Brenna’s life abroad was everything an adventure-lover could dream of — the perfect balance of excitement and stability.
“After college, I moved to South Korea to teach English. It was an amazing experience. I lived rent-free, my job was stable and I had great benefits. Plus I was always traveling somewhere new — Japan, China, Thailand. I even met and married my husband there”
But with a new partner came a new perspective, and Brenna found herself itching for a change.
“After five years in Asia, my husband and I both started to feel a little restless. He wanted to go to nursing school and I was ready for something different too. I had always dreamed of being a writer, so I thought it might be a good chance to get into that.”
Leaving with countless memories and the promise of a new beginning, she and her husband packed their bags and moved back to the U.S. She was surprised at how quickly she found her place — or so she thought.
“I got a job as a teacher’s assistant right away. I already had a lot of experience under my belt, and I really enjoyed teaching in South Korea, so I thought it would make sense to continue down that path. I just figured I’d put my writing dreams on hold for a bit while we got settled.”
A blessing in disguise
It didn’t take long for Brenna to realize that teaching in the States was more than a little different than teaching abroad.
“I got along great with my co-teachers and we worked really well together despite some challenges in the classroom. It was exhausting work and there were a lot of politics that I didn’t like, but I stuck it out and gave it my all every day.”
But she was blindsided when, despite her hard work, her job was ripped out from under her feet.
“I was fired. Totally out of the blue. My boss never even gave me a warning. She told me she wanted someone with ‘more experience.’ I was baffled — I had experience, and I was doing well on the job, so what was the problem? I got zero explanation.”
But once Brenna took some time to think things over, she realized her situation wasn’t as awful as it seemed.
“I finally acknowledged to myself that I had been burning out for a while, and I didn’t want to do things that I didn’t love anymore. Life is too short. I took it as a sign — it was time for me to get out there and do something I loved — even if it meant taking a risk.”
Not wanting to settle yet again, she started thinking about the dream she had put aside when she arrived in the U.S.
“I had always wanted to be self-employed, so I started seriously looking into how I could make that happen with my dream job: professional writing.”
Lots of options, but not many good ones
Brenna wasted no time getting real experience in her new career.
“My mom was writing a novel. This book was a pretty big deal for her, so she took my job search as an opportunity to hire me for editing and proofreading. In the meantime, I was still searching for something more full-time.”
Stretching her writing legs felt good, and she was excited to find more work. Like many freelancers, she turned to the internet to explore her options.
“I found Upwork through a quick Google search. At first, it looked like a pretty good option for freelancers — it was laid out nicely compared to some other online marketplaces I’d seen. I went ahead and made an account and started to look around the site.”
But it didn’t take long for her optimism to fade.
“I was worried about working through an online platform because I couldn’t talk to anyone personally. I also started to feel intimidated, because my initial impression was that payment was based strictly on experience, and I didn’t think I had enough.”
Even though Brenna had limited ‘formal’ writing experience, she wasn’t about to settle for anything less than what she knew she was worth.
“I knew I had writing talent and good interpersonal skills. I could deliver work as good as some of these other freelancers — maybe even better. But I had no idea how to get my work in front of a client. And even if I did, I definitely wasn’t going to start at $5/hour. So I got off Upwork and looked elsewhere.”
A closer look reveals some secrets
Undeterred, she hopped back on the internet. Upwork kept popping up, but she dismissed it — until she found something that sounded a bit…different.
“A lot of what I read about Upwork went along with my first impression: low-paying jobs and a never-ending rat race. But then I saw this Freelance To Win article about the Upwork mistakes Danny made when he started. I realized I could figure this all out, but I’d need to read between the lines.”
All of a sudden, Brenna had a whole new outlook. And this time, she started to believe that she had what it took to make it on Upwork on her terms.
“I went back and looked at it again with a different lens. The low-paying jobs didn’t have high standards. But when I looked carefully, I found high-quality, high-paying jobs. I knew if I could talk to these clients and get more details, I could absolutely do the work they were looking for.”
The once-impossible task of becoming an online freelance writer suddenly seemed like a worthwhile challenge.
“I started to get excited.Now Upwork wasn’t this unbeatable thing where I could never get ahead. It felt more like a puzzle, and I just needed to figure out how it all fit together. First and foremost, I needed to know how to connect with clients online.”
