I witnessed something extraordinary in Austin this weekend. Something that's keeping me up at night, compelling me to write this at 2 AM because it can't wait until morning.

While the city slept, I watched the future of work unfold in real-time. In 24-hour coffee shops and late-night coworking spaces, I saw professionals of every generation hunched over laptops, teaching each other new AI tools, debating industry futures, and actively reinventing themselves. The energy was electric, contagious, unstoppable.

The contrast with my corporate meetings last week was stark enough to give me whiplash. Same industries, different universe. In those fluorescent-lit rooms, I witnessed the other side: professionals treating each new tool like an invasion, each change like a personal attack. The energy difference wasn't just noticeable – it was seismic.

Welcome to the great bifurcation of 2025.

A Tale of Two Workforces

Think of your career like a car. The traditional view – what I call the "retirement mindset" – treats it like a vintage collector's item. You maintain it carefully, keep it garaged, protect it from change, and one day, you simply park it for good. It's comfortable, predictable, and for decades, it worked.

But in today's world, that's like keeping a Model T in the age of Teslas.

The alternative – the "re-tiring mindset" – treats your career like a high-performance vehicle that needs regular upgrades. Yes, changing tires is expensive. Yes, it's hard work. But each new set lets you handle different terrain, greater speeds, new challenges. You don't just change tires when they're worn out; you upgrade them to match the road ahead.

The Entry Paradox: When "Re-tired" Isn't Enough

Something ironic emerged in my university lectures this week. These students embody the re-tiring mindset – they're digital natives, AI-fluent, and perpetual learners. Yet they're facing unprecedented barriers to entry in their careers.

Here's the painful truth: being "re-tired" is becoming table stakes, not a differentiator.

Think back to our car analogy. These graduates are like Tesla Model 3s trying to enter a race where everyone else is already driving Model S Plaids. They're advanced by historical standards but still playing catch-up in today's market. Why?

• The experience gap is widening: Companies want "entry-level" workers who somehow have 3-5 years of experience with tools that have existed for 18 months

• The tools are evolving faster than curricula: What they learned in freshman year is often obsolete by graduation

• The bar for "technical skills" keeps rising: Today's marketing grad needs to understand machine learning; today's finance major needs to code

Yet in my corporate role, I see a stunning disconnect: Teams desperate for fresh thinking and digital fluency are rejecting the very candidates who could provide it.

Breaking Through: The New Rules of Entry

For students and recent graduates, the path forward requires a counterintuitive approach:

1. Leverage Your 'Digital Native' Status

   • Document your AI experiments and tool mastery

   • Show how you're using emerging tech to learn and create

   • Position your adaptability as experience

2. Build a "Learning Portfolio" Instead of a Resume

   • Showcase projects that demonstrate rapid skill acquisition

   • Highlight cross-disciplinary applications

   • Document your learning process, not just outcomes

3. Reverse Mentor While Job Hunting

   • Offer to teach senior professionals about new tools

   • Create content explaining emerging tech to experienced workers

   • Build bridges between traditional and new approaches

Staying Sharp: The Mid-Career Reinvention Playbook

For established professionals, staying relevant requires a fundamental shift in how you view your expertise. Your experience isn't your safety net – it's your launching pad.

1. Weaponize Your Experience

   • Map your deep industry knowledge to emerging technologies

   • Use past project success patterns to spot AI opportunities

   • Turn your "we tried that before" into "here's how we can try it differently now"

2. Build Your Innovation Sandbox

   • Carve out 10% of your week for experimental projects

   • Create a personal R&D budget for new tools and courses

   • Find one process you know intimately and completely reimagine it with AI

3. Master the Art of Unlearning

   • Identify which of your "best practices" are actually legacy handcuffs

   • Challenge one fundamental assumption about your role each month

   • Document which parts of your expertise need updating vs. replacing

4. Become a Cross-Generational Catalyst

   • Partner with digital natives on high-visibility projects

   • Translate emerging tech benefits to skeptical veterans

   • Position yourself as the bridge between traditional and new approaches

The Re-tiring Readiness Assessment

I created a quick, real quick, assessment to see where you are at based on my experience.

