I woke up last week to these messages in my Inbox:

I dedicated 3.5 years to this company and got completely kicked to the curb in an instant. No severance, no PTO payout. Got our last paycheck, and that was it. I don’t think my former “managers” are going to be doing anything to help me either. Just a huge disappointment all around. I haven’t heard a peep from either of them, which is another huge disappointment.

I’m reeling from just how savage these layoffs can be.

That combined with the uncertainty of the markets (e.g. the S&P 500 dropped 10.5% in just two days, one of the worst days since 1950)…

This is the reminder that our careers are more fragile than we think.

It’s not enough to think about stability.

Or just thinking about how to land that next remote job.

We have to work to create a recession-proof career.

Here’s what you’ll learn today:

• 🛡️ The 4-step AI playbook to future-proof your career (even during layoffs)

• 💰 How to quickly start earning additional income streams using AI tools

• 🔗 The scripts and systems to build powerful professional relationships at scale

…and more!

We assume that if we’re doing good work, we’re safe.

We assume that if we’ve been at a company long enough, we’ve earned some job security.

Gina Sapien shared this wild stat:

24,000 tech workers laid off this year so far, across just 90 companies.

The message is clear: job security is an illusion.

Elena Verna put it well.

“Most people still equate full-time jobs with stability, which makes sense—they’ve been the default for so long. But that stability? It’s an illusion.

If recent waves of layoffs didn’t already shatter this belief, they will. Full-time roles are disappearing faster than we think, and the open roles that remain are getting harder to justify—especially with AI on the rise.”

Source

What’s worse is that most of us aren’t prepared to re-enter the job market.

Why would we be? For years (decades?) we’ve been told we’re doing great work. So we never expected tomorrow would look any different from today.

The solution?

Make your career layoff-proof.

When you see layoffs in the headlines, don’t just breathe a sigh of relief and move on.

• Dig a deeper moat.

• Fortify your position.

• Build systems that make you stronger—even in the middle of chaos.

Here are 4 ways you can use AI to help become recession-proof.

💰 1/ Learn to Sell Your Time

🧰 Recommended tools:

ChatGPT

Perplexity

There are lots of ways to make money. But when you’re trying to get income coming in quickly (especially during uncertain times) selling a service is the fastest path.

That just means doing something you’re already good at… but as a consultant or freelancer instead of a full-time employee.

You don’t need a fancy offer. You don’t need a landing page. You don’t even need a personal website.

You just need to know:

• What you’re good at

• Who needs help with that

• How to reach them

Here’s how to use AI to discover profitable services you can offer:

Step 1/ Copy your LinkedIn profile

Be sure to go and manually copy the text from the profile, (e.g. the headline, summary, and all the experience).

Do NOT just copy the URL.

Step 2/ Use ChatGPT to discover what you can offer

💡 Here’s a prompt I’d use:

I’d like you to act as a positioning strategist and business advisor. I’m sharing the content from my LinkedIn profile below. Based on what you read, I want you to help me answer two questions:

What consulting or freelance services could I credibly offer, based on my experience, strengths, and how I currently present myself?

Who are the ideal personas or types of companies I should target for these services? Be specific—name industries, job titles, company size, stage, etc.

When answering, focus on:

What problems I appear well-suited to solve

Where there’s a clear “willingness to pay” for that kind of help

What differentiates me from the average generalist consultant

Please break your response into these sections:

Summary of your read on my positioning

2–3 consulting offers I could start with

Target buyers (including job titles, company types, industries)

Bonus: how I might start validating or selling these offers

Here’s my LinkedIn profile:

[Paste LinkedIn profile content here]

You’ll get back a list of ideas—probably more than you expect.

Step 3/ Use Perplexity to find real companies to pitch.

Perplexity is an AI-based search engine. It’s great for searching and providing summaries of unstructured data.

Now that you’ve got a rough idea of what service you could offer (and what kind of companies might need it) next you need to answer:

Who’s hiring for this right now?

That’s where Perplexity comes in.

💡 Use a prompt like this:

Which [insert your target buyers here] have recently raised funding or are currently hiring for [your services]?

You’ll get a list of real, current companies with money to spend and open roles to fill.

Those are your target customers.

You’re not trying to spam 100 people.

You’re trying to find 5–10 companies that:

• Need your help

• Have money to pay

• Would benefit from what you already know how to do

Start there.

2/ Take stock of your finances

🧰 Recommended tools:

Monarch

ChatGPT

Suggested reading: The Psychology of Money by Morgan Housel and I Will Teach You To Be Rich by Ramit Sethi

In The Psychology of Money, Morgan Housel summarizes his personal finance philosophy:

More than I want big returns, I want to be financially unbreakable.

Here are steps to become unbreakable.

Step 1/ Use Monarch to take stock of your finances

Monarch is the best tool out there right now for managing your personal finances, IMO.

It’s fast, mobile-first, and makes categorization of your transactions a breeze.

Once you start using Monarch, you can export all your transactions into a CSV.

Step 2/ Use ChatGPT to review your transactions

ChatGPT will review your spend and understand where all your money is going.

Monarch does a decent job of categorizing this for you. However, there is still some manual work in recategorizing transactions. Plus, the dashboard gives you a pretty but surface-level view of where your money is going.

Augment this with ChatGPT to get greater insights and suggestions on how to improve your finances.

Step 3/ Stash money in your emergency fund.

This is priority number one.

