💸 6 Steps to Be Financially Unbreakable During Your Job Search

Hello there 😎 

Got back from a family holiday this weekend. Now desperately chucking things into boxes because we’re moving house in a few days 😂

Anyways, taking a break from wrapping stuff in towels and ripping packing tape to send out this email.

Here’s a quick story:

I'll never forget the morning I got laid off.

It was almost a year ago, to this day!

It was my first morning back from paternity.

I logged in.

Checked my calendar.

And saw that a 15-minute meeting was booked with HR.

My first thought wasn’t:

“How long can I survive without a paycheck?"

Because I already knew the answer.

Instead, it was:

See, I’ve been through this financial uncertainty before:

• Moving to Ireland

• Starting consulting during the COVID-19 pandemic

• Quitting the entertainment industry to chase this idea of remote work

One thing makes these moments less overwhelming: financial clarity.

When you’re in the thick of your job search, financial clarity gives you:

• The freedom to make strategic decisions instead of desperate ones

• The ability to focus on making yourself the best candidate possible

• The patience to hold out for the right opportunity instead of grabbing the first one

Today, we’re covering the five steps I followed to feel financially unbreakable during my job search.

Here's what you'll learn today:

• How to calculate your real financial runway (most people get this wrong)

• AI-powered decision frameworks for your biggest career choices

• The exact timeline strategy that aligns your finances with your job search

...and more!

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

🚦Breakthrough the Noise and Land The Interview

I’m opening up more spots for my Land The Interview service.

The results have been too good not to:

I’ll be opening more spots in the next few weeks.

If you want your resume and LinkedIn to break through the noise, click below to join the waitlist.

🔮 Step 1/ Get Financial Clarity (Know Your Numbers)

You gotta know three numbers:

• How much do you spend

• How much do you make

• Your runway (how long until your money runs out, also called your burn rate)

During the job search, your runway usually equals:

“How many months can I cover expenses without new income?”

For example, if you have $30,000 in savings and your monthly expenses are $5,000, your runway would be 6 months.

Look, I 100% get that there’s a whole psychological side that can make this really tough. That for many people, talking or even thinking about their financial situation can feel unbearable (I spent years working on this and studying it).

But what I’ll say is: it’s never been easier to figure out these three numbers.

The tools today make it simple.

I've played with Mint, YNAB, Tiller, Kubera, even manually with a spreadsheet.

My biggest tool recommendation is Monarch Money. The team makes tracking your finances easy. I can’t recommend them enough.

Use my referral code when signing up and get 50% off your first year.

(Disclaimer: I get something too. TBH I don’t know what 😂)

👉 Do this:

Step 1: Set up Monarch Money (15-20 minutes)

• Connect your main accounts (checking, savings, credit cards)

• Let it pull in your transactions automatically

Step 2: Quick categorization (don't go crazy here)

• Make sure transfers between your accounts show as "transfers" (not expenses)

• Same with credit card payments (so you're not double-counting)

• Check that your salary/income is labeled as "income"

• You don't need perfect categories, just the basics

Step 3: Export and analyze

• Export 3 months of transactions from Monarch

✍️ Use this prompt in ChatGPT:

That's it. Spend 15-20 minutes setting up Monarch, then let AI do the heavy lifting on analysis.

You'll end up with three critical numbers:

1. Current monthly burn rate (what you spend now)

2. Lean monthly burn rate (cutting non-essentials)

3. Survival monthly burn rate (absolute bare minimum)

Most people only calculate their current spending and panic when they realize it's unsustainable. Having all three numbers gives you options and removes the guesswork from financial decisions.

♟️ Step 2/ Decide Your Strategic Options

Great. You know your numbers.

Now you can map your financial clarity to your job search strategy.

Here are some of the key job search questions you can start to answer:

• Can I afford to hold out for the right job? (How long can I be selective?)

• If you’re employed and hate your job, can I quit? (Do I have 3-6 months of lean spending covered?)

• What are my realistic career plays? (Remote-only, geographic flexibility, freelance bridge work?)

This sometimes comes up with my clients. Questions like:

When facing big career decisions, the first most helpful thing is to have someone whom you can trust to talk to and bounce ideas off of.

But maybe you don’t have that person in your life.

Or maybe they’re not available.

In any case, the second best thing is to have an AI-powered framework to help you think through these questions.

