How to make the jump to freelancing full time

One of the biggest questions I get through my site is from creatives who are wanting to quit their jobs and freelance full time.

They know they want to do it, but they are afraid to make the jump. 

Over the course of the past year, I have interviewed numerous creatives on my podcast who have made the jump to freelancing full time. I even made the jump myself about a year and a half ago.

The one thing I have noticed throughout these stories is that everyone does it differently. 

Everyone has a different tolerance for risk.

In this post, I will share with you two strategies for making the jump and stories of freelancers who have done it. 


1) Reduce your risk by freelancing on the side

Kaleigh Moore -


Kaleigh was working in the marketing role for a non-profit as her full time job. Slowly over the course of a couple years at her job she started picking up clients on the side. She worked extra hours and around her work schedule to serve these clients and provide them value.

Eventually, Kaleigh hit a point where she realized her monthly freelance income was equal to the income she was making from her full time job. At that point, she turned in her resignation so that she could focus full time on freelancing and continue to grow her income.

Kaleigh made the jump a very smart way. There was almost no risk involved because she had already lined up enough clients to match the income from her full time job. 

Alicia Waters -

Alicia Waters had spent a majority of her professional career working at different design agencies. Yet throughout all of it, she still managed to take on freelance projects on the side. She used the money from her freelancing to help pay down student loans and build a cash buffer.

When she was finally ready to leave her job, she wasn't completely terrified about finding work. She had been freelancing on the side for several years now and had a small client base built up. It wasn't enough to provide a full time income for her right away. But with a slight cash reserve and decent network of prospects, she knew she could make a living if she hustled and put the time into it.

Alicia mitigated her risk by freelancing on the side even while she had a full time job. Those projects allowed her to put money away and build up a portfolio. That stability gave her the foundation and confidence to dive into freelancing full time.


2) Quit your job and then just figure it out

Danny Margulies -

When Danny Margulies quit his job, he woke up the next morning and decided "I am going to become a freelance writer and figure this out."

Danny had a few months cash in the bank, but he had a wife and kids to feed as well. Danny hopped on eLance the next day and started applying for jobs. 

He buckled down, hustled and applied to as many jobs on eLance as he could. Danny maxed out his eLance applications and then purchased more so he could keep applying. He even woke up at 3am so that he could apply to jobs right as they were being posted in Australia.

Danny hustled and it paid off. Within two years Danny was making more than $100,000 per year doing freelance writing on Elance. 

While some may look at Danny's approach as risky, in many ways it wasn't. Searching in hopes of another full time job was equally as risky. The amazing thing is that Danny now makes significantly more in income than he would have if he had sought out a replacement full time job.

My story -

Prior to starting my freelancing career, I was working at an investor backed startup. It was a poor decision to get into on my part as I wasn't passionate about the project or the industry. I slugged along at the startup for about 8 months and then I had enough.

Eventually, I decided I was couldn't do the startup anymore. I had closed one small web design client on the side but it was by no means enough to make a living, and I had hardly anything in my pipeline. 

My cash reserve was pretty weak, I had about two months living expenses in the bank. Then I did what some would consider even more risky. I bought a one way plane ticket to Mexico for my girlfriend and myself.

With two months of cash in the bank, and two months until we moved to Mexico, I hustled to find more clients. I landed a few that gave me a bit more runway.

Then when we got to Mexico, my cost of living dropped by nearly 2/3rds which made the cash I had stretch even longer. We buckled down in Mexico where our cost of living was extremely low as I built up a remote freelancing career.

My style was probably more risky than how I have seen most others do it, and I wouldn't recommend it to those without tough skin. There is nothing scarier than being down in Mexico and hitting near rock bottom on your finances.

The bottom line

Everyone has their own tolerance of risk, everyone has their own way of making the jump. 

There isn't a secret formula or a right way to do it. It all comes down to you and how you want to handle it. Some people need the jolt of the life changing event to get them motivated. Others prefer the safety of overlapping their freelancing with their full time job.

It honestly comes down to you and the person. Figure out what path works right for you, and start building a plan of action to take it. 

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