My Freelance Life: Why I Started On The Road To Self-Employment

“Nobility, to me, is using your creative talents to invent a job for yourself and getting paid a decent wage to do it.”Michelle Goodman, My So-Called Freelance Life

The thing about freelancing is that you gotta have the chutzpa to carve out your own spot in your industry and dance to the beat of your own drum. It’s not always easy and being new to freelancing (like me) it can sometimes be really scary! Here are some stories on what started these alterna workers on their freelance path!

Liz Andrade, CMD+Shift Design

Web design and Front-End Development.

I made the freelance leap just over 8 months ago. It’s been both exhilarating and terrifying. I have had an ebb or two in my flow, but nothing catastrophic. My daily mantra is “make it work”, and I am doing just that.

It wasn’t until only about a year and a half ago that the prospect of working for myself even occurred to me. I had a stable staff position at a small local creative firm but was not feeling financially or creatively satisfied and began looking for a new 9-to-5 gig. I spent every night after work reading job ad’s and after just a couple weeks had my first interview lined up.

After going over the interview basics like education, skills and experience, the interviewer asked “So what do you think you’d like to do in say, 5 years from now. What’s your dream job?” I admitted “I’d love to freelance! Start my own business.” He nodded and marked something down on his notes then replied “and what’s stopping you from doing that now?”

So now I’m sitting there in this swanky conference room, and I was dumbstruck! flabbergasted! My mind had officially been blown! I spit out some answer about needing stability at this time in my career and blah blah blah. But by the time I walked out of the building, I’d already made up my mind. I was going freelance!

2 weeks later the prospective 9-to-5 offered me the staff position and I turned it down, stating I had already committed to another position.

Jeff Fisher, LogoMotives

Engineer of Creative Identity

In my case I didn’t choose to work as an independent designer – it chose me.

In 1980 I moved to Portland, in an economy much like today’s. Several design and advertising agencies has closed, and many creative types had been laid off. There were no jobs to be had.

Many firm principals, art directors and creative directors took the time to participate in informational interviews with me. With a portfolio of real world work, from my college job as advertising designer for the daily university newspaper, these individuals saw something in me that resulted in contract work coming my way from their firms and those given my name.

Nearly 30 years later, I have worked independently all but about 3.5 years when I took on full-time positions to gain additional experience I felt was necessary for me to better work on my own long-term.

Niki Brown

Graphic Designer & Illustrator

I decided to start freelancing shortly after graduating. I was afraid that my design skills would grow stagnant because I had an in house web design job. So my motivation was to keep all my skills sharp and to try new things. I had a lot of free time on my hands and decided to go for it. I caught some lucky breaks and ended up with some great and interesting clients! Eventually I would like to be a full-time freelancer, but that’s a ways down the road. For now I’ll just enjoy the extra income to blow on cool designy things! :)

Joshua Mauldin

Art Direction, Design & Photography

My decision to go freelance was a gradual one. I started to see more and more benefits for working on my own as I grew in design.

Working freelance gives me an amazing ability to jump from one kind of project to another. Since I do more than design (I do light development and photography, too) I don’t have to worry with being too bored or getting sapped creatively. It’s also very helpful in dry times when one specific kind of work runs a little scarce. All I’ve got to do is beef up on another skill and I keep moving.

Being in an office or studio can be fun, but they’ve got some pitfalls. For instance, I’ve never been in a place where there wasn’t some degree of drama or office politics. I don’t do office politics personally; they’re inane and very high school. Working freelance insulates me from that.

One of my previous jobs was being a project manager and designer for a small firm, and I got to see lots of things designers didn’t normally get to see. Namely how much money came in for a project and how little of it you got. It’s true you’d have more responsibility if you went it alone, but the benefits of doing it would be immense.

I also realized you have just as much to lose staying in a job you don’t love as you do striking out and going it freelance to pursue jobs you do love.

I get such a sense of satisfaction working freelance. I can take on the projects I love and leave the ones I don’t. I get to work directly with my clients to make sure they get the best service I have to offer. If I feel like relaxing a little during the day, I can take the afternoon off and play Wii or read a good book with no problems.

Thanks to those who contributed to this post! I’d love to do an other edition to this entry, so if you have a story to share, email me.


  1. Smart topic, Liz! I’m halfway through Michelle’s book and am thoroughly enjoying it. :)
    Good bg everyone! Great reading other perspectives.
    While I’m a tweener walkin’ the fine line of freelance and 9to5, my hope is to get all the way to freelance and then I’ll tell ya my story. LOL.

  2. as a freelancer, i sometimes wonder and worry if web workers have a sustainable future. it certainly makes sense from a time, flexibility and cost saving perspective, as a whole lot of tasks can be done from home. if you have the right personality (ability to self motivate), skills, and tools (i use HyperOffice) web work is for you!

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