June 13, 2026

Read Time - 4 minutes

"Would you tell me, please, which way I ought to go from here?" "That depends a good deal on where you want to get to." ~ Lewis Carroll, Alice in Wonderland

Stay in higher ed long enough and you'll watch a lot of people retire. What I've come to pay attention to isn't the milestone itself — it's the stretch right after the announcement, those last months between "I'm done" and the final goodbye. That's when you see how someone really felt about the place.

Some go strong all the way to the end. They keep showing up for their students, hand off what they know, and have an energy about them — proud of the work, ready for what's next, a little wistful on the way out. The years clearly meant something to them.

I've seen others handle it differently. The moment the announcement is public, they're already gone — checked out, counting down. Whatever frustration they'd kept in check for years starts to surface: a sharp comment in a meeting, a door that stays shut, a flat "I won't miss this place" that they plainly mean. After decades on the same campus, they cannot wait to be done with it.

I want to be careful here, because these are good people — nobody plans to end a career bitter. It accumulates, a frustrating year and then another, a long stretch where the place asks a lot and gives little back, until one day the disappointment is just the water they swim in.

The difference between the two, I've come to believe, is whether, somewhere along the way, the person actually decided to be there. The ones who finish well re-chose the place, more than once, with their eyes open. The bitter ones often didn't. Because staying is the easiest thing to do when nobody makes you choose.

It's a hard season for a lot of us. Some are at institutions watching individual rights dissolve, funding vanish for the things we care about, or the mission shift in a direction we can't get behind. Others still believe in their campus but are living through a hard stretch of growth or decline. And then there are the more personal questions: Can I still grow here? Do I need to move to get the role, the responsibility, or — let's be honest — the salary I want? It all comes back to the same question: should I stay, or should I go? No one can answer it for you. But asking it periodically is how you tell a place that's still worth it from one that's only become comfortable, a genuine pull from plain restlessness. Read it right and the decision gets clear. Read it wrong, and it costs you either way. Stay when you should have gone, and you give your best years to a place that stopped deserving them. Leave when you should have stayed, and you land in the same trouble with a new email address.

I don't think it's possible to make this decision easy. But I do think there are a handful of questions we can ask ourselves along the way — the kind that keep us from sleepwalking through our careers.

5 Questions Worth Asking

1.) Am I burned out, or am I genuinely called elsewhere?

This is the one to start with, because a lot of us are running on empty right now. One in four higher ed employees say they're likely to look for another job this year. Some of that is a real pull toward something new. Some of it is simply exhaustion looking for an exit. The two are hard to tell apart because they surface the same way: a low, steady urge to be anywhere but here. Burnout can make your current job feel wrong, so getting out feels like the cure. A true calling pulls you out too — the difference is that it pulls you toward something specific, not just away from this. And that difference hides under the feeling. Burnout is about your tank, not your job; when you're empty, almost any role would feel unbearable right now. A calling is about direction. Which is why the two need opposite things: burnout needs rest, a calling needs a move. So before you trust the urge, get some real rest. Take the leave, protect a few weekends, get to the far side of a hard semester. Then ask again. If the pull is still there when you're whole, it's real. If it eases with rest, you've learned where it was coming from.

2.) Have I asked for what I need, or just assumed the answer is no?

Gallup found that 42% of people who voluntarily left a job said their manager or organization could have done something to keep them, and nearly half said no one in leadership ever asked about their satisfaction in their final months. Read that again. A huge share of departures were preventable, and the conversation that might have changed things never happened. We assume the schedule is fixed, the role can't flex, the answer to what we need is already no. So we never ask, and we leave certain the place wouldn't have moved. Before you decide this place can't give you what you need, find out. Name the one or two things that would actually change your experience, and ask for them plainly. You might get a no. But at least it'll be a real no, and not one you decided on the institution's behalf. It's worth turning around, too. Someone on our own team may be weighing the same decision quietly, and we may be the leader it describes: the one who never thought to ask.

3.) Is there a version of this job I haven't tried yet?

This is often the most overlooked move. We treat a role as a fixed box we either fit or we don't, when most jobs have far more give than we ever use. Researchers Amy Wrzesniewski and Jane Dutton named this job crafting, the small, deliberate changes people make to the tasks, the relationships, and even the meaning of their work, without waiting for anyone above them to redesign it. The chair who offloads the committee that drains her and trades for the one that feeds her. The dean who carves out the mentoring he loves and delegates the reporting he doesn't. Before you conclude the job is wrong, ask whether you've been living the assigned version of it or the one you'd actually design. Feeling stuck can mean a lot of things, and sometimes you've hit a ceiling. But it can also be a design problem in disguise, and design problems have design solutions.

4.) If I stay five more years, who do I become?

Picture the version of you that five more years here would produce, on the current trajectory, with nothing dramatic changing. Is that someone you'd be glad to be? This is the question that takes you back to those retirements. The bitter ones didn't set out to become bitter. They just stayed, year after year, in a place that slowly drew down their generosity and their hope, until the depletion was the most visible thing about them. Environments shape us, quietly and relentlessly. We become the meetings we sit in, the colleagues we absorb, the standard the room keeps. So look down the road. If staying makes you more of who you want to be, that's a powerful reason to stay. If it makes you someone you'd rather not meet, that's something a higher salary can't fix.

5.) Am I moving toward something, or just away?

If the read points to leaving, leave well. The cleanest test is whether you can name what you're moving toward in a sentence that doesn't mention what you're escaping. "I want to build in a place whose mission I believe in." That's toward. "I just need to get out of here." That's away, and away is the one to be careful with, because whatever you're fleeing has a way of packing itself in your bag and meeting you at the next place. The stakes are higher than they were a few years ago, too. Robert Kelchen calls this moment in higher ed the "Great Hunkering Down", hiring slowed, postings down, people staying put because the doors barely open. In a market like this, a move made only to escape is one you may not get to take back. So make sure you're running toward something worth the leap.

The Bottom Line

Work through these questions and you'll usually know. Sometimes the answer is go. Sometimes it's stay. And sometimes it's the option we forget we have: reshaping the work we already have. Whatever it turns out to be, the goal is the same — to enjoy the work we do and, if we're lucky, the people we get to do it with.

Try This Before Friday

Look back at the five questions. You probably gravitated toward one of them. Start there. Block twenty minutes this week, away from your inbox, and answer just that one on paper.

Until next week.