I’m working really hard this week to find the sweet spot. I have a group of rising seniors that is just small enough to manage each student’s needs on a case-by-case basis, as I have in the past. This year, however, I have online support from College Planner Pro (I was a total newbie this time last year to CPP), and when I start to factor in the parents—their personalities, their anxiety levels (or what I can gather about them)—as the other parts of this equation, I’m realizing how important it is to have a system of organization that everyone can plug into. I need a template that can largely keep everyone on the same page; better to create it now than to put it off until next year—which is so tempting—when urgency for such a system is likely shooting through the roof. It seems stupid to implement a system intended to circumvent stress as an act of triage.

I started by making a list of everything I’d like to have each student finish by the time school starts back up. Main college essays should be in near-submittable shape. The “Why [college]?” template framework should be solid, easily adaptable to specific schools based on student research. The brag sheet, resume, and cover letter should be polished and ready to hand over to recommenders. The college list should be all but locked and balanced based on admissions likelihoods. We should have a week-by-week schedule of college-application tasks that stretches all the way through our agreed-upon final deadline. Et cetera.

So I spelled all these things out and then broke them into their sub-tasks, and then assigned them deadlines through the end of August. After that I cleaned the list up, made sure everything was intelligible and well ordered, and worked it into an email addressed to these students and their parents. And then I sent myself a preview.

Reading it was AWFUL. I broke out in a sweat. I had heart palpitations.

The list was so long and impenetrable—like a dark cloud blotting out the sun. Except this dark cloud was really a flock of angry birds, threatening to crap all over everyone’s summer. I started with an image of parents printing this thing out and sticking it on the fridge, and then this whole montage of family discord played out in my head, culminating in my students coming to my office twisted with rage or completely checked out, starting senior year utterly exhausted. Or, worse, they just choose to stop showing up to meetings.

Feeling into the student and family experience is useful and totally necessary. I just have the tendency to catapult myself directly into worst-case scenarios.

It took a couple of days for the nightmare to dissipate, but now I’m on to figuring out the appropriate way of chunking all the information. For the parents, I’ve gone back to condensing the extended list into overarching goals for summer, which fills one email window and reads as  much simpler and more manageable. For both parents and students, it’s now a matter of emailing one set of tasks every couple of weeks. If I’m lucky, it will make about half my seniors close to self-sufficient. The others are probably the one who’d need the hand-holding one way or the other. We’ll see.

By Nick Soper