Career Pivots, Reskilling, and the Last Years of Work: How to Stay Employable as Machine Intelligence Reshapes Everything

Why Employability Now Has Less to Do With Skills and More to Do With Judgment

For decades, careers were built inside a single, largely unspoken assumption: growth was the default state of the economy.

Revenue would increase. Headcount would expand. New problems would be solved by adding people. Even when technology changed how work was done, the underlying logic stayed the same. Complexity meant more roles. Output meant more staff. Careers unfolded horizontally inside that expansion.

That assumption no longer holds.

What we’re living through now isn’t a temporary downturn or a cyclical correction. It’s a structural shift. Organizations across industries are exiting growth mode and entering constraint mode. They’re designing themselves to operate with flatter headcount, tighter margins, and heavier reliance on automation, not as a stopgap, but as a permanent operating condition.

That shift changes what “employability” actually means.

I explored this in depth in a recent edition of my LinkedIn newsletter, Human Systems Review, titled “Career Pivots, Reskilling, and the Last Years of Work: How to Stay Employable as Machine Intelligence Reshapes Everything.” This post is the short version of why that conversation matters, and why so many well-intentioned conversations about reskilling miss the real point.

The real risk isn’t job loss. It’s structural redundancy.

Public discussion around AI and work tends to focus on whether jobs will disappear. That framing is incomplete. The more important shift is role compression.

Organizations don’t need everyone to vanish. They need fewer roles that look like pure execution. Fewer people whose primary value is processing, maintaining, or moving work that can now be standardized, centralized, or automated. Experience doesn’t disappear, but it becomes harder to translate if it’s tied too tightly to tasks rather than outcomes.

In a constrained system, companies stop asking who can do the work well. They start asking which work still requires a human at all, and how few humans they can rely on without increasing risk beyond tolerance.

That’s a structural change, not a personal failure.

Why traditional reskilling advice falls short

Much of what’s marketed as “future-proofing” focuses on tools. Learn the latest platform. Get certified in the newest system. Stack credentials and hope visibility equals safety.

It rarely does.

Tool knowledge decays quickly. When everyone reskills in the same direction, the market simply adjusts expectations downward. Competing with automation on execution is a losing strategy, because automation improves faster than humans can.

What actually holds value in a constrained, automated environment isn’t doing more work. It’s operating at a different level of the system.

Where human value is consolidating

As automation absorbs execution and middle layers compress, value stacks vertically. At the base are tasks and processing. Above that are coordination and optimization. At the top are judgment, trade-offs, accountability, and responsibility for outcomes.

Machines are excellent at pattern recognition and optimization. They’re poor at understanding consequence. They don’t weigh ethical trade-offs. They don’t decide which errors are acceptable. They don’t own outcomes when systems fail.

Humans who operate near decision choke points, who can anticipate second-order effects, identify unintended consequences, and constrain automation where it introduces unacceptable risk, become more valuable as headcount shrinks, not less.

That’s the core argument of the newsletter.

The strategic move isn’t sideways. It’s upward.

Most careers were built horizontally, moving from role to role within the same layer of work. That worked when expansion created slack. In a constrained system, horizontal movement just relocates you within the same pressure zone.

The durable move now isn’t into management by default, and it isn’t into endless reskilling. It’s toward decision-bearing work. Work where a human remains necessary because removing them degrades judgment, accountability, or trust.

This is why second skill spines matter more than total reinvention. Recruiting moves into workforce planning and hiring governance. Operations moves into resilience and continuity. Marketing moves into narrative integrity and trust. IT moves into security and AI risk. HR moves into organizational design and accountability.

Same background. Different altitude.

Why I wrote this

I wrote the full piece because too many capable professionals are being told to work harder, learn faster, and adapt endlessly, without anyone naming the structural reality they’re adapting to. This moment isn’t about effort. It’s about alignment.

Organizations are no longer building for expansion. They’re building for endurance.

The people who stay employable won’t be defined by age, title, or technical novelty. They’ll be defined by judgment, systems awareness, accountability, and the ability to operate where automation introduces risk rather than eliminating it.

That’s where employability lives now.

👉 You can read the full essay here:
Career Pivots, Reskilling, and the Last Years of Work: How to Stay Employable as Machine Intelligence Reshapes Everything