the money I lost. But I never forgave myself for my financial fuckup. Going to my parents at 30 to beg them for money was the most humiliating thing ever. Now they thought I was a total fuckup. Forget about all the jail cells I ended up in when I was in my teens and twenties, I was a shitty businessman at 30. That was even worse in my head.

Now I was doing all these live streams for this Guinness Record road trip and looking back at myself on camera staring at my gray hair. Is this what a 31 year old dude should be doing? No way. But people will admire me and that’s the most important thing. People will know I’m the real deal.

I Better Do All The Things I Can’t Do in my Forties Now…

So, after I broke the record and broke up with my ex-girlfriend, I thought: I better travel the world one more time before it’s too late to stay at hostels. I can stay at a hostel before 33, but after I turn 33, it’ll all be too late. So I spent another year traveling the world and staying in hostels in South America and fucking chicks that were in their early twenties. That made me feel like I wasn’t that old yet.

Then I finished doing that and thought to myself: fuck. I better find somewhere to live. I’m almost 33 and I’m living on a pull-out couch in my parent’s basement. I hope nobody finds out about this…

Around that time I met my fiance and thought: maybe I should stop floating around the world sleeping with chicks who I can never build an actual life with. So I committed to the girl I was falling in love with in Brooklyn and decided to find an apartment upstate in the Hudson Valley. 

I decided to “get old” and the strangest thing happened: I began to build the life I always wanted. I mean, backpacking the world and breaking the road trip record was fucking incredible. Getting sober in LA was great. Nothing is replaceable. But since then I’ve built a brand-new life, one with a community of friends, neighbors, and income. I got engaged. I won’t be alone forever after all… 

The moral of the story is to do whatever the fuck you wanna do no matter how old you are and just be a nice person along the way and don’t worry about where you’re supposed to be. You’re supposed to be where you are. If you can be okay with where you are, you’re successful. That’s the measure I now use for success: learning to be nice even when I feel shitty sometimes. That’s how an adult should act: like everything will be okay. Cause it always is unless it’s not, and if it’s not usually it’s not in my control anyway.

Anyway, that’s just how I feel about that. But I kinda wanna tell you about how it felt when I was a homeless runaway teen at 16 years old…

WANT STORIES THAT THE INTERNET WON'T PUBLISH?
Get Consistent Good Shit

Get humiliating stories told with honesty... it'll make you feel better about yourself

Invalid email address
Give it a try. You can unsubscribe at any time.

Pin It on Pinterest