Podcast: Unemployed for a Living
Hosts: Cory and Ken
Episode Summary
Making decisions is easy when you have a boss handing them down to you. But when you’re working for yourself? Suddenly, every choice feels massive. Should you start that side hustle? Quit your job? Take that big risk?
In this episode, we break down what it really means to trust yourself as a decision-maker when you’re self-employed. We share how we personally approach risk, the biggest mistakes we’ve made, and why overthinking can be your worst enemy. Plus, Cory reveals his highly scientific way of determining your risk tolerance (hint: it involves butt-puckering).
If you’ve ever talked yourself out of a great idea because it might fail, this one’s for you.
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💡 Key Takeaways from This Episode
- Why decision paralysis keeps so many people stuck in jobs they hate
- The false sense of security in a 9-to-5 job (it’s not as stable as you think)
- How to start making confident decisions—even if you’ve never worked for yourself
- The difference between risk-taking and stupidity (trust us, there is one)
- Why perfectionism is just another form of fear
- Ken’s secret to making a pro and con list that actually helps
🎯 Episode Highlights
- [00:00] – Intro: Are you comfortable making decisions for yourself?
- [05:30] – The real reason most people never leave their jobs
- [12:10] – Cory’s approach: Take the risk now, figure out the details later
- [19:45] – Ken’s approach: Overanalyze until the opportunity disappears
- [28:00] – The “Butt-Pucker Scale” for determining your risk tolerance
- [34:40] – The #1 mistake new entrepreneurs make when deciding to start
- [42:30] – Final thoughts: How to trust yourself and just start
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- YouTube: Unemployed for a Living
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