You can't skip the hard part

Everyone wants a shortcut past the hard part.

Reskill. Rebrand. Take a course. Learn to prompt. Adopt a framework. Stay relevant. The entire industry of AI-age career advice assumes the problem is technical and the solution is a new set of skills.

It isn’t. The problem is you. And there’s no workshop for that.

Here’s what’s actually happening: the version of yourself that you’ve been performing at work—the compliant, productive, machine-like version—is being exposed as replaceable. Not because you’re bad at your job. Because the job was designed for machine-like behavior, and now actual machines do it better.

The reskilling pitch says: learn the new tools, stay ahead of the curve, adapt. As if your skills are outdated and the fix is updating them.

But your skills aren’t the problem. The problem is that you defined yourself by your skills in the first place. By outputs. By what you produce. When a machine produces the same thing faster and cheaper, the identity you built around production collapses.

No course fixes that. No certification addresses it. No framework helps.

I write about this in the book as “the abyss”—the moment when the old answers stop working and nothing rushes in to replace them. The job title, the expertise, the productivity metrics: they stop answering the question they were supposed to answer.

What am I for?

The instinct is to rush past this. Find solutions. Reinvent yourself. Treat the collapse as a problem to be managed. But solutions offered too early are just new forms of denial.

If you don’t actually sit with what’s collapsing—if you don’t register the loss—then whatever you build next gets built on the same lie. You’ll grab onto slogans and call it transformation. You’ll perform optimism while the fear stays unmetabolized, appearing as anxiety, resentment, or frantic reinvention that never quite lands.

I’ve watched this happen. People who skip the hard part don’t become hopeful. They become brittle. Every setback feels catastrophic. Every comparison feels like a threat. Every success feels temporary. Because the ground was never secured. They just started running again before they noticed it was gone.

The reskilling industry depends on you not noticing this. It depends on you treating the crisis as technical—a skills gap, a knowledge deficit, a training problem. Because technical problems have technical solutions, and technical solutions can be sold.

But this isn’t a technical problem. It’s an existential one. The question isn’t “what should I learn?” The question is “who am I when the role falls away?”

And you can’t answer that question by taking a class.

When I was consulting, I’d meet executives who had been through three or four “transformations.” Agile transformation. Digital transformation. Now AI transformation. Each time, they adopted the language, hired the consultants, reorganized the teams, updated the strategy decks.

And each time, nothing actually changed. Because transformation was treated as something you implement, not something you undergo. The hard part—examining what you’ve built your identity around, admitting what you’ve suppressed, facing the possibility that the professional self was never the real self—that got skipped every time.

You can’t implement your way out of an identity crisis. You can only sit in it long enough to discover what’s underneath.

Here’s what’s underneath: the capacities you suppressed to fit the machine model. Judgment. Discernment. Creativity. The ability to ask whether the work matters, not just whether you did it correctly. The willingness to sit with uncertainty instead of reaching for the nearest framework.

These aren’t skills you acquire. They’re qualities that develop over years of practice. They’re precisely what the industrial model trained out of you. You can’t reclaim them in a weekend workshop. You can’t develop judgment through a crash course. These capacities grow slowly, through reflection and failure and learning.

Which means you need to start now. Not with a course. Not with a framework. With the uncomfortable practice of becoming someone who doesn’t need the role to know who they are.

The window is closing. Not immediately. The transformation will unfold over years. But the people who wait until the crisis is undeniable will find themselves without the foundation they need.

Look honestly at the version of yourself you’ve been performing at work. Ask whether that version is really you or whether it’s a machine-self you constructed to fit a model that’s already dying. Consider what you’ve suppressed. What you’ve neglected. What parts of your humanity you’ve kept locked away because they didn’t serve the organization.

Those are the parts that matter now. And there’s no shortcut to reclaiming them.

The denial is thinking you can reskill your way through this. That the fix is external—a new tool, a new credential, a new strategy. That if you just stay busy enough learning the next thing, you won’t have to face the harder question.

You will. Everyone will. The only variable is whether you face it on your terms or whether it catches up to you after years of running.

The abyss is not a problem to be solved. It’s a reality to be acknowledged. You have to sit in it. Not forever. But long enough to know what you’re sitting in. Long enough to discover that the scaffolding that fell away was never you. Long enough to find what is.

That’s the work. Not reskilling. Not rebranding. Not staying relevant. Becoming actually human in a world that trained you to be a machine.

This is what The Work of Being is about. Not tips for the AI age. The uncomfortable, personal, un-shortcuttable work of reclaiming what you suppressed.

If you’re ready to stop running: The Work of Being: Staying Human in the Age of AI