Everyone thought Ari Zelmanow had a dream job — so why did it feel more like a pair of shackles?
Something was missing. “I wasn’t enjoying my work. It felt like I was missing out on doing something that really makes me happy.”
Okay, a few things were missing: “I was always chained to the clock, when I really wanted the freedom to control my own schedule. And even though I had a great salary, there was always that cap on how much I could earn–no matter how hard I worked.”
Many of the people closest to Ari didn’t understand his frustration. They wondered why he couldn’t just be happy with his “secure” 9-5 job.
That’s understandable. To hardcore believers in the American Dream, the void Ari was feeling didn’t make much sense.
After all, here was a guy who’d made all the “right” choices in his life.
He went to college, then grad school. He held a stable job with the police department for nearly a decade. Now, he was crushing it in the corporate world.
Yet he’d found this version of the “dream” to be more of a nightmare.
And he was looking for a way out.
A way to make money doing work he truly enjoyed.
To have the freedom to work how and when HE wanted to.
And, most importantly, to be in control of his own destiny.
“Don’t get me wrong, there are a lot of excellent things I’ve accomplished. I have a beautiful family, own my own home, and I’m healthy. But it was time to find work that made me feel fulfilled, so I could give my family the life and dreams they deserve.”
Looking for work he loves
At first, Ari thought entrepreneurship might be his ticket to freedom.
But it was slow going.
“I invested a few thousand dollars in online courses to help me figure out how to launch my own online business. But I realized it can take a long time to start making real money. You need to build a website, develop a product, do lots of promotion…it’s not fast. Don’t get me wrong, that’s okay for some people. But I’m 42, and I’m an Ironman Triathlete – I was ready to RUN, not walk. ”
Ultimately, he knew he needed a vehicle that would help him achieve his goals quicker.
So, he started looking into freelancing.
He’d always been interested in writing. And, though he didn’t have any formal experience or training, he’d heard stories of people who’d turned similar passions into successful freelancing careers.
Freelancing would allow Ari to work on his own terms. He could start out part-time, doing work he enjoys on the side. And — if it went well — he could transition into being a full time freelancer.
After doing some research, he settled on the idea of becoming a copywriter. “I was instantly fascinated with how copywriters use their creativity to help businesses sell products and services. I noticed my own reaction to reading sales letters and marketing emails, and how they got me excited about online courses. I wanted to be able to do that.”
But there was one hurdle Ari still needed to overcome: he needed to figure out where and how to land clients who were willing to pay him good money for his services.
After months of trying the conventional route of sending out cold emails and networking, Ari had yet to get a single paid gig.
By this point, he was starting to doubt himself. “I’m a tenacious individual. Quitting and failure go against the core of my being. But I had to wonder…what am I doing wrong? It was demoralizing to try so hard, and not make any headway. I felt beat down and emotionally drained.”
Freelancing to win
Just as Ari was nearing the end of his rope, he opened up an email from Ramit Sethi’s “I Will Teach You To Be Rich” newsletter. In it, he read about Freelance To Win — and immediately clicked through to see how it could help him.
“The timing was perfect. I was so impressed with your approach to being an online freelancer, and started to realize that Upwork would be a great way to find my first clients, and build up my freelancing career. I’d used the platform as a client myself, but for some reason I’d never tried making money on Upwork as a freelancer. When I read about how well you’d done, it all just clicked. I thought, this could really work!”
Ari didn’t waste any time. He wanted to learn how to make money on Upwork quickly, and he wanted to start charging premium fees right out of the gate.
So he immediately signed up for Secrets of a Six-Figure Upworker, and never looked back. “I was willing to put the effort in. I just needed someone to show me HOW to do it.”
Getting his first Upwork client — and beyond
Ari trusted the process. He did the work.
But after a couple of days, the nagging doubt came back – with a vengeance. He’d submitted over a dozen proposals, and hadn’t heard back from a single client.
He was almost ready to give up for good, and resign himself to his 9-5 fate once and for all.
That’s when a message popped into his Upwork inbox. One of the clients he’d reached out to wanted to hire him.
Ari was over the moon.
Just two days into his Upwork journey, and he’d already landed his first client.
He almost couldn’t believe it.
But even though he could barely contain his excitement, deep down Ari couldn’t help but wonder if his quick win was just a fluke. “Keep in mind I’d experienced my share of setbacks. I didn’t want to be overly optimistic here.”
Would his success continue? Was it really possible to keep making money on Upwork like this?
A full blown side income from just 8 weeks on Upwork
Ari chose to push his doubts aside and keep working. “I decided have faith in the system — I knew it worked for others. I put my head down and kept running.”
The last of his doubts quickly vanished as he started hearing back from more and more clients.
One by one, the jobs started to roll in.
Ari was shocked by how quickly he was getting new clients. “Secrets of a Six-Figure Upworker worked faster than I expected. It would have taken me months, maybe years of trial and error to figure it all out on my own. Yet here I was with a full blown side income in less than 8 weeks.”
Quitting his job and going full time
It wasn’t long before Ari had more freelance work than he could handle.
