Imposter syndrome and success paradox

Description:What does it mean to be okay when nothing is okay?

Not fixed.

Not optimized.

Not cured.

Just… okay.

This week, Jen and Amy sit down with bestselling author and professional weirdo Jenny Lawson to talk about surviving — and sometimes even thriving — inside a brain that does not always cooperate. Jenny’s new book, How to Be Okay When Nothing Is Okay, is a field guide for tender humans: a collection of tiny tools for when the big solutions feel impossible.

Today, we talk about:

• Living with “tiny erratic squirrels” in your head

• Why imposter syndrome gets louder with success

• Learning to live within your real capacity

• Why you’re not failing if it’s just not for you

• Helpful tools like “weird walks”, “body doubling”, “writing Zooms”, 

• The radical courage of simply staying

This conversation explores what happens when we stop trying to override our nervous systems and start listening to them instead. Midlife has a way of stripping away illusion — about productivity, about comparison, about who we’re supposed to be.

Jenny reminds us that sometimes grit looks like finishing the book. And sometimes it looks like taking a drink of water and calling it enough.

If you are exhausted, if you feel behind, if your brain tells you you’re the only one struggling – YOU ARE NOT ALONE. And being “still here” is no small thing.

Thought-provoking Quotes:

• “Self-help books are super helpful for the right kind of person but I’m not that person.” – Jenny Lawson

• “Keep in mind that what worked for you in the past might not necessarily work for you now or in the future, and that doesn't mean you failed. It just means that's an opportunity.” – Jenny Lawson

• “If you throw humor into a really dark subject, it gives people permission to laugh. And then that big monster becomes so much smaller.” – Jenny Lawson

Resources Mentioned in This Episode:

• How to Be Okay When Nothing Is Okay: Tips and Tricks That Kept Me Alive, Happy, and Creative in Spite of Myself by Jenny Lawson – https://amzn.to/4qWKZi5

• Samantha Irby – https://www.samanthairby.com/

• A Ghost and His Gold by Roberta Eaton Cheadle – https://amzn.to/405lMH8

• Anne Rice – https://annerice.com/

• Dean Koontz – https://www.deankoontz.com/

• Mexican Gothic by Silvia Moreno-Garcia – https://amzn.to/475Qp31

• Focusmate (Body Doubling App) -  https://www.focusmate.com/

• Let's Pretend This Never Happened: (A Mostly True Memoir) by Jenny Lawson – https://amzn.to/4rGEBN7

• Furiously Happy: A Funny Book About Horrible Things by Jenny Lawson – https://amzn.to/4u4RBxG

• Broken (In The Best Possible Way) by Jenny Lawson – https://amzn.to/4r3Bhuh

• Jenny Lawson Book Tour - https://thebloggess.com/2026/02/25/how-to-be-okay-when-nothing-is-okay-on-book-tour/

• Jenny Lawson’s Nowhere Book Shop in San Antonio, TX - https://nowherebookshop.com/
  

Guest’s Links:

Website - https://thebloggess.com/

Instagram - https://www.instagram.com/thebloggess/

Twitter - https://x.com/TheBloggess

Facebook - https://www.facebook.com/jennythebloggess

Pinterest - https://www.pinterest.com/thebloggess/

Substack - https://thebloggess.substack.com/

Connect with Jen!Jen’s Website - https://jenhatmaker.com/

Jen’s Instagram - https://instagram.com/jenhatmakerJen’s Twitter - https://twitter.com/jenHatmaker/

Jen’s Facebook - https://facebook.com/jenhatmakerJen’s YouTube - https://www.youtube.com/user/JenHatmaker

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