I was eleven when I removed two of my front teeth with a pair of needle nose pliers.

Many use the phrase, “like pulling teeth” to describe a very difficult process. If you’re just starting out as a freelancer, chances are good that you’ve not yet encountered the tooth-pulling part of the gig.

If you’re a veteran, you already know what I’m talking about. You know about the late nights, uncertainty, and self-doubt in the face of impending deadlines. You know the depth of character and creative tenacity it takes to succeed as a freelancer. It’s not easy. But nobody said it needs to be. I believe freelancing, especially in its early stages, should be much like pulling teeth.

I was eleven when I removed two of my front teeth with a pair of needle nose pliers. The family dentist had said my teeth would be just like my older sister’s. Instead of her upper canines (you might call them “eye teeth”) pushing her baby teeth out, they poked through the front of her gums like poorly crafted vampire teeth.

I had seen my sister’s embarrassment over her teeth and discomfort wearing braces. I had seen how she never wanted to smile because people would suddenly break focus to look at her mouth. I was terrified of the same thing happening to me.

I knew what I had to do.

I went to my father’s toolbox and found a pair of needle nose pliers. I had seen my mother sterilize a needle over a gas flame before removing a splinter from my hand. I did the same with the pliers. The metal was still warm as it touched the inside of my upper lip. The pliers were the locking type and I had to adjust the lock setting so I could close the pliers on my tooth.

I watched in the bathroom mirror as I placed the pliers over my right tooth. I heard the slight crunch as the metal grooves on the pliers dug into my tooth. There was a click as the pliers locked. I let go of the pliers and they rested against my chin. My head felt heavy.

I wrapped both hands around the pliers, squeezed, and pulled as hard as I could. The tooth dropped into the sink in a rivulet of blood as I unlocked the pliers. I bit down on a wad of paper towel to slow the bleeding. I tightened the pliers on the second tooth and yanked it free.

I drooled blood into a cup for a few hours. Then it was over. My father had the odd habit of keeping all the teeth his children lost in a glass bottle. I held my drool cup in one hand as I dropped the washed teeth onto his desk with the other. He looked at the teeth and saw the marks from the pliers but said nothing.

It was done. I never got those dreaded vampire teeth or needed braces.

There are times when freelancing is going to feel “like pulling teeth.” I’m here to say that you need not be fearful of the hard times. I’ve put together five steps, inspired by my childhood recklessness and proven in my own career, to help guide you forward. If you’re already a veteran freelancer, I hope you’ll add a few of your own tips in a comment.

Define your desired result

Why do you want to be a freelancer? “I want to be my own boss and make lots of money” is a popular reasons to jump into freelancing. Sadly, most of us want to be our own bosses for the wrong reason. We focus on the negative traits and habits of authority figures instead of figuring out ways to be more productive and enjoy life more!

The trick, and this is where it gets truly difficult, is to clarify what you want out of your freelancing experience. I’m talking about digging deep and figuring out what will drive you to keep trying even when everything goes wrong. What will be your guiding light?

Take a 3×5 card or a piece of scrap paper and write down a few lines describing what you want out of your experience. What do you want for yourself? What do you want to provide to others? Now put that piece of paper in a safe place. You’ll need it when you forget why you started doing all this.

If you’re going to make a real go of freelancing, you’ll need a reason to pull your teeth out. What’s your reason going to be?

Gather as much information as possible

Now that you’ve clarified what you want out of freelancing, the world is your easily-pried oyster. It’s time to get some grunt work out of the way. There are 3 basic motions that worked well for me when I first started freelancing:

1. Join a community - Pick up a book on freelancing, join an online community, and dive headfirst into everything you can find that covers your area of expertise. Track down successful freelancers in your intended area of business and soak up as much information from them as you can. Blogs can be a great way to meet freelancers willing to share advice based on real experience. If you have specific questions, forums like the one on this site can prove very helpful.
2. Practice your craft every chance you get – If you can’t stand doing “dry runs,” pick some local non-profits and put your skills to use for them. A quick note about working for non-profits: Make sure to clearly describe what you’ll be doing and what you can be counted on to do in the future.
3. Start a blog – You’re the smartypants intent on making it big as a freelancer. Why not let the world into your head and share your innovative thoughts on changes taking place in your field of expertise? You don’t need to write ponderous articles about the state of your industry. Share things you find interesting and do so regularly.

Don’t waste money on frivolous gadgets

Make a list of the basic tools you’ll need to get your work done and spend as little money as possible for the best quality you can find. It’s okay to have a list of things you’d like to purchase once you’ve made it big. Until then, get excited about how much you can produce with the lowest possible capital investment.

An easy way to keep from stacking up unneeded expenditures is to force yourself to write budget proposals. When Aunt Gretna’s PayPal payment for $35 clears, you’ll be tempted to raid your piggy bank and splurge on a new laptop. Sit down and write a budget proposal. If you can explain on paper why $35 in gross income warrants a $1,000+ expenditure, your future as a copywriter is paved with gold. The more likely result is that you’ll get back to work on your clunker and wait for real income before you start spending real money.

Look for the least inopportune moment

There is almost never a perfect time to do anything. It will rain on your wedding day, your website won’t be perfect, or your teeth might not be perfectly loose. That won’t matter to you though. You have your goal. You know what’s driving you to find success. You’ll find that success by looking for the least inopportune moment. That’s just another way of saying to find the best possible moment while giving yourself room to make a few mistakes.

You’re going to have doubts, misgivings, and questions about things might be done differently. If you’ve done your research, connected with the right people, and have good tools, you’ll be able to make adjustments on the run. If you’ve taken this whole freelancing thing seriously, you’ll be in a good position to start. The trick is in giving yourself a chance to start!

Pull as hard as you can

When it comes to pulling teeth, personal experience dictates that a firm grasp and a hearty pull make for the best results. The same goes for freelancing. If you’ve got the right tools and a firm grasp on what you’d like to accomplish, you need simply to pull as hard as you can. It won’t be easy but you can do it if you work harder than you’ve ever worked before and ask for help when you need it.

Many use the phrase, “like pulling teeth” to describe a very difficult process. But when I hear those words I’m taken back to a moment early in my life when I saw my future and decided to change it. You have a chance to do something similar now. I don’t recommend doing your own dental work but I do suggest leaping at this opportunity with everything you’ve got. In the heartfelt words of Conan O’Brien,

“If you work really hard and are kind, amazing things will happen to you.”

If you have any questions, check out these tips for new freelancers, join in the forum, or just leave a comment below. We’re glad you’re here!