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When Is The Best Time to Quit Your Job and Freelance?

quit your job and freelanceI’m often asked by folks who have started writing for pay, “When is the best time to quit my job and freelance?”

Truly, I’m tempted to say ‘Now!’

But that’s usually not helpful.

Some will say you can quit your job and freelance as soon as you have six month’s income in the bank. Others will say “never quit your job!”

The issue, of course, is that jobs (mostly) pay a regular wage. It comes every week or two. Jobs are nifty. They often pay even if your sick or spend an hour or so goofing off each day. Many provide things like health insurance and offer 401ks, maybe even with matching funds for retirement. It’s fairly easy to form at least causal friendships at your work place. It’s predictable and it feels secure.

Some problems with jobs

Of course, no job is truly secure. The health insurance benefit will change, and probably not to your advantage. The company may move, or merge or get a new CEO resulting in layoffs. The friends you have at work will probably subtly or directly tell you it’s stupid to quit your job and freelance


Jobs are often boring, even soul killing.

They also control your time, or at least your time during the workweek.

Still many, even most people make jobs work. Some do this really well, although even those will at least occasionally wonder if they shouldn’t step out and freelance.

Before you quit your job and freelance consider these things

You need to know your financial situation before you quit your job and freelance.  By that I mean you need to know what your current expenses are so you can decide how much you need to earn. You also need to be aware of your debt. Set up some sort of budget and see where you might reduce your expenses without going into feelings of deprivation.  Maybe you’ll decide you do need to wait for six months income in savings; maybe you won’t.

If you’ve got a family, you’ll discuss this possible move with them thoroughly and get them behind you.

See if you can line up some freelance work before you quit. Your current company is the place to start – maybe when you give notice. You probably already know if they tend to hire freelancers or not.

Start looking for freelance work so you’ll be able to jump right into a gig or two.

If you get fired

If you get fired it may be a real blessing. You’ll collect unemployment which can make your transition easier.  Getting fired or laid off is the perfect time to make the transition to freelancing. At least in my opinion.

What questions do you have about when to quit your job and freelance?

Write well and often,

{ 9 comments… add one }
  • Ola, that’s ideal… doesn’t always work that way.

  • maybe… at least get a website going and a wordpress site is probably the simplest

  • Well, maybe….

  • Hi Anne,

    Never quit a job until you get fired. Doing freelancing should be a part-time work. Unless you have a financial back-up or any real support don’t do freelancing as a full-time job.

    Thanks for writing this.

    Reji Stephenson

  • Sorry, I mean studying and blogging should they continue both? As a student, should I do blogging along with studying?

  • Ravanchal, is your blog making enough money to support you? If not, it’s probably best to do both until it does, unless you have another source of income.

  • I’m sorry, I don’t understand your question… want to try again?

  • Ola, I agree. I don’t advise that but when someone does I help them celebrate

  • Ola

    Hi Anne,

    You have shared and discussed an interesting topic. To be fair, the best decision to take lies in your gut and ability to truly look deeply into the future.

    From a personal perspective, I will never advise anyone to leave his/job for a freelance writing if the fellow is just starting out. However, if you discover that you are making close to about 70% of your actual job wages with your part time freelance writing stuff, then you can give it a go.

    That is just my little cent from my own experience.

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