Growing up, I was an honor student; in high school I was voted runner-up for best smile. It may sound pie in the sky, but I genuinely thought I'd go on to write New York Times best-sellers, have torrid love affairs, take meetings with publishing VIPs, and host legendary dinners at my Harlem brownstone with 150 ethnically diverse friends. My Aunt Patsy told me I'd be a star—and I believed her.

Instead, as I approached 36, my love life was laughable, I'd yet to write a book, and I could barely afford my cell phone data plan, let alone real estate. I'd made a habit of feeling sorry for myself, writing mournfully in my journal and complaining to friends about all the happy-couple photos on Facebook.

But eventually, I got tired of my own whining. I knew in my heart that I didn't long just to get married or buy a house, but to celebrate these achievements. I'd watched as countless friends became brides and homeowners, and despite being thrilled for them, the fanfare made me anxious. When will it happen for me? I wondered. Just once, I wanted to stand in the spotlight, surrounded by everyone important to me, to scan their faces and see love, admiration, and, yes, envy of my incredible dress.

Rather than continue to wallow, I decided to do something. I'd throw a blowout bash in honor of my 36th birthday—not a milestone by any means, but at the rate my discontent was growing, I couldn't hold out until 40. I billed the event as a party, but it quickly grew into something bigger: a one-woman spectacular. I called it Penny Sings the Hits. I'd been performing with hairbrushes in the mirror since I was a little girl, and I'd always wanted to strike that classic R&B diva pose—one hand to my ear, the other toward the sky—before an audience. I obsessed over every detail like a bride. More than a few times (while rehearsing in the shower or writing out my between-songs audience patter) I thought, Oh, this is silly, or Who do I think I am? But I pressed on, swept up in my fantasies of friends from college nodding their heads to my Lauryn Hill rap and the crowd hollering as I jazz-scatted a sca-bah-dah-bee-bee-do.

As the big day drew closer, I hired acquaintances as my backup singers (and by hired, I mean promised Häagen-Dazs) and spent an embarrassing amount of time editing a list of songs on my BlackBerry, adding a few I'd heard in the grocery store ("Jack & Diane") to old favorites like the theme song from Grease. This left little time for a guest list or actual invitations, so I just invited everyone I knew on social media.

Picture a low-lit, intimate club packed with 70 of my closest friends, friends of friends, coworkers, a former boss, and even an ex or two. By showtime, it was standing room only. As the lights flashed, I made my entrance, clutching the hem of my plunging silk halter dress as I weaved through the crowd and ascended the stage. Cold feet? Ha! I felt immediately like I belonged there, front and center. So often in my life I'd been weighed down by guilt or embarrassment over the state of my dreams or my bank account. But in that instant, I'd done good. Or at least good enough. Surrounded by everyone I loved, I felt something richer than happiness—it was gratitude. I understood why people chase these moments, spend hours trying on gowns to star in shows of their own making. For one night only, I had everything I'd been waiting for.

Nowadays, when working on something big, like reactivating my dating profile—or even a small thing that feels big, like a sink of dishes—I try to conjure that Penny Sings the Hits feeling. I remind myself that I'm the girl who knew what she wanted and made it happen. The girl who, when the crowd was cheering and the lights flashed bright, gripped the mic and sang her heart out.

Penny Wrenn lives in Harlem and her work has appeared in Essence and Esquire.


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