Freelance In the Arena
Freelancing

What It’s Like to Be in the Arena: My Foray into Freelancing Full-Time

October 22, 2015

For as long as I can remember, I’ve prided myself on my observational abilities and liked hiding from the world.  I was way more comfortable watching my brother play video games than taking at stab at leveling up on Sonic the Hedgehog myself. Even though I’m known to be a “loud introvert” and a bit hammy, I see myself as an in-the-background type of person, a fly on the wall, the ultimate observer. I don’t even really feel comfortable talking about myself on my own blog.

So when I started Cheapsters back in 2009, it was originally a way to help my friends through the Recession. It was an ultimate testament to my Cheapster livelihood, to a life of frugality and yearnings for financial independence. And just a few years ago I’ve started to focus on helping my friends who freelance. I lived vicariously through them, to understand what it takes to do amazing things, like build an uber successful Etsy Store, or to do so much with less.

Although I blogged about it, I wasn’t totally part of it. Sure, I saved my beans like a mofo, but I was passively watching from the sidelines. I was secretly jealous of how free they all seemed, how they managed to break from the 9-5 grind. I was really drawn to the idea about saying no to money and saying yes to your free time, to what you love to do. Aren’t we all?

I’ve been a 9-5er for nearly 10 years. I think a bit part of why I did it was due to my natural inclination toward what seems “safe”. It was also partly because I think of my self-image as being “the steady one,” at least in a financial sense.

And in just a short amount of time, that has seemed to change.

About three months ago I took a mini-leap of my own: I went from a steady, full-time job with benefits (a job I actually enjoyed) to accept a contract assignment that I felt was more along the lines of what I really want to do: write and educate others about personal finance. It was super scary, and it felt like a big risk.

That assignment ended much shorter than anticipated, and the funny thing was that although it was a shock initially, I wasn’t totally bummed about my situation. I realized that it was time to do what I truly wanted: to write, make time for my passion projects, and go crazy! (No, not really.) I think deep down I was waiting for this opportunity to present itself. So I decided to just roll with it.

I’m going maverick, y’all.

And you know what? I’m only at Week Four, and what an interesting four weeks it’s proven to be. I am quickly realizing that preserving your freedom means fighting for it.

There is this longish quote by Teddy Roosevelt that I remember reading when I was a teenager that really spoke to me:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.

I know it’s a little hokey, but I’ve financially managed to “take the leap” and give this freelance life a real go.

Sooo…here is:

The Freelancer Pact I (Jackie) Am Making to Myself

I will commit to this freelance life for a year, reassessing my progress and goals every three months. I am trading money for time instead of time for money.

I will go on a minimalist spending purge, meaning:
-Minimal paid entertainment (eating out, movies with friends).
-Only necessary gift giving.
-Will spend money on only essentials such as food, household items, and items related to growing my business.

This isn’t about making tons of money. This is about survival and experimentation, and creating the life I’ve always wanted to live. I am curious to see what I can learn, and how far I can take this so-called experiment.

And the truth is, I’m a little scared. Terrified, in fact.

Wish me luck, guys! (gulp)

 

 

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