“Be Careful Little Man” – Advice from Your Future

06/22/2025
By Kate Stone Lombardi
Published on Substack

Photo of police car lights
Photo: Michael Fortsch for Unsplash

One writing exercise I like to assign is having the men write letters to their younger selves. It’s a vehicle for reflection and can often lead to more polished pieces. But responding to these letters as a writing teacher is hard for me. Let me show you what I mean.

Here’s an excerpt from “L” :

“Hey Little Man,

I hope I didn’t catch you at a bad time. I know that by now you have flipped the script on a lot of things you have been going through for the last several years. Instead of getting bullied and made fun of in school, you have become sort of a bully yourself. Watching your dad get put in handcuffs and being placed in a patrol car for hitting your mom across the back with a dining room chair was confusing. It made you angry, I know, because your mom and dad have had many fights before, but your father has never been taken to jail. I know you asked yourself why the police didn’t mind their own business? But I want you to know that it was their business because your dad hurt your mom, the only woman who will love you for the rest of your life.

If you let that anger build up inside you, it will affect your decision-making in the very near future, and you will go against your gut instinct every single time. Your first girlfriend will break your heart because she will be afraid of you. The anger you will begin to express at any provocation will make some of your best friends dislike you. Family members will abandon you when you need them the most, and you will stop caring about life.

Well let me tell you little man, life is beautiful. Please enjoy it. I know it’s not easy for you right now, but I need you to do something for me. I need you to smile. Start practicing to smile more often every day. Lighten up your mood and please don’t take life so seriously yet. I don’t want you to miss the best years of your life. I don’t want to tell you why, but you have to trust me. You are good. Just always try and think before you act. You have a lot of people who love you and if you don’t care you will end up hurting them all.”

So how would you respond to this as a writing teacher? While I am frequently overwhelmed by the emotional content of these pieces, I have to force myself to focus on how the writing can be strengthened. That said, I’d feel like an idiot saying “Nice use of detail on your dad using the dining room chair across your mom’s back. Can you give us more? Was it a metal chair or a wooden chair?” Or: “You tell the reader that your girlfriend will become afraid of you. Can you show us instead of telling us?” Actually, I could say the second thing.

But it’s a challenging balance. Since the men share their writing by reading their work out loud, I try to stay quiet, at least initially, and let the other class members respond first.

“Dear T,

As you already know by now due to constant reminders of mom and pop, these streets aren’t all fun and games. Although you should always enjoy the light side of life, also be prepared for the darkness in an instant.

T, I wanted to take some time out of your day, before you go out and party with your friends, to impart some wisdom to you, in the hopes that you do not follow down the wrong path. I know you are at an age where you feel you know everything and us old people can’t teach you shit, but remember that old adage Mom used to constantly say to us: ‘a hard head makes a soft ass.’

Be careful. I know J’s block is where most of the kids your age hangout at, and it’s the popular place to be seen, but that area is a ‘Red Zone.’ The police constantly stop, frisk and harass young black men, but especially over there. I once got stopped five times in one day by the same cops who gave me a different reason each time. T, be aware that when the police stop you (not if) because you’re a black man, listen to their directions PLEASE! Hands out of your pockets, put them in the air, face the wall, place your hands on the wall, spread your fingers and your legs, maintain your balance and please DON’T COME OFF THE WALL. It will be taken as an act of aggression, and their hands and feet are going to be all over you. I know it feels degrading, but survival of this ordeal is much greater than disgust. Make sure you carry your identification card everywhere. You’re in no position to forget it.

T, I know the thought of these things happening to you seems scary because you’re a good kid and a good student who gets good grades. But this doesn’t matter, the actions of the police are just a sad reality of the way they perceive us as young black males, they have a shoot first mentality, and are most definitely not going to pay the price for their actions because time after time no matter the circumstances, the courts always justify their actions by saying that the officers felt in danger for their lives.

I hate the fact that you have to live like this. You should be able to live life freely, without the worries of, ‘will this be the day I die or lose my freedom at the hands of racism?’ I don’t mean to scare you, no actually, I do, because fear will heighten your sense of awareness to the fact that they are always watching. Unlike your counterparts, you will rarely ever get a second chance if you make a bad decision.

Love, your Self.”

Okay, on this piece, what feedback do I give? Again, I had class members respond first, and most of that discussion was on related experiences they’d all had. Then I tried to steer it back to the writing. It felt like T’s instructions on how to respond to the police might be somewhat generic. Should I ask him to focus on his more specific, detailed experiences of being detained? And was that relevant to the letter or prurient on my part? And of course, as an older white woman what the hell did I know? What T advised his younger self was most likely good advice.

Instead I asked him to think about the emotions behind his letter – his urgent need to protect this younger version of himself, the frustration of trying to impart wisdom when he knows that his younger self would likely reject it.

Both letters touched me by the tenderness they showed – the nickname of “Little Man” in the first and the signature of “Love” in the second. These guys are locked up for the rest of their adult lives and they are reaching into their past, trying to warn themselves.

But it’s too late. So much potential, so much regret and so much pain.

And so much for not reacting to the emotional content of the pieces.

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