Dutch Scammers, $5 Gigs, and Nearly Half a Million Words Later

This is what I learned in my first year of freelancing.

Technically, my first job after college was “DoorDash delivery boy”, but my second was “freelance writer”.

I spent my first few months after graduation applying for countless full-time, “grown-up” jobs at digital marketing and copywriting agencies, and after getting rejected after every single one of the few interviews I was granted, I was stuck delivering Chipotle on DoorDash in the evenings to make up for the cash I’d lost by sitting on my ass all day doing nothing.

Because of the pandemic, I couldn’t even teach Jiu-Jitsu lessons anymore, which was my trusty side-hustle back when life was “normal”. My weekly income was about $75, most of which came from DoorDash tips. My friends were all building real careers, and I was a bum with a martial arts addiction and absolutely no career prospects.

Then one night, in the middle of yet another “purpose-based” existential crisis, I discovered an article about freelancing on this very platform, and I immediately created an UpWork account and applied for 15–20 jobs on that site, along with creating a Medium account. I had never published any writing and I had no copywriting experience besides 2 undergraduate internships and my degree in Communications, but I applied for everything that seemed interesting.

At first, UpWork wasn’t very good to me. I received only 2 replies from my initial stack of applications. One of which was to tell me I wasn’t “a good fit” for the client (probably because I had zero experience), and the other was a 3-day long episode with a man from the Netherlands (I think) which eventually ended with me realizing I was being scammed just hours before I gave him my social security number.

I was young, ambitious, and a complete idiot. I also needed money badly. Nonetheless, I started writing, kept applying for work online, and hoped that someone would throw me a bone.

In the time since I was nearly scammed out of my (small) life savings, I’ve gone from zero clients to more than 10, and I’ve learned a thing or two about the whole “freelancing thing”. I couldn’t find a grown-up job to save my life, so as a 23-year-old fresh college graduate I leaped headfirst into the world of full-time freelancing, without even realizing that that was what I was doing.

12 months later, this is everything I’ve learned.

Freelancers Are Not Entrepreneurs

So we shouldn’t work like them.

When I started freelancing, the main motivation behind my decision was that I believed I could freelance on the side while focusing on my martial arts career. I could write for clients in the morning, train during the day, write in the evenings, and still have time to travel the country and fight in tournaments. It was a strange but powerful source of career motivation, and it seemed like the perfect scheme to build my dream life.

Well, on paper, it seemed perfect. In practice, it’s been a little bit more difficult.

As I’ve started to add clients, my time has slipped right out of my hands. Having essentially two part-time jobs (one as a semi-professional Jiu-Jitsu fighter and another as a freelance writer) essentially has become the equivalent of having one very demanding full-time job. Between my passion and my job, I’m “working” 10–12 hours per day, all to avoid the safety net of a “9–5” that would force my fighter dream to die.

This is sort of similar to what you hear from entrepreneurs, but I’m not an entrepreneur. Entrepreneurship is sexy right now, freelancing is not.

I may have some entrepreneurial tendencies, but I do not have a company. I am the company. This detaches my feelings from my clients and allows me to focus on what I do well: writing. I’m not running a business, I’m helping other people run their businesses. This is an important distinction.

In the beginning, I was working on writing content for my clients like their business was my business, and it was killing my mental health and creative capacity. I’ve learned that when you freelance, you are still working for someone else. Your “business” is you, not the client’s business. When you create content for someone on a freelance contract, you have to work diligently, but not like it’s your life’s work. This is a surefire path to burnout and creative deficiency.

That weekly company blog on jerk chicken is a work project, not a passion project. I’ve learned to spare my creativity from projects that don’t require it. Ultimately, I’ve developed my ability to work below my limits.

Jobs Can Come From Weird Places

Of all of my clients, I only actually have one who I received from UpWork, which was the first site that I used to find freelance jobs. The rest of my clients have come from my own personal network, my advertising attempts on social media, and word of mouth.

I started out by sending out 2–3 applications on UpWork every morning as I drank my coffee and read the prior day's rejection notes, but the constant rejection was starting to ruin the taste of my morning brew. So, instead of applying for every possible ghostwriting and copywriting job on UpWork that I was impressively unqualified for, I’ve learned to focus on building my own brand and using that to help me establish credibility as a writer.

This doesn’t mean that applying on UpWork is useless (I’ve found one particularly well-paying client from that site), but it does mean that it’s probably a good idea to diversify the places that you look for work. Heck, one of my jobs came from my childhood best friend’s dad, who connected me with a digital marketing agency that’s given me countless projects to work on in the last few months.

