Episode
Why Don't My Clothes Feel Like Me Anymore?
- Published
- Apr 6, 2026
- Duration seconds
- 358
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Summary
This is a free preview of a paid episode. To hear more, visit moonshotmentor.substack.com Remember when lockdown happened and there were all those stories about people showing up to Zoom meetings looking perfectly presentable from the waist up — and if you got a peek below the camera line, you’d find them in their underwear and socks? I loved that. It was so human. So real. It was a great contrast to the pressure to get my wardrobe choices right. All those spoken and unspoken rules: Women wear heels, men keep shirts tucked. Dress for the role you want, not the one you have. First impressions happen instantaneously and last a lifetime — so be careful of what your sweater says about you. When we all worked remotely in 2020, those rules — and a gazillion others — started feeling more like suggestions. But here’s the thing about rules going soft, whether by a global pandemic or a career transition, chosen or not: it’s disorienting. When the pre-approved look comes off, a lot of people don’t know what to put on instead. Because for years, the job dressed them, in every sense of the word. And when the job changes, so does the style guide. When I made the transition out of corporate and into indie filmmaking, my Manolos and Pradas were not only inconvenient on set — they genuinely felt like a costume I’d been wearing for decades. If you’re in the middle of a career change, contemplating one, moving up, or been pushed into one, you may no longer feel confident about what to wear — or even who you’re dressing for anymore. When you open your closet, do you stand there longer than you used to? What Your Wardrobe Is Actually Asking You Here’s what I’ve come to believe: getting dressed during a career transition isn’t really a fashion problem. It’s a values question. Let me explain…