Money Rehab with Nicole Lapin
From Losing Dream Jobs to Booking First-Class Flights: Reinventing Success with Daryn Kagan and The Miles Husband
24 Nov 2025
Chapter 1: How did Daryn Kagan redefine success after losing her dream job?
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Chapter 2: What lessons did Daryn learn about financial security during her career transition?
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Money rehab.
Today's episode is a double header with a power couple I know you're going to love. In the first part of the conversation, I'm talking to the one, the only Darren Kagan. And let me tell you, if teenage Nicole had a vision board, this woman's face would have been front and center.
Before the world of social media and influencers, Darren was a trailblazing journalist covering some of the biggest stories of our time, from the Gulf War to 9-11, as a lead anchor at CNN. I never, ever even dreamed that our worlds would intersect, but they did. And we tell that story today. Darren was not only working my dream job at CNN, it was her dream job, too.
But as you'll hear in this episode, even dream jobs can come to an end. Darren opens up about how she found out her contract at CNN wasn't renewing and the questions that she will never have the answers to. She told me what came next and how she redefined success on her own terms. If you have ever felt like your career took a left turn that you did not see coming.
This conversation is one you need to hear. After the break, you'll hear from Darren's husband, Trent Swanson, a.k.a. Miles' husband. What started out as a small experiment to earn two free flights to Miami turned into jet setting across the globe in first class. Yes, I have seen the receipts. Emirates, Japan, champagne in the sky, all for literally $5.
Trent breaks down exactly how they hacked the travel points game, and they even helped my executive producer Morgan plan her honeymoon to Japan.
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Chapter 3: What strategies does Daryn use to create the role she wants?
So from losing your dream job to living your dream life, this episode is full of hard-earned wisdom, inspiration, and some Seriously game-changing money tip. Darren Kagan, welcome to Money Rehab.
I cannot believe we're here. I'm so happy we're here.
If I had a poster of you growing up, it would have been next to Christy Yamaguchi as like my idols, truly.
I mean, that's beyond, beyond, beyond, beyond.
And some say don't meet your idols. Chris Yamaguchi taught me how to ice skate, actually. And you taught me how to be a good person.
And in the order, ice skating, far more important.
Truly, you know, growing up, all I heard was like Darren Kagan, Darren Kagan, Darren Kagan. Like one day maybe you could meet her or smell her hair or like be in her presence because she's the one that made it out of the journalism class that both of us were in. Same high school.
For the record, I believe I graduated before you were born. However, we did not only share the high school. There's one legendary journalism teacher who taught there forever, Mr. Chesterton.
May he rest in peace.
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Chapter 4: How did Trent Swanson start his travel hacking journey?
But we should also say the reason we did meet was because at an incredibly young age for this kind of career, you landed CNN, which took me quite a few more stops to get to.
Yes. Back in the day in journalism, you... We're supposed to go through these small markets. And I thought like I would live and die in Poughkeepsie. And maybe one day I would get to Los Angeles and local news. And then I would die a happy woman.
NBC Los Angeles was my ultimate dream.
But then you were out. crushing it, covering 9-11, covering the Gulf War, like all the things at CNN, like the queen that you are. And yeah, I thought that, you know, maybe one day, like I would meet you somewhere and did not expect at 20 to get called for this thing, this internet thing at CNN. And I truly, truly, we were talking about it.
This morning, as we were thinking about you guys coming in, I thought I would audition there and it would be such a great experience. As it would have been. And I would leave and I would never, ever forget. And on the off chance I emailed you and I thought, maybe, I don't know, like maybe she would write me back. But you did. And it and it was it's something that I'll never forget.
And you invited me to sit with you on the anchor desk.
And here we are. And I'm so proud of everything that you've done. And yeah, I mean, that's just what you do. You be good and you be nice. That's what I always tell people. Be really good at your job and be nice to other people because, well, just because. But also that person you're being good to might one day just be a badass boss woman who you're thrilled to be on her podcast.
But you know, in that space too, oftentimes like women are pitted against each other, that there's some competition. And you bucked that trend for me.
Thank you for that credit. I would also say I felt like at CNN, that really was not my experience.
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Chapter 5: What tips does Trent have for maximizing credit card points?
It was women for women. People like Judy Woodruff, Greta Van Susteren, women supported each other. I can think of a couple that maybe passed a rumor or two. But in general, it really was about women supporting other women.
So when you see my email, I'm sure you don't remember this at all, but just based on that culture, you thought, okay, I'll help this young whippersnapper out.
Well, not to make you not feel special, but I'm sure you're not the only one that I invited to come sit on the anchor set. Like that's, that was not a lot out of my day. I'm sure. It's not that hard to be nice and it's not that hard to share.
Well, it was so gracious of you. And then three months later, I got a call. They're like, come to Atlanta. I was like, am I getting punked? Is this a joke?
I think what's interesting about your CNN experience, it was probably five to 10 years ahead of its time for the project that they brought you in to do. It was a streaming service. Like here was a crazy idea. We're going to have people that are just going to be streaming the news on the internet. Like, what is that?
