After finishing his service in the military, Kasey went back to school — but couldn’t help feeling a little out of place.
“I went back to finish my undergrad degree. It was a little weird though because I was already married and older than all the other students, and I remember thinking ‘Am I really back in class?’”
As if the stress of raising a family while attending school wasn’t enough, his wife surprised him with some exciting — yet nerve-wracking — news.
“While I was studying, my wife was busy working and doing a lot to run the house. Then one day we found out we were going to have our second child.”
Kasey was excited to hear the news, but he quickly realized that several things would need to change, and fast.
“The GI benefits from my time in the military had helped us pay the bills in the beginning, but it wasn’t going to be enough to support our larger family. So I knew I needed some extra money coming in soon.”
To make matters worse, his long hours of commuting to and from class made adding a “real” job into his schedule virtually impossible.
“I drove an hour each way to get to and from school. Leaving college wasn’t an option, so I needed something that gave me enough flexibility to not upset my schedule.“
An unlikely solution
This led Kasey to begin searching online for a creative way to earn money from home.
“I found one of Danny’s blog posts on Freelance To Win, where he talked about getting freelance jobs on websites like Upwork even though he started with zero experience. Up until then, I didn’t know that something like Upwork existed!”
Inspired by Danny’s success, he wondered if Upwork was the solution he had been hoping for.
“I thought to myself, ‘If this guy is able to a make a six-figure income, why can’t I do the same thing?’ I figured that if I could even do half as well, I’d still be happy.”
There was one hurdle to get past though. Kasey needed to figure out which service he should offer.
“Danny made his money as a copywriter, but I’d never written professionally before, and I didn’t even know what copywriting was. So I decided to look for tech-related jobs since that’s what I’d been studying in school.”
A shaky beginning
Kasey set up his account on Upwork and started searching for jobs. But things didn’t go as smoothly as he’d hoped at first.
“I submitted a lot of proposals and got almost no response. I started to have doubts, and I wondered if this was a bad idea. But this felt like my only option, so I decided to stick it out.”
He devoted more time to implementing the tactics he’d learned to improve his proposals and communication with potential clients. When the results started to trickle in, Kasey breathed a sigh of relief.
“After I used Danny’s strategies to fix up my proposals, I got a few replies from clients telling me about bugs they needed fixed, and other tech services they were looking for. I felt like I could finally start to see the light at the end of the tunnel.”
Not long after the first replies came in, Kasey landed his first job on Upwork.
“I was hired to fix a bug that the client wasn’t able to fix himself. I identified the problem and explained that it could only be repaired if we made major changes to his system. Even though I wasn’t able to fix the problem, the client was extremely grateful.”
Even though it was a small job, the experience was eye-opening.
“I realized that I didn’t necessarily need to have the answer or know how to fix something in order to make clients happy. Sometimes you just need to show them the problem.”
Taking things up a notch
Kasey continued to rack up successful jobs on Upwork, but he wanted to grow his freelance business even further.
“Danny’s free blog posts were already paying off, so buying his Secrets of a Six-Figure Upworker course was a no-brainer.”
Right away, Kasey started picking up some counterintuitive insights about charging premium rates.
“One of the most surprising things I learned was that when you’re charging high rates, like $100/hr, clients are much more likely to treat you like an expert. Most freelancers don’t realize they’re actually shooting themselves in the foot by charging a low price tag because they diminish their value, and are less likely to be hired.”
And when he found himself in an unusual predicament, Kasey went right back to the course materials for the answer.
“One of the clients I’d worked with before wanted to hire me again, but he wanted me to lower my rate from $100/hour to $80/hour. In the past, I would’ve taken it because he was a great guy to work with. But now I knew it’d affect my positioning and would actually change the way the client saw me.”
Kasey considers himself lucky to have discovered these non-traditional approaches to freelancing before launching his career.
“I feel like I dodged a bullet by learning about freelancing through Freelance To Win. I’ve heard so many horror stories about freelancers who beat their heads against the wall and often give up when they can’t make freelancing work. I definitely had a shorter learning curve than if I’d just tried it on my own.
Rapidly raising his rates
During the course, Kasey put the strategies he’d learned to work and skyrocketed his rates.
“I had more projects than I could handle, which put me in a great negotiating position. I had been charging $20 an hour, but as I got more clients and the projects got bigger, I was forced to push my rate up to $50 per hour. Later, I decided to ask for $75 an hour and clients were still more than happy to pay that.”
As his rate continued to climb, he made a surprising discovery.
“Clients don’t look at rates the same way freelancers do — for a client, it’s a business expense. One of my clients hired me without ever even bringing up my rate at the time. And when the project was complete, he paid me $50 an hour without batting an eye.”
Now that he’d achieved an hourly rate that was beyond his expectations, he completely shifted his mindset.
“Once I saw how high clients were willing to go, I realized that I’d been undercutting my value. A corporate IT employee providing the same services earns over $100/hour. I realized that if I could charge $100/hour, I’d only need to work 10 hours each week to bring in a solid income and I’d get to spend more time with family.”
Going beyond “glitch-repair”
Kasey likes to develop a personal connection with his clients, an approach that has helped him broaden his skill set and advance his career.
“When I develop a relationship with a client and they trust me, they’ll often come to me with more work. A lot of times it’s completely unrelated to the original project and it might even be something that I’ve never done before. But they trust me to figure it out.”
It’s impossible to predict how far these relationships can go. Now, even “one-off” jobs can turn into something much bigger.
“One of my clients initially hired me to do a small, simple job. When that went well, he kept hiring me for more projects. We’ve really hit it off, and now I’m his business consultant for everything tech-related.”
Always looking to improve his abilities, Kasey has gone from being a guy who repairs glitches to a technology expert whom clients rely on to help make big decisions.
“One of my clients does a lot of investing, and when he’s considering buying stock in a Silicon Valley startup, I help him assess the company’s value and make sure it’s a solid investment. It’s one of the coolest things I’ve done so far.”
Avoiding “job-board hell”
During his final semester in college, Kasey got a small taste of the life he was going to be missing…and it felt great.
“My classmates were under a lot of pressure to find jobs and internships. They were vying to get hired by anybody, regardless of who the company was. I never had to go through that. When I look for new clients, I have the freedom to step back and ask ‘Is this a company I’d like to work for?’”
With Upwork, he never needs to hassle with “red tape” or suffer through a long, drawn-out hiring process.
“I don’t have to submit a resume, be interviewed, or wait a long time for a response. I just speak with the client for about 10 minutes to see if it makes sense for us to work together, and if the answer is no, I move on to the next guy.”
Living the good life
Now that Kasey earns more than enough to support his family, his wife finally has the freedom to pursue her dreams too.
“When my wife told me she hated her job, I told her to quit and go back to school. Now she’s becoming a nurse, which is something she’s dreamed about doing for a long time.”
And because he works remotely, he can go virtually anywhere at anytime and not miss a day of work.
“My wife and I both love to travel. As soon as she finishes school, we’re going to have the freedom to go wherever we want, and we plan to take full advantage.”
Proud of her husband’s rapid rise to success, Kasey’s wife surprised him with a creative gift, which has led to a healthy “addiction.”
“One year, my wife gave me kiteboarding lessons as a Father’s Day present. I was instantly hooked from the moment I hit the water, and it’s been my ‘go-to’ hobby ever since.”
One of Kasey’s favorite parts of freelancing is that unlike a “traditional” job, he has the freedom to “play hooky” whenever he needs a break.
“If I’m working on a project and I feel like I’m not being productive, I look out my window and if the wind’s blowing, I drop what I’m doing and head to the ocean.”