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Travis
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You're listening to the Travis Makes Money podcast presented by gohighlevel.com for a free 30 day trial of the best all in one digital marketing software tool on the planet, just go to gohighlevel.com travis.
Travis
What is going on, everybody? Welcome back to the Travis Makes Money podcast where it's a mission to help you make more money. Today on the show, I have a new friend, Yasmin. Cheyenne. Yasmin is a three time HarperOne author and today's show wellness expert who's guided hundreds of thousands of people back to who they were before the world had a say. Through her writing workshops and teachings, she helps people reconnect with their purpose and step into their comeback era. And her new book, the Comeback Era, helps you reconnect with the little version of you and reminds you that it's never too late to start again. Yaz, welcome to the show.
Yasmin Cheyenne
Thank you for having me. I'm excited to be here.
Travis
Yes, ma', am. Of course. So I want to go back in time a little bit first before we talk about the book. Tell me the first time that you ever made a dollar that got you really excited. Like, you couldn't believe that somebody PA paid you money to do xyz.
Yasmin Cheyenne
Oh, I absolutely love this question. When I was in fourth grade, I started a magazine. It was similar to a tabloid, honestly, but it was the gossip of what was going on within the classroom. And a friend and I started selling it and we sold it for like $2 and 50 cents. And I was like, oh, crap. Like, this is a really.
Travis
You wrote a gossip column about your class and then sold it to your classmates?
Yasmin Cheyenne
Yes.
Travis
Wait, did the school shut it down?
Yasmin Cheyenne
The reason the school shut it down is because we didn't realize that printing it on school paper was a problem.
Travis
So, yeah, yeah, it's funny because, like, every time I ask that question a lot and I get some of these, like, creative school stuff, and almost every time the school ends up shutting it down, which, I mean, I guess they probably should, but I. I hate to see it, you know?
Yasmin Cheyenne
Yes.
Travis
The Discouragement of young entrepreneurship. So it was sort of in your blood then it seems like, what. What did your. What did your parents do?
Yasmin Cheyenne
It was so interesting. Both of my friend and I didn't get in any trouble. They were actually so proud of us for thinking of a way to start our business. It was a magazine, so yes, it was like a little sleazy in that it was gossip, but they were really impressed with the way that we had turned it into something that people were interested in. We found a solution for what people wanted.
Travis
And were your parents entrepreneurs or what did they do for work?
Yasmin Cheyenne
Yeah. So I watched my work a 9 to 5 and have her own business. Growing up, she did party planning events. And I saw that from early on I would help her make the favors to the parties and do things. And so I think that was also ingrained in me from that experience of watching her do that.
Travis
So was that what you wanted to do as a kid was entrepreneurship, or did you go a different path first?
Yasmin Cheyenne
So if you had asked me, like, let's say in elementary school, what do you want to be when you grow up? It was definitely a lawyer. I thought that that was a safe way to find, you know, money, access, opportunity.
Travis
Sure.
Yasmin Cheyenne
And from experiences like the magazine one or watching my mom have a side hustle, I knew that having a job wasn't going to necessarily be the thing that was going to help me get to where I wanted to be. But I just didn't think entrepreneurship was an option early on. Honestly, I thought I needed to pick a safer route.
Travis
Yeah. So what was that safer route?
Yasmin Cheyenne
The military.
Travis
Really? Wow.
Yasmin Cheyenne
Tell me that.
Travis
Tell me about that.
Yasmin Cheyenne
So I served in the Air Force for five years on active duty. Thank you for my. Thank you. I joined shortly after high school. And when I think about that, I'm mystified because it's 20 years ago now, but we were like at war. And I don't remember having that be a part of my consideration. It was no. And that's the power of being young. Because you're just. You just don't realize. I just saw the opportunity and I joined what the Air Force has, which is called jag, it's the legal department of the Air Force. And so I got the opportunity to have the experience of what I thought I wanted, which was to be an attorney. So it was very strategic. Strategic. And why I didn't.