✍️ Here's a prompt you can use (I recommend ChatGPT for this):

h/t Louis Gleeson for the idea for this prompt

⏳ Step 3/ Build a Job Search Timeline

Your financial runway is an important input into your job search strategy. Here’s how to integrate the two:

✍️ Use this prompt in ChatGPT:

Here’s an example 8-week timeline if you had three months’ worth of runway:

Weeks 1-2: Research & Foundation

• Build your target company list (15-20 companies)

• Research decision makers and recent company challenges

• Optimize your resume and LinkedIn profile using AI tools

• Create your "show your work" project for 1-2 top target companies

Weeks 3-4: Proof of Work & Direct Outreach

• Complete and polish your proof of work projects

• Begin direct outreach to hiring managers with your analysis/deck

• Start informational interviews with people at target companies

• Apply to 5-7 highly targeted roles per week

Weeks 5-6: Scale and Network

• Expand outreach to 10-12 applications per week

• Leverage warm introductions from informational interviews

• Follow up on proof of work projects you've sent

• Consider adding hybrid roles in commutable areas

Weeks 7-8: Intensify and Reassess

• Increase application volume to 15+ per week if needed

• Follow up on all outstanding conversations and applications

• Evaluate what's working vs. what isn't in your approach

• Consider expanding criteria (role type, location, company size)

💵 Step 4/ Extend Your Runway (Without Going Broke)

Sometimes you need to buy yourself more time. Here's how to do it strategically through two approaches:

💸 Part A: Quick Expense Cuts & Financial Adjustments

The fastest way to extend your runway is by reducing what goes out and optimizing what you have.

If you don’t have a list yet from Step 1, Getting Financial Clarity, do this:

✍️ Pull from Monarch and use prompt in ChatGPT:

Example monthly expense cuts:

• Pause gym memberships (YouTube workouts exist)

• Downgrade phone/internet plans

• Cancel streaming services (keep one for sanity)

• Negotiate insurance rates

• Use generic brands for groceries

• Pause non-essential subscriptions (software, apps, magazines)

Also, here are more strategic financial decisions to have in the back of your mind:

• Pause retirement contributions if cash flow is tight

• Move some investments to more liquid accounts

• Don't panic sell unless absolutely necessary

• Know your withdrawal options if the search extends

In general, look for cuts that save $50+ per month with minimal life impact. A $100/month reduction adds an extra month to a $3,000 monthly budget.

For investments, prioritize liquidity over growth during your search period.

🔥 Part B: Strategic Freelancing & Consulting

I’ve written about this before. You can generate income while staying in your field.

Here’s how you get started, and read the rest of guide to learn more:

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:

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.

✍️ Here’s a prompt I’d use:

Remember: The goal isn't to build a freelance empire. It's to buy yourself time to find the RIGHT full-time role instead of settling for the first one that comes along.

My friend Dexter at The Portfolio Path writes more about combining multiple income streams. I strongly recommend checking out his stuff.

💪 Step 5/ (Optional) Build Financial Resilience for the Future

This job search is temporary.

Building financial resilience is permanent.

And I think reading the right books will change your relationship to money and career risk (it did for me).

There are four books I recommend to my friends, in this order:

For getting started:

1/ I Will Teach You to Be Rich by Ramit Sethi – Always my go-to recommendation for someone getting started in their financial journey. Ramit sets you up for success. This is where you learn all the blocking and tackling (e.g. credit cards, getting out of debt, which savings account to open, etc.)

2/ Psychology of Money by Morgan Housel – This book is a perfect follow-up to Ramit’s, diving into why we handle money the way we do. It’s super insightful about the weird ways our brains work when it comes to money and risk, showing you how to make better financial decisions. If IWTYTBR is the block and tackling, then this is the mental game of personal finance.

3/ The Millionaire Fastlane by MJ DeMarco – I didn’t love this the first time I read it. It gave very “Rich Dad Poor Dad”. But on the second and third reads, the ideas here changed how I think about diversifying income sources.

4/ Quit Like A Millionaire by Kristy Shen and Bryce Leung – This one has a strong FIRE vibe (Financial Independence, Retire Early), which isn’t for everyone. But even if retiring early isn’t your goal, it’s packed with straightforward tips on how taxes work with different investments. Useful as you dive deeper into exploring how you want to design an investment portfolio

You’re never going to be perfect with money.

Or your career choices.

But cracking into even one of these books is going to 10x your decision-making abilities.

💫 The Bottom Line

Morgan Housel says:

When you're financially unbreakable, you can make career decisions based on strategy, not desperation.

You can hold out for remote work instead of settling for the first local offer. You can build proof of work instead of just sending resumes. You can negotiate knowing you have options.

If you want freedom in your career, buy yourself time. And that starts with financial clarity.

The job search isn't just about finding work. It's about having the runway to find the RIGHT work.

I love meeting new people. Say hi on LinkedIn 👋

🤝 When you’re ready, here are 2 ways I can help you with remote work:

That’s a wrap. See you next week 👋