Side Hustle Struggles: From Startup Dreams to Freelance Fails

The Alluring, Yet Terrifying, World of Side Hustles

Honestly, I thought I had it all figured out. You know, the whole “escape the 9-to-5” dream. A side hustle, they said. It’ll be fun, they said. Make extra money, they said. Well, let me tell you, it’s been more like a rollercoaster than a relaxing walk in the park. And sometimes that rollercoaster is terrifying. I mean, who even knows what’s next when you decide to jump into the side hustle game? One minute you’re brainstorming brilliant ideas, the next you’re staring at a blank screen wondering where it all went wrong. It is not, I repeat, NOT all sunshine and rainbows.

I remember back in 2018, I was SO hyped. I was convinced I could launch this amazing online store selling handmade jewelry. I envisioned piles of money, freedom to travel, and basically living the “laptop lifestyle.” I even stayed up until 3 a.m. researching Shopify themes and learning how to run Facebook ads. Ugh, the naive optimism of my past self! The jewelry was… let’s just say it wasn’t exactly flying off the shelves. I think my mom was my best customer. I lost a solid chunk of change on the ads, and the ‘laptop lifestyle’ felt more like the “stressed-out-in-my-pajamas-at-4-a.m. lifestyle.” It was a harsh lesson, but hey, you live and learn, right? Or, in my case, you fail and then try something else. But the burning desire to make something happen, something *mine*, never really faded.

Freelance Fumbles and Lessons Learned

After the jewelry debacle, I decided to pivot. Startup dreams were clearly not my forte. Freelancing seemed like a safer bet, right? Use my existing skills to make some extra cash. I signed up on Upwork, feeling all confident, and quickly realized the competition was fierce. Like, ridiculously fierce. I was bidding against people who were charging like, five dollars an hour. Seriously? I started low, too, hoping to snag some clients and build my reputation. And I did get some work! But it was mostly tedious, low-paying projects that made me question my life choices. I mean, I was writing blog posts about…garden gnomes. Garden gnomes! Was this really what I envisioned when I dreamed of financial independence?

There was one client, in particular, that stands out. He was super demanding, constantly changing the brief, and always finding something to complain about. I swear, every email from him gave me heart palpitations. He finally approved the project, gave me a mediocre review, and then disappeared without paying. Ugh, what a mess! I ended up having to file a dispute with Upwork, which was a whole other headache. It took weeks to resolve, and I only got a fraction of what I was owed. Honestly, that experience almost made me give up on freelancing altogether. It felt like I was pouring my heart and soul into these projects, only to be taken advantage of. But quitting wasn’t really an option, was it? I had bills to pay, and that side hustle money, even the little bit I was making, was helping.

Finding My Niche (Eventually)

So, I took a step back and re-evaluated my strategy. I figured if I wanted to succeed in the freelance world, I needed to specialize. I couldn’t just be a generalist writer. I needed a niche. After a lot of soul-searching (and scrolling through endless articles about profitable niches), I decided to focus on content marketing for tech companies. It seemed like a good fit – I had some experience in the tech industry, and there was definitely a demand for skilled writers.

It took time, but I started to land better clients who valued my expertise and were willing to pay decent rates. I learned how to write compelling website copy, create engaging blog posts, and even manage social media campaigns. It wasn’t always easy, but it was definitely more rewarding than writing about garden gnomes. And the best part? I was finally making enough money to actually make a difference. I even managed to pay off some debt and save a little for a future vacation. I remember when I got my first big check, I felt…relieved. It was like all the struggles and frustrations had finally paid off. Still, there were, and sometimes still are, days I question everything. Was I the only one confused by this whole side hustle journey?

The Side Hustle Reality Check: It’s Not Always Glamorous

Let’s be real, the side hustle life isn’t all Instagram-worthy photos of working from a beach in Bali. It’s a lot of late nights, early mornings, and juggling multiple projects at once. It’s dealing with difficult clients, managing your finances, and constantly learning new skills. It’s a constant hustle, hence the name. It’s easy to get caught up in the hype and think that you can become an overnight success. But the truth is, it takes hard work, dedication, and a healthy dose of resilience. And a good understanding of what you are actually good at.

Looking back, I’m glad I didn’t give up after my initial failures. The jewelry store flop and the dodgy freelance clients taught me valuable lessons about entrepreneurship, resilience, and the importance of finding your niche. Would I do it all again? Probably. Even the bad parts. Because even though it’s been a messy, chaotic, and sometimes frustrating journey, it’s also been incredibly rewarding. And who knows, maybe one day I’ll actually make it to that beach in Bali. Okay, probably not. But a girl can dream, right? If you’re as curious as I was about escaping the 9-to-5, you might want to dig into researching various online business models. Just go in with realistic expectations, okay? You have been warned.