Instructor
Kristen Proctor
6-figure freelancer, Upwork recruiter, & freelancing mentor
About me
I'm Kristen, your teacher and freelancing bestie. I spent years stuck in a toxic job with 70-hour workweeks, chasing promotions from an abusive boss who left me with PTSD (instead of a Christmas bonus).
When I finally broke free, I spent a year solo-traveling to recover. That’s when I found freelancing. And for a while, it felt like freedom.
But after a health scare, I got spooked and went back to a “stable” corporate job. Within two years, I was burned out again, caught up in office politics, and had a job-related mental breakdown so bad I had to take a grippy socks vacation (IYKYK).
After lots of therapy and soul-searching, I realized: I needed to build a life that was about living first and working second—one with less stress, more freedom and flexibility, and more joy.
So I gave freelancing a second chance. But this time with more intention and strategy.
And my old friend, Upwork.
For the last five years, I’ve earned a six-figure annual freelance income from Upwork clients working only 20-30 hours a week, doing work I genuinely enjoy with long-term clients who respect me.
I moved abroad to Barcelona on a digital nomad visa that my freelancing made possible. I wake up without an alarm, have chill work days, and feel happier than ever.
I’ve also been on both sides of the Upwork hiring table as a recruiter for my clients (kind of like a secret freelancing double agent). This gives me a unique, behind-the-scenes perspective on what clients are actually looking for across many different types of freelancing roles (not just how *I* got hired by clients).
Here are some stats to back up my experience with Upwork:
- Over $600k earned from Upwork clients in the last 5 years
- Thousands of profiles & proposals evaluated as an Upwork recruiter for my clients (and you'll see me evaluate other freelancers on Upwork live in this course)
Since January 2025, I've also been helping other freelancers (like you) create the same fulfilling life of freedom and flexibility with sustainable freelance businesses (without all the typical hustle/grind bro culture BS you’ll find from the other Upwork guru guys).