How to Start Freelancing: 3 Questions to Answer Before You Quit

How to start freelancing comes down to three honest questions before you quit: how much career time you have left, how much money you need to keep your current life running, and how much going solo actually excites you. Then you stress-test the answer against a worst case. The timing will rarely feel perfect, so the goal is to know you will be okay if it isn't.

That is the advice Andy Milligan, founder of MMG Design and the Columbus Marketing Organization, gave a community member who asked a simple question: "I'm employed and I'm looking to build my resume and transition to a business owner when the time is right. When do I know when the right time is?"

If you have already decided and want the client side of the equation, start with how to get your first client.

The timing rarely feels perfect

Andy starts with a disclaimer worth repeating: he doesn't know your exact situation, and the specific answer changes depending on who is asking. But one thing he does know: "the timing is rarely ever going to feel perfect."

His own start proves it. Andy was laid off from his first full-time design job when his side business had about $1,200 in revenue. He was 22, had about $10,000 in savings, and was paying $1,200 a month for his mortgage. That flexibility let him, in his words, "burn the candle at both ends" and grow the business by "doing outreach, attending networking events, and fixing my lack of experience by throwing my own time at it."

He is also clear that his situation isn't everyone's. If you have kids, a mortgage, or debt and need to make money quickly, he says, "it's going to be really hard to do that starting from net zero."

You would not be alone in making the jump. The U.S. Bureau of Labor Statistics counted 11.9 million independent contractors, 7.4 percent of total employment, in its July 2023 contingent and alternative work survey, released in November 2024.

Question 1: How much time do you have left in your career?

"Life is a lot shorter than we all think it is," Andy says. He admits he falls into the same trap he warns against: telling himself he won't do the next thing until he reaches some other milestone first.

Applied to a career, that loop never ends. There will always be a reason to wait one more quarter. Andy's suggestion is to zoom out and ask how much time you realistically have left in your working life, then decide whether waiting for perfect conditions is worth those years.

Question 2: How much money do you need to maintain your current lifestyle?

Andy recommends doing "a full assessment of how much money you need to maintain your current lifestyle." Get specific. List rent or mortgage, debt payments, insurance, and the fixed costs you can't pause.

Then account for what changes when you become your own employer. Self-employed people in the U.S. pay both halves of Social Security and Medicare through the self-employment tax, a combined 15.3 percent rate according to the IRS. Your monthly number as a freelancer is higher than your number as an employee, even before you buy your own software and equipment.

Question 3: How much does going on your own excite you?

This is the question people skip. Money and timing are math. Excitement is what carries you through the months when outreach feels slow and the pipeline is thin.

Andy's own early growth came from effort he could only sustain because he wanted it: daily outreach, networking events, and long hours spent closing his experience gap. If the idea of running your own business doesn't pull you forward, the spreadsheet won't save you.

Stress-test the worst case

Once you have your answers, Andy suggests one more exercise: calibrate against "the worst case scenario if you were not to make any money for 2 months, 4 months, 6 months" and play it out.

He isn't predicting it will happen. The point is confidence: "just knowing that in your back of your mind that you will be okay even if the worst case scenario happens is really helpful."

A simple way to run it:

1. Multiply your monthly number by 2, 4, and 6. Compare each total to your savings.
2. Decide what you would cut first. Know which expenses go if month three is slow.
3. Name your fallback. Contract work, part-time roles, or a return to a full-time job are all fine answers. Knowing yours lowers the stakes.
4. Start building demand before you leave. Andy had $1,200 in revenue when he was laid off. Every client conversation you start while employed shortens your worst case.

Find your people before you jump

Freelancing alone is harder than freelancing with peers who have done it. Columbus Marketing Organization is a peer community for marketers, freelancers, and service providers in Columbus, Ohio, founded by Andy Milligan. Members share leads, introductions, and job opportunities, including the weekly Columbus Marketing Jobs newsletter.

For the full story of how Andy's first year went after that layoff, read his guide on how to become a freelance marketer. For practical outreach once you're out, see how to find freelance clients.

How to start freelancing with a plan, not a perfect moment

Knowing how to start freelancing is less about the perfect moment and more about honest answers: your time, your number, your excitement, and your worst case. Run the exercise this week. Then come meet Columbus marketers who have already made the jump at an upcoming Columbus marketing event, or join the Columbus Marketing Organization community on Skool.