I pursued the idea for a little bit, but then the job at the University of Chicago came along, and while it didn’t fit my goal exactly, it seemed at least a step in the right direction. That job lasted a few years, then evolved into my current freelance career, and while it’s been wholly satisfying and successful, I still think about what it’d take to get myself closer to the classroom.

So when Ruthie—who I’d known only tangentially for many years—started twittering about all the fun she was having as a Lab School computer science teacher, the gears started turning again. I dropped her a note out of the blue, basically an offer for lunch if she’d spend an hour telling me about her career and letting me bounce ideas off her about my interests. She obliged, and we met up a couple weeks ago. It was great—she got me excited about seeking this kind of work out again, which led into a brainstorm of how I could help her out with her program.

The upshot is: I’m now helping her plan out the curriculum for a course she’s teaching this summer on web design. The kids will be middle schoolers, mostly, both from the school and the community. The mission is pretty broad—it’s a class on “web design,” and beyond that, the details are up to us.

I’m pretty stoked about it, of course. Who wouldn’t want to the chance to mold the minds of a couple dozen little web designers-to-be? But at the same time I’m worried. From what Ruthie told me about her experience teaching a similar course last year, these kids get it, and fast. My fear is I will woefully underestimate their abilities to pick up the material, that within days they’ll be the ones teaching me, and I’ll be left feeling like the old man in his jalopy who still swears by the slide rule.

The solution, I think, is to focus on fundamentals. Cheap coding tricks are a dime a dozen online; it takes a lot more time and experience to know what actually works. Ruthie and I brainstormed this weekend and I think we’ve got a pretty good list started on what’s relevant to teach. (Relevance being really difficult to gauge with this group—some of these kids are likely to start up their own web design business before the summer’s over. Not joking.) I’ll probably write up a post about it once it gets refined, but until then, I’m curious:

If you had the chance to teach a group of ten- to twelve-year-olds the fundamentals of web design, what would you tell them?

I went into the building Wednesday morning with a notecard in my back pocket. This is more or less—more more than less—what it said:

• When I was in high school, the web had just been invented, and there was no such thing as a web developer. No one could have told me what I was going to do. New jobs are invented all the time. There’s a good chance you’ll end up doing something you can’t even dream of yet.
• It’s okay to change your mind about what you want to do, as many times as you want to. Don’t worry about picking the right major the first time around. Or the first job. Or second, or fifth.
• The story of my rise from immigrant bean picker to CEO of a multi-thousand-dollar organization.
• College is about trying new things and finding what fits. When I was in college I spent half my time in my major and half the time at the newspaper with J-school dorks. Explore.
• Endearing story about living in CRC, the best dorm ever. I went with Illumi-Hinman.
• What they don’t tell you is that college is about making connections, building a network. Seems like cheating, but it’s true. Real, honest, human connections is what propels you along in life and allows you to have the confidence to do risky, scary things. It’s what’s helped me.
• You guys are smart. You know what’s right. Be skeptical. Don’t be distrustful, but skeptical. Make sure the things people are telling you (including what I’m saying here) make sense to you before buying it. Trust yourself.

Which took me to the five minute mark, because really, shut the boring adult up already. At this point, I’d ask for questions, which would usually come slowly, so I’d turn it around and ask the kids a few things, like who knows what they want to do? Or who has parents who are insisting they do something in particular? One of those got us going, and then we’d riff for the next fifteen minutes until it was time for the next speaker.

Fortunately, it was wasn’t my intention to recruit them into web design or computer programming, because I would have been deflated to learn LPHS doesn’t offer programming or web design classes. Instead I probed them about what they really wanted to do. It was uplifting to find that a lot of kids had really specific ideas. Nurse anesthesiologist. Computer animator. Stock trader. Musician. I made my pitch for web design anyway, and told them to use their resourcefulness to research it online and try it out on their own time.

