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  • keyboard_arrow_right How To Transition Your Career To Upwork with Robert O’Kruk | Ep. 44


How To Transition Your Career To Upwork with Robert O’Kruk | Ep. 44

Filip Stankovski May 25, 2020

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The coronavirus forced us to stay at home but that doesn’t mean that we should spend our free time laying around and watching Netflix. Since everything is becoming remote, UpWork is the perfect platform to find fun projects you are passionate about, even make a good and steady income for yourself.

No matter what level you are on UpWork, you always need something you can improve. That’s why we invited Robert O’Kruk to help us out.

Robert O’Kruk is one of the leading educators and coaches for remote workers and digital nomads. He’s been privately trained by Google in Canada and has been part of the Upwork Pro Sales & Marketing team as well as their Top Rated freelancer program.

He is the founder of the 12,000+ member remote worker community, the Digital Nomads Forum and is also the founder of the Mindful Nomads Retreat, a mindfulness and remote work lifestyle based educational program.

Robert is focused on bridging the gap between working remotely and mindfulness. His goal is to help educate, inspire and empower remote workers to live purposeful, meaningful and happy lives.

Remotrepreneur’s Insights

  • Optimizing Your UpWork Profile – Robert says that your profile on UpWork is your biggest weapon. That’s why it’s crucial to optimize it and polish it to maximize your chance in landing a job.
  • Apply Fast – Time is of the essence even on UpWork. You have to one of the first to apply for a job in order to give you a head start of the competition. Robert explains the importance of timing.
  • The Perfect Proposal – If your profile is your biggest weapon, the proposal should be your ammunition. Robert gives us some tips on crafting the perfect custom-tailored proposal to grab the client’s attention.

“Ideally the proposal is inviting people to have a free 30 minute phone call. Free 30 minute phone call where you just talk with the client to talk if you guys are a good fit. Phone calls give you a higher chance to get hired.”

Key Podcast Milestones

05:00 – How Robert started working on Upwork

09:06 – Four key principles in getting a job on Upwork

10:36 – Principle #1

20:30 – Principle #2

28:10 – Principle #3

31:40 – Principle #4

38:32 – When to know the right time to close the job

47:24 – Where to find Robert and his coaching courses

55:45 – Should you start an agency on UpWork?

Top Key Quotes

“You have to realize that UpWork is not a computer or an algorithm that’s going to actually hire you. It’s a human. So, you need to learn how to craft your profile, interact with clients on UpWork in a way that’s optimized for the algorithm as well as the actual human and the business that’s going to hire you.”

“You can’t have good results on Upwork if you don’t have a good profile optimized for the algorithm and the human”

“People post an opportunity on Upwork. Then all the freelancers jump on it and usually 10 to 30 or so people who apply for each job. If you just kinda jump in there with everybody else, your just in the pile, you have no control. The key to avoiding in being at the bottom is learning to be the first person to apply for the job. On Upwork they give you all sorts of tools to refine and narrow down the entire list of job opportunities they provide.”

“The key to a good proposal you have to do two things. The first thing is you have to be time-efficient. You have to send an epic proposal in 3-5 minutes. You have to send a minimum of 10 – 20 if you have no reviews. If you have a crappy profile you have to send some more.”

“The proposal has to be custom tailored. We have to remember the human will have to hire you. What do they want to see? They want to see someone who has read the description of their job and they replied in a custom way that acknowledges everything they need. “



Gary V


Robert O’Kruk – Robert’s website

Robert O’Kruk – Robert’s YouTube channel

Robert O’Kruk – Robert’s IG



Don’t forget to get even more great episodes and resources to help you break out of the Matrix and grow your own remote empire at the Remotepreneurs website.

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Filip Stankovski

I'm a top rated sales freelancer on Upwork and Level 2 Seller on Fiverr. I believe that the new entrepreneurs are remotepreneurs and the purpose of the podcast is to teach people how to adjust to the new future of doing business - REMOTELY!

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