You’ve made it to what some would consider middle age — in spite of stumbling over every possible mistake along the way. But instead of enjoying your triumph over the odds, you can’t shake the feeling that it’s past time to get off the hamster wheel and make a difference. You’re frustrated and fearful of disappearing from the world without leaving your mark on it or handing down a legacy, some security, and a vision of what’s achievable to your kids, so we’ll do our best to help you figure out how on this Feedback Friday!

And in case you didn’t already know it, Jordan Harbinger (@JordanHarbinger) and Jason DeFillippo (@jpdef) banter and take your comments and questions for Feedback Friday right here every week! 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 Now let’s dive in!

On This Week’s Feedback Friday, We Discuss:

  • Interested in doing some prison time with Jordan next February? Reach out to for details!
  • Does a 32-year-old need to tell Mom before getting tattoos?
  • How do you say no to an insurance pyramid scheme?
  • Should you begin with your professional or personal life when overhauling for a fresh start?
  • What steps could you possibly take to get both of your bickering siblings to grow up?
  • How do you get your employer to see the value in letting you work from home once the baby you’re expecting is due?
  • Is it a mean-spirited, drama-loving academic advisor who is holding up your thesis progress, or is it secretly you?
  • You’ve made it to age 50 and feel like a frustrated nobody, fearful of never leaving your mark on the world. How can you turn things around?
  • Your spouse of three years is just now telling you about their massive debt. How can you be supportive without ransacking your own savings?
  • Life Pro Tip: When starting your day at an amusement park with kids, take a full body pic of each person individually so that if anyone gets lost, you can show security exactly what they look like that day.
  • Recommendation of the Week: The Family
  • A quick shoutout to Brett Jesperson!
  • Have any questions, comments, or stories you’d like to share with us? Drop us a line at!
  • Connect with Jordan on Twitter at @JordanHarbinger and Instagram at @jordanharbinger.
  • Connect with Jason on Twitter at @jpdef and Instagram at @JPD, and check out his other show: Grumpy Old Geeks.

Like this show? Please leave us a review here — even one sentence helps! Consider leaving your Twitter handle so we can thank you personally!

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Resources from This Episode:

in Feedback Friday, Podcast Episodes