Get Clear on the Job You Actually Want Next
- Darren Webster
- 6 days ago
- 4 min read

Key Takeaways
AI is reshaping or replacing roles, especially in operations, support, and middle management. Align your next move with the future, not just your passion.
Mass layoffs across industries mean fierce competition, even for experienced professionals. No one’s immune.
The market now favors strategic clarity, adaptability, and measurable outcomes over credentials or loyalty.
It’s not about what’s familiar, it’s about what’s sustainable and resilient.
A smart pivot that diversifies your experience increases long-term career durability and relevance.
Why This Matters
The job market of 2025 isn’t the one you entered five, or even two, years ago. AI is replacing task-based roles across functions. Middle managers, support staff, and even entire departments are being automated or eliminated.
If you've been laid off, or fear you might be, it’s not necessarily about your performance. It's about how the game has changed.
If you're considering a pivot, this isn’t just a moment to "follow your passion." It’s a moment to think clearly, act deliberately, and position yourself to win the next round, not just survive it.
AI and the Middle Management Squeeze
There’s a massive reshuffling happening in corporate org charts. AI tools now perform tasks previously handled by analysts, coordinators, and even first-line managers. As a result, organizations are flattening, and middle management is being squeezed out.
Amazon plans to cut 14,000 managerial roles in 2025, about 13% of its global management workforce, aiming to save up to $3.6 billion annually (TechStartups).
According to Goldman Sachs, AI could automate or significantly reshape up to 300 million jobs globally, with administrative and managerial layers hit hardest.
It’s not just tech. Industries like banking, healthcare, and retail are all redefining which roles are “essential.” What was once a secure path to growth, climbing the management ladder, is becoming riskier by the quarter.
Ask yourself:
Am I targeting a role in a layer that’s shrinking?
Do I know how automation is changing what employers actually value?
Am I learning how to leverage AI, not just avoid being replaced by it?
This isn’t just disruption. It’s a chance to reposition yourself as someone who provides the kind of value AI can't replicate: strategic thinking, emotional intelligence, leadership, and creative problem-solving.
The Market Is Crowded
You’re not just planning a transition, you’re entering a saturated arena.
Job postings for white-collar roles are down nearly 13% year-over-year, and professional services openings hit a decade low as of Q1 2025 (Revelio Labs; Salesforce DevOps).
Even experienced, credentialed professionals are competing for fewer roles. Middle management especially is under pressure, not just from AI, but from companies looking to streamline and reduce layers.
This means a few things:
You need more than transferable skills, you need strategic clarity.
Being passionate or qualified isn’t enough, you must also be market-aware.
The safe move might not be the smart one. In some cases, lateral or even step-down moves into durable sectors or high-leverage roles can pay off longer term.
Translation
This isn’t the time to casually follow your passion or cobble together side gigs unless you have a plan. It’s time to:
Identify which of your skills drive revenue, reduce cost, or lead transformation.
Double down on cross-functional value, not just niche specialization.
Decide whether to stay in a traditional lane or pivot into an emerging one, and build the case to do so.
My Story: Trading Comfort for Range
When I left Verizon, I was leading large organizations of teams. We hit our numbers, built a strong culture, and delivered consistent results. But did I want to go and work for some other telco? No way.
I knew that staying in telecommunications would narrow the number and quality of opportunities I'd be in the mix for, and I wanted to expand into new areas.
That meant gaining more experience in SaaS. It meant trading a clear path for a steep learning curve. I had to learn a new industry, market, and product, so I leaned in, absorbed as much as I could, and made it my mission to grow outside the domain I had felt so comfortable.
Why? Because telecom wasn’t going to be the future. SaaS was still booming and I didn’t just want another job, I wanted greater range, if only to mathematically increase the opportunities I’d have vs. being pigeonholed as a leader in the wireless business.
The priority for me in the search was to add a new dimension to my experience, even if that meant a lateral or even step back to do it.
Map the Future, Not Just the Past
Too many people treat their resume like a rearview mirror (what they’ve done, vs. what they’re progressing to). But in this climate, you need a forward-facing plan. If AI is changing what work looks like, and if layoffs are eroding the middle, your next role should meet three criteria:
Durability: Will the role or industry still exist (and grow) in 5-10 years?
Leverage: Will it give you more visibility, influence, or optionality?
Alignment: Does it reflect where you want to go, not just where you’ve been?
According to LinkedIn’s 2025 Workforce Report, professionals who upskilled into AI-adjacent roles or product environments saw 37% higher job security than those in purely operational roles.
Final Thought
Choose the role that moves you forward, not just out of your current situation.
This isn’t about finding your dream job. It’s about building a resilient, future-ready career, especially in a market that’s changing faster than most companies can keep up.
If AI can do it, it will. If a spreadsheet can replace you, it might. But if you bring vision, synthesis, adaptability, and leadership to the table, you become the moat.
Choose your next role not based on where you feel safe, but where you stay irreplaceable.
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