Don’t have an emergency fund?

Create a free online savings account.

I recommend either Capital One or Ally.

Start small: $50/month, $100/month, whatever.

You goal is to save up to 3 months worth of living expenses. Then work up to six. Then 12.

Step 4/ Increase your earnings

See above 🙂

🌉 3/ Build Opportunity Bridges

🧰 Recommended tools:

Google Sheets + Mail Merge

Taplio

Perplexity

ChatGPT

If you’ve ever gotten a job from a friend-of-a-friend or a past coworker you hadn’t talked to in years… you’ve already seen this at work.

Sociologist Mark Granovetter spent 50 years researching this and found something surprising:

“Weak ties—not close friends—are your most likely source of new opportunities.”

New jobs.

New ideas.

New information.

To recession-proof your career, start building and strengthening these opportunity bridges:

1/ Keep connections warm

You don’t need to be an extrovert. You just need a system.

A simple Google Sheet + Gmail Mail Merge can go a long way.

Here’s how:

• Open a new Google Sheet and list 20–50 people in your network: former coworkers, mentors, peers, even college classmates.

• Add columns for their name, how you know them, and the last time you talked.

• Use a Mail Merge tool (see documentation here) to send personalized check-ins at scale.

Keep it casual. Example:

“Hey {{Name}}, hope things are going well at {{Company}}! I came across something that reminded me of that project we worked on at {{Shared Context}} and wanted to say hi. Would love to hear what you’re up to lately.”

This keeps the door open and the relationship alive.

I cover this system in more detail here.

2/ Leverage a content engine

The best way to stay top of mind? Share your ideas publicly.

Posting online gives you a passive way to stay connected with your network, at scale.

Here’s how to get started:

• First, find top-performing posts from others in your niche. You can try Taplio the Chrome extension to help you

• Second, rework these top-performing posts with your own take. If you pay for the Taplio app, you can do this in-app. If not, use ChatGPT

• Then tweak and post.

It removes the friction of staring at a blank page and helps you find your voice faster.

💡 Prompt to try

“Based on this post from {{LinkedIn profile or paste text}}, help me write a version in my voice. I work in {{your industry}}, and I want to make a point about {{your point}}. Give me a draft that uses the same structure but reflects my expertise.”

The more consistently you’re in someone’s feed, share, the more they’ll remember what you’re about. And that leads to opportunities.

3/ Create new bridges

Cold outreach doesn’t have to be sleazy.

Done well, it’s just a way to connect with someone you admire or want to learn from.

Here’s how AI can help:

First, find people working in your target industry or companies using Perplexity.

💡 Prompt to use in Perplexity:

“List 10 rising startups in the fintech space that have raised funding in the last 6 months and are hiring for product roles.”

Next, use ChatGPT to draft your cold outreach message:

“I’m reaching out to {{Name}} because I admire their work at {{Company}} and saw they recently posted about {{Topic}}. I’d like to ask for 15 minutes of their time to learn how they got into {{Field}}. Write a short, warm message I can send via LinkedIn or email that’s respectful of their time.”

Then tweak it to sound like you.

The goal here is to make a genuine connection and not just send more noise into the void.

🧠 4/ Build a Career OS (and never start from scratch again)

🧰 Recommended Tools:

Notion, Airtable, any notes app

ChatGPT

When layoffs happen, most people scramble to update their resume, remember their accomplishments, and spin up new materials from scratch.

You don’t want to be most people.

Instead, build a Career OS—a system that helps you:

• Document your wins as they happen

• Save time by reusing high-quality components

• Make your skills, wins, and contributions easy to reference

When you do this right, your Career OS becomes a living portfolio. It helps you move faster in job searches, win clients as a consultant, and perform better at your current job.

1/ Capture your wins as you go

Create a “Wins Journal” inside your notes app. This can Notion, Airtable, Google Docs, Notes, etc. (I use Roam). Use it to track:

• What the project or task was

• The business impact or result

• Feedback from customers or teammates

• What you learned

This doesn’t need to be polished—just save the raw material. You can always refine it later.

💡 Paste in your emails or Slack messages and ask ChatGPT:

“Summarize any notable accomplishments or wins from this message thread I can add to my portfolio.”

It’ll help you pull insights you’d otherwise forget.

2/ Save and tag your best reusable components

Each time you create something useful, e.g. slide decks, templates, onboarding docs, interview guides, save it in your system.

Tag it by type (e.g. GTM, Hiring, Research) and use case. Add a quick note about where and how you used it.

Over time, you’ll build a library of reusable assets that let you work faster and smarter.

💡 Paste in details about your project and ask ChatGPT:

“Based on this project I led, what assets could be reused in a future project? List them with suggested names and tags.”

3/ Set a recurring reminder to update

Your system is only as good as your updates. Every month, block 30 minutes to review your work and update your Career OS.

This is about building leverage, not just a portfolio.

So when the next opportunity (or challenge) comes, you won’t start from scratch. You’ll have receipts.

💫 The Bottom Line

Layoffs aren’t just a company problem. They’re a career wake-up call.

And in a world where full-time roles aren’t as stable as they used to be, the best time to protect your career was yesterday.

The next best time is right now.

Here’s how you can use AI to build a career that’s more flexible, more resilient, and harder to take away.

1. 💰 Learn to Sell Your Time

2. 💸 Take Stock of Your Finances

3. 🌉 Build Opportunity Bridges

4. 🧠 Build a Career OS