How to Go Full Time as a Freelancer: Five Painful Steps

Note: After a few horrified responses to this post, I should point out that I am wearing the pointy hat for much of this screed…that is to say I may have actually DONE this, but remember that all editors are slightly crazy and I’d never expect anyone to seriously take this advice unless they are as much of a rabid workaholic and certified nutter as I am.

There is no one tried and true way to make the jump from part time to fulltime…except possibly ONE method, the one I tried myself with great success. (How egotistical is THAT? There’s no way to make it except MY way, HAH!) Yet, when I think about it, this is the only method I know that makes any sense at all IF you have a day job you need to dump with extreme prejudice, and want to get yourself into a freelance situation where you wake up and tell yourself that your job is getting in the way of your career.

Naturally it’s a painful, isolating and downright masochistic path to follow to fulltime freelance success, which is why many people shy away from it. And who can blame them? Do you really want to suffer for your dream? You’ll find out just how committed you are when you contemplate doing “the Crazy Joe Wallace Method”. Also known as “Leaving Las Vegas, For Writers.”

What you do is decide, sort of like Nicholas Cage in that uber-depressing movie, that you’re going to write yourself to death.

Well, not quite. The actual trick is to write so hard that you WISH you were dead, but manage to take care of yourself in the meantime enough to maintain your madness. What madness would that be?

STEP ONE: It’s simple, really. You begin by committing yourself to one more full year at your day job. You won’t KEEP that promise, but you have to be clear with yourself that ditching the day job is NOT an option–at first. And at every single step of the way, remind yourself that you are taking this journey ON PURPOSE. You actually MEAN to do all the crazy things you’re going to wind up doing to go fulltime.

STEP TWO is to find a steady writing gig on the side. Any steady, paying gig will do. Commit yourself to doing five Associated Content or Helium posts a day, for example. Get hired as a blogger. Form a relationship with an editor willing to give you regular work. Start small. Think small. Think STEADY rather than GOOD PAYING. Take literally ANY steady paying work and throw yourself at it as hard as you can.

STEP THREE: Establish the trust you need with that one gig, but all the while try to find ANOTHER paying gig. Steady or not. Again, take ANYTHING. Get that second one going and look for a THIRD paying gig. Steady or not. Cram all of this into your off-work hours. Weekends, late nights, early mornings. Lunch hours. You want to start juggling your free time. You need to work yourself into a situation where you have to make serious time management decisions. Sacrificial ones. If you significant other hasn’t started expressing concern for you at the end of Step Three, you’re doing something wrong. The dark circles under your eyes aren’t dark enough, the late nights behind the computer aren’t going late enough. Think MASOCHISM. I’m SERIOUS.

Step Four: Add some additional paying work to your already tottering pile of deadlines. Force yourself into a position where you can’t possibly meet all your deadlines AND show up for work. Then, call in sick and finish your work. You are nearly there now. Remind yourself that you are overtaxing yourself ON PURPOSE. You are pushing the limits to see how much money you can force into your bank account in a single month with your words. At some point during step four, if you are doing it properly, you will be forced to resort to “daylighting”. This is where you work on your freelance projects on the company dime at your day job. Once you make it to daylighting, you are very nearly ready for full time freelancing and you will KNOW it. Remind yourself that the boss is EVIL, and then when you go fulltime freelance you can call the boss a jackass out loud when he or she is in the room…because YOU will be the jackass.

Step Five: You know you have arrived at Step Five when you have a dilemma; you are making more money now than you have in ages because of the combined income from your day job and your insane freelancing schedule. Do you stay in your day job for another six months to a year and bank a huge sum and lose your mind in the process? Or do you take a pay cut and go full time freelance? You know your pay will go up eventually once you have the whole day free to be a workaholic, but the idea of losing your big mad paydays still makes you cringe. What to do?

NOW you are ready for fulltime freelance work.

5 thoughts on “How to Go Full Time as a Freelancer: Five Painful Steps”

  1. WAITTTT!!!!! OMG!!!! JOE!!! NO!!!! WHAT HAVE YOU DONE????? Okay….so this is a…overview, but there are some MAJOR considerations missing. I think anyway….of course, I am still a corporate tool…but…think about retirement plans at work- are you close to fully vested? Is it worth it to wait until you are? That extra 20% could be really valuable! Can you afford COBRA? Your expenses will go up when you freelance since you don’t have sick time, vacation time, health insurance. You need to make sure you are making enough to cover that. Do you have a back up plan? If one of your big, steady jobs falls through, can you work for Starbucks part time to supplement? How are you planning on advancing your skills? There are always newer, better, younger, thinner freelancers nipping at your heels- can you take them? I mean, I could go on…but maybe I am too careful?

  2. Yolander,

    Oh, DETAILS? Heh….I suppose I should have mentioned that when I did all that I lived alone and had nobody to worry about but MEEEEEEE. If you have kids (I don’t and never will, luckily for the rest of the planet) or health issues or other concerns, maybe –just maybe–my insane plan isn’t a good one. Me, I lead with my face for better or worse.

    I didn’t have a 401K but have managed to get a nice little toehold on the future using the Henry Rollins method: Live below your means and live to work. I have no car payments and only one credit card bill, so maybe I’ve left a lot out of my ranty screed there….this fulltime business is NOT for the faint of heart, that’s to be sure!

    As for younger, thinner freelancers, well…I love the old saying: Age and treachery outwits youth and skill. But I ain’t a geezer yet 🙂

  3. OH PS–I ALWAYS work when “sick” unless I am just out of my MIND with fever or somesuch…but thanks to my regular exercise, penchant for red wine and vitamins, I only fall down about once a year.

  4. What about the plan where you get fired unexpectedly and realize it’s either write full time or watch your son starve to death?

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