How I Got into Freelancing

Posted on Oct 18, 2011 in freelance | 0 comments

When I was in college, slogging through mountains of reading as an English major, I had this grand idea that I would one day have my own freelance business.

At that point, I was already freelancing a fair amount for various companies, so the thought didn’t seem crazy to me. I liked the idea of having control of my time and creativity on a long-term basis. I wanted to be a career woman but still have the energy for a future family. Freelancing seemed like the perfect fit for me.

I fell into freelancing in college at the encouragement of my dad—a successful financial consultant with a nicely groomed network. With his help, I landed my first corporate clients and an editorial internship at that later led to more freelance projects.

Through my freelance work, I built an impressive resume that paved the way for a decent in-house writing job after college.

That initial freelance work also gave me a taste of a lifestyle that I’d never be able to fully forget.


My Intro to the Corporate World

When I got my first job out of college, I was a fresh writer with a fresh perspective. I was enthusiastic and optimistic and hard-working. I ran circles around many of the older employees, who often lacked spark and ambition.

But my eyes were soon opened to the plague that can set in on companies that aren’t careful. As my company grew, things were changing, and the work life that seemed so great at first was slowly turning sour.

I learned first-hand the effect that a bad work environment can have on a person—particularly a creative person. With its control and mind games, I saw the workplace squash the life out of the intelligent, fun-loving, ambitious people around me. We were all on our way to becoming dull-eyed, mechanical, pessimistic, gossipy creatures.

The 9-to-5 schedule that had been tough right after college suddenly felt brutal. It was too much of my life to give to a cause I didn’t believe in. So much of the system seemed inefficient to me, with two-hour-long meetings that went nowhere and projects that never seemed to end.

I struggled with the politics of the corporate world—I consistently found myself back in high school, questioning whom to trust. I was ambitious and wanted to excel faster in the corporate system, but I felt so many things holding me back. I also wanted a mentor to help me learn the ropes better and faster, but my options were limited.

I had not been prepared for this in college. This was what people were willing to give for (limited) money and stability? What was I willing to give? What mattered more to me?

I understood that not all companies are like this, but that knowledge didn’t matter much. In the end, the whole environment depressed me, and I wanted out.


Jumping from a Burning Ship

A bad work environment can make you do desperate things—particularly if it is your first real job out of college and it is all you’ve ever known of corporate life.

One day in 2009, I decided I had hit the limit of what I could stand, and I quit. Out of the blue. I gave 12 days’ notice and waited to be done.

I didn’t have another job waiting—I hadn’t really even been looking. I was jaded, and scared to enter into another potentially disastrous workplace. But I couldn’t yet get past the fear of NOT having a stable job. I still valued money and health insurance over my sanity and ultimate fulfillment.

When my last work day came and went, I took a two-week break from it all, then started searching for something else. I found my next company and had another stable job within a week.


Burn Out

The environment at my new company was a hundred times better, but I soon discovered that the actual job I was doing was the exact same. I was a copy monkey, required to churn out writing but not think too much.

Suddenly, I realized this was also a problem for me. I already knew I could do this job; I needed a new challenge and new ways to keep my mind and interest alive. I found myself in a brand-new job with a desire to look elsewhere, which felt wrong.

I was so burned out by this point, I hardly knew how to think straight.

The idea to freelance full-time was never very far away, but it still seemed impossible. How would I manage to support us—to put my husband through his final year of college—if I quit my job like this? It seemed so selfish; there was no guarantee that it would all be okay. So I stuck with it.

The new job was fantastic. I could actually stand behind the company’s products, mission, and executives. I adored so many of the employees that I worked with. But there were still problems, of course. I was one of the only professionals my age. I was surrounded by managers but not actually a manager myself, which was difficult at times. There were still lots of politics and gossip, and problems seemed to be escalating.

I was also sacrificing more to be here. My first company had been a 7-minute drive from my house. This new company was a 45-minute drive. I had to figure out what to do.

Perspective is an important thing to note here. Yes, I was dealing with frustrations, but I was also allowing those frustrations to affect me emotionally. I allowed my situation to kept me in a perpetual state of burnout–which fueled the idea in my mind that the grass must be greener on the freelancing side of life. Mentally, I was too far gone to be happy in my corporate life again. I had gotten the idea in my head that it was time to try something new, and I wouldn’t be happy until I got there.

So my desire to leap built and built over the course of several months–and I let it build until it ultimately pushed me back into a crazy risk-taking mode. I found myself asking those self-seeking questions again: What was I willing to give up to keep my sanity? What was I willing to change within myself to make it happen?


Getting the Ball Rolling

In winter 2009, I finally latched onto the idea of quitting my job and starting a full-time business. In truth, I was feeling a bit reckless and overly hasty about freelancing, though, which is never a good state to be in when you’re trying to make an important life decision.

The good thing about such a wild state of mind is that it really helped me to relax and reevaluate the importance of certain things. I had spent years obsessing over the supposed importance of money and the idea that I didn’t have enough of it to feel stable. With the onset of my newfound interest in freelancing, I suddenly didn’t care about money or health insurance anymore. Money was just a means, and it would come. Living life more slowly and truthfully was now more important than living the fast, material life. I was no longer willing to sacrifice myself to an imaginary system, and I felt a huge relief from that new mentality.

Through all of this, Ryan was my rock and my stable sail. He was completely supportive of the full-time freelance idea. Thank goodness he was also practical. I was ready to quit right then and there, but he convinced me to stick it out a bit longer. He saw a safe way out for me, which would help give me what I wanted without destroying the financial stability I’d worked hard to achieve.

The safe way was this: in spring 2010, Ryan’s industrial design program required that he do an internship. If he could find something that paid well enough, he could support us for a few months while I got my feet under me.

It took all I had to not quit immediately, but it helped to finally have a reasonable plan—and a deadline.


Leaping with a Safety Net

Once a plan was in place, I wanted to tell my boss, so she would have time to find a replacement for me. In early 2010, I walked into her office and shared the news that I’d be leaving in a few months. I explained that Ryan had to get an internship for school and I wasn’t about to let him have all the fun without me. I also explained that it would be a jumping-off point for a freelance business I’d been dying to start for years. She was very supportive, though I think a little panicked that I was leaving her.

Then the countdown to my release began. 4 months, 3 months, 2 weeks, 1 day.

In the time that I waited, I read a shelf of freelance writing books and made a lot of goals and plans (all overly general and ambitious). There were days I was a bit terrified and couldn’t believe I was doing this, and there were days that I wanted to jump the gun and start my new life immediately.

April 22 couldn’t come fast enough, and then suddenly it was here. And I felt stress in other ways. Okay, was I actually ready for this? How would I handle the freelance life? Did I have any idea what I was getting myself into?

The short answer: no, I did not. But that was okay.

Ryan managed to land an awesome internship in Cincinnati that paid unbelievably well—as in, better than my salary at any of my professional jobs. (I admit to only a hint of jealousy.)

His full-time work that summer helped to support us while I pushed past the incredibly overwhelming task ahead and slowly figured out my new system, my new life.

This whole experience–from corporate life to freelance life–gave me (us) a solid foundation on which to build a more flexible life. It also gave us the freedom we needed to take a random trip to Europe. It’s amazing how way leads on to way, isn’t it? Even today, I find myself wondering if I shall ever really look back.

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