This transcript was generated from the episode audio and may contain minor errors.
An overworked freelancer gets stressed out, and what does she learn through this process? What does this freelance writer learn, who struggles a bit with organization, kind of creates a scheduling nightmare? How does she overcome this obstacle and move forward positively? Welcome to Side Hustle School. I'm Chris Guillebeau, your host, episode 2876 here, and this one takes place on Friday.
What comes out on Friday? You could be listening anytime, but it is in the segment known as Failure Friday. You get to hear from a side hustler who has struggled in some way, you get to hear a short story of something that goes wrong and what they learn from the process. So it's kind of about how we adapt, how we evolve, how we maybe choose better ideas at the outset, or how we change it up as we go along. Whatever the case may be.
So today's short story features Samantha from Seattle, and as you might guess, her business had a couple of challenges, in particular with organization, but let's hear her share the details. I'll have a few words to wrap up at the end. And by the way, thank you so much for being out there. Hi, my name is Samantha Chen, and I live in Seattle, Washington. I've always thought I had a way with words, so when I decided to start freelance writing on the side, I thought it would be fairly simple.
My day job as a marketing coordinator paid the bills, but I dreamed of building a writing business that could eventually become my full-time gig. At first, things were going well. I landed a few clients through online platforms like Upwork and word-of-mouth referrals. The extra income was nice, and I loved the variety of projects. One day, I'd be writing blog posts about sustainable fashion, the next crafting website copy for a local bakery.
As my confidence grew, so did my ambition. When a former colleague reached out to me about some technical writing work, I jumped at the opportunity. Then, a week later, a small startup needed help with their email marketing campaigns. Of course, I said, without any hesitation. Before I knew it, I was juggling five clients alongside my full-time job.
I was writing the hive, the thrill of it all, imagining the portfolio I was building and the money that would be coming my way. But there was one tiny problem. I had no system for managing it all. My scheduling system consisted of sticky notes plastered around my computer monitor and half-finished to-do lists scattered across various notebooks. I convinced myself I could keep it all straight in my head.
After all, I had always been good at multitasking. The crack started to show, though, when I mixed up two clients' brand guidelines, sending a quirky, pun-filled article to a serious financial services firm. They were not amused. I stayed up all night rewriting it, promising myself I'd be more careful next time. But next time came sooner than I expected.
I completely forgot about a deadline for the startup's email campaign, remembering only when they sent me a frustrated follow-up. I scrambled to put something together, but it was rushed and below my usual standards. The final straw came when I submitted a technical document. A full week late. The client understandably refused to pay and terminated our contract on the spot.
I was overwhelmed, exhausted, and on the verge of burning out. My side hustle drink was turning into a nightmare, and I realized I was dangerously close to jeopardizing my day job, too. It was time for a serious reality check. I reached out to a friend who had been freelancing successfully for years, hoping for some advice. She took one look at my chaotic "system" and shook her head.
"Samantha," she said, "you're talented, but talent isn't enough. You need structure and systems to succeed in freelancing." She introduced me into project management tools like Notion and helped me set up a proper scheduling system. More importantly, she taught me the art of saying no to projects that would overextend me. This was the way forward. I had to swallow my pride and reach out to the clients I'd disappointed, offering discounts and revisions where I could.
Some were understanding, others weren't. I learned the hard way that in freelancing your reputation is everything. Slowly but surely I rebuilt my hustle on a foundation of organization and realistic commitments. I now have a clear picture of my capacity and stick to it rigorously. My client list is smaller, but the quality of my work and my stress levels are much improved.
This experience taught me a crucial lesson. Your time and your reputation are your most valuable assets. Protecting them isn't just good practice, it's essential for both you and your clients. All right, Samantha, thanks so much for sharing the story. And always, listeners and Samantha, remember, never confuse a single defeat with a final defeat.
I too have struggled with organization. I like this line about how Samantha is talented, but talent isn't enough. You need structure and systems to succeed. I feel like structure and systems were my nemesis for a long time. It's still definitely not my strong suit, but I did have to adapt and learn some things and it's helped me to just feel better.
It's not just about being more productive. We are talking about creating a profitable business and being productive and effective, but it's also about your own well-being and when you're stressed out all the time because you lack structure and systems. One way to fix that is to improve your structure and systems and then be less stressed out. It's a lesson that I tell myself from time to time. If you have a question or an update about your hustle, sidehustleschool.com, I'm excited to come to the midpoint of November in the calendar 2876-2876.
Of course, new episodes come out every day, seven days a week. I hope you'll continue to listen. My name is Chris Guillebeau. This is Side Hustle School. From the Onward Project.
