Podcast: Unemployed for a Living
Hosts: Cory and Ken
Episode Summary
In this episode, we’re taking a step back to reintroduce ourselves—both for our longtime listeners and those just discovering Unemployed for a Living. How did we end up self-employed? What pushed us to walk away from traditional jobs? And what lessons did we learn along the way? Spoiler alert: one of us had a literal “crappy” job experience, and the other was a model employee who stuck it out for 32 years.
If you’ve ever wondered whether self-employment is right for you, this episode gives a candid look at two very different paths that led to the same outcome—ditching the 9-to-5 and working for ourselves.
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💡 Key Takeaways from This Episode
- The exact moment Cory decided he would never work a 9-to-5 again (it involves a porta potty disaster)
- How Ken went from a 32-year printing industry career to full-time reselling
- Why some people thrive in structured jobs while others crave independence
- How every skill you pick up along the way can be used to build your own business
- The false sense of security in traditional employment—and why layoffs can happen to anyone
🎯 Episode Highlights
- [00:00] – Intro: Why we’re telling our stories today
- [05:30] – Cory’s long and winding road through dozens of jobs
- [12:40] – The day Cory got covered in human waste and swore off working for anyone else
- [22:30] – Ken’s structured career path and his surprising pivot to self-employment
- [34:20] – The importance of stacking skills from past jobs
- [42:15] – The one thing Cory and Ken completely disagree on
- [47:30] – What’s coming in next week’s episode: Decision-Making Without a Boss
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