No Perfect Answers with Caroline Stanbury

What happens when you stop choosing the “right” answer… and start choosing the honest one?

In this bonus game episode of The Iconic Midlife, Roxy Manning puts reality tv star Caroline Stanbury in the hot seat for a rapid-fire round of impossible trade-offs, power plays, social dynamics, ambition, relationships, image, control, and the real cost of living life on your own terms.

There are no safe answers here.

From choosing between power or peace, privacy or visibility, control or freedom, Caroline is forced to answer the kinds of questions that reveal how someone actually thinks when there’s no perfect option on the table.

The result? Funny, sharp, revealing, and at times surprisingly honest.

Inside the episode:

• the trade-offs behind confidence and success
• whether being respected matters more than being liked
• the hidden cost of always being “on”
• ambition vs ease
• visibility vs privacy
• control vs freedom
• what Caroline values when both choices come with a price

And yes… some of these answers get very real.

🎧 If you’ve ever wondered what someone like Caroline Stanbury actually prioritizes behind the image, this is the episode.

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Apple Podcasts: https://podcasts.apple.com/us/podcast/the-iconic-midlife-with-roxy-manning/id1817484587

Spotify: https://open.spotify.com/show/4FRDzq3AalXaqfpfWq7dlm?si=7e91db12ba1f4bfa

Amazon Music: https://music.amazon.com/podcasts/ff905ad8-332f-430e-a040-ce1ba5047483/the-iconic-midlife-with-roxy-manning

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Social media: @theiconicmidlife (show) | @redcarpetroxy (host)

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I love the journey. I don't want to get to the end so fast. Enjoy the process.

Right now, the standard I hold for my life is blank.

Extremely high. If it doesn't work for me or it doesn't bring me joy, it's out.

Life is too short.

Friendships too.

It doesn't make sense to carry a friendship that is toxic. Especially now.

I'm shedding very fast right now, and I'm not that upset about it. The best things come. If you make uncomfortable choices in uncomfortable times.

And you can be a little scared, that's okay.

You can shit your pants. Do it. Leave. If everyone tells you, don't do it. Jump.

The conversation around aging and beauty is completely wrong about blank aging in general.

I mean, I think that, you know, it's inevitable, but that's what they say, but it's not anymore.

We can do all the tools and all the things that we want.

We can do all the things.

This is a just a rapid fire. Whatever comes to mind first. Just say what's on your mind, my friend.

Go for it.

The biggest misconception about me that most people think is blank.

I'm a bitch.

I have the proof. You're not. People underestimate me when it comes to blink.

Everything I'm building.

I know it sounds exciting. And a house in Africa, too.

Well, that's the community I'm building. Yes.

What country in Africa?

Tanzania.

Oh, wow. Amazing. The conversation around aging and beauty is completely wrong about blank aging in general.

I mean, I think that, you know, it's inevitable, but that's what they say. But it's not anymore.

It's not. We can. We can do all the tools and all the things that we want.

We can do all the things.

The part of making unconventional life choices that people don't understand is blank.

The best things come if you make uncomfortable choices in uncomfortable times.

That's a good one. And you can be a little scared. That's okay.

You can your pants. Yeah.

Full blown shit pants.

Full blown. Do it. Leap. If everyone tells you, don't do it. Jump.

Most people build businesses for blank, but I build mine for blank.

Most people build businesses to make money, which I do too, but I also build mine for the journey. Like, I love the journey. I don't want to get to the end so fast. Enjoy the process.

Okay. Okay. That's. That. That seems very evolved.

Be careful what you wish for because, you know, with businesses, you want to get bigger and bigger. But that's not the fun bit in the end. The fun bit was when you were the founder and the. The creator of it and building it like that.

And then when it gets too big for you, it actually takes a lot of the joy from a business.

The difference between being liked and being respected is blank.

I think your Persona, what you put out there for people, you know, everybody wants to be liked, but, you know, everybody needs to be respected because everybody's journey is different and everybody is going through their own shit. Really.

Was there a shift for you? Were you. Did you always like to be liked and then respect became more important?

