The Other Side of the Game Part 1

BottlepopI have to give a nod to Boyce Watkins for putting me on to  “’25 Sitting On 25 Mill’: Why Rap Culture Is Ruining Our Generation’s Perception of Money”. Writer Jennifer Sanchez put into words an issue that I’ve thought about often, but for some reason I’ve never written about.  Sanchez (hilariously*) writes:   Here I am: 25 and employed by a company that pays me pretty well. That’s all well and good, but where the hell is my Lamborghini?!   This is bullsh*t.

Our generation has grown up thinking that we are young, we are talented, and we deserve boats and h**s.

It seems as if somehow, we have all seen the exception, and now believe that this is the standard of living.  Every time I go out with my friends, the boys in our group decide that we have to get a table. No matter the financial situation any of us are in, we are going to party at a table that costs a grand.  We are going to drink Ciroc that is way too expensive and sit in a crowded room that is way too sweaty, and we are going to take Instagram pictures because THIS IS HOW WE LIVE.

We have rented limos to drive us around for nights of club hopping, planned weekend trips to Atlantic City to stay in presidential suites, and bought VIP tickets to events that were completely unnecessary. Why?  Because Big Sean does it. A$AP Rocky does it. Because Tyga hasn’t had a hit since “Rack City”, and even he does it. So, why don’t we?

The reason why I share this is because I know I’m not the only one.  One conversation with coworkers, or a quick scroll through my Twitter timeline, shows that our whole generation is buying Louis Vuitton belts, going to Miami for our best friend’s birthday, and trying to finance things we really can’t afford. I call this hilarious-- and strikingly honest--  because it’s a woe as old as time itself. That, and change the name brands and the rappers mentioned and nix social media, and I could have written this excerpt 9 years ago, but far less well.

So now I have to tell you a story (or three).

This year was the first in four that I didn’t work July 4 weekend. When I worked at The Magazine, I worked—all day and all night— at their annual music festival. The year after I left, a sponsor picked up the tab to send me down to work their booth, and of course, enjoy the festivities.

I wanted to go this year too—since it was now a tradition and all—but eh… I wasn't paying for it because I've never paid for it. Why start now?

So over the holiday weekend this year, I’m prancing around Brooklyn and run into a good friend, who I connected with while working at the festival all those times. Currently, he is on a network TV show and has had a long career as a working actor. If I told you his name, you’d immediately know who he is.

“What’re you doing here?” I asked when I saw him hanging out CBW’s favorite spot. I expected him to be in New Orleans as usual. He was a staple at the festival, there every year I was, and many years long before that.

“I was about to ask you the same”, he said.

I laughed. “Brands wasn’t paying, so I ain’t playing,” I said.

He smirked, and laughed too. “Same here.”


A decade ago, I moved to New York. I had a city job that barely covered the bills and had great benefits. I freelanced for magazines on the side back when even as a novice, writing a quick profile of a new artist for a black publication could put enough in your account to afford a RT plane ticket to Miami. Every other week, I worked Friday night after working my main job, and 14 hours on both Saturday and Sunday as a fact checker for a sports magazine that paid exceptionally well by the hour.  With all the jobs combined, I was able to etch out a living that allowed me to hang out with my finance crew—on the rare occasions I wasn’t working—and not be considered the “broke friend.”

I had a friend—genuine friend, no “” needed—  then, a guy who recently moved to NYC and taken an entry-level job on the business side of a popular magazine. He rolled with these “older” guys who worked there and did parties on the side, but called themselves “a brand marketing group” instead of promoters.

As the newbie, my friend took pictures at their events. He never told me how much he made and I never asked. I knew about what his job at the magazine paid, so I guessed we were in the same income bracket on the 9 to 5, but I figured he must make crazy money taking pictures because he lived a life I could only fathom.

Between the two jobs, he grinded—sun up to sun coming back up on some nights when he was working parties with the group.  And he rewarded himself handsomely. Fresh outfits and fresh kicks for every event. A bottle or a table every place he went even when it wasn’t “his” event.  When he traveled—often and to every major industry event in another city — it was first class and suites at the best hotels in Miami, LA, Las Vegas, etc. Tickets to every artist performance, and front row at that.

Clearly, I was doing something wrong. I worked. I grinded. 13 days on, 1 day off for that first year. If I budgeted (and had the time off and didn’t have a deadline), I could treat myself to traveling coach and stay in a standard room in a nice hotel. I could buy a bag, a pretty dress, and afford a fancy meal and a concert. But those were treats, not a lifestyle. I didn’t want to splurge every now and again. I wanted to live The Life like my boy.

I knew women my age who lived The Life—largely off their backs, even if they would swear up and down that wasn’t the case. I had one friend who received a large inheritance—I knew the amount—and even she didn’t have it like that. I wanted to live it and I was willing to work for it. But try as I might, I couldn’t figure it out.

I was doing something wrong, but what?

Part 2: Wednesday