I have the absolute pleasure of speaking to quite a few people, usually 2-3 per week on average, and a great majority of those discussions are career oriented in some way. These people trust me enough to be open, honest, and in many cases vulnerable, and that trust is humbling.

Over the last few months there has been an uptick in discussions where the person is in a quandary over a career choice. Because I’m lucky to do this on the regular, I see patterns, and there’s a lot of very similar situations. Most people I speak to, I’ve never met and do not know well, so I’m only reacting to what I hear and can extrapolate, but there are some that I have deep insight into and can help with a more balanced conversation.

There are also a few where people have assumed I’ve provided help to a common friend but I haven’t. There’s no expectation that anyone shares anything in these conversations, but I’d strongly suggest getting as many inputs as you can from as many people as you can. I’ve made the mistake of not doing that, trusting what I was told. Do not recommend.

Two lists, same ledger

Career change usually gets sorted into two buckets.

  • Involuntary: the RIF, the layoff, the performance-out, the startup that ran out of runway. Anything that involves “that call” and a same day access cutoff.
  • Voluntary: losing faith in leadership, outgrowing the role, whether that means more scope, people management, or the next title. Or the plainer pull of wanting something else, sometimes as one deliberate step toward an end state you’ve already mapped.

The involuntary list deserves more than a bullet point, because getting laid off still sucks even in this world that has seen years of watching big tech hire in a boom, then cut in the correction that follows.

That cycle has a name: binge and purge. Everyone half expects it in the abstract. That doesn’t make it hurt less when your name is the one on the list. Knowing a pattern exists and being ready for it to hit you personally are two different things.

The involuntary ones are more emotionally charged, but the path is clear. The voluntary ones are more intriguing because they immediately get complex.

An interesting aspect I observe: no matter which path, there’s a commonality, a weird feeling of sadness and nostalgia. The reason is simple. We all buy into the same myth, that a change you choose isn’t supposed to cost you the way a forced one does.

The reality is that it costs you either way. The only difference is the timing and control. The bill arrives on a different schedule, not a different account.

Which is where the two lists stop looking like opposites. They’re two entrances to the same room.

The grief shows up either way, just on a different clock

Strip away the cause and the aftermath looks familiar. Disorientation. Some version of anger or resentment. Bargaining with yourself about what you could’ve done differently. A stretch where your identity feels unmoored from your job title. And eventually, the rebuilding.

The involuntary path front-loads the shock. The grief starts immediately, often before you have any capacity left to plan. Planning has to happen alongside the grieving, or right after it. That’s part of why it’s so impactful and stressful.

The voluntary path inverts the order. You plan first. You make the call, you walk, you feel decisive and clear.

Then in the days and weeks later, once the decision’s adrenaline wears off, the grief shows up anyway and it’s disorienting precisely because you didn’t expect it. You chose this, right, so why does it still feel like a loss. My experience is that it’s usually the people and the day to day experiences you forget about when looking at a sunnier alternative.

One nuance worth stating is that on the voluntary side, what people feel often isn’t grief exactly, it’s more … disappointment. In a leader who let them down. In a role that didn’t become what they’d hoped. In a company that stopped matching the story it told when they signed on.

Disappointment and grief aren’t identical, but they run on the same nervous system. The feeling of flatness, the sadness, the low hum of “this isn’t what I thought it would be.” It shows up close enough to grief that people who left voluntarily talk themselves out of feeling it.

You’re allowed to feel it. Disappointment is still a loss … it’s a loss of an expectation instead of a role.

Why the sequence matters more than the cause

The list you’re on matters less than whether you know the order the reckoning is coming in.

If you’re on the involuntary side, the discipline is assuming it’s coming before it does. Not paranoia, just practical prep: money set aside, a sense of what comes next, a network kept warm.

Big tech’s “binge and purge” cycle shows no sign of slowing. Treat a layoff as a “when,” not an “if,” and do the unglamorous prep while things are calm. That prep won’t stop the grief from arriving first. It will stop it from arriving and catching you unprepared.

If you’re on the voluntary side, the discipline is different. It’s checking in on yourself often enough that you’re never making the call from a standing start.

That means regularly asking where you actually are, not just when a recruiter calls. Two things ride on that habit. First, whether a new offer’s timing actually matches the next step you’ve mapped, so you’re reacting to fit, not flattery or fear. Second, catching it early if you’re the one sliding: quietly checking out, coasting, letting resentment build, catching it before it hardens into something you can’t see from inside it.

This is the same underlying habit, aimed in two directions. Don’t wait to be forced into clarity. The involuntary version points outward, toward the market. The voluntary version points inward, toward yourself.

The map still matters most

Underneath both lists sits the real differentiator … not whether you saw it coming, but whether you have any sense of where you’re trying to end up.

Involuntary change forces you to build that map under duress, with no notice and no runway. Voluntary change is supposed to mean the map already exists, and to my experience, often it doesn’t. That gap, deciding to leave before you’ve decided what you’re leaving toward, is its own quiet source of grief.

Where that leaves you

However you got here, give the grief its due. Don’t skip it because you think you weren’t entitled to it, and don’t be surprised when it shows up late even though you made the call yourself.

Assume the market will surprise you, and as the Scouts say, Be Prepared. Check in with yourself on a cadence, not just in a crisis. Whatever list you’re on right now, mapping where you’re headed deserves the same energy as processing how you got here.

The door you walked through matters less than the room you’re heading to next.

Adam