Brenna was on a roll. She devoured the rest of the content on FTW and got ready to succeed on Upwork.
“When I’m trying to learn something new, I normally ‘shop around’ to get the big picture through a variety of different people. It’s very rare for me to feel like I can trust one individual enough to read their whole blog. But everything on the blog just made so much sense to me. It was almost like, ‘Why didn’t I think of this stuff?’”
Putting her best foot forward
Making a career out of online freelancing was starting to look like a real possibility. But she also knew that she wanted to go about it the right way from the very beginning.
“I had a lot of life experience at that point and was pretty confident in myself. But I also knew that there was a lot to learn about becoming an online freelancer. I wasn’t about to just randomly apply to jobs. I wanted to know how everything works.”
She knew she’d want to lean on someone who’d been there before. Considering how much she connected with FTW, Secrets Of A Six-Figure Upworker seemed like the perfect place to start.
“It was a risk for me to buy the course. I didn’t take it lightly. But I read the success stories, all of them, and they all made sense. All of it just seemed very logical to me.”
Once she was in, there was no looking back. She went through the course front-to-back and then back again, soaking up every detail along the way.
“I knew that completing the course would help me get jobs faster. I decided to go slow and steady. I didn’t want to go out and try to get a bunch of jobs and then go back and look at the course and realize my mistakes. I wanted to save myself time in the long run.”
The proof is in the pudding
One of the first lessons Brenna put to the test was overhauling her profile.
“Before listening to the lessons, my tagline was something really vague. But I learned how to change it to make it more exciting so it stood out to potential clients. I also learned exactly what clients are looking for when they come to Upwork, so I tailored my overview to fit what they needed.”
And even though she was prepared for a few rejected proposals before receiving an offer, she was shocked at what happened next.
“I’m not kidding, within a week I got my first private invite. At first I thought it was a scam. I thought there was no way it would work that quickly. But I got on a call with the client and he told me he invited me because my overview was exactly what he was looking for.”
Brenna didn’t even have time to consider that her first invite might be a fluke — a second invite came in right on the heels of accepting the first.
“This client said that he immediately trusted me based on my profile. In fact, he had already decided to hire me before he even called. I literally got chills down my spine because in that moment I knew that everything I had learned was going to work for me.”
Her hunch was right, and the proposals have been rolling in ever since.
“I haven’t applied to any jobs since I got my first invite, because I’ve been so busy with my private invite clients. I actually don’t even have time to apply other jobs. But that’s okay, because I’m still getting at least one private invite a week, sometimes more.”
Finally “settled” in the most exciting way possible
Even though Brenna isn’t applying for new jobs, that doesn’t mean things are getting stale.
“I’ve had thousands of dollars worth of work, all because of private invites from clients who liked my profile. And as soon as my initial batch of clients saw my work, they each offered me repeat work. They’ve also referred me to other people, so I’ve got a bunch of projects going at once.”
And while she’s thankful for her years of teaching in South Korea, she’s dead-set on never settling for the 9-5 lifestyle ever again.
“I will never go back to a ‘normal’ job, ever. Having to get in your car at the same time every day, arriving at the same place every day, taking your lunch break at the same time every day…the thought of it kind of feels like being in prison to me now.”
Not only does she get to finally live out her dream career, she gets to do it all on her own terms — every last bit.
“The time freedom is just incredible. I like to be active, so now I can choose my favorite yoga class every week, even if it’s in the middle of the day. Even on days where I wake up and realize I have a ton of work to do, I still get to choose when and where and how I’m going to do it.”
Writing-as-a-job, working from home, and dictating her own schedule were the top requirements in Brenna’s job search. But she’s starting to realize there may be one more (big) bonus.
“I wasn’t looking to be rich. I just wanted to pay the bills doing something that I loved and allowed me to work from home. But I’m quickly realizing that I can make more money doing this than at any job I’ve worked in the past, with fewer hours.”
Believe it or not, there is someone who’s not so thrilled with Brenna’s new career…
“My mom is desperate for me to come back and be her full-time editor again, but I’m so busy right now with my other clients that I don’t have time! I’m told her I’d put in some time on the weekends for my very first (and favorite) client.”
