carefree is a myth

post number forty four

Note: An update on the subscriptions/donations, through forty-three days (a little over 1/4th of the way through this newsletter.)

As of May 29, 2020 (9am PST):

$7923.53 raised from subscriptions / $7173.63 distributed to orgs/funds/individuals (including this morning, a $1000 donation to the Louisville Community Bail Fund).


Almost 12 years ago — 08/11/08 — I got on an Amtrak train in Atlanta, Georgia. I had two big bags with me, some snacks, and three identical, fit-in-your-back-pocket Moleskin notebooks. They were purchased with purpose.

Like most 21 year olds, I’d just made a questionable decision. My final destination on this Amtrak was Hanover, New Hampshire (with a train change at Penn Station in New York City).

I remember vividly the decision to not fly back to college. What I (told myself I) needed: 18 hours to clear my head and collect my thoughts before showing up for my senior year.

While I regretted this decision by the time I made it to South Carolina, this trip was the beginning of the rest of my life. It was the first time I’d prioritized creativity over comfort, passion over peace.

At 9:20pm, my train left Atlanta. 18 hours later, I’d mapped out my senior thesis, gotten deep into writing a play about a group of teenage boys, and fully filled out a notebook with essays and letters, addressing some of everything.

On days like today, ones that follow nights filled with terror and sadness, I often go back to these old notebooks. Each time, I’m hunting for something — answers, clarity, a feeling — something.

I’ve opened these notebooks, and read these same words, probably over 100 times since 2008. And each time, I leave with a new take, either about myself or the world.

“In the past 2 days, Bernie Mac and Isaac Hayes have died.

Welcome to August 2008.

Why the hell am I doing this trip? Why would I ever board an 8pm train (it’s now 9:20) that arrives in Penn Station 18 hours later?

I don’t fully know. I think, perhaps, I’m trying to find myself.

Damn, I can’t believe I just wrote that. “Trying to find myself.” That’s the corniest bullshit I’ve ever read.

But I don’t know how else to say it. What I do know — I’m scared to dig into the past. The reluctance is real.

Hopefully, by 3pm tomorrow when I get off this train, I’ll have an answer.

And hopefully, in 18 hours, I’ve figured out what it means to be a young Black man in 2008.

Black. Male. Atlanta. Middle-class. Only child. Educated. Fatherless.

These are my buzzwords. In that order.

Every five seconds, I’m tempted to close this pretentious Moleskin and chat with the woman next to me. But I have to keep going. Because this might be my final moment for “me” time until I die. So I guess it’s now or never.

Where to start?

Well, I feel like 2008, in many ways, has been a rough year for us.

Us meaning my people. Black people. Capital B.”

Three months before Barack Obama was elected President of the United States, that’s how I felt. It’s easy to only remember the elation from November, and not the hardship that existed on this triumphant moment’s eve.

I then went on to write a letter, to Barack Obama. How it began:

I’m sorry you had to do this, run for President.

How it ended:

If you win, I will cry for days. If you lose, I’ll cry for weeks. Either way, thank you.

Also inside: a scathing letter to Kwame Kilpatrick, a letter of appreciation to Claude Brown, feedback on every performance in We Are The World, and this:

To the lady in front of me on the Amtrak

“I just realized why people don’t take 17 hour overnight train rides up the East Coast anymore. Your snore sounds like my friend Ben’s busted subwoofer back in 11th grade after cranking the Intro to Speakerboxxx up to 19.

If snoring wasn’t a sign of life, I would assume you were dead, because you are the only one who isn’t phased by the sounds.


And finally, my letter, to Malcolm and Martin.

“Everyone knows the timeless arguments:

Magic or Bird? (Magic)

Sampras or Agassi (Sampras)

Tupac or Biggie (T-Pain)

I think the greatest argument of them all, however, is between you two — Martin and Malcolm.

The impact is profound.

Even though you both are so different, I always thought it was clear how you both shared some common heroes.

Time will only tell who will be talked about more, 100 years from now, long after both of you have left this earth.

I was too young to catch either of you in your primes of popularity or influence, but all I can say is thank god for syndication.

I owe the world to you two strong brothers.

To Martin Lawrence and Malcolm Jamal-Warner,

I salute you.”

What did I find this time, on this trip down memory lane?

It was a reminder, of my lifelong journey with the word “carefree.”

Feeling free is powerful, especially when your ancestors were in chains. Freedom is the goal. Carefree is the dream. Carefree is a myth.

It’s a myth I’ll always hope comes true, a myth that I know will never exist.

For most of my twenties, I wanted nothing more than to be a #carefreeblackboy. And each time someone referred to me that way, it felt like a stamp of approval.

But what I thought at 21 — and what I now know at 33 — carefree is not in the cards.

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In the past, after reading through these notebooks, I put them away, where they belong. But not this time — artifacts (including your own) aren’t simply time capsules and points of nostalgia. They’re hopeful guides, on how to simply make it through the day in one piece, in a world that’s both unprecedented and discouragingly cyclical.