Behind the Shade: Housewives, Hustle & the Midlife Game with Cynthia Bailey & Dana Hill-Robinson
What happens when a Real Housewife and a powerhouse attorney sit down for The Iconic Midlife Manifesto Game?
Cynthia Bailey and Dana Hill-Robinson are here—and they are not holding back. From navigating narcissists to chasing peace over drama, they’re dishing the truths, throwing a little shade, and revealing what really matters in midlife.
Expect laughter, lessons, and one very spicy round of “Iconic or Insane?”
🎧 Hit play to hear their bold takes on dating, confidence, boundaries, and what they'd tell their younger selves.
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Transcript
A boundary I'll never break again is.
Dana Hill-Robinson:Blank, allowing anyone to try to dim my light.
Cynthia Bailey:Oh, that's a good one.
Roxy:Did you hear that, Real Housewives of Atlanta? A red flag I no longer ignore is blank.
Cynthia Bailey:I am well researched on narcissistic personality disorder. I can spot it from a mile away.
Dana Hill-Robinson:We should have had a cocktail while we chatted.
Cynthia Bailey:I know, right? I think I'm gonna have one after.
Roxy:I'd love to play a quick rapid fire game with you. We like to wrap up the show with a little game.
Cynthia Bailey:Okay. I love games. Okay. All right.
Roxy:Okay. This is the game segment that is called Midlife Manifesto. So I will start a sentence and you finish it with whatever comes to mind first.
Cynthia Bailey:Okay?
Roxy:In midlife, I finally learned to blank.
Dana Hill-Robinson:Love myself, pamper myself.
Roxy:O. Those are both really good. Okay, next one. A boundary I'll never break again is.
Cynthia Bailey:Blank allowing any kind of disrespect.
Roxy:Do you hear that? Real Housewives of Atlanta.
Cynthia Bailey:I don't think they're included in this one because they've already been disrespectful. So.
Roxy:Yeah, I can only imagine.
Dana Hill-Robinson:Allowing anyone to try to dim my light.
Cynthia Bailey:Oh, that's a good one.
Roxy:Yeah, that one is really good and very.
Cynthia Bailey:Oh, you know what I want? I want to change mine. Okay. I love that one. I won't allow anyone to make me feel like I have to dumb myself down.
Roxy:Yes. We're done with that. That's, like, old news. That's not happening anymore.
Cynthia Bailey:Shine bright.
Dana Hill-Robinson:Shine bright.
Cynthia Bailey:Yeah, that's right.
Roxy:Okay. The sexiest thing about getting older is blank.
Cynthia Bailey:My confidence. Self confidence. Like, I. This is it.
Like, you know, you get the wig, you get the wig off, you get the makeup, you get the makeup off, you get the real body. Like, you. You get. Everything is you. You get the real. So I would say confidence.
Dana Hill-Robinson:Yes.
Cynthia Bailey:And just.
Dana Hill-Robinson:Just feeling comfortable. Comfortable being yourself. Like, my husband always teases me. Like we were first dating. In, like, one of the first nights we were together.
I said, you know, I'm not taking off my scarf.
Roxy:Your scarf?
Dana Hill-Robinson:Oh, my God.
Cynthia Bailey:Not messing up my hair.
Dana Hill-Robinson:Right. That scarf.
Roxy:You're like, okay, there's gonna be one thing that you're not going to touch tonight, and that will be the hair.
Cynthia Bailey:Right?
Roxy:Hey, I don't blame you. I don't blame you.
Cynthia Bailey:I love it.
Roxy:A red flag I no longer ignore is blank.
Cynthia Bailey:Oh, a red flag. I.
Dana Hill-Robinson:Nice.
Cynthia Bailey:You don't say narcissist. Yeah, I was getting ready to say I am well researched on narcissistic personality. Disorder. I can spot it from a mile away. No narcissist.
, I'm not doing narcissist in: Roxy:Goodbye. Got your fill? And they walks amongst. Amongst us, not only in our romantic relationships, but even our female friendship groups.
