Reading · The Midlife Sabbatical

New format today: co-authored post.

I teamed up with Sharon Chae Haver of The Sabbaticalist to write about a growing trend we’re seeing (and our potential solution) that merges two areas we’re both very passionate about: the sabbatical experience and AI. Specifically, we’re looking at the pinch point of corporate layoffs as the opportunity to reimagine how we support people through the coming significant shift in the US labor market.

If you like this piece, you’ll love The Sabbaticalist. Definitely check her out.

We’ve been thinking a lot about the next era of layoffs.

This era looks different. Instead of the cyclical, painful and ultimately, absorbable labor market that over time rebalances, this next era brings brand new territory.

Layoffs where it isn’t “your job went away,” but “your category went away.” Layoffs where the “next job” isn’t obvious because the thing you did for 10, 15, 25 years is being absorbed by software. It’s not happening overnight but steadily and then, we expect, suddenly.

What happens when large numbers of people aren’t just laid off from a company, but laid off from the concept of their role?

We think the current iteration of outplacement services (you know - the “support” companies provide to someone that they let go) could be a critical piece of this changing world assuming it starts to look much different.

For most of modern corporate America, we’ve treated layoffs like weather. A front that can be devastatingly cold but eventually the sun returns. Awful, but also fundamentally temporary. Something you “get through” by doing the normal things: updating your resume, getting active on LinkedIn, activating your network, practicing your interview skills, and pushing forward.

What’s coming (or already here) with AI is different.

It is rewriting how value gets created, how work gets done, how teams are staffed, and what “entry level” even means. And the credible forecasts (while they vary from 3 to 20 years) agree on the same underlying point: disruption is going to be broad, and it will touch a surprising amount of white-collar work that once felt insulated.

The IMF estimates AI could affect roughly 40% of jobs globally, with advanced economies more exposed. Goldman Sachs has estimated generative AI could expose the equivalent of 300 million full-time jobs to automation globally. McKinsey has estimated that by 2030, activities accounting for up to 30% of hours worked in the U.S. economy could be automated - with generative AI accelerating that shift. The World Economic Forum projects millions of roles displaced by 2030 even while new roles are created, meaning churn and mismatch will define the decade rather than smooth replacement.

Even the near-term signals show this is no longer speculative. Challenger, Gray & Christmas (a company that tracks layoff announcements) began separately tracking job cuts where “AI” is explicitly cited as a reason. That alone tells us something: AI is now a boardroom narrative used to justify workforce redesign.

So yes, jobs will be created. But the transition is not going to feel like job creation. It’s going to feel like displacement, confusion, and identity whiplash.

Outplacement, as it exists today, is generally built around a narrow but clear promise: help someone who lost their job get another job as quickly as possible. It’s typically a blend of resume updates, LinkedIn profile revisions, job search tactics, interview practice, and networking strategy. Some services include confidence coaching or light emotional support, but most of the value is positioned around faster reemployment.

In some cases, the program is genuinely helpful. But, that assumes the underlying system is stable.

Even the pricing model reveals what outplacement is designed to do. ADP notes that outplacement may cost a few hundred dollars per employee for basic support, rising to $20,000+ for executive-level packages. INTOO similarly describes a range spanning from roughly $100 to $10,000+, depending on the employee level and depth of support.

The structure implies a belief: that “landing the next job” is mostly a question of tactics, confidence, and process. That might be true in a world where roles remain intact.

But that is not the world we are entering.

Traditional outplacement assumes the labor market is fundamentally coherent. That those roles still exist. That job ladders still make sense. That job descriptions are stable enough to be targets. That your experience is still legible in the way it was five years ago. That key to success in this situation is execution rather than reinvention.

But we’re heading into a world where many resumes won’t be “wrong” so much as irrelevant. Not because the person didn’t do valuable work. No. But because the way the work is done is changing. Whole functions are being redesigned around a new baseline: one person with AI can often do what used to require multiple people. That changes hiring. It changes org charts. It changes what “qualified” means.

This is why the resume will no longer be the central artifact of modern career transition. Resumes are built for stability. They are evidence of progression inside known systems. But if the system itself is changing beneath our feet, then outplacement can’t keep focusing on historically-proven processes.

It has to shift toward capability and identity.

There is another reason outplacement isn’t equipped. And it’s not technological. It’s cultural.

In the U.S., as well as many other parts of the developed world, work doesn’t just provide income. It provides identity. Status. Belonging. Direction. Structure. Community. A reason to get up. A story that makes sense of our effort. A way to explain who you are to someone you meet.

