When Your Parachute Says Cliff-Diver: What I Learned About Being a Freelancer

Richard Nelson Bolles wrote the book What Color is Your Parachute? in 1970. The job-hunting classic is all about how the job hunter has just as much to offer the employer as the employer has to offer the potential employee. The gig economy of today has created a completely different job market than what existed when Bolles was writing, but the overall message still rings true. But I didn’t realize just how true it was until I decided to become a freelancer.

In March 2013, I took a big leap — perhaps one of the biggest leaps of my life. I decided to quit my job and become a freelancer. Unlike other writers who delved into freelancing while working a day job, I quit my old job having made just $15.00 in freelance income. If this sounds like a potentially foolhardy proposition, that’s because it was… why on earth would I take such a dramatic leap into the great unknown!?!

Well, it all started when I was at a crossroads with my office job, which was veering into territory that was in conflict with my values. But even without that drama, I always knew I wanted something more. I had an entrepreneurial mindset and I wanted to see what I could do for myself. Most of all, I realized that I didn’t want to be an office worker.

I embarked on a new career with nothing but the clothes on my back and a few key strings in my parachute: expertise from years of reviewing books and managing websites, sales, research and management skills I developed working in a law office and bookstore, plus a some college degrees I hoped were not as useless as they sometimes seemed.

As I walked toward the edge of the cliff, I reflected on how I got here. I had been convinced that my Master’s Degree in Corporate Communications was the key to the $60k job, and that job would come with benefits. After I graduated in 2009, I realized that this job didn’t quite exist. In addition to a few years of working full time in real estate, law and retail, I had also acquired a supportive spouse who believed in me and didn’t think this was the craziest idea ever. I am married to a solo lawyer, so I know the power of hard work and belief. So I did it. We were about to enter into a world where our household depended on the incomes of two people who were self-employed. Were we wise? Yes.

Our household depended on the incomes of two people who were self-employed. Were we wise? Yes. Click To Tweet

Now, four years later, I’ve learned a lot. I’ve increased my income enough to get an office that I can pay for without my spouse’s help every month, I pay many of our bills, and I am so far away from that $15.00 I made while working from a coffee shop.  I’m not the writer pictured on the Facebook ads, you know the one: “I was struggling to make ends meet and now I make $6k a month OR MORE working three hours a week! Click here!” No, that’s not me, but that’s okay. I never stop learning about this wild world of freelancing and I keep adjusting my approach toward the job. This is what I’ve learned:

You have more skills than you think you do.

If you’ve ever looked at your resume, concluded it was trash and gave up in a huff, then we have something in common! No one is immune to feeling like they haven’t accomplished enough, but the most important thing you can do is look at your experiences and realize that they all give you marketable skills.

All those years I spent in high school, college, graduate school (and yes, even after graduation) working as a bookseller have served me well. Selling books taught me self-confidence, how to communicate effectively with other human beings and also how to sell. I always enjoyed making the just the right book recommendation for the parents and kids who would approach me in the bookstore, but it took me a long time to realize that this was also a valuable skill.

I started book reviewing and blogging about books as a hobby, and I was fortunate enough to interview some bestselling authors before I called it quits as a blogger. But what did that have to do with my present, when I needed to make money and hoped to do it through writing? Actually, it had a lot to do with freelancing. Communicating professionally with writers and publishers, completing reviews on time, and promoting my website gave me a few skills, not to mention the ability to navigate programs like Canva and WordPress.

After I graduated, I found a job in an office that had nothing to do – or so it seemed – with my degrees in English or Corporate Communications. Although this particular industry was unrelated to the things I loved, it exposed me to another world. That job taught me about SEO, digital marketing campaigns, sales funnels, call-to-action and so much more. This job also taught me how many businesses were outsourcing their writing, editing and social media marketing tasks, often finding freelancers on websites like Fiverr, PeoplePerHour, Upwork and other third-party sites that are designed to connect freelancers with businesses.

I promise that you too have skills you take for granted. If you have kids, for instance, then you know all about time management, communication, negotiation, organization, collaboration and guess what? People online will actually pay you to do stuff like this for them.

When Your Parachute Says Cliff-Diver: What I Learned About Being a Freelancer

Know your worth and be willing to work.

The most common complaint I hear from new freelancers is that they don’t want to work for just $5.00 or $15.00 per project. No one does! But in my experience, starting at the bottom and being willing to work many hours paid huge dividends more quickly than I could have imagined. Like everyone, I would love to earn enough money to pay the mortgage simply by writing about pop culture for some online magazine. Instead, I went where the money actually was – with corporate clients.