Travis
Did you. Did you like complete schooling and things like that in the Air Force for that purpose?
Yasmin Cheyenne
I did. I got the opportunity to. I got my four year Degree. I got to second chair, which is be next to the attorney who is presenting the evidence. I got to. I learned everything that you would need to go to law school. It's just by the time I got out of the military, we were in a recession and I knew that I was not going to take on hundreds of thousands of dollars of debt in an economy where people were not being hired. And so that's where entrepreneurship kind of became the only, the only option for me. It's. It felt like if there's so much of a risk here, then I might as well take the risk on myself.
Travis
Yeah, sure. Like, if, if, like there was sort of this overwhelming evidence that even if you, even if you took the quote, unquote, safe path, that it wasn't actually the safe path for sure.
Yasmin Cheyenne
And so many people I knew who had master's degrees, law, law degrees, they had no. They were struggling to find a job and they had those big bills to pay. Those, those big student loan bills to pay.
Travis
Yeah. Mortgage payments, basically.
Yasmin Cheyenne
Mortgage pay. Yeah. So, yeah, that's what's, that's what gave me the, the encouragement to start doing business on my own.
Travis
It all of a sudden seems like a little bit less courage is required when it's like, you know, like, take your pick. You know, one of these, like all these paths are going to have a level of danger to them, so you may as well pick the one that, that has the most outsized reward, which most of the time be the entrepreneurship path. So what, what exactly did that look like for you practically?
Yasmin Cheyenne
So I want to be honest too. So I did have a 9 to 5 still. So I was working for the government at the time. I was working for the Veterans Affairs.
Travis
Okay.
Yasmin Cheyenne
As a government employee. And then I was also writing on my own and coaching on my own. At the time. It wasn't really. It was called coaching, but it wasn't what we know as a coach Today back in 2012. And I knew that I wanted to be doing it full time, but I also knew that I didn't want to have to depend on my business to pay my bills because it was just going to be too much stress. And so I was just doing jobs on the side, taking clients on the side in my off time, doing events on the weekends, and then having my 9 to 5 during the week. And I did that for almost 10 years until I left my 9 to 5 in 2021.
Travis
2021. Okay. What made you make the decision to leave the 9 to 5?
Yasmin Cheyenne
Finally I got to a place in my business, honestly, where I had to turn opportunities down because I was working and because I was a government employee, I couldn't do a lot of media. And I really wanted the opportunity to get my business out there. And it's the wildest story because I left my job on a Friday, and that Monday, the Today show reached out to me. And I always think that that's such an interesting experience of what it's like to take a risk on yourself. I had no idea that that would happen. But had I not been leaving my job, I would have had to turn down because I wouldn't have been able to go on and do it. And so sometimes we need those winks from the universe to let us know that we're kind of on the right path. And that felt like one of those for me.
Travis
When you're. If you're talking to somebody who is maybe in a similar situation where they're doing stuff on the side, they're pulling, you know, extra hours to work on this side, hustle, work on their dreams type of a thing, but they're still in their nine to five.
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Travis
and maybe maybe they they have a family and they have expenses and they have a mortgage payment and they have some of these things that you know that you don't really have when you're maybe 2021 type of a thing. Are there any I Guess mindsets, parameters, tools, like anything that was helpful for, for somebody like that to decide when and how and if they should be leaving their nine to five in order to pursue this. Like, is there a certain dollar amount in the bank account, a certain number of months of expenses saved up, certain amount of income coming in from the business to offset what you're making 9 to 5. Do you have any sort of advice for somebody in that position?
