Freelancing is a form of rebellion

Table of Contents

• The background

• Choosing the “right” path

• The worst year of my career

• The turning point

• Discovering freelancing

• Becoming a full-time freelancer

The background

I’m a rule follower.

Ever since I was little, one of my biggest fears was breaking the rules.

Skip school? Absolutely not. Toilet paper a house? No way. Cross the street without looking both ways?? I would never.

I pride myself on following “the rules” and doing the right thing. Not only am I risk-averse, but I also never want to disappoint anyone, especially my family (raise your hand if you’re also the eldest daughter 🙋🏻‍♀️).

Choosing the “right” path

This follow-the-rules-always-do-the-right thing mentality followed me through high school and all the way to college. In this case, doing the “right” thing meant working towards the ideal career path: graduating, getting an entry-level job, working my way up the ladder, and padding my resume with well-known companies and impressive titles.

When it came to choosing a major — and ultimately a career — I didn’t know exactly what I wanted to do. (Isn’t it crazy that we’re expected to choose a career at 18 years old before we have any real-world experience?).

All I knew was that I wanted to work in media à la Lauren Conrad on The Hills (IYKYK). During freshmen year, one of my professors told us that public relations typically offered a lot of job opportunities, so that’s what I chose. Because it sounded like a fail-safe career.

Once I chose this path, I did everything I thought I was supposed to do to set myself up for success after graduation. I got good grades, joined student organizations, networked, and learned everything I could about PR and media.

I even had four internships (3 of which were unpaid…yikes) so I could get real-world experience. One of these internships was at a local PR firm and required making media appearances on behalf of one of the firm’s clients, a local sandwich shop that hosts an annual Turkey Trot.

This wasn’t exactly like the glamorous internships I’d seen on The Hills, but hey, it was a step in the right direction. Everything would be worth it when I graduated college and landed my first real job, I told myself.

I graduated in May 2015 ready to hit the ground running and start my new adult life as a working woman.

The worst year of my career

I spent the next year going to countless job interviews. I’d get an interview, make it to the final round, and then get ghosted or rejected. Each time, it felt like I was one step closer to actually getting the job. But it always ended the same way. I can’t even remember how many job interviews I had, but I can tell you that none of the rejections got any easier.

Fast forward to May 2016, one year after graduating college, and I still did not have a job. I was living back home with my parents and picking up random gigs in between interviews.

I felt like a complete failure.

In my mind, I did everything right. I went to college, decided on a “stable” career, and got multiple internships to prepare me for that career. I networked. I passed my resume around to everyone and their mom (literally, one of my friend’s mom’s tried to help me get hired).

But nothing. No one would hire me. It was depressing and demoralizing.

If you’ve ever struggled to find a job, you know this feeling all too well. Job searching takes over your life and every day you don’t have a job is worse than the last. The process makes you doubt your capabilities and question every choice you’ve made that led to this point. 10/10 would not recommend!

The turning point

Finally, in 2016 I got a part-time job with a very small local marketing agency. I was an independent contractor and worked about three days a week out of a coffee shop with the agency founder. Was it the big girl office job I had dreamed of when I graduated? Not even close. But it was more than I’d had up until this point, and I was grateful. (I also want to note that I was still living at home during this time and I’m immensely grateful to my parents for supporting me. I know that not everyone has this option, so I don’t take this lightly!).

I continued to interview for full-time jobs in PR and marketing, thinking that landing a traditional 9-5 would be the ultimate marker of success. At one point, I had three part-time jobs in completely unrelated fields in hopes that this combination of experiences would somehow help me get hired somewhere full-time.

Eventually, I was tired of waiting around for someone to hire me, so I took control of my own career. 

Discovering freelancing

During a shift at one of my part-time jobs, I was scrolling a job board when I came across someone looking for a freelance blog writer. I had experience writing blog posts for the marketing agency I worked with so I figured, “Why not?”

I got the gig, and within a week I wrote my first freelance blog post for my first freelance client. I got paid a whopping $20 per post — and I was so proud. This was the first time I felt in control of my own ~destiny~ so to speak.

I started pursuing more freelance work. I did all types of writing, from journalism to blog writing to copywriting to ghostwriting. I even did social media work for a while. I worked with companies of all sizes from small businesses to media conglomerates, and across a range of industries from fashion brands to cybersecurity websites.

Looking back, it’s crazy to think that I tried so many different types of work (and with very little experience).

But that’s the beauty of freelancing — you can just decide you want to try something and no one can stop you. There are so many opportunities to learn new skills, explore different industries, and figure out what you’re good at.

Becoming a full-time freelancer

In 2019, I officially gave up on my search for a full-time job and decided to go all in on freelancing. I stopped trying to follow the “ideal” career path.

I tried that, and it didn’t work for me. What did work was freelancing — so I bet on myself.

Freelancing was the first rebellious act I committed.

It wasn’t the typical career path. No one in my inner circle was familiar with freelancing, and sometimes people were confused about what I did for work. (I think people also thought “freelancing” was code for unemployed or in between jobs).

I’m not gonna lie — my lack of 9-5 experience certainly made me question my worth more than a few times. I wondered if this was the right move and if I’d ever be taken seriously without an impressive resume to fall back on.

But five years into full-time freelancing — and nearly 10 years since graduating — I can say that I finally feel confident in my career. And breaking free from what I thought was “right” helped me get here.

If you’re at a turning point or you’re feeling lost in your career, I’ll tell you what I wish someone had told me during those early days: there are no rules. 

There’s not one “right” career path. You don’t have to pursue a full-time job if it doesn’t feel right. There’s nothing wrong with getting a part-time job at a coffee shop or a restaurant or a retail store.

Our careers are long. If you want to try something different for a while, you can. If you want to experiment with freelancing on the side, no one’s going to stop you. If you want to completely start over, I bet there’s a way you can make that happen.

If there’s anything I know to be true it’s that our careers aren’t meant to be linear.

If you’ve made it this far, thank you. 💛 

I appreciate you for taking time out of your day to read this. I hope that you’re able to take away something from my story and apply it to your own. (At the very least, you got to see me dressed up in a Turkey costume, so consider it an early Thanksgiving gift from me to you).

Now that we’ve gotten my backstory out of the way, I’ll be back in your inbox on Tuesday, December 3rd with a much shorter story (promise).

Until then, enjoy the rest of your week! (And to my US friends, I hope you have a restful holiday next week 🦃).

-Sam