This newsletter is my process of writing a self-help book, tentatively titled How To Make Money: Financial Advice For Poets.
Though I recently thought of another title: Single Digit Millionaires. I guess we’ll see.
In any event paid subscribers should get the book for free, maybe. Or a discount. It’s hard to say. But it is true that I would like to be rich. And if I could tell something to my younger self I would say, “Don’t listen to anyone who says money can’t buy happiness.” Of course I know, as a practical matter, money cannot buy happiness, but neither can art. Not even integrity can buy happiness. So if nothing can buy happiness why is it only money that gets devalued in this way?
Here is something that money can buy: tools.
Anyway, today’s letter is about how to go to college for free. I’ve decided to only send one letter a week from now on. Please share.
In 1987 or 1988 I lived in a group home on the north side of Chicago. I was 15, or had just turned 16, and it was my 4th placement in 2 years.
I went to a school called CSC, a three story red brick building with a buzzer entry system (I have no idea what CSC stood for). It was operated by the Jewish Children’s bureau, though the majority of kids weren’t Jewish. The school was a mix of private and public children. Wards of the court, like me, for whom the state was our legal parents, and also children who lived with their relatives and attended because they had special needs.
It was a big step up for me, though I didn’t appreciate it at the time. When you’re a ward of the court, to be in a facility with private kids is significantly better than a facility that is only public. To share space with children who were not yet wards was to share space with children who still had advocates.
The classes were intentionally small, 3 to 5 kids per teacher. We had a smoking lounge, because the administrators preferred to keep us inside the building. There was often someone being restrained. Knives were drawn, or lunged for. The girls were all victims of sexual violence, and most of the boys were too, though less open about it. But it was considerably less violent than my previous placements.
There was lots of individual attention and no homework. Some of the kids left after lunch to go to work. There was no focus on learning. The point was to keep people out of trouble, help them acquire skills they could use in the real world, like typing. We were not being prepared for college. Despite the ease of the schoolwork I never attempted to do any of it. I liked to drink; I liked to get high. Sometimes I just didn’t show up at all. I don’t think I had ever passed a high school class at that point, though I’m not fully sure.
The staff at the group home I lived in didn’t care too much. That’s not actually a fair statement. I think they cared quite a bit. They just didn’t know what to do with us. Nobody in the world knew what to do with us. By the time an adolescent arrives in a group home (as opposed to foster placement or adoption) they’re already damaged beyond repair. If they don’t end up more damaged than when they come in that’s already a miracle.
There I was, in that red brick school building with the locked doors, watching from the window as the kids crossed the avenue to the high school across the street.
Mather High School was a “normal” Chicago Public School. It served the children of West Rogers Park, an almost comically diverse neighborhood. The majority of students were children of immigrants. There were Iraqi Kurds, African Americans, Mexicans, Koreans, a handful of Russian Jews brought over thanks to Project Exile, mixed in with the Greeks and Irish who had been in the area longest. If you look it up on GreatSchools, which the real estate boards use for evaluating neighborhoods to invest in, Mather is a 2 out of 10.
I wouldn’t say there was a gang problem at Mather, but there were definitely gangs. You had to pass through a metal detector to get in the school, which wasn’t common pre-columbine. The point I’m making is Mather was not a perfect school, but it also wasn’t terrible by Chicago Public School standards.
It’s over 30 years ago, so I’m certainly not getting things exactly right, but I remember it clear as day. I looked at those kids going to the school across the street, none of whom were being groomed for greatness, and I thought, “they’re not better than me.”
I went to the CSC principal and told him I wanted to go to the normal school across the street. Some of the better kids already went there for a class or two, but I wanted to go full time, and I was not one of the “better kids.”
I asked Dr. Blum, “If I get straight A’s in every class, can I go to Mather full time?”
“Alright,” he said. And why wouldn’t he? Why not encourage me? I doubt he believed I would do it, but nothing was at stake for him.
Then I asked him to sign a contract.
And that’s how I ended up at the normal school. It was my first success in my young life, which had been kind of hard up to that point. I’d left home two weeks after my mother died when I was 13. I had no foundation and anything I was going to learn I was going to have to teach myself. That would be true all my life, which is why I’m writing this book. Not because I’m wildly successful, or the best at any one particular thing.
Here’s what I learned from the experience of turning my life around at age 15.
First: Everybody wants to be on a winning team. Help yourself and you’ll be amazed at the support you receive. It’s not hard to get A’s at a group home school, really just a matter of showing up. I had to quit drugs, and I didn’t start getting high again until after college. But the support I received was tremendous. All the adult attention I had been craving but didn’t know how to access, or even how badly I wanted it, was now mine. I felt self esteem, perhaps for the first time. Suddenly I had something people wanted, even if it couldn’t be seen.
This is similar to how successful founders attract talent to a startup (though you also have to be careful when you’re attracting ambitious people, for other reasons). I was allowed to get a job working nights at Freedy’s Fine Dining On A Bun, which I would not have been allowed to do if I wasn’t already doing things correctly. So I had some money. I no longer had a curfew at the home. If I needed a ride there was always a volunteer ready to help. I even made out one night with one of the social workers managing the group home, which I know is frowned upon and is statutory rape maybe, but at the time it seemed like the greatest thing that ever happened to me.
That kind of support can be intoxicating. I was so inspired that I graduated high school in just over 2 years so I could graduate with my age group. I tested well and received a full scholarship for college. Because if you’re a ward of the state, and you actually survive and go to college, you don’t have to worry about things like tuition. There is a lot of money out there for people who turn their lives around, especially children, and much of it is unclaimed.
But here’s another other thing I learned, eventually. I went to a big state school, which was hard for me as I had never written an essay before. During college I didn’t know where to go on the holidays when the dorms closed. There are consequences to not having a foundation and they don’t magically go away. I graduated college. I started working as a stripper and shooting heroin. Then I had a massive overdose resulting in a stroke and I couldn’t move and spent 8 days in the hospital. It’s not a straight line; it’s peaks and valleys.
In every group of people that should make it there will be some that don’t. And in every group of kids that shouldn’t make it there will be some that do. If we want to change the world we have to focus on those percentages. If we want to change ourselves we have to leverage the difference between what we can and cannot control.
The best advice anyone can give you is to be born rich. On the other side of that is you don’t have to pay for college if you make it out of the group homes in one piece. The space between is infinite.
Life isn’t fair and I’m not that interested in the advantages other people have over me or I have over them. You have to believe in yourself and take initiative not because it’s a level playing field, or because you’ll make it as far as someone who grew up with two parents and healthy role models, or went to a high end boarding school followed by Yale. You have to try because it’s the only thing you can do to help yourself; it doesn’t make sense to focus on anything else.
p.s. I hope nobody reads this as being critical of Mather or the wonderful teachers and social workers I met there, who gave so much and asked for so little. I don’t care what GreatSchools says, Mather will always be a great school to me.
Thank you for reading. As always please share on social media, it helps a lot! Liking and leaving comments also helps, in a different but no less important way.
p.s. 2 Someone wrote me after my last letter, about trading stocks, and pointed out that the best investors did not trade with other people’s money, as I had inferred (though not explicitly stated). They mainly bought and held with their own money. Or they’re rich because of how much they own of their own companies. Option traders who never actually hold stock, no matter how good they are, are working a job, which is the opposite of passive income. Which is something I want to get into in an upcoming letter (probably the next one) about how to run a short term rental.
Something about poets makes them the best writers of prose.
Great read. Thanks Stephen.