Compression Season

U.S. job cuts hit over 806,000 through July 2025, already surpassing all of 2024 — with tech leading the way (Harvard Business Review).

In tandem, tech companies like Amazon, Google, and Meta are embracing flatter structures, slashing manager roles to boost efficiency (Business Insider). Directors are being cut, managers dismissed, senior ICs are gone in 72 hours — and “team reorg” emails keep rolling in, written in the flattest passive voice.

It’s not personal. It’s structural. The middle is collapsing — not because it wasn’t working, but because the old system can’t support the weight anymore.

For decades, middle management was the glue.

They translated vision into action.

Held context. Kept things moving.

They made systems feel human. But here’s what’s happening now: Companies are flattening to move faster, look leaner, and save money — 41% of employees say their management layers have already been cut. At the same time, AI and software are taking on oversight; three in five managers admit technology now does chunks of their job. Without someone holding the middle ground, leaders tend to either micromanage or disappear. And trust is eroding fast: only 32% of employees trust senior leaders, and just 29% trust their managers — a steep drop (People Element). The result? A lot of “senior leaders” are now expected to be both visionary and executional — with no buffer in between. And early-career folks are left without mentorship, growth paths, or guardrails.

Compression feels brutal. But here’s the upside hiding in the mess: it reveals everything the middle used to cover.

The gaps are visible. The inefficiencies surface.

And the people who thrive are the ones who don’t wait for permission.

This is the rise of the high-agency operator — people who can:

✅ See across functions
✅ Make decisions with incomplete info
✅ Handle ambiguity
✅ Self-direct
✅ Rally others

If the ladder is gone, then the edge becomes the path.

People aren’t waiting for next steps — they’re inventing new tracks.

If your role got compressed, eliminated, or blurred — don’t panic — pivot.

This moment is calling for something different: clarity, adaptability, and creative control.

You can still lead, even if no one gives you a title.

You can still grow, even without a direct manager.

You can still earn — in new formats, new contexts, new structures.

Think:

Your move this week: Pick one of the above and sketch a 30-day experiment. Small scope. Low stakes. Just enough to see what’s possible.

Compression isn’t just about who gets cut — it’s about who steps forward.

Which brings us to this week’s AI Academy skill — turning messy information into a clear, actionable plan, fast.

Skill: Distilling complex info into a clear plan

Tool: ChatGPT (or any AI chatbot)

Prompt Potion: “Turn this into a simple action plan with 3 main priorities, 3 bullet points each, written for someone new to the project: [paste text, notes, or meeting summary].”

XP Earned: Clarity Creator

Time Saved: 30+ minutes of rewording, restructuring, and wondering if you forgot something

🎧 Listen: What Role Do Middle Managers Play in an AI-Driven Workplace? — A sharp 10-minute hit from Upwork’s Work Week, unpacking whether middle managers are being replaced—or just reimagined by AI. No fluff, all insight.

📚 Read: The Rise of Fractional Executive Leadership — The ladder’s gone, but the gigs are good. Fractional C-suite roles are up 3x since 2018—proof you can lead big without sitting in the big chair full-time. (HR Executive, July 2025)

📺 Watch: Why Are Middle Managers Disappearing Everywhere? — A concise, insightful YouTube video exploring why corporate org structures are flattening and what that means for workforce dynamics.

🧠 Tool: Notion — Our ride-or-die. We use it to run projects, track client work, map career experiments, and keep all our “brilliant” ideas in one place. Free for individuals—and dangerously satisfying to organize.

Change will keep squeezing. Ladders break, gaps open — that’s where the funemployed step in.

On the edge with you, till next week,
— The Funemployed Team ✌️

Careers aren’t static, so why are titles? We’ll unpack the moment you outgrow your role — and what to do about it.