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This is the second of several posts I’ve put together about my journeys as a writer. Please laugh when and where appropriate.

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“You always gotta do things the hard way, don’t you?” my one-time professor Barbara Sizemore said with some sighed frustration. It was in response to me telling her I had decided to stay at Pitt, to pursue my history doctorate at the University of Pittsburgh and possibly transfer to Carnegie Mellon to complete it. It was April 1992. We were standing in the main corridor of the third floor of Wesley Posvar Hall (née Forbes Quadrangle), I was on my way back to my grad student cubicle in the History Department. Sizemore was heading back to her office in the adjacent Africana Studies Department. If I had known this would be my last conversation with the prickly educator, her of squinty eyes and well-manicured afro, before she return to Chicago, took a position at DePaul, and passed away in 2004, I would have done more than given Sizemore a blank stare. As the tall, lanky, and sarcastic 23-year-old I was, I probably would’ve said, “Why yes, professor, I really do!”

I knew what Sizemore was really saying. It was about attending a lily-white university, where there were only four tenured Black professors out of 800 total faculty. My advisor Joe William Trotter, Jr. was one of them. Sizemore assumed that going to Ohio State or Temple to earn a doctorate in Black studies would have been my best move. But even though Sizemore was incorrect about my education decision, she was definitely correct about me taking “always doing things the hard way” paths toward so many of my goals.

Claudia Menza became my first (and so far, only) literary agent in July 1999. The idea of finding a literary agent to help me publish my first book was something I had played with as an idea for nearly a year. At least once I had begun to emerge from my state of rage, depression, and sheer burnout from my years finishing my doctorate at Carnegie Mellon and having Professor “running interference” Trotter as my advisor. I made the decision to turn my doctoral thesis into a book that would straddle the fence between the scholarly and the general. I wanted to publish what would become Fear of a “Black” America for a larger audience, to include both the academic and the personal in the same book. No one told me this was impossible. No one said this was the harder road for a first-time book author. I owned books by scholars that had mainstream imprints and labels. And many, if not most of them, had an agent helping them.

Soon after I finally found my full-time gig with the nonprofit Presidential Classroom in the DMV, I went ahead, did some research in those big, thick books on books and lit agents at Pitt’s Hillman Library, and wrote pitch letters to seven of them. Three weeks later, Menza wrote me back offering to represent me.

She started querying publishing house editors in October 2000, just as I was leaving Presidential Classroom for a higher paying nonprofit job working in social justice in DC. I was so busy with work and my New York family and with married life that I took my eye off the process. One year went by, with a few rejection letters here and there. Then 9/11 happened. I met up with Menza in New York six weeks later. I was already there to do a site visit with a social justice fellow. That’s when I learned Menza at this stage of her time as an agent predominantly represented fiction and poetry. Still, she had some high-powered authors under her belt. I remained confident in her and the mysterious process of finding an editor willing to publish me, in between bites of delicious pasta at a wonderful Italian bistro in the Village.

Two more years went by after that. I received rejections from Basic Books, Random House, Palgrave, Oxford University Press, Farrar, Straus, and Giroux, among others. Some stood out because the acquiring editors met to debate the merits for my book before ultimately rejecting it. Some stood out for being two-sentence rejections. I remember Menza saying, “I don’t understand why they don’t want your book.” That was at the end of 2002. By then, even though I remained outwardly confident, I had given up on finding a mainstream commercial publisher. “Maybe I need to go learn how to write again,” I said to my partner more than once. This, just after she became pregnant with our first and only egg.

With the ugly transition between jobs within my nonprofit organization and the birth of and caring for our one and only son, I knew I didn’t have it in me to continue the process of pitch-and-reject with Menza. I was also thinking about writing a memoir, something that could explain how I got to be me. I wrote Menza in March 2004, formally cutting ties with her as my agent. “I wish it had all worked out,” she wrote back.

That July, with some encouragement from my new boss and from my significant other, I decided to look at Fear of a “Black” America one last time, but this time, to self-publish. I went and found a house that did its own reviews of manuscripts and provided adequate enough copyediting to make sure I didn’t embarrass myself. Sometime in that process, Barbara Sizemore died. I read about her death in a nicely done obituary DePaul University put out (The Washington Post obit, not so nice about her years as DC Public Schools chancellor). I imagined Sizemore looking down at me that July and August, shaking her head.

The book came out at the end of August. Somehow, despite myself, I sold over a thousand copies in 16 months, did radio and newspaper interviews and talks and signings all over the DMV. I was happy and a bit bitter, like a cup of black coffee not sugary enough for my taste buds. This book could’ve been so much more, I thought so many times in 2004 and 2005.

But none of this is Menza’s fault, or Trotter’s, or even my fault, not in any direct sense. The world of book writing is more mysterious than the cloistered world of academia, and much more mercurial, too. It’s a popularity contest cloaked in American -isms, especially individualism and elitism (which of course contains racism and misogyny, too). It puts all the effort and blame on you and me. In my case, for not having a job in academia that lined up with my expertise in writing Fear of a “Black” America. For not having a degree from an Ivy League institution, or for not having enough successful writer contacts in my genre(s) or in general. For not living in New York as a writer. Maybe even for not being light enough or good-looking enough.

And, even in the four-and-a-half years of having an agent, for not paying close enough attention to how the industry had become a set of six monopolies. All with independent presses being squeezed, to sell out, to fold, to become niches for a small group of aspiring authors. It went from being an industry where you could pitch your books directly to publishers with or without an agent to “Get outta here!” unless you do have an agent. So many agents would prefer DIY schlock or books that easily fit the tastes of elite or hokey white readers than to ever read a query from me. I’m too eclectic, too determined to write for Black folk and beat up on white ways of thinking. I received more than 130 rejections from agents for my memoir Boy @ The Window, between 2007 and 2011, including one that read, “Alas, another book on childhood abuse!”

So, is it really me making it more difficult, because I like to “do things the hard way?” Is it because I have frequently put the need to pay bills and eat over pursuing my art and craft first? Is it because my writing sucks and agents see that immediately? Is it because I don’t know what I’m doing, or because of all of the above? Well, fam, what I do know is that I need help. I don’t quite know what I need to know to navigate this strange world of finding representation. I don’t quite know what I need to know to make publishing with a reputable press work without representation. Kenny Loggins says “when you can’t give love, you give out advice.” Advice with love is preferable, and usually, specific to where I am.