Well, I think respect comes when you start to do things that people don't necessarily like. Right. So, you know, to gain respect, you have to do things that other people wouldn't necessarily do, I suppose.

Yeah, you have to chart your own way, you know. Yeah, people underestimate me when it comes to blank.

Lots of things. I think being a housewife, people automatically dismiss anything you're doing.

There goes another reality star who thinks she, you know, this people love to underest, underestimate. But now it's all coming to fruition.

I'm, you know, you can be a TV personality and do multiple things and I think, you know, back in the day, used to say, jack of all, trade, master of none. That doesn't apply anymore. I think, you know, you need daps. I. I took it on board.

You need to have at least seven businesses today to make you money because things change on the, you know, flip of a coin. And if you're not ready or if you put all your eggs in one basket, that doesn't always work out.

Yeah, that's a very good point, actually, is don't put your eggs in one basket, especially with business, because you're right, it changes the market, changes, like, everything.

So life is. Life is very different.

When we were growing up and people told you, you know, become a lawyer, become a doctor, do all that, you know, you didn't have what we have around right now with Chat, gbt, Claude. You know, AI, like, all of these things will come obsolete. You better know how to do different things, you know, like really different things.

So, like, I've always, always been a serial entrepreneur. I've done loads of different things. But if you know numbers and you understand the business, you can do any business.

It doesn't matter if you are building a bank or building a yogurt company, they're the same bloody thing. In the end of the day, if you, when you get down to the.

Numbers, where does that entrepreneurial spirit come from? You? Is it something you've just always.

Always had. Yeah, always at school. I just wanted to know. I think I went to boarding school.

I wanted, you know, I was controlled by my allowance, my parents, my teachers. And I thought, fuck this shit. I'm going to make my own money and no one's ever going to tell me what to do again. And it was as simple as that.

And I never did.

Right now, the standard I hold for my life is blank.

Oh, I have so many boundaries. Extremely high.

I can imagine, lady.

Yes. Much higher than I think I've ever had because I absolutely at the top of everything right now.

So if it doesn't work for me or it doesn't bring me joy, Mary Kwondo says it's out.

Life is too short, you know, Friendships too. Yeah, friendships. That's a thing. Especially now. I mean, shedding the baggage. It doesn't make sense to carry a friendship that is toxic.

Especially now, right?

Oh yeah, I'm shedding. Like I'm shedding very fast right now. And I'm not that upset about it.

For 25 year old Caroline, what advice.

Would you give her not to take life so seriously? To slow down? I think I was in such a rush to grow up, I really wanted to be the next net, a porter and to, you know, raise all that money.

And I, you know, took on all these staff and I just, you know, I was running around like a lunatic, which I still do, but I do it much more, as you said, intentionally now.

And I'm creating this life where I know that, you know, this project will pay this project which will pay for the rest of my life so that I can retire and be peaceful and I, instead of rushing around all the time, time. Now I'm enjoying my holidays with my children. I'm going away next week with my husband.

I will, you know, not look at my phone all day and I will, you know, run into the water and snog him for hours and, you know, have the most magical time that I would not have had time to do before or wanted to do before because I was just so in love with making money and like building what I was building. And you know, ultimately when I lost my business, I've learned that, that sometimes you don't get what you are. You know, what you need is. Right?

You don't get what you want. You get what you need. And that happened to me, I believe, to make me a much nicer, softer human and to realize that actually that wasn't my path.

I don't want to be the CEO of a hundred million dollar business.

I want to be the CEO of my world that is like, oh, you know, my little pink golf cart, my husband, my kids, my pink Bentley going around town like I love it. That's it. I'm happy.

Do you have any regrets?

No. God, no. Never regret, never look back. Once it's over, it's over. No.

What is the biggest lesson you've learned in midlife?

The boundaries are super important. Stop being used by people. I think has been a big one.

Would you have considered yourself a people pleaser before?

Yes. Oh, yeah, many times.

Especially because everybody, you know, you feel you owe it to people to be extra nice because I think, you know, you're well known and so you just do things as favors. And I've realized, you know. No.

Yeah. That.

Thank you for having me.