At 32*, I wrote about not finding that fine line between between being a brand and being well, me. I never figured out which side to fall on. In fact, I’m more confused now than ever. I just habitually line step and hope for the best.
There was a time when I could say what I wanted with out much clapback other than a call from my father about the number of f-bombs I drop. I was essentially a fart in a mitten, the term once used to describe the societal usefulness of Paris Hilton. I was mostly writing for myself to get the thoughts out of my head so I could sleep at night.
Over time, I’ve been fortunate enough to have people give a f*** (sorry, Dad), which is a blessing and a curse (more on that later). A blessing for the obvious reason—I love what I do and I can do it from anywhere. Writing has brought me a freedom, professionally and personally, that I never imagined. On good days, I marvel at how I operate. The idea of sharing my thoughts and being paid for what I love doing from anywhere in the world? Every time I deposit a check, I’m amazed.
I listen to Alicia Keys’s new album a lot. On "Brand New Me", she sings “It took a long, long road to get here/it took a brave, brave girl to try.” The long, long road? I get that. But I don’t think of myself as brave. More like risky. I wonder how long this lasts. I’m sure about today. It’s the tomorrows that occasionally keep me up late.
The curse is my doubts. I like to think of myself as a hustler—not the get over kind, more like put in work. I met with the publisher of Uptown once, my hustle icon. And he told me when you work for yourself, “you eat what you kill.” When my back is against the wall, I kill. I like that about me.
I lost a cushy contract last month, and didn’t even take time to sulk. I’d talked to my Dad just after I got the news, when he was on his way to the airport. I hit up my contacts, landed two to replace one in six hours. By the time he landed, I was straight again. He was impressed. So was I.
But sometimes I wonder if I’m just a dreamer who’s luck hasn’t run out yet. Most of what I do is easy. I can write with my eyes closed. I’ve honed a skill that comes naturally. I feel lucky more than I feel talented.
That sounds self-depreciating and I thought that meant something was wrong because I’m supposed to be confident, right? But then, I talked to other women and many say the same thing. I think that’s supposed to make me feel “normal”, but I think no, maybe we’re all just screwed. And maybe that is normal too.
I don’t think I’m supposed to say that as a life coach or advisor though. Life coaches are supposed to have it all figured out. Isn’t that why people hire us? Like if I have fears and doubts, does that make me unqualified to help people work through theirs? Or does that make me more equipped?
I do know that anyone who tells you they have it all together is bold-faced lying and you should run because they are sociopaths. I know a lot of things that are true. Trying to apply them? Sometimes I say and read things that are empowering, but I occasionally have trouble believing them or practing them. Faith is believing what you can’t see or touch. So I have faith, and I hope. I haven't mustered the audacity to wish.
Over the years, I stopped writing about my life so much. I always held back certain details, but I wrote this story once, inching up the curtain higher. It was how I came up, where I go, what I do. I wasn’t bragging, just being honest and setting the scene to make a larger point. What I said wasn’t even impressive to me, as everyone I really know lives a similar life. But I received this huge backlash. Apparently I grew up in a bubble, was living in one and I was bragging. By then there was a book coming, and I was one of the faces of The Magazine and I was popping up on TV. I panicked about the brand, me, being unrelatable. If they don’t like me, will they still buy the book? Will they read the column and blog? Will they watch? Will “they” care? I spent way too much time thining about “they”.
Ultimately, I decided: I didn’t work this hard to self-implode here. So I shut up.
In some ways, I felt like I was becoming unrelatable. Of course, there were people who got it, but many more who didn’t. And I blamed “them” for not getting it until I called Tariq to tell him about who called, and what they offered, and who I met that knew my name and where I went and was going and he would just say, “Wow, baby girl!” And then, I called him to complain about this deal and that one and how they conflicted and I how they wanted X in exchange for Y and should I go with A, B or C? And I wondered if I was being greedy to want both when I "should have been" happy with just one. And my boy, who had always had all the answers said, “Damn, I don’t know. It’s over my head.”
Shit. Mine too.
My world it moves so fast today The past it seems so far away, And life, squeezes so tight that i can't breathe
There was also just weird sh** happening that I'll never get used to. Women come up to me shaking and teary and they say what my blog or my story or my writing did for them. Nothing prepares you for that. I say, “thank you” and really mean it because I’m glad just writing could resonate with someone. But in my head, I think, “all I do is write. Really?” And then I think about how I couldn’t get my words straight the first time I met Terry McMillan. I’m good, but I’m no Terry McMillan. (Yet?) Other times, I meet people, and they immediately start talking about what they read that I wrote. And I get being a published writer is a big deal in some circles. But I’m a writer. It’s what we’re supposed to do, write, right?
