Handling Your Fear of Starting a Freelance Career


Fellow Webcomic Alliance member Dawn Griffin tossed this question out on Twitter the other day:

“Would you rather have a steady, reliable job that you simply tolerate, or do what you love but be terrified about bills and insurance?”

Easy answer for me: Do what you love.  Not so easy for most folks, so let me try to ease the pain and tear off that band-aid most folks wear.  And that’s the pain of giving up a steady paycheck vs. the ups and downs of freelance work.

First off, I disagree with the fact that Dawn put in the word “terrified” into that question, because it’s not terrifying IF YOU PLAN!  Let me say it again: IF YOU PLAN.  Like anything you do, you can’t just jump into a freelance career and expect to be floating in cash the next day.  It will not happen, no matter what may fall into your lap.

I could end the article right here simply by stating:  Plan and promote, and you’ll be successful in your freelance career.

fl-fired-2But what you REALLY should be terrified of is being laid off or fired from your job.  The days of working for a company all your life, getting the “gold watch” at retirement and die happy are gone.  That’s the really scary part.  A company today will not think twice about protecting its shareholders over keeping you on.  So why slave away for nothing?

So ask yourself: How did the company you currently work for get to where it is?  Luck?  Rich parents?  Insurance fraud?  No.  They planned and then WORKED that plan, making adjustments along the way.

Then the real question is this: Do you want to work at a job where you’re making SOMEONE else money, or do you want TOTAL control of your life and income?  That makes it much easier, doesn’t it?  There’s no fear there, simply logic.  Why the hell toil away at a job… especially a job you’re not in love with… knowing that at a whim your employer could let you go for any reason.  They can, and they will if they think it will save THEM money.


Let me give you an example.  There’s a rule in Vegas: The house always wins.  It’s true too.  Why?  They came up with a plan which was to design games that give the players a false pretense that they can win.  But the odds are always in favor of the house.  Everyone’s heard stories of folks who took their last $100 and walked out with tens of thousands from Vegas .  For every one of those, there are a MILLION suckers who lost their shirts gambling.  The house always wins.

The key to your success is to become the house.  Be the “designer of the game” and you’ll be in control.  Now I’m not saying open a gambling house.  No, it’s a metaphor.  So don’t write me nasty emails when you get busted for running an illegal poker game in your garage.  We’re talking about freelance work here.  🙂

fl-scaredMost people let their fears run them.  They have all these “What if…?” type questions:  “What if I pay the mortgage late?” “What if the furnace breaks?” “What if I get sick?”  These are ALL negative statements that you feed your brain.  So your brain, being only so smart, BELIEVES those statements and makes them come true for you.  You can’t live your life in fear.  What if your house gets hit by a falling meteorite?  OH MY GOD!  So calm down and think about it rationally and leave those nasty “What if…” questions behind.

If you truly do your homework, you’ll be successful.  Don’t let the statistics about businesses failing in the first year fuel your fears.  But, take heed and PLAN.  Then when that plan doesn’t go perfectly (it won’t), be sure to stay calm and have an alternative plan at hand.  Soon, you’ll become so good at making plans, and adjusting them, that you won’t notice you’re also making money.

Will you be rich?  No.  But was “being rich” in your dream job statement?   No.

fl-drawingSo, what is it that YOU want to do that you love?  I doubt the words “Be rich” will part your lips.  More than likely it will be “Draw my comic” or “Make great art”.  Notice how “be rich” wasn’t in there?  But, that doesn’t mean you can’t make money and live a good life.  I’ve done it for nearly 30 years now.  You will have your failures… I have.  How you react to those failures and move on will be the true test if you can survive as a freelance person.

I know this is not for everyone, but I hear SO MANY folks complain about their jobs and say “I want to make my comic my day job.”  Then do it.  Stop talking and start doing it.  For it is true: If you build it, they will come.  I’m proof of that.


fl-pros-consI come on hard about this subject and I know there are lots of people whose path in life is NOT to be self-employed.  It is very hard work and for many the risks out-weigh the benefits.  Do a simple PRO and CON list.  You know, put on the PRO side “Be my own boss” “Total control of my career” and put in the CON side “Holy crap there’s no money in the beginning” “High liability” and see which column is shorter.

If you take the fears out of the CON side, I think you’ll see that the PRO side will win.  If not, then accept that and find a way to do what you love as a hobby.  That is totally fulfilling as well.


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  1. Really good article, Byron! Fear can be crippling to a lot of people, especially creative types. We are such sensitive creatures already. Who doesn’t experience doubt and fear of failure? I think you’ve opened a doorway to a series of informative articles for people interested in making changes in their lives towards doing what they really want to do, and finding a way to make it work financially, as well. You mention planning as being a really important part of that transition. Could you go a little more detail as to what a good plan might entail?

  2. Entrepreneurs also have a certain “financial profile”. They tend to be people with a high risk tolerance and a high propensity to save. They thrive off the uncertainty of the business and are able and willing to live on a tight budget. They also find spouses who are willing to support the business. The spouse either is working for the business full-time, help with the business on the side, or have no problem with the uncertainty that owning your own business can create and willing to sacrifice when things are tight and uncertain.

    So do you fit the profile? Do you thrive on uncertainty? Can you live on a tight budget? Will your spouse support you and not divorce you?

  3. Yep, I was thrust into my current situation by the good old outsourcing of my job. Which really gave me little time to formulate a plan and had to wing it to survive (hint: it hasn’t been going too well). Hindsight, wishing I had known about being outsourced (company said my position was the safest in the department, was called into a meeting and supervisor shrugged and said probably giving you your duties as the only employee of the department) so I could’ve laid the foundation of a plan, but alas, lied to by many parties (supervisor stayed in the company, same office, just a different title…because he was the director’s brother-in-law…oh, and the director kept his place in the company too…so I think they all knew my fate but chose to lie) and didn’t have that luxury. Hole I was tossed in turned out to be mighty deep, so I am still trying to form a plan that actually works. It’s never easy playing catch-up.

  4. I just came across this article. I didn’t know where to post it. This subject I think is a common theme in the podcast. It’s not about just being a good artist or a good writer, it’s about combining your various skill sets to become successful.

    How To Succeed When You’re Not Good At Anything In Particular

    Read more: http://oliveremberton.com/2013/how-to-succeed-when-you-have-no-special-skills/#ixzz2nJBxcEIA

    “Individual skills are common. Combinations are rarer. If you want to raise your value, take a step back from your strengths, and consider building a broader combination of them.”

    I’ve managed to this with my existing career and I am trying to do the same as a web comic entrepreneur. I’m building some new skill sets but they will be complemented by my existing ones.

  5. Thanks for this advice I’m about to launch my new web comic and go 100% freelance and at present feel a bit like Im about to dive from a cliff ,but hay ho.

    • Aron, good-luck! It’s a very hard first step and filled with lots of doubts and questions. Take it day-by-day at first. Don’t think about your rent and/or mortgage payment in 3 to 6 months, think about next month’s and how to leap that goal. Each month it will become easier.

      There are days when I’m broke I question whether I made the right decision or not. But then I look at my three sons and I know I was around them while they grew up and their memories of me aren’t just me leaving for work in the morning and coming home exhausted late at night.

      To me, that makes it worth it. 🙂

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