The kids were genuinely engaged and interested. It wasn’t hard to have a conversation with them for fifteen minutes. They had relevant follow-ups to the points I made. One girl really latched onto the point about networking, saying she found it so frustrating that she’s having to compete against kids her age who are unfairly ahead due to the networks their parents built for them. I tried to encourage her to go out and make her own connections right now; she was a sophomore, after all. If you start now, I told her, you’ll be ahead of most of your peers in no time.

As good as it all went, I’d change some tactics for next time:

• Lean heavily on the personal anecdotes, and less on the fortune cookie wisdom. No one likes to have someone preach to them. Much more effective is first-hand accounts of the benefits of all these lessons.

• Come prepared to drop names… Every class asked about two things. The first was “Have you worked with anyone famous?” I didn’t have a good answer.

• And numbers. The second: money, money, money, just like Lilli predicted. When I told them I charged $5000 to make a website, their eyes lit up and I swear for a few seconds they all wanted to be web designers. But then they asked the gynecological oncologist how much she made, and they immediately forgot who I was.

• Offer a way to stay in touch. I brought my business cards with me, but forgot about them until the last period. When I offered them out, at least 12 kids came up after the class to take one. I was floored. I don’t expect to hear from most of them, but if even one writes me, I’ll be thrilled.

• Collect addresses. Knowing how short their attention spans are, I would love to have a collection of their emails, so I could follow up with an invitation to talk more about web design or programming as a career, if they were interested.

• Have an answer prepared for the inevitable “what good is all this?” question. As in, why do I give a shit about how to calculate the derivative of a quadratic? I was caught off-guard by this one, especially when it was asked by the math teacher, and didn’t have an answer ready, so I kind of stumbled through a riff on how college teaches you about how fun it is just to learn for learning’s sake. It’s an important question, one that I remember wondering when I was in high school. Next time I’ll come with something prepared.

Recently, I registered with the Alumni for Public Schools, an organization that connects Chicago Public Schools with the volunteer arms of local college alumni clubs. I signed up on behalf of the Northwestern Alumni Club, a group that’s been hooked up with local heavyweight Lincoln Park High School. A couple weeks ago, they sent me my first mission: speak to the high school students as part of their career day. Or, as they’re calling it, “Meet Your Future—Career Motivation Morning.”

If I was in high school, and saw “Meet Your Future Day” on my calendar, and couldn’t find a way to fall down a flight of stairs or contract a 24-hour cold the night before, I’d use that morning’s commute to steel myself against the onslaught of irrelevance and banality that was about to fill my day. Which means that even if, as an invited presenter, you come with good intentions and possibly even a message chock full of meaning, you’re going to start off against the ropes and down a few points.

Despite all that, I said sure, I’d be happy to show up and play the part of the kids’ future. That was a couple weeks ago. Now it’s three days before C-Day, and I’m still stuck figuring out what to say. The invitation email encouraged a sort of theme: “The content of your twenty-minute informative/motivational/inspirational message should incorporate the value of post-secondary education and how a career unfolds.”

I’m assuming a few things:

• Dressing up as a Wal-Mart employee, prisoner, or cadaver will be looked upon unkindly.
• When they say “value,” they actually mean “positive value.”
• The bar for what stands for inspirational to high schoolers climbs ever higher, and a twenty-minute soliloquy by a computer nerd talking about his stirring rise from post-collegiate ASP programmer to 31-year-old PHP programmer isn’t likely to drive anyone to break out the SAT study guide over lunch.
• When they say “twenty minutes,” they don’t mean “four minutes on your job and sixteen minutes debating who’s the best ottoman humper.”

Right. So of course, college is valuable. Happy to preach it. And for most high school kids, especially those at the 47th-best high school in the country as rated by Newsweek, absolutely I’d recommend going to college if you’re the slightest bit interested. I’m just wondering how to make that message interesting to a class of high school seniors without talking down to them or telling them things they already know.

So I’m soliciting advice. What do you wish someone would have told you about college and careers when you were a senior?