131: How to Know When It’s Time to Start a Side Hustle | Feedback Friday


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Dec 07 2018 50 mins   7

Jordan Harbinger (@JordanHarbinger) and Jason DeFillippo (@jpdef) banter and take your comments and questions for Feedback Friday right here every week!


Friend of the show and Entrepreneur on Fire John Lee Dumas (@johnleedumas) joins us to tackle one of our trickier questions about starting a side hustle!


If you want us to answer your question, register your feedback, or tell your story on one of our upcoming weekly Feedback Friday episodes, drop us a line at [email protected]. Now, let's dive in!


On This Week's Feedback Friday, We Discuss:



  • Are once-friendly people really avoiding you for some unknown reason, or is their perceived lack of interaction largely in your own socially anxious head?

  • When you're young and in long-distance love but also looking for a new career path, should you follow your heart and move closer to your sweetheart or follow your head and pursue local educational opportunities in your chosen field?

  • What's the most graceful way to turn down a retention bonus without sending a signal to the company you are looking for another job?

  • You're newly single and going to yoga classes. You want to ask out someone who seems to be expressing interest in you, but you also want to respect the yoga space and not tarnish your ongoing practice at this studio. What's the right next move?

  • You've recently been made privy to sensitive information about your clients from a well-meaning but careless business contact. How do you make this contact understand -- without being ungrateful for their effort -- that such information in the hands of someone less ethical could jeopardize their career and the integrity of your organization?

  • Your boss treats you as a liability rather than an asset thanks to fabricated and unsubstantiated accusations made against you in the past, but rumor has it this person is leaving in a few months. Is it worth your time to get this person to see your value, or should you just stay under the radar until the (fingers crossed) new boss arrives on the scene?

  • Your morale is low at your current company, and in spite of skill stacking to position yourself uniquely in any number of other companies, you can't seem to land an interview elsewhere. Is it time to scratch that entrepreneurial itch you've been feeling with at least an honest foray into the side hustle?

  • What can you do to mend the divide between you and someone with whom you shared a relationship when you empathize with why that person isn't exactly the president of your fan club?

  • Recommendation of the Week: The Final Table

  • Quick shoutout to Dr. Brad Block of the Physician's Guide to Doctoring podcast!

  • Have any questions, comments, or stories you'd like to share with us? Drop us a line at [email protected]!

  • Connect with Jordan on Twitter at @JordanHarbinger and Instagram at