I skipped an annual party I live for to go to Tariq’s wedding in Maryland. It killed me to miss it, but there was no way I was missing my best friend’s wedding. There were a lot of people from college there. These are guys who I vacay’d with, who have crashed on my couch and/or floor, who I’ve driven home because I’d stopped drinking when I realized everyone else wasn’t going to. I’ve been one of two human crutches to get them upstairs and in a bed face down so they didn’t choke on their own vomit. But that was years ago. They’re husbands and responsible fathers now.
I spoke to one of them at the wedding, one of those dudes I looked out for and had looked out for me. I offered a big “Heyyyyyy” and he said, “hello” respecfully and introduced me to his wife as “Tariq’s friend. The one who wrote the book.” Really? That's it? I wasn't going to start telling old stories there (I've never even written about those years). Plus, I had my ring on and CBW was right there. I wasn’t some perceived threat of a single girl. His wife beamed and told me she read my book and loved it. I thanked her as my heart broke.
Later that night, Tariq’s wife thanked me for coming to their wedding. Huh? “You thought I would miss it?” She said sincerely, “I don’t know. I just thought you might be too busy.” For your wedding?!
I wondered then if it was something I was giving off. It wasn’t the first time I’d been treated apart. It had become something quite common. And I had grown used to it in some circles, but not from my friends. They matter, but somehow I didn’t feel they felt that they did. There was this weird distance between all of us. I talked to Tariq about it after his honeymoon and he said, “You’ve been in New York a longtime. They see you on TV more than they see you, D.”
There are so many stories I want to tell, but there are unspoken rules now. You don’t talk about what happens behind the scenes and confidentiality contracts are iron-clad. That and I never want to be perceived as bragging again. Also, I feel like if I speak about something before the ink is dry, then it won’t happen. And after a good run, I don’t want to look a failure when I say, “I met XX and they promised YY” and then nothing ever comes from it. So I talk to a small group of five people. And I talk to myself in the mirror too. I say, sometimes through tears, “God didn’t bring you this far just to drop you off here.” And for awhile I’m convinced and then I doubt again. And I start over. When it's nice out, I ride my bike to the park and talk to the ducks. I’m sure people see me and think I’m crazy, but that’s actually how I keep myself sane. Go figure.
I read a Samuel L. Jackson profile in New York Magazine once. He talked about being a stage actor and wanting to do Hollywood. His manager told him to be patient. “If Hollywood wants you, they will call,” he said. So Jackson waited, and waited, and he called his manager every now and again to ask if they called and the answer was “no”. He kept going until one day they called. And then he went to Hollywood.
I got that call, actually three times. I packed my bags with my best dresses and headed West. I had pool side meetings and sat in cushy offices with big windows with views overlooking the hills and sometimes the ocean. I looked out and allowed myself to dream that what I want now is possible. I talked to executive producers at the top production companies and networks. I did my little song and dance, telling my story and selling myself (but not my soul), trying to make them like me, really like me. They told me I was great I what I’d be perfect for. And I beamed. And they called back and took calls from my team, which my manager swears is a good sign.
I went back and shimmed some more. And a third time. And they still take the calls, and they say, “yes, she’s on our radar.” And I do the auditions and everyone raves. But then projects gets delayed or dropped or they haven’t found the vehicle for me just yet. “Soon” they say. “Soon.” My manager insists this is part of the process. I trust her or maybe I just want to believe my effort isn't in vain. Actually, both.
And so I wait. I watch others get on. And I’m genuinely happy for them. I think of them as paving the way. I watch how they move and adopt the best practices. Tweak that, fine tune this, expand into uncharted territory. But I still wait.
The wait is what kills me, makes me think about giving up, getting a day job at the library (surrounded my books) and calling my dreams a wrap.
My manager isn’t just the woman who books me for gigs, she’s also my therapist. So is one of my lawyers. So is CBW. So is my wife. They, along with Tariq, share the full-time job of managing me when I get to listening to Lauryn Hill Unplugged and start equating my life to scenes from The Wire.
“Remember when Stringer Bell wanted to kill Senator Davis?” I begin. CBW knows this is his cue to pause whatever show he’s watching on TV or look up from his laptop. “And Avon told him that Slim Charles wasn’t built for that and Stringer needed a jackal? And Stringer had this plan to get out of drug dealing? And Avon told him he was caught between two worlds? Maybe too good for the street and not good enough for what’s beyond that? Remember that?”
