

Jason Weiss
Mar 1, 2024
The Parable of Bob's Pants: Liberation From the Closet of the Past
I was on a coaching call the other day with a client we’ll call “Bob.” Bob's a great guy, with a loving family and a fulfilling career. But Bob had a problem—a problem that was taking up space in his closet and cluttering his mind. He confessed to me, with a sheepish grin, "I've got too many pants that don't fit anymore, way too many to count." Ah, the eternal optimism of the human spirit, or is it the eternal denial? Let's find out.
These pants, Bob believed, were the silent judges of his success, or rather, his lack thereof. Each time he'd swing open his closet, those pants whispered (rather rudely, if you ask me), "Hey Bob, remember us? Still not fitting in us, huh?" It was as if his worth was stitched into the fabric of these trousers, trousers that hadn't seen the light of day in years. Bob was clinging to a version of himself that no longer existed, his self-esteem tethered to a waistline from yesteryear.
The more we talked, the clearer it became. Bob was in a relationship with his pants—a toxic one at that. Every encounter with them served as a reminder of a goal not met, a dream deferred. It was his daily dose of "You're not good enough," served up by denim and khaki messengers.
But here's the kicker: Bob was working out, eating healthier, and genuinely taking better care of himself. He was making strides, but because he hadn't reached that arbitrary metric of success—the Great Pants Fit of 2015—he couldn't see his progress. He was blinded by the fabric of failure.
So, I told Bob, "It's time to break up with your pants." Yes, you heard me. Get rid of them, donate them, free yourself from the tyranny of cotton and button flies. Why? Because success isn't about fitting into an old version of you; it's about embracing the journey towards the best version of you. And let's face it, if and when Bob reaches his goals, those old pants won't just be out of style—they'll be relics of a past self that Bob has since outgrown, both literally and metaphorically.
By the end of our chat, Bob saw the light. He decided to liberate his closet and, more importantly, his mind from the chains of those pants. And you know what? If Bob ever does fit into that size again, he's going to treat himself to a brand spanking new pair of pants, ones that reflect who he has become, not who he used to be.
So, let this be a lesson to us all. Our closets, much like our lives, need a bit of decluttering now and then. Holding onto the past, especially a past that makes us feel inadequate, is no way to live. We must let go, move forward, and make room for new experiences, new successes, and yes, even new pants. Remember, it's not about the pants; it's about the person wearing them. And Bob? He's doing just fine, walking a little taller these days, even without those old pants.
“I wear my sort of clothes to save me the trouble of deciding which clothes to wear.”
- Katharine Hepburn
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