Now I am a writer for hire. I’ve written about locksmithing, music, plumbing, television, celebrities, animals, asphalt, dentistry, artificial grass, makeup, beer, weight loss, health and yep, even kitchen sinks. I never thought I would be writing in these areas, but a job is a job. Without these opportunities, I also wouldn’t have been able to land my dream job, which is collaborating on the website FairyTalez.com. Sometimes I have to pinch myself to realize that it is not a dream, I get paid to write about fairy tales! I also have fun writing viral content about all kinds of things, and who would’ve ever thought that I’d earn writing about “Celebrities you didn’t know were a twin!” (Not me.)

For me, knowing my worth started with creating my own lane. I built a portfolio on several sites that connect freelancers with corporate clients. I proved my worth by churning out copy that was memorable, informative and did exactly what my clients wanted it to do. After I built a reputation, I started raising my rates. It’s often scary to ask for more money, but I have clients who have stuck with me for four years and multiple rate hikes.

I have no doubt that if you are reading this, you can create your own niche, too.

No one will make you work but you.

You must be a self-starter in freelancing. It can be all too tempting to sit inside and watch TV for hours, especially if you’re not feeling well or the weather is poor. I admit sometimes I stay inside and work in front of the TV, but most days you’ll find me “grinding it out” in my office. If I don’t have a routine, I lose hours of work, and hours lost means money lost. I work for hourly clients, as well as clients who pay for batch work, so I have to be mindful of what I’m completing so I know what’s my rate is. However, the temptation to not work can be great, and you have to circumvent it. For me, getting an office was the way to make sure I used my time well.

This doesn’t mean that everyone needs an office in order to maximize work time. Do you have a room with a door? Does your town have a library? What about a shared co-working space? I know many freelancers who work using some combination of these spaces and it helps them earn more money than they would make otherwise.

This is no 9 to 5…yet.

Try as I might, I haven’t made my freelancing work 9 to 5. I will check email before bed, often at 11 P.M. or 12 A.M. This isn’t a good habit to get into, but it’s my habit. I try to work 9 to 5, but like most of our best intentions, it doesn’t always work that way. Sometimes I just couldn’t sleep, or I want to take a look at a project really quick, or I’m responding to a client halfway around the world, and then it’s 2 A.M! If you are considering freelancing, know that it’s not a 9 to 5 unless you make it. On the other hand, freelancing provides you with greater flexibility. As long as your projects get turned in on time, your clients don’t care when you did the work.

Never compare yourself to others.

It’s easy to say but harder to practice: don’t compare yourself to others. If you’re freelancing and you see one of those ads — the “I earned _______” type of ads — don’t start doubting yourself or comparing yourself to others’ success.

Don’t be afraid to say no, but also don’t think everything is going to be the perfect job either.

I say yes to projects a lot. Sometimes it means that I take on too much and I’m scrambling. Sometimes it means that I’ll learn something new, which I can then use for future projects. Sometimes it wasn’t a good match but I didn’t want to say no, so I said yes. Don’t do that!

If you want to say no, just say no if you feel the reason is right. I get offered some jobs that I just don’t think I can do, or I think the pay is too low or maybe I don’t feel right doing them, and I say no. I hit decline on the job invite or I write a personal response.

I am, however, realistic about jobs. Sometimes not every project will be a passion project for you, but instead, it’s something to pay the bills. That doesn’t mean you can’t do it with passion, however, and you should endeavor to do all of your jobs with passion, because it will show in your work. I am so very happy to work at Fairytalez.com as its Editor in Chief, but I am also happy to work with talented content companies, web designers, and other clients. If you go into freelancing, don’t think that you’ll be writing about just things you love, because that isn’t realistic, nor is it a way to challenge yourself.

...at least I know that I’m working for myself, on my own terms, and paying my own bills. Click To Tweet

Freelancing isn’t perfect. I work when I’m sick, sometimes it takes awhile to get paid, and often it’s feast or famine. But at least I know that I’m working for myself, on my own terms, and paying my own bills. That’s more than enough to keep this freelancer soaring above the ground.


Be sure to follow Bri on Twitter at @briannaahearn and check out her work at whatthefangirl.com and ahearncreative.com.

There are 5 comments

  1. I am standing on the edge of this cliff and looking over with equal parts trepidation and glee. I am so close to making the plunge…

    Thank you for this article. It is quite encouraging 🙂

  2. I love your practical approach. I’m honestly tired of hearing all of the “instant” success stories, and would rather read about someone who put in the work for longer and realized a slower, but stable success.


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