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2026 Financial Planning: Why Your Best Investment is Career Insurance

December 29, 2025

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If your stomach drops every time leadership mentions “organizational shifts” or “streamlining for the new year,” you aren’t being dramatic. You’re being observant. 👀

In 2020, I watched 300 directors disappear in a single afternoon under the cover of “performance reviews.” These were the sharpest people in the room, yet their security was an illusion. Whether it’s a “quick chat” calendar invite or a subtle shift in leadership language, reorg dread is a signal that your financial plan needs more than just a 401(k) contribution. It needs career insurance.

A severance plan helps you once; a safety net helps you forever. As we look at 2026, it’s time to move past traditional budgeting and start building options. Here is your practical checklist to become layoff-proof this year.

1. Assess Your Vulnerability

Most financial planning starts with “how much can I save?” We’re starting with “how long can I last?”

Depending on a single paycheck is the single greatest risk to your financial health. You wouldn’t drive a car without a spare tire, yet millions of professionals are driving their entire lives on one “paycheck” wheel.

The first step in your 2026 plan is a brutal gut check. You need to know exactly how exposed you are if that paycheck ghosted you tomorrow. This isn’t about fear; it’s about clarity. Clarity is the only thing that cures the “shaky job” feeling. It’s the difference between panicking during a town hall and sitting back because you know your numbers.

The Move: Take five minutes to run your numbers. Use a tool like the $$ Safety Net Check to see where you stand and exactly where you need to start shoring things up.

2. Map Your Reality

Once you know your vulnerability, you have to get honest about your resources. I’m not talking about your bank account — I’m talking about your life.

When corporate pros try to build backup income, they often fail because they pick a plan that doesn’t fit their season of life. If a “side hustle” makes you want to hide in a dark corner, it’s because you’re looking at the wrong models. You don’t need a second job that feels like a second job.

Mapping your reality means looking at:

  • Energy: Do you have 30 minutes after the kids go to bed or an hour before the emails start?
  • Skills: What do you already do at your 9-to-5 that people would pay for outside of your employer?
  • Risk: Do you need to build this quietly to protect your professional brand?

Don’t build a plan for the “future version” of you who has endless motivation. Build it for the smart, tired version of you who needs a plan that respects her energy.

3. Pick One Stream (And Keep it Low-Drama)

The biggest mistake is trying to “diversify” by doing five things at once. That’s not a strategy; it’s a recipe for burnout.

For 2026, your goal is to pick one way to make money that fits your reality. It doesn’t have to be a “passion project” or a “get rich quick” scheme. It just needs to be a second faucet of income.

Think about these options:

  • Consulting: Using your corporate expertise for a different audience (think small businesses that need your big-company brain).
  • Reselling: A simple system like my resale shop, which uses a simple iOS shortcut to calculate profit while sourcing.
  • Travel or Franchise Models: Structured, system-based models where you don’t have to reinvent the wheel.

The goal is to find a “right-fit” stream — something that feels professional and doesn’t require “influencer cosplay” to succeed.

4. Run a Tiny Test

Before you go all-in on a website, a logo or a fancy LLC, you need proof. In 2014, I launched an Etsy shop selling digital prints that went absolutely nowhere. It was a great lesson: test fast and cut losses even faster. That “failure” was just data.

A “Tiny Test” is a small, low-risk offer that proves someone will actually pay you for your idea.

  • Can you get one person to pay you $100 for a one-hour consultation?
  • Can you sell five items on a resale app?
  • Can you book one commission-based trip for a friend?

First dollars earned quickly will do more for your confidence than any “manifesting” ever will. Once you have proof, you can engineer the system to make it repeatable.

5. Build Your Career Insurance

The ultimate goal for 2026 isn’t just to “make more money.” It’s to have options.

When you have more than one way to earn, the vibe of your 9-to-5 changes. You stop being at the mercy of a single paycheck. You can say “no” to the promotion that would pull you away from your strengths. You can walk into “quick chat” meetings with calm confidence because you know you have a net.

You don’t need a secret formula. You just need a system that starts with a single step.


Ready to start your 2026 plan?

Step 1: The $$ Safety Net Check. Take five minutes to see how long you’d last without your paycheck and get a clear roadmap for what to do next.

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