CBW nods dutifully. We’ve had this conversation a million times.
“What if that’s me?” I ask. "Too good for a cubicle, but not good enough for anything else?"
He assures me it isn’t the case. And I want to believe him too, but I want what I want and I want it now and all I hear is “soon.” Sometimes there’s even a date, but those deadlines come and go. And new unfulfilled promises come too. I‘ve learned not to believe in anything until it actually happens. I think it's making me jaded.
My manager reminds me, “success isn’t an sprint, it’s a marathon.” She reminds me of my best traits and what’s on the table: plenty of offers that come with contracts and hefty lawyer fees. I look at my dwindling account, the money from my book advance and writing round-the-clock. I repeat to myself, "this is an investment in your future." But I also think of how I lived this crazy life to write this blog, to get that book to get that check and I see the money flying out the window. I’m gambling and I sometimes I have the sinking feeling that maybe I’m not the investment that I thought I was. Maybe I should have bought stock.
In the 3AM hours, I think about this woman I sat on a panel with at NYU once. She was pushing for a news anchor job and getting rejected over and over and over. And then someone told her “go where the water’s warm.” So she executive produced her own Internet show, and she’s been thriving ever since. Writing is warm water. Coaching is lukewarm, but getting warmer. Maybe this is where I should stay. Writing and coaching work out for me consistently. TV is like the water in Cape Town. Cold. Is swimming where I am settling or is it sensible?
I don’t know. And that’s when I go stand in the mirror and talk to myself.
In the quiet hours when I don’t have a deadline hanging over my head, I wonder if I’m crazy. If I should have stayed in my cubicle and chosen building someone else’s dream over my own. Enough people told me I should have been happy with that and I wonder if I thought too highly of myself by trying to do something different. I remind myself that if I stayed, I wouldn’t be able to "see some world" or earn in a couple days what I used to clear in two weeks at 100 hours. The Magazine had a future mapped out though. It was certain, at least for awhile longer anyway. I liked my work there. I liked my co-workers. It held a prestige. I’d say, “Oh, I work for The Magazine” and people were automatically impressed. I liked that feeling.
I didn’t want to leave. I had to and I was in the position to, so I did.
No time soon will I tell what my breaking point was—the moment that made me reach across the conference room table to my mentor and say, “I can’t do this anymore.” (A month later, I was out.) But I will tell you about the social media conference I watched on YouTube. It was a new entrepreneurs panel, and this guy talked about how he started this side business while he had a full-time job. It was rapidly successful and he ended up on The Today Show. He talked about how it’s so hard to get to that level of exposure, and you have a six-month window to capitalize it. That same day, a prominent new author was on Twitter complaining that Black authors didn’t get the same exposure as white authors. “We don’t get the Today Show,” she wrote.
Actually, I’d taped the Today Show that morning. It would air the next day.
Early one morning, I got all dolled up, and hopped in the black car the studio sent. Traffic was heavy and I was late, but I tried to look at the bright side: more time to practice for whatever questions they might lob at me. (No, they don't give you the questions in advance.) I rehearsed answering every possible question in front of my laptop camera for weeks.
My make-up artist was even later than me. She beat the hell out of my face in 15 minutes, and I ran upstairs to the set barefoot. I waited backstage, nervous like I’d never been as I slipped into unsteady heels, poofed up my falling hair (not enough spritz) as I prayed with my eyes open, “If You gotta drop me off, not here. Just not here.”
After the taping, I kept my fancy dress on to walk in flip-flops around the corner to my office where I changed into a comfier outfit. I sat in my cubicle and pretended the biggest moment of my life hadn't just happened. I'd become annoyingly good at that.
So I watched that live stream, and I read that tweet. And I went to that meeting where what happened, happened, and I reached across the table and said what I said because I had a rare chance, and too I was tired of pretending that what was a big deal wasn't and I thought it would be stupid not go after my dream. Chasing it was "urgent like a motherfucker" (Sorry, Dad.) I had a lot to lose either way. But I’d tried the cubicle and that was that. What would happen if I tried something else, if I tried Team Me?
I couldn’t be okay with not trying.
When I’m feeling optimistic, I re-tell myself that story like it happened to someone else. I remind myself that writing got me to where I was, and to where I am and if I’m not able to get any further, then at least I got here. I tried. If I fail, I can go back to a cubicle, knowing at least I gave me my best shot. I can be okay with that.
I think. I hope. I pray.
*(I'm at not 33 in this pic. I think this is my 27th birthday)