Dana Hill-Robinson:Oh, yes.
Roxy:That's some of the worst of it.
Cynthia Bailey:Oh, and family members. And family members. Don't forget the family members and business people in the year.
Roxy:You know, they're everywhere. They're everywhere. It's crazy.
Cynthia Bailey:Yeah.
Roxy:Yeah, absolutely. My power shows up strongest when I blink.
Cynthia Bailey:I would say for me, in mom mode, when I'm with Noelle, like, I feel like that is my. Being a mother is my biggest and most proudest accomplishment. I feel very powerful as a mom. Like, I'm definitely. All I need is my cape.
Because when it's time to clock in, as a mom, I am all the way in. And that is the job, the responsibility that I take the most serious. So, yeah, I think for me.
Dana Hill-Robinson:I think being able to deal with conflict and handling it in a balanced way and maintaining my composure, that is handling.
Cynthia Bailey:Power and handling it in a smart way. In a smart way.
Dana Hill-Robinson:Yeah.
Roxy:Correct. Yeah. If you can handle it in a smart way and not, like, just let it get to you, like, that's. That is a superpower.
Dana Hill-Robinson:Trying to stay, you know, maintain my emotions and just, you know.
Roxy:Yep, absolutely. One thing that used to scare me but doesn't anymore is losing friends.
Cynthia Bailey:Like, honestly, I feel like sometimes in life, you know, people are just with you for a reason and a season, and it's okay for one or two to fall off every year and two new ones to come on. Like, it just. It doesn't. I don't second guess it. I trust myself. I trust my discernment. I trust timing. I trust energy.
And, you know, sometimes it's just time to let go. And it's not even a bad thing. It's just you guys no longer energetically and spiritually, mentally, and emotionally have that connection anymore.
And that's okay.
Roxy:And that's okay.
Cynthia Bailey:Yeah.
Roxy:It's a season. Like, you're saying it passes. Mm. Yeah. And you have to be okay with letting it go, which we need to sometimes. Okay.
I used to chase blank, but now I attract blank.
Dana Hill-Robinson:I think I would say I attract opportunities.
For example, even the birth of Gloisima came from an opportunity of just out into the universe and speaking to people and speaking it into Existence and. And just being at the right place at the right time with the right people helped us to bring gluism to fruition.
Roxy:That is amazing. I mean, you say something and then you create it, and here it is.
Dana Hill-Robinson:Yes.
Roxy:Yes.
Cynthia Bailey:I feel like I used to chase money. Coming from very humble beginnings. Like, I always was.
Like, if I had money, I would have more options, I would have more choices, more power to do the things that I want to do. I won't be in a position of being stuck because I would have the means to do what I need to do.
So I feel like I used to chase money, and now I feel like I attract it. I feel like at this point, I built a brand for myself that people resonate with. I think as a person and as a brand, I'm very authentic. Yeah.
So opportunities and the money sing by me.
Roxy:Happiness to me now looks like blank.
Dana Hill-Robinson:Being in control of my destiny.
Cynthia Bailey:You.
Dana Hill-Robinson:Know, and that means, you know, like, for, you know, just working, being able to, you know, have my own businesses and. And not, you know, it's. It's great having the. Having that level of.
Of comfort of getting, you know, a paycheck every two weeks or whatever it is, but, you know, you never know when that's going to be taken away from you. So just being able. Control of that, for me, is. Is happiness.
Cynthia Bailey:Happiness looks like. Looks like peace to me. I feel like. And when you have true peace, you have happiness. You do because you have peace. Yeah, Peace. Peace equals happiness.
Like, when I'm at peace, I am genuinely happy. I'm in my happy place.
Roxy:Yeah, that. That is the key, being at peace. Ladies, I love chatting with you. It's like sitting with girlfriends at dinner. I love it. I love it so much.
Dana Hill-Robinson:We should have had a cocktail while we chatted.
Cynthia Bailey:I know, right? I think I'm gonna have one after. After we.
Roxy:Exactly. We're like, oh, yes, a margarita sounds good.
Cynthia Bailey:It.
