AI Is Moving Faster Than Your Career Plan — Here’s What to Do

I Was Wrong About One Thing...

(An update to my post: The Silent Job Market Decline: What's Really Happening in 2025)

I called it "silent."

It's definitely not silent anymore.

Back in February, I wrote that the job market was quietly transforming. That post was popular because people felt something was shifting beneath the surface.

Seven months later, the data is in. And it's not great.

But there's also a story within the story that nobody's talking about. Some people are finding real opportunity right now.

Let's look at both sides.

The Numbers Don't Lie Anymore

Here's what's happened since February:

Job openings dropped below 8 million for the first time since 2021. That's not a seasonal dip. That's structural change.

Tech job postings fell 25% year over year (Indeed, September 2025). Entry-level roles? Down 31%.

Administrative, HR, marketing, and analyst positions — the jobs most vulnerable to AI automation - are disappearing faster than they're being replaced.

Remember when I said companies were just "not backfilling"? That was only the beginning. Now they're actively restructuring around AI-augmented teams that need fewer people to produce the same output.

The Quiet Part Said Out Loud

Here's what makes this different: the people making the decisions are now saying it publicly.

Amazon CEO Andy Jassy has openly discussed planning for a workforce structured around AI capabilities — not because of temporary cost-cutting, but because AI tools are fundamentally changing how much human labor is needed per unit of output.

He's not alone. CEOs across industries are discussing workforce transformation in earnings calls. They're not planning to hire back to previous levels.

Here's the reality: AI companies haven't automated entire jobs yet. What they've done is automate portions of jobs — the tasks that used to fill 30-50% of someone's day.

When you eliminate half the tasks across a team, you don't need the same headcount anymore.

And it's accelerating. AI labs are working on:

• Omni models that can process and generate video, audio, images, and text simultaneously
• Advanced reasoning systems that can break down complex problems
• Autonomous agents that can complete multi-step tasks without supervision

Each capability breakthrough exposes more job categories to automation. Not entire roles disappearing overnight — but tasks and projects moving further along the automation spectrum every quarter.

But Here's What Gives Me Hope

While traditional employment is contracting, something else is happening.

A small group of people are moving quickly to learn AI tools and positioning themselves differently are creating new opportunities — consulting work, AI-powered services, new integration projects, and side income that sometimes exceeds their old salaries.

What I'm seeing: they're not waiting for the perfect moment. They learned AI tools, built things, and started solving problems.

The shift from "employee seeking a job" to "problem-solver with AI capabilities" is creating real outcomes for people willing to leap.

And here's the key part: this doesn't have to be all-or-nothing.

The Portfolio Career Approach

In an earlier post about Portfolio Careers, I discussed the importance of skill-proofing your career. This is exactly the moment that the concept becomes essential.

You don't have to quit your job search or abandon traditional employment to build AI skills and side income.

In fact, the smartest approach right now is parallel paths:

Path 1: Traditional job search (if unemployed) or current employment (if working)

Path 2: Building AI skills through side hustles that could generate income

Think of it as a portfolio approach to your career:

• You're building skills that make you more valuable as an employee
• You're creating demonstrable proof of AI and other capabilities that differentiate you from other candidates
• You're potentially earning side income
• You're building optionality — if the side hustle grows, you have choices

At worst, you become a dramatically stronger job candidate. At best, your side hustle becomes substantial income or even your primary path forward.

This is about creating certainty in an uncertain market by building real capability.

The Difficult Truth

We're in a race.

AI capabilities are advancing rapidly. Human adaptation? Still moving at, well, human speed.

Can you adapt fast enough while dealing with rent, stress, and uncertainty? That's the real question.

And here's what I believe: you most definitely can. But only if you start treating this as a portfolio problem, not an either/or decision.

Your Personal AI Roadmap

You need to create your personal AI roadmap — right now.

Where are you today?

• What tasks in your current role could be AI-augmented?
• What tasks are at risk of being automated?
• What skills do you have that AI can't easily replicate?

Where are you going?

• Which AI tools are transforming your industry?
• What new capabilities are coming in the next 6-12 months?
• What role do you want to play in an AI-augmented workplace?

How do you get there?

• What can you learn this week?
• What can you build this month?
• What can you demonstrate this quarter?

The people who navigate this transition successfully won't be the ones with the most experience. They'll be the ones with a clear roadmap and the discipline to execute it.

What Actually Works: The Portfolio Approach

Here's the practical playbook:

Weeks 1-2: Build Foundation

• Pick the #1 AI tool in your industry and use it 2-3 hours daily
• Join communities where people share AI workflows
• Document what you learn publicly on LinkedIn or Twitter/X

Weeks 3-4: Create Proof. Build 3 examples of AI-enhanced work in your field. Marketing? Create a campaign. Operations? Automate a workflow. Development? Build a tool. This serves double duty: job applications AND side hustle foundation.

Weeks 5-8: Execute Both Paths

• Keep applying to traditional roles
• Target 5-10 companies with custom AI solutions to their problems
• Start offering your AI skills as paid services
• Share your work publicly and engage in communities

The goal: become a stronger job candidate while building a side income. You're creating options, not limiting yourself.

If You're Currently Employed

You're in the best position to execute the portfolio approach.

Do this immediately:

• Keep your job (this is your stability and runway)
• Start documenting every process you do
• Learn the AI tools that could enhance (or replace) your work
• Build a portfolio of AI-augmented projects on the side
• Position yourself internally as the AI expert → Create your personal AI roadmap with 90-day milestones
• Start taking on small side projects to build proof and income

The people who survive the org restructures are the ones who make themselves essential by bridging old expertise with new capabilities. And if the restructure happens anyway? You'll have skills, proof, and potentially side income already flowing.

The Realistic Timeline

Let's be honest: most people won't replace their income in 60 days.

But here's what IS realistic:

Month 1: Build foundation, create proof, become noticeably more capable Month 2: Start getting noticed, land first small paid project, become a stronger job candidate Month 3: Build momentum, potentially earn $500-2000 in side income, get job offers OR grow side income. Month 6: Either land a better job than you would have otherwise, OR build a side hustle to $2-5K/month, OR both

This is a portfolio approach. Multiple experiments. Real progress. Actual options.

The Uncomfortable Part

Not everyone will navigate this transition easily.

Financial pressures don't allow for weeks of experimentation. Some industries are being hit harder. Some are competing against younger, AI-native workers.

I get it. This is genuinely hard stuff during a genuinely difficult and confusing time.

But here's what I know from some uncomfortable experiences: Waiting for things to go back to "normal" is the riskiest thing you can do.

The portfolio approach isn't about having unlimited time or resources. It's about making strategic use of whatever time you DO have to build multiple paths forward.

Even 30 minutes a day for 60 days can completely change your position.

Bottom Line

The job market I described in February has evolved into something more serious.

The displacement is real. The anxiety is valid. CEOs are openly planning for smaller, AI-augmented workforces.

But there's also a genuine opportunity — if you're willing to think in portfolio terms rather than single paths.

Your expertise still matters. Your experience still matters.

But now it needs to be combined with AI capabilities to create a competitive advantage — whether you're seeking employment or building your own thing.

The next 6-12 months will separate the two groups:

1. People who've built their personal AI roadmap and portfolio approach
2. People who hoped it would slow down

Which group will you be in?

Take Action Right Now

Follow me for daily insights on AI and the future of work

Subscribe to my newsletter for the complete AI adaptation playbook + portfolio career strategies, or DM me if you need personal guidance for your situation

The best opportunities won't go to the most experienced. They'll go to the most adaptable.

It's your choice.