And it ultimately didn't make it not because of you or because of the people who weren't involved, but I really do think it was too early.
Yes. The entire department got let go, which was a fascinating experience for me. But when I started, so I got there 2006 and you were leaving and,
Yes, that's exactly when I was leaving.
At the time, I had no experience with announcements. I just thought when people say I'm moving on to do other things, those are true. And so I had no idea why he left or what the story was.
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Chapter 6: How can anyone start their own travel hacking strategy?
And there was an email from the big boss. I think it was John Klein at that time and said, Hey, when you get off the air, why don't you come see me? I thought he was calling me up to tell me what a great job my team and I did on breaking news that day, which I assure you we did because we were very good at that. Yes.
And instead he called me up and he said, your contract is up the end of this year. And I want to let you know we're not going to renew you. But I'm not going to let you go. I'd like for you to stay. Well, I think I would. I'll let you know. So every day I came to work after that for like nine months. I didn't know if that was going to be the last day that I spent.
I mean, I'd spent 12 years there, which was a little stressful. But it also was a gift because I didn't know the thing. I hadn't figured out the thing I was going to go do next. So it was kind of quiet. And then about Labor Day, they called me and they said, OK, now we're sure. Now we know we're going to let you go. And then that was it.
But what's so unusual about that, usually with on-air people, you know, when you're done, you're done that day because they don't want to kind of put you on the air and... Let you say whatever you want.
Like I... this guy, John Klein, boo.
And I never asked why. People go, well, why did they let you go? I was really clear I was never going to ask why. Why? Why? Because why doesn't matter. I mean, you know how subjective that business is. It's kind of like toothpaste.
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Chapter 7: What are the common pitfalls in travel hacking that people should avoid?
If they decide they don't like you anymore, they don't. You work by contract, two, three-year contracts. It's not France where you're guaranteed employment for life. And I also probably figured I wouldn't hear the truth. Is it because you make too much? Is it because we didn't like who you were dating? Is it because any particular thing? It was enough to know they didn't want me anymore.
So it's like, all right, peace out.
Wow. I mean, that was so grown up of you because when I got the call from HR, all I said was like, why? Why? What did I do? I didn't know. But I, yeah, it was the first time I had ever experienced like a layoff or a firing or anything like that. And probably with breakups at the time, later on you learn it doesn't really matter why.
Although I would say there are plenty of guys I did ask why, but I wasn't going to ask you. But did they tell you why?
No, it was HR mumbo jumbo. But I didn't know that you're never going to get like satisfying answer. You're never going to get that closure.
So now you're the big boss woman. But if this situation happened to you again, where somebody was going to discontinue you or you did get fired or not continued, would you ask why?
No, I don't think so.
Everything ends. That's where I kind of come to my life. Every job, every life, every relationship, everything will end. And the kind of the why it ends eventually doesn't matter. It just ends.
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Chapter 8: How can listeners apply these insights to their own financial journeys?
And that's not people like, oh, that's so dark. But I actually think it's light because then you appreciate what you have while you have it, knowing that it's not going to be forever.
Well, the good and the bad. Yes, exactly. Exactly. And did you think when you heard around Labor Day that there was going to be no other role, like maybe originally you thought you would be reassigned to another hour?
Well, no, I knew that wasn't going to happen. So the gift of not being let go that day did give me time. First, I had my sad where, you know, I crawled under my covers and had my cry. And then I kind of started looking around. Well, what am I going to do? So the options then were. Try to get on with another network, like get up to MSNBC or Fox or one of, you know, ABC or CBS.
That would have meant moving. And I really didn't want to do that. Going back to local, I really didn't want to do that. I also had kind of a realistic look of, well, I could go to the next thing, but I knew I was going to age out. It's not like all women can't. There are some women who go forward, but eventually some 20 something comes up.
And at that pay rate, that pay rate, they will kind of scoot you out. And I came up with my idea. I decided I wanted to do uplifting and positive news. And it was just the beginning of journalists being entrepreneurs. I mean, by the beginning, I mean the very, very beginning. So I went and had my own website built.
I came up with what I thought was a good business model, which actually wasn't, but it was a thing to go do. And so when they said, now it's time, I was like, okay. I did go, I did say to the big boss at the time, I said, hey, I actually have this idea and it might be good for here. And they never asked me what. They didn't say what it was. I said, oh, good luck to you. And they let me go.
And then meanwhile, after I left, then they started like CNN Heroes. And they did start a lot of kind of good news, positive things. But that's okay. That was their thing. And I went off to do mine.
I want to double click on the age out situation. So did you feel like there was an expiration date?
I think there was. And I will be so bold as to say there is an expiration date, not for like if you're a really big star, not for the Barbara Walters or whatever. For heaven's sakes, Gayle King is 70 years old leading that. But if you're in that weekend, midday, those slots that can be really used to develop an up-and-coming talent, I think as a woman at a certain point, yeah, I think there is.
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