#76 How To Dress for The Woman You Are, Not The Job You Had
Episode Summary
When I walked away from my corporate 9–5 to start my business, I didn’t just quit the job—I left behind the wardrobe too. No more dressing to fit in or impress techies in sneakers and Patagonia vests. As we all know, the tech world isn’t exactly crawling with fashionistas.
In this episode, I sit down with Andie Sobrato, a Silicon Valley-based stylist who helps women dress like the leaders and people they really are. We talk about what happens when you stop choosing clothes based on approval or optics—and start dressing from a place of confidence, creativity, and self-respect.
This episode is about more than outfits. It’s about how to shed the corporate mask and fully be yourself as a business owner.
You don’t need a brand-new wardrobe. You just need a new way of seeing what’s already hanging in your closet and maybe a small hit of confidence.
In this episode you’ll learn:
[03:12] — Why so many of us used to dress to be taken seriously in rooms that weren’t built for us—and why that approach needs to change when you work for yourself.
[06:45] — How we’ve lost the creativity and fun in getting dressed, and why feeling stuck doesn’t mean you need to shop.
[10:01] — That “I’ve already worn this in a photo” nonsense—and how it’s keeping you from fully using the wardrobe you already own.
[14:26] — How to build a closet that reflects your brand and feels like you (think cozy CEO energy, not stiff and overdone).
[19:03] — The magic of a simple style system that saves time, reduces stress, and boosts your daily confidence.
[22:37] — Why dressing for yourself—not your Instagram feed, not your audience—is the most freeing move you can make.
[28:55] — Three ways to create “new” looks using what’s already in your closet (and no, this isn’t about capsule wardrobes).
[33:40] — Our final thoughts on using personal style as a form of self-leadership, ownership, and joy.
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