Square Peg Round Hole
Ever feel like you don't fit? Like you can't be real? In other words, you have to fake it because you're not accepted as your true self. Yeah, that seems about right. And ridiculous.
Every day people from every background—not just you—put on masks to make it through life. Talk about exhausting. But we keep doing it because no one wants to talk about the insanity of it even though it keeps us from being our best.
Well, that's about to change.
Welcome to Square Peg Round Hole with Timothy Eldred, writer, speaker, and friendly disrupter of the status quo on a mission to end aloneness and help people live and lead with authenticity in an artificial world.
Square Peg Round Hole
Ep.30 | Maybe
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I got an email last week that I've read fifteen times.
Someone had been reading the book. And at the end of it, they wrote: "Maybe I might just be okay."
I had to put my phone down.
A few days later, I got a phone call—different person, same word. After a long silence, they said, "Maybe I can do one more day."
Not a declaration. Not faith. Just — maybe.
This episode is about that word. What it costs to say it. Why we spend so much energy crushing it before it can get out. And why maybe is actually where everything real starts—not certainty, not breakthroughs, not finally having it figured out.
Just maybe.
SHOW NOTES
We treat "maybe" like weakness. Like it's the embarrassing rest stop on the way to healing—something to push through as fast as possible so you can get back to certainty and confidence and having it together.
But Tim has sat across from enough people at the end of their rope to know that's exactly backwards. Performed certainty is just another word for performance. And performance is what's keeping people stuck.
In this episode, Tim talks about what it actually cost him to stop manufacturing certainty—and what he found when he finally did. He shares two stories about the same word landing in two completely different lives in the same week. And he makes the case that maybe isn't failure. Maybe is the most honest thing you can say. And honest is the only place real change has ever started.
If you've been performing certainty you don't have—this one's for you.
Try this before the next episode: → The next time you feel a maybe surfacing—don't crush it. Don't reframe it. Don't find a verse or a framework to make it go away. Just let it be there for sixty seconds. See what happens when you stop fighting it.
The Shift — Tim's book — is out now. Order here.
Connect with Tim:
Substack: Square Peg Round Hole or timothyeldred.com
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Thanks for listening. Please follow on Facebook, Instagram, and Twitter. You can learn more about Tim here.
