April 10, 2023

You’re Failing in Your Twenties…Or At Least You Think You Are | E93 Paul Angone

You’re Failing in Your Twenties…Or At Least You Think You Are | E93 Paul Angone
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I’m turning 30 next month and I’ve been unsure how I’ve felt about that. I’ve had countless conversations with guests that shared with me how silly it was to think they needed to “make something of themselves” by 30. Yet here I am, wondering if I’ve done enough to really make my 20-year-old self proud how I’ve spent the last decade.

That 20-year-old Justin had high expectations about where he was going to be at 30. I’ve learned over the last decade that you can set your sights on something but life has a whole lot of serendipity. And I don’t know, that’s kind of the fun of it right? I mean, at 20, I would have never predicted podcasting would be such a significant aspect of my life.

So here’s to me for letting go of any expectations, being proud of everything I have accomplished, and excited for what’s to come in this new decade.


I’m done with my poetic monologue but it does set up my conversation with my friend, Paul Angone.


Paul spent most of his 20s thinking he was a failure. Working at dead-end jobs to support his real dream of becoming a best-selling author, Paul grinded and hustled any moment he had - lunch breaks, late evenings, weekends - with the hope of creating something that sparked a fire.


Sure enough, it eventually happened (although much longer than expected) and Paul has gone on to author best-selling books including 101 Secrets for Your Twenties, 101 Questions You Need to Ask in Your Twenties, and 25 Lies Twentysomethings Need to Stop Believing. His newest book, Listen to Your Day: The Life Changing Practice of Paying Attention, is out today and I recommend picking it up.


Paul has spent so much time researching and understanding the unique struggles of being in your 20s. We get into a whole lot of conversation about these struggles including finding your purpose, feeling like a failure, and when to make sacrifices vs when to move on. You’re really going to like this one.


100 reviews before our 100th episode (consider it an early birthday present). If you’re a listener of the show and haven’t left us a rating and review, we’d really appreciate it if you did. And if you’re new, welcome, sit back, relax, and let’s learn something new.


I hope you enjoy my conversation with…”20-something failure” turned 5-time author…Paul Angone. 


Key Takeaways:

  • Why to consider sacrificing spending for time
  • When to keep going and when to give up a dream
  • How to find your “signature sauce”
  • Defining yourself in multiple ways
  • A lesson learned from the Mayor of Starbucks
  • How to find your significance by embracing failure
  • The possibility of greatness and embarrassment in the same space
  • Why you can’t label something a failure or success too early
  • How to listen to the small details of your day to find the answers you’re looking for



Searching for Sugar Man: https://www.imdb.com/title/tt2125608/


More of Paul:

Website: www.AllGroanUp.com

Listen to Your Day: https://allgroanup.com/books-2/

Instagram: https://www.instagram.com/paulangone/

Signature Sauce course: https://signaturesauce.com/


More of The Struggle is Real:

Find show notes and more athttps://www.tsirpodcast.com/

Follow us on Instagram athttps://www.instagram.com/tsirpod/