Hello there 😎 

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

I’m reeling from 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:

Our careers are more fragile than we think.

It’s not enough to think about stability, or how to land that next remote job.

We have to work to create a layoff-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!

But first, let’s look at some open roles I’m excited about.

We assume if we’re doing good work, we’re safe. If we’ve been at a company long enough, we’ve earned security.

Gina Sapien shared this wild stat:

The message is clear: job security is an illusion.

Elena Verna put it well.

Source

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

Why would we be? For years, we’ve been told we’re doing great work. We never expected tomorrow would look so 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 four ways you can use AI to help become layoff-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 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 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

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:

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:

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:

Here are the steps to become unbreakable.

Step 1/ Use Monarch to take stock of your finances

Monarch is the best tool available right now for managing your personal finances, in my opinion.

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 spending 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:

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 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:

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 Chrome extension to help you.

• Second, rework these top-performing posts with your take. If you pay for the Taplio app, you can do this within the 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:

The more consistently you’re in someone’s feed, 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:

Next, use ChatGPT to draft your cold outreach message:

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 be 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—save the raw material. You can refine it later.

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

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:

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

I love meeting new people. Say hi on LinkedIn 👋

That’s a wrap. See you next week 👋