At the same time that I’ve been focusing on copywriting and building a client list, I’ve also been focusing a lot on developing my personal portfolio and sharing stories from my own life on Medium and on my personal blog. As someone who naturally loves to tell stories, this has been not only good for my brand building but also for my mental health. Don’t tell anyone, but my favorite thing to write is my personal writing. Everything else is writing for work, but that’s an okay distinction.

At the end of the day, it’s all writing, and it all makes you better. As a new writer, the most important thing to do is write. Constantly write, because you never know who’s going to be reading.

You Have to Speak Up For Yourself

Though I’m technically not an entrepreneur per se, I have learned a lot about being a better freelancer from entrepreneurs.

One thing that natural entrepreneurs do exceptionally well is that they speak up and assert themselves in business interactions. I don’t mean this in an aggressive, domineering sense of “establishing authority”, but really just that I’ve learned how to speak up and ask for the things that I’m owed or that I need for my work.

This is everything from asking for replies on job applications, asking for money that’s owed, and asking for solutions to any other problems that have arisen during my time writing for other people’s businesses. Business owners tend to be very busy people, and they’re most often not trying to withhold resources from you, they’re just sidetracked with other more pressing tasks than shooting a Zelle payment to the guy who writes their company blog and newsletters.

As someone with a lot of social anxiety, this was a tough but necessary lesson to learn.

When you jump into the freelancing world, you’re jumping into a world where you’re constantly surrounded by entrepreneurs. The best thing you can do is learn how they think, and learn how to speak with them in ways that both force them to respect you but also show that you respect them.

Plus, speaking up might even open the door to larger paydays and more interesting projects.

Being Good at Deadlines Is Crucial

A lot of freelancers struggle to meet deadlines.

The best thing you can do as a new freelancer is not only turning your work in on time but turning it in early, without slipping on quality. Freelancing isn’t middle school, and it does pay to be an overachiever. Every company owner I’ve talked to has been surprised when I’ve been able to promise rapid turnarounds on assignments and projects, and the result of this consistent behavior has only been more work and as a result, more money.

Freelancing is not about how much work you can take on at once, it’s about how much work you can complete and complete well, consistently. It’s the same thing as the difference between an amateur and a pro. If you’re a professional creator, you must create consistently. Every single day, even when you absolutely do not want to.

In my short time as a freelancer, the two contributing factors to my small successes have been that I say “yes” to almost all of the assignments that I’m offered and that when I say yes to a project, I complete that project as soon and as efficiently as possible. I procrastinate on a lot of things in my life, but I try to not procrastinate on work that I promise to do for other people.

Having the ability to churn out content quickly also allows a bit of room for error. If your client is reasonable, they’ll likely be able to work with you at making a less-than-stellar piece of content better if you’ve turned it in early rather than just 45 minutes before the due date.

As a recent college graduate, meeting deadlines has been the easiest part of freelancing for me, but it’s also been the part that has led to the most positive feedback, additional projects, and additional financial compensation. I always end every email with “what’s next?” instead of “your welcome”.

I should point out, I’m not saying you should lie about your capacity for work.

Despite the benefits of “deadline hacking”, I also believe that honesty is an important part of contract work. Do not say you can do something that you physically can’t. You will burn yourself out and piss your clients off in the process. Be honest, ambitious, and attack each project with excitement. I mean, you’re getting paid to write, what more do you want?

Closing Thoughts

Freelancing is hard work, and it’s not very glorious.

When I started, I didn’t know anything about what I was doing, and I’m lucky that I was able to start from the safety net of my parent’s house as a fresh college grad. I felt embarrassed to be living at home while all of my friends were taking on fancy consulting jobs and moving into beautiful downtown apartments, but I’m proud of where I’m going and what I’ve done.

So far, it’s honestly going pretty well, and it has the potential to keep getting better and better. This time last year, I had never written anything on the internet besides school homework assignments, and now people pay me to write. In my book, that’s pretty cool. Plus, I still get to compete in martial arts all over the country and travel frequently to train. Life isn’t too bad right now.

When you freelance, you’re going to have weeks where you feel on top of the world, and you’ll have other weeks where even just going out for a cup of coffee is out of the question. That’s just the nature of the beast.

To quote a friend of mine who’s been in this game a lot longer than me:

“You’re going to have your steak weeks, and you’re going to have your bologna weeks.”

If you’re okay with that, and the thought of creating a life free of typical restrictions excites you, freelancing might just be the first step on your journey to freedom.