The plane touched down at O’Hare early Sunday morning, jolting me awake. I looked around to see other passengers in varying states of awareness.

I flipped my phone off airplane mode and noticed I had no messages.

I checked my email quickly. Same thing.

Everything was quiet.

What a difference two years makes.

The last time I touched down on the first leg of a trip back from a college media convention in this metropolis, my life had gone from bad to worse. I had just traded some labor for airfare and a room so I could head to Austin, Texas in hopes of finding salvation for the newspaper I advised. We had been told a week earlier that we were too far in debt for our student government to tolerate, never mind they had no say over our finances or budget. As a result of the SGA’s prodding, an administrator told us that if we didn’t have $5,000 paid off of that debt in less than four months, we might be forced to close.

I found myself at this convention, begging funds from former students and offering services to fellow advisers for donations to the cause.

In one such circumstance, I had been given a tin can with a slot on the top with a simple message: Go beg for life.

So I did. And at that point, I thought it could never get worse.

When I flipped that phone on two years ago, alone and cold on a red-eye flight into the Windy City, the text messages came pouring in like a dam had broken free.

“Check your email.”

“Check in when you get this.”

“OH MY GOD! DID YOU SEE YOUR EMAIL?”

“Can they DO THIS?”

“Where ARE you? Call when you get this…”

On and on it went. I had no idea what was going on, but I checked my email. There it was in black and white: The student government was putting forth a resolution asking me to resign and if I failed to do so, a request that the chancellor fire me.

I called a couple of the kids and talked them off of their various ledges.

It’ll be fine, I told them. Everything is just fine.

Did I believe that? Not for a fucking second, but what could I do? I’m on a plane in Chicago on a Sunday, taxiing to the gate for a two-hour layover before heading to Milwaukee. It really did seem like the beginning of the end for me.

I detailed most of the tumult that followed in this post, aptly titled, “Heroes Often Fail.”

What followed that post was a set of truly dark days, the kind that lead you to question what exactly it is that you’re doing here or why you’re bothering at all.

The one thing that kept me going was what A and I used to say to each other quite often when sussing out some level of student-media bullshit:

“Is this the hill you are willing to die on?”

The odd thing was that we often used that phrase as a deterrent to action. It was a way of saying, “Look, we got bigger fish to fry here, so don’t go all great guns after this stupid thing.”

The answer was always, “No, it’s not. Now, where are we on this other thing…”

As I watched my own staff have to write what should have been my career’s obituary, I could hear her asking me that question. Not “Is this the hill you WANT to die on?” but rather “Is this the hill you’re WILLING to die on?” The distinction being simple but profound: I wanted to live but I would give everything I had if it meant we could win this one and keep this paper alive.

So I stuck with it. I hung in there. I pushed back.

We got through a meeting with what seemed like every administrator in the entire university and we gained ground.

A day later, I got a call from my contact in the area of fundraising. I figured she wanted to see what our next move would be to raise money to help defray the debt. It turned out, an anonymous donor had turned up with a matching-funds challenge grant.

If we were successful in pulling in the entire match, the debt would be gone and we’d have cash to spare.

It was the first miracle in a string of miracle, each one slightly more outlandish than the previous one. We chipped away at the debt a buck at a time, with me pulling in every favor I ever earned, calling in every marker I ever collected and begging every alumnus I ever met.

We rebuilt the staff, refocused our efforts and restructured our funding, in large part thanks to a chancellor who understood that you don’t kill off something valuable just because some little dipshits have a need to feel important.

Two years later, I could afford to take eight kids with me for the trip of a lifetime: A media convention where they earned national awards and learned from incredible pros and advisers. A trip they will never forget as long as they live.

The reason?

One alumnus made a donation to our cause, but asked that if we had money left over after the debt was repaid that we use “his” portion of it to give the students an educational opportunity that linked travel and passion. If the looks on their faces throughout the convention were any indication, we did exactly that.

We have money in the bank and fund-raised cash to boot, all as we expand the paper and improve education. The kids this year, even the most senior among them, only vaguely recall what happened back then. It’s like a bad memory mixed with a foggy dream.

Still, those who went through it remember. I posted a photo of myself to Facebook from the convention and one of those kids who went through hell with me responded:

“No tin can for donations this time?”

No, but I still have that can. It sits on a shelf in my office and I look at it every day.

It’s a reminder of what can happen when you finally find your hill.