Before You Leap: A Safety Net for Leaving Your 9-to-5

Leaving a steady job for your own thing is a perfectly good plan, as long as there's a net under it. This is general guidance, not financial advice; a fee-only financial planner can look at your actual numbers.

1. Build the safety net first

Add up what you actually spend in a month: housing, food, insurance, debt payments, and the subscriptions you forgot you had. Then multiply. Six months of expenses is a common rule of thumb for a cushion, and many people aim for more when they're leaving a paycheck on purpose, because new businesses usually take longer to pay than their owners expect. Keep it somewhere boring and easy to reach.

2. Price out what your job quietly pays for

In the US, health insurance is the big one. You generally have two routes. COBRA lets you keep your employer's plan, usually for up to 18 months, but you pay the whole premium yourself, up to 102% of what the plan costs, which surprises a lot of people. Or you can buy a plan on HealthCare.gov: leaving a job, even quitting, opens a special window to enroll, and you have 60 days after your coverage ends, or can apply up to 60 days before.

Then list the rest: retirement matching, life and disability insurance, your phone, your laptop, paid training. Add whatever you'll keep paying for to the monthly number from step 1.

3. Let the side hustle prove itself first

Pick a “leap number” before you get excited, and write it down. For example: the side hustle covers half your monthly expenses for three months in a row, with more customers lined up. While you still have a paycheck, every month it earns is a month your cushion doesn't have to cover. How to get your first 10 customers and What should I charge? are the guides for getting there.

4. Talk to the people it affects

A partner, family, anyone who counts on your income. Show them the real numbers, the cushion and the plan, and agree ahead of time on what happens if it's harder than expected. It's also worth an hour with someone who has made the jump themselves; they'll ask the questions you haven't thought of yet.

5. Decide your checkpoint before you jump

Write down a date and a number: “If the business isn't paying $X a month by [date], I start looking for a job.” Share it with the people from step 4. Deciding it now, while you're calm, makes going back part of the plan instead of a decision you have to make on a bad week.

6. Leave well

Give the notice your role expects, write a real handoff, thank the people who helped you, and keep your references and contacts warm. Plenty of people go back to a job after running their own thing, sometimes to the same company, and you want that door open.

Your exit interview is not the moment to finally share your thoughts on the reorg.

If you signed anything about competing, inventions or confidentiality, have a lawyer read it before you give notice.

To put all six steps on paper, print the Leap Worksheet.

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Questions people ask

How much money do I really need saved?

It depends on what you spend, what your health coverage will cost and how quickly the business can pay you. Six months of expenses is a common place to start. A fee-only financial planner can work it out with your actual numbers.

Should I quit before the side hustle makes any money?

The safer path is to let it earn first while you're employed. If the business truly can't start until you're full time, plan for a bigger cushion and a firmer checkpoint.

Can I go part-time instead of quitting?

It's worth asking. Some employers will agree to reduced hours or a contract arrangement, which keeps some income and sometimes benefits while you build. Check your company's policies first.

What if it doesn't work out?

Then your checkpoint does its job: you start looking for work with new skills and a real story to tell. Leaving on good terms makes that much easier.

Sources

Last checked October 3, 2026.

Before you leap