Cover art for podcast The Freelance Podclass

The Freelance Podclass

85 EpisodesProduced by Craig CanningsWebsite

The Freelance Podclass is not your ordinary podcast! It features a series of actionable lessons designed to help you solve the biggest challenges you are facing in launching and growing a profitable Freelance Business. Join the founder of Freelance University, Craig Cannings, and an amazing faculty … read more


The Digital Nomad Lifestyle Class with Robert O'Kruk

In this class, I’m joined by Robert O’Kruk, a Digital Nomad expert who shares his insights on how to build a thriving freelance business working from anywhere in the world. He unpacks three key principles to help you be successful on remote work platforms and other client networking opportunities. And he shares his opinion on the top three destinations for Digital Nomads. The principles discussed here can help you achieve the lifestyle you want and make a positive impact.


Podcast Outline:


0:00 - Opening thoughts

1:05 - Introduction to Robert O’Kruk

2:26 - Robert describes the journey that led him to freelancing as a Digital Nomad

5:33 - The pros and cons of being your own boss

6:36 - Craig’s journey and the benefits of working remotely

8:30 - Is a Digital Nomad or Laptop Lifestyle attainable?

12:10 - The importance of a supportive community


12:51 - Practical steps to building a Digital Nomad lifestyle:

  • 13:13 - Two buckets of how it happens:
  • 1) The logistics
  • 2) Earning money remotely


15:46 - Three key principles people need to cover to be successful using remote work platforms:


  • 17:07 - 1) Create the perfect profile based on what’s working.
    • Create a list of 20-30 profiles of people on a remote work platform like Upwork who are matching those characteristics.
    • Go through the profiles in depth:
      • Take note of trends and unique fits.
    • Research what’s working for others and then use that as your inspiration to create your profile.


  • 21:12 - 2) Get instant automated notifications for the ideal jobs:
    • Free tools you can use when you’re using Upwork or other platforms


  • 25:09 - 3) Send a custom tailored proposal in a time-efficient manner.
    • Two keys to a proposal:
      • Being custom tailored - Read specifically what they need help with and then write something that’s tailored to that.
      • Being time efficient - You need to send 20 proposals to land your first job, taking 3-5 minutes apiece.
        • How “The Tactically Tailored Template” can help


  • 29:18 - Two takeaways: 
    • You want to be contextually relevant.
    • It’s easy for people to give up as a freelancer - There is a numbers game.


  • 32:25 - How the three principles apply in many places in life and lead to success


34:38 - Dispelling some myths about Upwork

37:12 - Advice for applying the three principles in other ways

37:35 - Robert’s top three destinations for Digital Nomads

39:33 - Final thoughts and how to find out more about Robert

Resources and tools discussed in this episode:


How to connect with Robert O’Kruk:


The Tactically Tailored Template:


Google in Canada: 




Google AdWords (now known as Google Ads):

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