In addition to the new clients he was taking on, he was also getting lots of repeat business from existing clients.
“They started emailing me out of the blue, asking me to do more work. That meant I could spend less time looking for new clients, and more time making money.”
Things were going so well that Ari decided to take the plunge and quit his job, becoming a full time freelancer.
“It was a little scary at first. But giving up my job freed me up to focus on my freelancing business even more. I’ve since been able to replace my income – and then some. In November alone I was able to book over $10,000 worth of projects, all stemming from clients I found on Upwork.”
By this point, Ari is finally convinced that it’s HIM — rather than luck — pulling the strings in his new career as a freelance copywriter.
“Everything I learned in Secrets of a Six-Figure Upworker was spot on. The strategies, and the psychology behind them–it all just works. I’ve taken other online courses, but it felt like they were just recycling the same information. None were as thorough as this. It was clear I was finally learning from someone who’d walked the talk.”
Writing Upwork proposals that work
Ari credits his proposal writing strategy as one of the keys to his Upwork success.
“As a client, I’ve seen the proposals most freelancers write. They’re usually very weak.”
Ari’s tips for writing winning Upwork proposals are powerful, yet simple:
1. Focus on the client’s SPECIFIC needs. “Read each job description carefully, and take a mental note of exactly what the client wants. Since I’m a copywriter, my potential clients may be looking to grow their email list, make their website more engaging, get more traffic to their site…it isn’t one size fits all. So you need to pay attention to the details of what the client is asking for in their job description, and make your proposal about that. That keeps you from sounding like everyone else, and shows the client you care about helping them win, which is what they really want.”
2. Overcome objections. “There are always barriers that can potentially keep clients from hiring you. For example, I charge over $100 per hour, which some clients consider expensive. So right in my proposal I’m already talking about the importance of investing in your business. I want to get them into that mindset of, ‘Okay, this isn’t cheap, but it’s important.’ I also mention the fact that I will edit the work until they’re happy with it. That eliminates the fear of what will happen if my first draft isn’t perfect. You can use this approach to remove any objection. The key is knowing what your ideal client is most concerned about, then using that information to make them feel comfortable. And you can do this right in your proposal.”
3. Start a conversation. “My proposals serve one purpose: To get a response from the client. That’s it. My goal is to get the client interested enough to write me back. From there, I’m going to try and move them to a voice call, either by phone or Skype. Once we’re talking, I can get a better understanding of how I can help them, and if I’m even the right person to help them. And then I have a much better chance of closing the deal if it’s a good fit. There’s no replacement for that human connection of just talking with someone.”
4. Under-promise and over-deliver. “It can be tempting to promise clients the moon in the hopes of getting their attention. Especially if you’ve sent out a bunch of proposals and haven’t heard anything back. Don’t do it! Stick to realistic timelines, and don’t promise anything you can’t deliver. Good clients are smart… If your proposal sounds ‘too good to be true,’ you’ll come across as desperate. Smart clients will sniff that out and it’s a turnoff to them. It’s better to be more low key in your proposal, and then impress the client by delivering your work better and sooner than they expected. That makes them feel like, ‘wow, this freelancer did a really great job.’
5. Be consistent. “You won’t always get a response to your proposals right away. Clients get busy, and it can take them a few days or even weeks to respond. And not every response will turn into a job. So it’s important to keep sending out those proposals. Pick a number to send out every week, or every day, and stick to it. That way you’ll always have plenty of irons in the fire at any given time. That’s what leads to success on Upwork.”
“It doesn’t feel like work”
Today, Ari is finally discovering what it means to do work he truly enjoys.
“It doesn’t even feel like work. Not in the traditional sense anyway. I’m excited to wake up in the morning. Corporate jobs claim they want creativity, but they don’t really encourage it. But as a freelance copywriter I get to use my creativity everyday. In fact, the more I use it, the more money I make.”
He’s also loving the “free” in freelance.
“Being my own boss is incredible. I’m not dependent on anyone else for my income. And there’s variety–I get to choose what I want to work on. Or if I want to go for a run instead of working, I can do that too.”
And the income potential? Ari sums it up well: “If you get hired at a corporate job at $70k a year, at the end of the year, you’ll make…$70,000. Whereas in freelancing there is no ceiling. It’s all up to you. You can choose to work harder, and earn more–if you want to.”
For these reasons, Ari couldn’t be happier about his decision to transition into full time freelancing sooner than later.
“My wife was a bit hesitant about me leaving my corporate job at first. But now she realizes that pursuing my freedom and my passion is what’s best for our whole family.”
Key takeaway: Everyone has a skill they can get paid for
Ari has a word of advice for anyone who’s considering jumping into freelance work without formal experience or training:
“Everyone has a skill that clients are willing to pay for. That’s why you get paid to work everyday. When you think about it, you’d be surprised at how often you do something as simple as writing an email. And yet there are clients out there who will pay you good money to do that!”
Ari also believes that having years of experience is overrated.
“I remember reading the book Rework by the founders of 37Signals. They explain how it’s almost impossible to tell the difference between someone who’s dedicated 6 months to their profession, vs. 6 years. I would have to agree.”