Rate yourself from 1 (Strongly Disagree) to 5 (Strongly Agree):

1. Learning Agility

   • I regularly experiment with new technologies, even when they're not required for my current role

   • The prospect of learning something completely new energizes rather than drains me

2. AI Mindset

   • I view AI as a potential collaborator rather than a threat

   • I've actively explored how AI could enhance my current work processes

3. Career Evolution

   • I can name three specific skills I've developed in the past six months

   • My role today uses significantly different skills than it did two years ago

4. Investment Mindset

   • I allocate a specific portion of my income to professional development

   • I track the ROI of my learning investments through career progression metrics

5. Future Orientation

   • I regularly research emerging trends in my industry

   • I can articulate how my role might evolve in the next 3-5 years

Scoring Guide:

• 40-50: You're a Re-tiring Champion

• 30-39: You're on the Re-tiring Path

• 20-29: You're at a Career Crossroads

• Below 20: You're at Risk of Obsolescence

Your Re-tiring Battle Plan

Based on your score, here's your immediate action plan:

For Champions (40-50 points)

• Next 24 Hours:

  • Document your learning system – what's working needs to be repeatable

  • Identify one team member who could benefit from your approach

  • Start tracking your skill acquisition ROI

• Next 7 Days:

  • Create a "skill stack" map of your current capabilities

  • Identify three emerging technologies in your field

  • Set up automated learning triggers (newsletters, RSS feeds, GitHub alerts)

For Path Seekers (30-39 points)

• Next 24 Hours:

  • Audit your current week – where is learning time being lost?

  • Select one AI tool to master in your current role

  • Find a "re-tiring champion" to mentor you

• Next 7 Days:

  • Block 30 minutes daily for structured learning

  • Join two communities focused on emerging skills

  • Create a skills gap analysis with your manager

For Those at the Crossroads (20-29 points)

• Next 24 Hours:

  • Honest talk: What's blocking your learning mindset?

  • List three tasks you do that could be automated

  • Schedule a "future of our industry" lunch with a mentor

• Next 7 Days:

  • Take a basic AI course (fast.ai or similar)

  • Set up job alerts for roles you find intimidating

  • Create a financial plan for skill investment

For Those at Risk (Below 20 points)

• Next 24 Hours:

  • Calculate the cost of skill stagnation in your role

  • Book three informational interviews in dynamic sectors

  • Start a "digital skills" journal – note what you don't understand

• Next 7 Days:

  • Get an accountability partner for learning goals

  • Audit your role for automation risk

  • Create a 90-day rescue plan with specific skill targets

The Mirror Moment: Your 2025 Fork in the Road

I'm writing this from my hotel room in Austin, still buzzing from what I witnessed this weekend. The future isn't coming – it's here, and it's sorting us into two camps faster than AI can complete your sentences.

In those late-night Austin sessions, I saw professionals who've made their choice crystal clear. They're not just adapting; they're orchestrating change. They're not just learning; they're reinventing the very concept of expertise. The energy they radiate isn't just ambition – it's the pure electricity of transformation.

Then there's the other side. In my corporate meetings, I see the resistance. The grip of "this is how we've always done it" has never been tighter.

Here's what a quarter-century in workforce transformation has taught me: There is no middle ground left to stand on. The bridge between these two worlds isn't just burning – it's already ash.

Let me be unequivocally clear: There's no shame in choosing to retire. Some of the most brilliant minds I know have made that choice. They saw their season changing and orchestrated magnificent exits. They're legacy builders, wisdom sharers, the foundations we stand on.

But there's everything wrong with becoming a career squatter – occupying a role while refusing to evolve with it.

I've seen both paths lead to fulfillment when embraced without reservation:

Path 1: Go all-in on re-tiring. Make disruption your comfort zone. Turn perpetual beta into your personal brand. Become the change that others resist.

Path 2: Retire with intention and grace. Orchestrate your knowledge transfer. Become the bridge between what was and what will be. Leave a legacy that amplifies progress rather than impeding it.

But here's what's become career suicide: Standing in the middle, hoping the future will politely wait for you to decide. That's not job security – it's professional hospice.

The choice is binary. The timeline is now. Those electric minds I saw in Austin? They're not just coming for jobs – they're coming to rewrite the rules of entire industries. The question isn't whether transformation is coming.

Look in the mirror. Make the call. But whatever you do, don't become the human equivalent of a loading screen – eternally spinning, never advancing.

Your move.

Jason Averbook is a global thought leader, keynote speaker, author and future of work visionary on human resources, the digital experience and workforce technology and voted by his peers as one of the top 25 human capital consultants in the world. Currently a senior partner and the Global HR Transformation Leader at Mercer, Jason has spent three decades advising executives, HR and people functions, and technology solution providers. He also drives Mercer’s global Generative AI strategy and services, spearheading innovative solutions across the HR technology landscape.

From January 2018 to March 2023, Jason was co-founder and CEO of Leapgen, a digital transformation company helping organizations shape their future workplaces. Through Mercer and Leapgen’s partnership, he has expanded resources and reach, bringing more value to a global market. At Mercer, he continues broadening executive mindsets to rethink how to better design and deliver employee services and drive the shift from doing technology projects to being a digital function.