5 Challenges I Had in My First Year as a Freelancer (and How I Overcame Them)

5 Challenges I Had in My First Year as a Freelancer (and How I Overcame Them)

Working as a freelance writer for nearly two years, I can’t say it’s been a smooth ride. I decided to become a full-time freelancer when I closed my handmade jewelry business. It wasn’t easy, (especially after all the effort and money poured into it) but it wasn’t my passion.

I’ve been a writer all my life. It’s the answer I’d always say when someone asked, “What do you want to be when you grow up?”

When I was younger, you’d find me cooped up in my room, sketchbooks everywhere, and me working on my latest story idea. No wonder why I gravitated to writing as a freelance career.

If you’re looking to do the same, challenges will arise to test your resiliency. To better prepare you, take a look at a few I overcame.

Not Feeling Good Enough

Call it imposter syndrome, call it low confidence—whatever you call it, it happens to all of us. As writers (or whatever your occupation), we’re constantly looking at other’s work. It’s people we admire, want to be like that fuel us to be great.

But it also creates insecurity. We see their success and wonder if we’ll ever get to their level.

It’s what I experience daily. Some days are harder than others to get over it but once I do, that’s when the magic happens.

I remind myself to just write. I put my fears and hesitations aside and those nagging, negative thoughts (this sucks; no one will be interested; this isn’t of high standard) are pushed to the back of my mind.

The best thing you can do in those moments of weakness is to just do. Write, create code, paint—something to get the wheels in your head spinning. Don’t worry about it being perfect right off the bat, just go in with an open mind and allow mistakes to happen.

Confused About What I Should Be Doing

When you start freelancing, there’s no manual that magically appears. Turning to the internet only creates confusion with loads of articles about success as a freelancer.

I won’t say I have it down pat. I don’t stick to a schedule nor a routine. I get up, decide how I’m feeling, then decide what I’m going to give my attention to first: writing or housework.

Doesn’t sound like what you’d expect, huh? That’s because every person is different. I have a hard time sticking to schedules because doing the same thing every day at the same exact time gets boring. I won’t stick with it if I’m constantly fighting boredom.

That said, half the time I feel as if I’m confused about what I should be doing. What does the average freelancer do in this stage of their career?

There’s no one-size-fits-all answer. You can follow what other people are doing but I learned a while ago how much that doesn’t work. Copying someone else’s journey impedes your own. There’s no stone path to lead you to success. You must continue walking, no matter how hard it gets. You should decide what the next step is to get where you want to be.

One thing I do to keep on some sort of path is create to-do lists. And if I don’t get to everything within that day, I don’t beat myself up. I plan it for the next and give myself a break.

Not Gathering Clients

Since there is no magic manual, I feel as if I went a different path than most freelance writers. Instead of building a client list, I got a freelancing gig writing for a marketing company. I’m still with them today.

The job is on a quota basis, meaning I must meet certain numbers weekly. I won’t get into much more detail but what I will say is I wish I started gaining clients sooner.

That would’ve allowed me to work on a wide range of projects for more money. I’d be able to spread my writing wings more so than being stuck with occasional undesirable topics and unsavoury clients.

However, it helped me develop and polish the skills I have today. It also gave me thicker skin so when those clients’ attitudes are less than ideal, I don’t take it personally (most of the time).

Focusing on Too Many Side Projects

I’ll let you in on a secret: I have way too many ideas rolling around in my head. I’ve been this way since I was a kid. I’d even joke that while the average person has at least a thousand thoughts a day, I have double.

That said, I tend to want to take on lots of side projects. Most of them consist of starting businesses or blogs (I have a problem, I know). But when it comes down to it, I think realistically. Can I dedicate time and effort to it? Will I follow it through or become exhausted after the details are worked out? Do I want to be a business owner again or can I help someone else with theirs?

When I thought blogging was for me, I learned it wasn’t early on. That resulted in an abandoned website and wasted time.

Since then, no side projects have been started, other than focusing on building my portfolio.

Not Focusing on Improving My Writing Skills

The opposite of imposter syndrome is a big ego. I think we all get that way too—thinking we’re the best upcoming thing in our industry.

I felt that way in my first year of freelancing. I had friends and family telling me how good of a writer I was. And for a while, I did nothing to enhance my skills. I quickly learned I couldn’t do that. No matter your industry, your occupation, there’s always something to be learned. Even if it’s not strictly job-related, it could be as simple as getting better at small talk.

If you think you’ve learned everything, you haven’t. Always aim to improve yourself or your craft in one way or another. The world isn’t what it used to be, where your experience spoke for itself.

Now, your skills and who you are as a person win clients over. Keeping improving, keep working, and most importantly, keep learning.

The first year will be rough. There’ll be challenges and you’ll feel lost half the time. But as long as you stick with it and do what’s best for you, there’s no telling how far you’ll go.

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By Kayla Peart

Kayla Peart is a storyteller and poet wandering through life and wondering about it. She shares her findings through stories and poetry on Moonflwr, her newsletter.

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