The Incredulity of Saint Thomas, by Caravaggio, c. 1601-02, uploaded April 13, 2005. (Dante Alighieri via Wikipedia). In public domain.

We all have doubters in our lives. Even if the only doubters turn out to be ourselves. As someone without much of a roadmap for any success, doubt has been a constant companion, one that I often had to ignore to experience any victories in my life. To have those with influence pretend to be on my side but add to those doubts, though. As a twenty-year-old, it was somewhere between bewildering and rage inducing. As a forty-five year-old who regularly advises students, love ones, friends and others about their futures, looking back at those doubters, it’s almost unforgivable the seeds they attempted to plant.

Of all the non-relatives in positions to advise me, few were worse than my high school guidance counselor Sylvia Fasulo. For four years, Fasulo forced me to listen to her “Are you sure…?” questions about difficult classes, the colleges I wanted to attend, the career paths I thought about taking. Her patrician Vassar arrogance toward me as the poor Black kid drove me up a wall every time I walked into her cigarette-filled office.

“Raleigh’s First Pipe in England,” an illustration in Frederick William Fairholt’s Tobacco (1859), June 8, 2014. (Materialscientist via Wikipedia). In public domain.

I hated having Fasulo as my counselor especially once it was time for me to apply for college. She was condescending, demeaning and chain-smoked up my clothes for my troubles. Most of all, I hated having to reveal things about myself to her that I otherwise wouldn’t have shared. Like my family’s financial situation. Fasulo became only the second person I would tell that we were on welfare, that my father and mother had divorced and that he hadn’t made a child support payment since ’78. I had to talk to her about my role in my family as acting first-born child and my responsibilities. It was necessary and humiliating at the same time.

Despite and not because of Fasulo, things worked out for me in the end. Going to Pitt, meeting the people and the professors I’d become friends and colleagues with, was probably one of the best decisions I ever made. Still, I had one parting shot from her in the middle of my junior year at the University of Pittsburgh. It was the holiday season in ’89, and I took time while home in Mount Vernon to visit my favorite teacher, the late Harold Meltzer. I had just missed him, but bumped into Fasulo. It was about as fortuitous as having diarrhea and being nowhere near a toilet with toilet paper.

She asked me where I was in school, and I told her about my considerations for graduate school, law school and the world of work. It was a toss-off sentence, my attempt to end a conversation, not begin one. “Being a lawyer’s hard work,” Fasulo said in response. She then went on to tell me about 70-hour work weeks and billable hours and the bar exam, as if any of this was supposed to be surprising or would somehow scare me. I cut her off, saying “You know, you’re not my counselor anymore, so thanks but no thanks for your advice,” and left her office while she tried to explain her idiotic perspective.

Tiki Barber, the personification of a doubter, at the American Museum of Natural History, October 16, 2008. (Jamie McCarthy/WireImage.com via http://thenypost.files.wordpress.com/).

A quarter-century later, and though I am more than content with the fact that I opted for a PhD over a JD thirteen out of every fourteen days (people with law degrees do make more money on average), I sometimes question if the PhD in history was worth it. After all, a JD is far more portable. A JD would’ve served me better in my nonprofit and consulting careers than having to explain a doctorate. I wouldn’t want to think that I went in the direction of a graduate program for five and a half years simply because I had a conversation with a racial elitist.

It’s probably more likely that I didn’t go to medical school to earn an MD because my Mom and my idiot late-ex-stepfather both told me I couldn’t be a surgeon because I had “ten thumbs.” By more likely, I mean highly unlikely on both counts. I ultimately did what I wanted to do educationally speaking, despite own my doubts, despite the doubts of those who believed it was their job to advise me. But constantly asking, “Are you sure, Donald…?” isn’t exactly the best way to advise or mentor anyone, especially someone in their teens or a literal twenty-year-old. You lay out options, you ascertain what’s going on in their heart as well as their mind. You introduce them to other people who could provide better advice, based on direct expertise or experiences. Otherwise, you’re a doubter, not an advisor or a mentor.