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Apr 28, 2023
Career CloseUp: Expert Upwork Strategy Consultant


Hey, my name is Robert O’Kruk, and I guess I just wanted to share a little bit about my Upwork story. So for me, it started when I was 24. I was working in a semi-corporate digital marketing job, I was doing Google advertising work and I've been doing it for a few years and kind of got to a point where I was dreading going into day to day. I really wasn't enjoying my work anymore and so I quit my job, I sold everything that I owned, and I took a one way flight to Bangkok, Thailand. A few months into my travels, I was having the time of my life and I was trying to figure out how could I get some work, like while I was on the go, so I could keep earning and keep traveling, and that's when I found Upwork. And I got on to Upwork and I started doing the same thing I already knew how to do, which was Google ads work at the time. I found that I was making a lot more money than I used to when I was just working locally where I was from. And I also noticed that a part that a lot of people struggled with, which was actually like winning the clients on Upwork, was something that I felt very confident in. And so I started Google ads and then I eventually kind of brought into general digital marketing and Wordpress website development.


I went through a few different niches of work until I actually got into the world of coaching on Upwork and specifically helping other freelancers get onto Upwork and do well. And for me now, after doing this kind of side of it, for more than three years full time, I've had a chance to work with more than 100 individuals, one on one. And, you know, over the years personally, I definitely have been really happy with the amount of income I could earn personally. And I've definitely helped a lot of my clients earn a ton of money, but honestly, none of that has ever really mattered to me. The wins, and the most important part about my Upwork story, has always been around what success on Upwork has meant in my day to day life. And for my clients' lives as well.


There's been so many stories and experiences I've heard from my clients where–because they were able to be successful on Upwork, they were able to go traveling on the adventure they've been dreaming of for years, they were able to spend more time with their son or daughter, or take care of their sick parents or whatever it was. And that's the beauty of successfully freelancing on Upwork, is that you have more flexibility to basically lead and live your life the way you want to be. So, it's always inspired me and fulfilled me to help other people create that kind of lifestyle for themselves. For me personally, it meant that I was actually able to continue my travels for more than three years around the world, working remotely, and exploring the entire way. 


Along the way, I was able to fall in love with the first woman of my life ever and I also began to fall in love with myself and I feel that those experiences were empowered by the travel I was on and the travel was empowered by the income that I was making through Upwork. You know, after a while, I got tired of traveling and decided, hey, I want to be in one place, and again because I'm able to work from wherever I choose, I decided to move to Nelson, B.C., in Canada. It's a small mountain town that's absolutely surrounded by world class mountain biking and hiking and skiing and just so many of the things that I’m personally really passionate about and if I think about, like where would I choose to live? There was anywhere in the world, it's here. And it's funded by Upwork.


At the time of this recording, I just got back from a month long bike packing trip, I did the Colorado Trail Race, and I was able to take a month off because I set my own schedule and way that I work with my clients on Upwork. At the end of the day, you know, nothing is perfect and that includes Upwork. But when I think about broad strokes, like how has it impacted my life and how do I see it impacting my client's lives? It's a tool, just like any other, and so we have the choice on how we wield it and how it affects our lives. And I can earnestly say that I'm just grateful for how it's helped me to live my life, to change my life, to empower all the adventures over roughly the last five years, so I love Upwork.


Connect with Robert on Upwork 

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