We pretend this is normal. But it has consequences.

When someone loses their job, the pain is often deeper than money. It can feel like a loss of relevance, a loss of confidence, a loss of dignity, a loss of narrative. In many cases, what breaks people isn’t just the job loss, it’s the question that follows: Who am I without this job / title?

The American Psychological Association has documented the mental health consequences linked to unemployment and job loss, including associations with higher stress, anxiety, and depression. Research on work and identity similarly suggests that employment is not merely economic; it is deeply connected to how people form meaning and self-concept.

Now zoom out and imagine what happens when the fear isn’t “I lost my job,” but “I lost my place in the labor market.” That shift turns a temporary setback into an existential threat.

And no amount of interview coaching can resolve existential fear.

When the scale of displacement rises, we will inevitably turn toward our government: workforce retraining programs, unemployment benefits, community college pathways, local economic recovery initiatives. Those systems matter, and they should be strengthened. But they also tend to move slowly, vary dramatically by state, and become politicized quickly.

If AI-driven displacement accelerates, public systems will be overwhelmed precisely when the need becomes greatest. And many of the needs aren’t even “job training” needs. They are identity and mental health needs, belonging and purpose needs. The kind of needs that require skilled facilitation and community, not bureaucratic process.

This begs the question: if corporations reap massive gains from AI productivity and lower labor costs, why is the burden of transition expected to fall almost entirely on individuals and public systems?

If frontier labs stand to make billions and companies are directly reaping the benefits of reduced employment, it seems that both would be in a position to fund this need.

And, what better time to do so than at the point where people are most likely to engage? People generally do not change unless the pain becomes so overwhelming they are forced to do so. A layoff is the moment where you could likely have their full attention.

If outplacement were designed for the world that is coming rather than the world we’re leaving, its goal would not be “get them hired again.” It would be “help them rebuild a durable work life in a volatile economy.”

That means it would need to do two things in parallel. One without the other won’t work.

People need new capabilities, yes. But they also need a rebuilt relationship to self. This becomes less about a system of optimization and more about reconnection and re-architecture.

If we were designing modern outplacement, we’d do so around two tracks: one practical and one human. Both are essential. And both should be treated as core infrastructure, not “nice-to-have add-ons.”

Most corporate AI training today is passive. It teaches tools. It teaches vocabulary. It teaches prompting. It rarely teaches agency. But what people need is not knowledge that AI exists; they need proof (and confidence!) they can build with it, and collaborate with it.

A modern program should start by understanding the person’s industry, role, expertise, and years of experience, then help them identify their next role in the context of this new world. It should teach AI fluency through building real assets in that problem space - workflows, prototypes, research deliverables, automations, content systems, client-ready outputs. People would leave not just trained, but also materially more capable. More valuable. More confident because they have evidence that, indeed, they can create again. And then use that to position themselves well in their next role and it’s reshaping based on AI. This leads people to be agents of change vs. passive recipients.

This part is not “soft.” It is survival. If someone has been defined by their work, the loss of that role creates grief, confusion, and shame. Outplacement must support people in separating worth from title, processing the emotional rupture, and rebuilding a coherent future narrative that isn’t dependent on one job category staying intact.

This track should include a mix of reflection, facilitation, coaching, and mental health-informed programming that helps people reconnect to values, strengths, and intrinsic purpose. Not in a vague inspirational way, but in a concrete “re-authoring your life” way. Because if we don’t address identity, people won’t be able to learn. And if people can’t learn, they can’t adapt.

Finally, these tracks should not be done alone. Modern outplacement must include peer cohorts. People heal faster in community. They rebuild faster in community. Isolation is where shame thrives and motivation collapses. But when people are surrounded by others navigating the same moment - together building, experimenting, learning, sharing - something changes. The layoff becomes less like a personal failure and more like a collective transition.

Most outplacement today is a corporate gesture and a “check the box” compliance measure. Sometimes a well-intended one, sometimes a legal buffer, sometimes a way to soften the optics. But it is typically built to help a person re-enter a system that is dissolving and reforming in real time.

In the AI era, outplacement has the potential to become something radically more meaningful. Not a placement service. A transition architecture program. A true investment in human resilience.

Because the goal isn’t just to help people get their next job.

The goal is to help them become the kind of person who can keep rebuilding even as the world changes faster than anyone would have imagined.

Before we wrap up, we want to invite you into this conversation.

Outplacement Is Built for a World That No Longer Exists

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