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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 what I mean.

When I was in an executive gig, I genuinely valued the stability of that world — the sense that I could build something there over decades. Wearing those Manolos was part of that deal. I knew the rules, I understood the culture, and I made a conscious choice to dress for it. It wasn’t always comfortable, but it was mine to choose.

My brother Jim is a great counterexample. Jim would sooner show up to a board meeting in a tuxedo than wear a suit to work — and he never has, except on his wedding day. He works in construction because he loves the outdoors, loves working with his hands, and is completely at ease getting grubby. His wardrobe is a direct expression of what he values. He just never had to think about it because his work and his values were two peas in a pod.

When you’re in a career transition, you get a chance to ask a question most people never pause long enough to consider: Does what I’m wearing actually reflect what I value? Or have I just been dressing for someone else’s idea of who I should be?.

The Difference Between Choosing and Disappearing

When I dress in a way that feels true to me, I can regulate my nervous system. I stay grounded. I stay clear. In high stakes situations — interviews, pitches, hard conversations — that is an incredible advantage.

At the same time, I’m not going to pretend the external piece doesn’t matter. It does. Every industry has a visual language. Every culture has unspoken dress codes. The goal isn’t to ignore that. The goal is to look at it clearly and decide — consciously, on your own terms — how much of it works for you and how much of it doesn’t.

That’s the distinction I want you to hold onto: there’s a difference between choosing to dress for a culture and being swallowed by it. One is a decision. The other is erasure.

Which brings me to someone I want you to meet.

And Then There’s Dacy

Dacy Gillespie is an anti-diet, weight-inclusive personal stylist whose Substack is about letting go of what you’ve been told to wear so you can find what’s actually yours. She also made a significant career pivot herself — from musician to stylist — so she knows firsthand what it feels like to rebuild your identity from the inside out.

Where my work lives in the values and identity side of this conversation, Dacy lives in the practical, embodied, what-do-I-actually-put-on-my-body side. Together we cover a lot of ground.

I’ve invited her to join me for a live conversation on Wednesday, April 9th at 12pm PST right here on Substack. We’re going to talk about her pivot, what it taught her, and what to wear when you’re job searching, interviewing, or just trying to figure out who you are now.

No registration needed. Just show up. And if you have questions you want us to tackle, drop them in the comments below — or bring them live on the 9th.

👉 Follow Dacy on Substack here.

If someone came to mind while you were reading this—please send it their way. You never know the impact a well-timed message can have.

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Journal Prompts

Here are three journal prompts for Solid Ground members. These are here to help you explore the connection between what you wear, what you value, and who you're becoming in this next chapter of your career.

Why Don't My Clothes Feel Like Me Anymore?