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Why I Failed at Freelancing For So Long

My road to full-time freelancing was paved with desperation, inconsistency and negative bank accounts.

Self-employment was never something I thought I could achieve. Ever since a freelance marketer visited one of my introduction to journalism classes and said that the most important part of freelancing was making connections and getting used to rejection, I wrote freelancing off as something that just wasn’t something that someone like me could accomplish.

I know it sounds dramatic. Because it’s just freelancing. Just working with people, and delivering them things they need for money. But in my head, it was a mountain lined with a lot of things that make me uncomfortable. Things like networking, selling myself, talking about money, and cold emailing were all once on my “avoid at all costs” list.

My road to becoming a full-time freelancer is not a straight one by any means. There was a lot of trying and failing. Straight up giving up because it was too hard, and being too lazy to put in the work. Before I committed to writing, I gave my shot at freelance graphic design, video editing, and marketing. I tried pretty much anything I could think of as a sellable skill. I was desperate to give anyone anything they needed for the promise of a paycheck and the ability to work from home. I had no plan other than that I knew I needed clients, and I would try and figure out a way to find them and make it work.

It took almost two years for me to lean into my own worth and find decent rhythm at doing the freelance thing full time. I am not saying that I’ve figured out all of the answers. But it has become abundantly clear what I need to do to sustain this life, and that I wasn’t doing it before.

I failed a lot before I got to a point where my freelancing provided me a decent enough income to say it was my full-time gig and to feel confident I can continue to make it work. I’ve taken stock of all of the things I did that led me here, and all of the things that held me back from getting here sooner.

Desperation is not a good look.

Looking back at my life, desperation has always played a role in some way or another, without me ever really realizing it. I feel like I’ve never been comfortable where I was and always felt like my back was against make-believe wall. There was still something to prove, a bill to pay, or just some sort of approval that I needed to find at any means necessary.

In the beginning, I was so desperate to be a freelancer and make that first dollar that I took jobs that probably should have been illegal. Things $5 articles, 1000 landing pages with spun content, pretty much anything that I thought would be good on “my portfolio.”

Desperation also presented itself as my selling myself as someone who could do anything. If they weren’t looking for a marketer, I would pitch myself as a video editor or a designer, or a salesperson. I’d dig up some random project I did in college that involved 5% of what they were looking for and spin my role to make it seem like I met their needs. It was scammy, desperate, and a waste of everyone’s time.

Of course, it’s easier to let go of being desperate once you have some stability (and some money). I wish I could go back and tell myself that playing the role of hopeless, broke graduate would get me nowhere, and to suck it up and put in the real work.

I was waiting for someone to give me a chance.

In the back of my mind, I always had this thought that someday I would meet the right person who would see something in me and give me a huge opportunity to help them build their company for a lot of money. I would put in the bare minimum effort because I thought that I was somehow owed something for even trying.

It wasn’t until I realized that I needed to create the space I wanted to occupy that I started working on things that I cared about. I never realized that freelancing is mostly about creating awareness of a problem that companies don’t even know that they have yet. Instead of waiting for someone to present you with a problem to fix, you need to identify the issues that they can’t see, because they are too close to it.

Now, I put in the effort to develop a space for myself within companies that I know I can help.

No consistency & no persistence = no work.

In the beginning, I would send out a few job applications and pitches here and there. As I said, I had the attitude that I was owed a job for doing the bare minimum. In other words, I was pretty lazy and entitled. I thought that having a master’s degree and a glowing recommendation was enough that I didn’t have to put in any real effort.

I had to teach myself discipline in order to be consistent enough to meet the quotas I set for myself.

But consistency has also come to mean different things to me since I started freelancing. At first, I thought it meant hitting a certain quota of pitches sent or jobs applied to. Now I realize I needed to be much more consistent in the quality of what I was sending out to get more consistent results.

In addition to being consistent, I had to learn how to be persistent as well. It’s not enough to send out an email and hope the person on the other end reads it and gets back to you. They’re busy, and they don’t know you. So being persistent about following up on projects you care about is so much more important than I ever realized.
I was afraid of talking to people.

Networking is my actual worst nightmare. That sounds dramatic, but it’s the truth. Before every conference or every event, I go to that involves talking to other people, I need to go into it with a game plan. A list of talking points, or a quota of people I need to talk to to make myself feel okay about what’s going to happen once I get in there.

I thought that I could make it as a freelancer just existing anonymously behind my computer, but as it turns out, people trust people that they know IRL, more than they trust random people emailing them on the internet. Once I started putting myself out there, not only did I get a few new clients, who then introduced me other clients, but it let me get a feel of what struggles business owners were having that I could solve.

Talking to people in person reveals so much more than auditing a website. I learned that people have a hard time trusting writers who can deliver content that gets long term results. I learned that a lot of companies don’t have the time to recruit for roles they desperately need, and so approaching them with a solid plan and understanding of their pain points helps them way more than it causes me discomfort.

Which brings me to my next point.

I was passively waiting for direction rather than taking initiative.

Remember what I said about always waiting for other people to allow me to do something? This expands on that. When I first started looking for freelance opportunities, I was looking for visible roles that companies were hiring for. I would scour job boards for companies that were hiring freelancers and contractors. I would follow their process and fill out their form and send it off into the ether, never hearing a word back. Why would I? I was a drop in the bucket of thousands of other freelancers competing for the same opportunity.

I learned how to be the leader in the situation. I needed to find companies who needed me and go directly to the source. It wasn’t enough to send them my credentials or resume. I needed to add extreme value upfront. I needed to do my research and present myself as an expert so that they would know they are hiring someone who will take charge and help them grow — not someone who would wait around for directions or be assigned the next task.

I can also thank my education and college professors for instilling in me that my resume and cover letter were going to be the determining factors for my career. I held on to this idea for way too long, and it turned out to be bullshit in the freelance arena. When you’re pitching to help someone grow their business and help them make a real impact, they don’t care about your skills, or your background or the fact that you once ran a video campaign and learned how to use Final Cut Pro.

They care what results you were able to get for previous clients, and the benefits and deliverables they’ll have in hand from working with you. This is something I wish I had learned sooner because I spent way, and I mean wayyyyy, too much time formatting my resume with buzzwords and making it pretty so it stood out.

Business owners care about how you’re going to help them make more money, and how paying you money isn’t going to end up being a loss for them. In the beginning, when I didn’t have many metrics for results I had achieved, I had to get creative without coming off as a scammy. I did some free work to test the waters and get some case studies under my belt that I could use in my pitches to show clients that I know what I’m doing.

Overall, becoming a freelancer took some major mindset shifts and a lot of unlearning everything I knew about finding a job. It took going so far beyond my comfort zone and what I thought I was capable of. But as cliche as it sounds, I wouldn’t take any of it back because it’s taught me how much I can continue to grow and learn. I still don’t think I’m a great freelancer. There’s a lot about this path that still scares me. But seeing how far I’ve come gives me the confidence that I’ll be alright to face whatever comes next.

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