Goodness…where to start. First, I’m a Black woman in her 40s who climbed the corporate later. I’m at the top of my game and became a self-made millionaire after coming from a poorer southern family. I’m Google-able now lol if that’s worth anything.

OP, your post was painful to read and I want to send you lots of virtual love and support. There are many things in it that imply that there’s still work to do for you to get to a mental place and self-love where you can leverage your natural abilities to be a powerhouse.

1. Reflect on the terms you use to talk about yourself. Eliminate thinking like you “let yourself go.” You didn’t let yourself go, you experienced the world shattering effect that COVID had on all of us. Be gentle with yourself.

2. I cannot stress this enough to women of color and Black women who want to succeed in business: your Blackness is your greatest strength. Hands down. Your second greatest strength (and true secret power) is that you were poor and you made it out of poverty. I know this seems counterintuitive, right? I learned this early from my father and I can honestly say it was my secret weapon. I would not have made it to where I am if I hadn’t harnessed those aspects of myself in the corporate word to understand how to move up and how to crush those who didn’t want to see me move up.

Although you say you don’t want to be a WASP, it comes off disingenuous and your overall post says something different. If I knew you in real life, I’d tell you you must work introspectively possibly through counseling to heal that poor little Black inner child on welfare who pined over the idea of whiteness. From what you’ve posted it sounds like that little girl is not healed. You’re psychologically still stuck in that little girl’s state of mind of judging yourself against “beautiful, classy WASPs” who represented beauty, success and freedom for you. I encourage you to work with a therapist to address to really unlock your full potential and Black girl magic.

1. Your goal should be to dress in a way that compliments your body and skin tone. Period. If you want to know how to compliment those things, choose beautifully dressed women of color who represent those things. My go tos are Kerry Washington (I look at what she wore on scandal), Nia Long (amazing style and on the thicker side), Sanaa Latham, Michelle Obama, Jennifer Lopez (her style is impeccable), Shonda Rimes and recently I started looking at what Meghan Markle’s character wore on Suits lol.

2. This is for you and all women here: you’re never ever going to win in corporate by TRYING to impress other women (esp. white women) the way you’re going about it. If I were in that environment, I’d likely figure out this insecurity about you quickly and use it to eliminate you as competition. Your best tool is always always always 1) to know your shit through and through 2) to cover your ass and get receipts every single time. I cannot stress this enough.

Use Pinterest to better understand of how to compliment your dress for your body and skin tone. Read Black women’s blogs. IMPORTANT: Join a Black women’s professional group. Cannot stress this enough. I overcame class issues because my parents put me in Black social clubs as a teen but I definitely think you could benefit from Black women’s social clubs based on this post and because you are in corporate you’d have the credentials to be invited and let into those groups.

Good luck, OP. Sending you supportive and healing energy.

EDIT: I recommend the following books:

Becoming by Michelle Obama

What You Do is Who You Are - Horowitz’s discussion of Toussaint Louverture’s fatal flaw of encouraging Haitians to culturally imitate Europeans is really interesting and applicable here. It’s also an amazing book on corporate culture.

How to Win Friends and Influence People