One of the greatest decisions any of us can make these days is whether we move on from high school to college, which colleges to apply to for admission, and how to get through all of the paperwork, essays, exams, deadlines. Not to mention working with counselors, teachers, administrators, community folks and parents in order to get everything ready. My college decisions weren’t life and death in the fall of ’86, but with so many issues in my life, the choices I made by December ’86 were life-altering ones. No sixteen or seventeen-year-old, no matter how smart, insightful or clairvoyant, can fully understand the implications of these decisions. And I was pretty insightful about most of what to expect in getting ready for life after high school.

My college application process began with my annoying condescending guidance counselor Sylvia Fasulo. She was a chain-smoking, four-foot-nine Vassar Class of ’49 graduate who never seemed to think that I was good enough to be in the gifted-track Humanities Program from the day we met in September ’83. During my senior year, she chose to render some sarcastic judgement my way. “There goes Donald, always daring to be different,” Fasulo said to me as I shuffled down the second-floor hall from AP English class early on in the school year. It referenced my refusal to join our chapter of the National Honor Society and my insistence on carrying three AP courses and applying to schools like Columbia, Yale and the University of Pittsburgh. When it came to helping me work through my preparations for college, Fasulo was about as helpful as redneck would be in giving me directions to my White girlfriend on the White side of a Southern town—if I had one at the time, of course. It’d be an exaggeration to say that Fasulo had it in for me. Yet she wasn’t exactly helping me with good advice about the quality of the schools I wanted to apply to, whether they had good history or computer science departments, or whether the schools had more than a handful of Blacks attending. These were the questions I wanted her to help me answer. I ended up doing almost all of that research myself.

What Fasulo was good at was communicating her low expectations of me. She emphasized “safety schools” over and over again, as if I didn’t stand a chance in heaven of measuring up with the more selective schools. “You need to pick a safety school,” she’d say. Or “SUNY Buffalo’s a good safety school,” she said a fair number of times. On her constant advice on this, I wasted an application and applied there. But not without insisting that Columbia, Yale, and Pitt would stay on my application list. Pitt, of course, was the one school that didn’t fit and the one that Fasulo shook her head about the most. “They’re out of state,” she said to me in a bit of exasperation about my choices. I explained that the University of Pittsburgh’s out-of-state tuition was actually less than the in-state tuition of any of the New York State schools, and by a wide margin. Not able to resist, Fasulo responded, “There you go again, daring to be different,” adding a frustrated chuckle. Because of my research, I also ended up applying to Rensselaer Polytechnic Institute, Rochester Institute of Technology, the University of Rochester and Hobart & William Smith Colleges. Five schools in Upstate New York, two Ivy Leagues, and Pitt. No wonder Fasulo was confused.

I hated having Fasulo as my counselor at this critical crossroads. 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.

I didn’t get much help from my teachers other than my late AP American History teacher Harold Meltzer. Of all the former teachers I decided to ask for a letter of recommendation from, I went to my eleventh-grade math teacher Andy Butler. What he wrote was eighty-four words of qualified support of my pursuit of postsecondary education. I was “a good student” when I “worked hard,” but I could also become “distracted sometimes.” I knew I probably should’ve asked someone else—almost anyone else—for a letter. Even some of my senior-year teachers would’ve done better by me.

Meltzer did help out in numerous ways, more than making up for Fasulo and Butler. He helped me get over some of my embarrassment as I wrote my college essays about my life as the adult teenager at 616. I needed to write this type of essay, since I had some explaining to do about my lack of extracurricular activities. Meltzer helped me interpret the multi-page green-and-white financial sheet that I picked up from the local welfare office outlining my mother’s income between ’83 and ’86. He set up an interview with a Columbia University alum living in the Wykagyl section of New Rochelle, a rich neighborhood full of small mansions and near a professional-level golf course and country club. The pompous alum seemed as interested in intimidating me with his soliloquy about Columbia’s great traditions as he was in helping me get in. He never asked why someone like me would want to attend. I guess he thought that of course this Black boy would want to go to an Ivy League school like Columbia. “Why do I have to go through this to get into college?,” I thought. I tried to not hold it against Meltzer that I had to witness opulence and arrogance in my college quest.

What Meltzer did that probably helped me most was to bolster my confidence in the college application process. His letter of recommendation was six pages of unrestrained praise. He used so many superlatives to describe my academic success and college potential that I thought that I was the great Dwight Gooden by the time I finished reading it. I was “a great kid,” a “diamond in the rough,” hard-working,” a “critical thinker,” the “best student [he] ever had,” an “intellectual,” smart “beyond belief,” and, well, you get the picture. It made me laugh and blush over and over again after I first read it. I said to Meltzer the next day in the Social Studies Department’s faculty lounge, that “you know more about me than I know about myself.” He just laughed and laughed about that.

In October, I took the old SATs for a second time. My 1050 from last fall wouldn’t cut it, not for Yale, and not for Columbia. Scholarship money was on the line as well, as the combination of my GPA, my AP score, and a higher SAT score would all but guarantee college acceptance and some academic scholarship money. So what little studying I did in September and early October was to go through Barron’s SAT prep book and its sample exams. By the time of the test, I thought I had a chance at a 1200, which is what I set as a goal. There wasn’t anything memorable about this day. I went through analogies and other useless sections of the Verbal section and struggled, as if I hadn’t studied at all. It felt easier than last year, but not by much. The Math section seemed about the same.

In AP Calculus and AP Physics class the following month, we were all talking about our scores. The top students of my class were neck and neck as best SAT test-takers. Their scores included a 1360, a 1350, a couple of 1280s, a 1220. Even one unstudious jerk scored in the 1200s, prompting him to say that “only an idiot would score under 1200” on the SAT. I assumed that the comment was directed at me, since the asshole looked directly at me when he said it. Given that I only scored an 1120, I kept my mouth shut. Little did I know at the time that most of my more entitled classmates had gone through an SAT test-prep course like Kaplan and Princeton Review.

It was all over by the middle of December. My Yale application was due on November 1, and several other applications had deadlines between November 15 and mid-December. A couple weren’t due until the new year, but given the amount of work I’d put into the Yale, Columbia, and Pitt applications, I just adapted all of my essays and materials for the other schools. By the week before Christmas, all of my college applications were in the mail.

It was an arduous and privacy destroying process, but it felt good, even at the time. After four and a half years of living with the realities of poverty and domestic violence, feeling a bit like an outcast in a room full of nerds and wannabe cool folks, and being run into the ground by my mother and younger siblings, I was looking forward to getting out of 616 and Mount Vernon. I also knew that most of the decisions I made were good ones, given my limited knowledge of the college world and the arrogance of my counselor and some of my teachers. It’s hard to imagine what I would’ve done differently given what little I did know back then, other than asking my AP English teacher Rosemary Martino for a letter of recommendation instead of Andy Butler.