Yasmin Cheyenne
Oh my God, I have so much. So I would start with this. You need to see a financial advisor if you're about to leave your nine to five. And I know that you might hear that word and automatically think, I can't afford a financial advisor. But you'll be surprised how many institutions offer it for free. I'm not affiliated with this organization, but there's like an Edward Jones Capital One. All these banks and all of these places often offer fees for free. And the reason why you want to sit down with them is because they're going to actually look at your expenses and then they're going to look at your future, AKA your retirement and let you know if you have enough money coming into your business and whether your business is actually sustaining that. Because a lot of people had a real big bump in their businesses maybe during COVID when people were spending in different ways and then now they're, they're really seeing the impact of how that's gone down and it's changed. And if you didn't speak to someone to help you be able to weather that change, it's. You might have to go back to working. And so that's the first thing that I would do, the financial advisor. The second thing that I would do is I would be honest about whether you can emotionally handle your business. Your passion being the thing that pays your bills. Some people really enjoy writing books and, or coaching or speaking, but don't want their gift to be the thing that they have to rely on. It does change the way you show up with it. It become, it's so fun, but it becomes business. And so that's something I would really offer people to really think about within themselves. And then the last thing that I would ask people to do is to be patient when you are often people who want to leave their job and go full time hate their jobs. And so it feels like I have to get out of here. It's almost like a scarcity of if I don't get out of here, I'm not going to survive it. It feels like that I felt like that sometimes at work too. But sometimes when you're in that position, you don't make this smartest of decisions, and you go after and chase hope and potential versus reality. So you really want to look at your business as something that not only is going to be paying for your bills, it's got to pay your taxes, it might have to pay your health insurance. And it's very different than what it might look like for, you know, like, if you have a family, if you have kids. I have a husband, I have kids. I have to think about the whole of my family, not just myself. And so I think it's a family discussion that also needs to be made before you make that kind of decision that can impact you in a way that it's just hard to come back from.
Travis
Sure. Yeah. It's a. It's a not easily reversible decision. So it requires a little bit more thought and patience to go into it. Because sometimes it might just be the simple fact that you just didn't get enough sleep last night.
Yasmin Cheyenne
You know, sleep, or because you're so stressed, you're making decisions from a place that you're making decisions from overwhelm versus making decisions from what feels good. And I think also too, like, I'm in the spirituality world, I'm in wellness. And so people will often say, well, my gut told me, or I had a dream where it feels, I want you to follow those things, but I also want you to do your human work, which is the numbers. And so we have to make the decisions from both places. The dream doesn't necessarily have to go away. It just might not be able to be the full breadth of what you want it to be in this moment. And I think that's something that we definitely don't do enough is have those conversations.
Travis
How did you feel when you were. When you were actually able to go all in on business?
Yasmin Cheyenne
It was the most freeing thing that I've ever experienced. I still can't believe it sometimes that it's been six years. It's 2026. So it's been six years since I've been in business full time. And I'm. I'm incredibly grateful. I have changed the way that I look at my business. I find the parts of it that it's fun, like the writing piece, and then I have the parts of it that are not fun that I dedicate a certain amount of time to so that I can still feel the excitement that I felt when I first got into it. So it doesn't become stale.
Travis
So tell me a Little bit about the book, the Comeback Era. Why this book? Why this topic? Why now?
Yasmin Cheyenne
It kind of leans into everything we've been talking about. I think a lot of people, especially as they begin to hit midlife, you know, they have this feeling where they wake up in the morning and they think to themselves, like, is this really what I'm going to be doing here? Like, is this all my life is going to be? And it might be your job, or it might be the mundane ness of you do the same things, or you eat the same foods, or you're in a relationship that's unfulfilling. And I wanted people to feel excited by this feeling because it feels like doom. What it actually feels like when your feet hit the floor and everything sucks is I built this life by trying to check all the boxes or trying to go down this particular path, and it caged me. And so how am I going to get out of this environment or experience that I built for myself? But it's an opportunity for you to realize that you're uncomfortable. And that's a gift because surprisingly, a lot of people never recognize that they don't like where their lives are. They never feel that tinge of discomfort because they're so detached from their experience. They're just kind of moving through, like, kind of like robotically. To feel that discomfort is actually a gift, and it's an opportunity to explore how you can make the changes that you want. And I think that's why people call it a midlife crisis, because you start to just experiment in the way that it may be a child would. You paint, you color your hair, you try something new. But I think it's actually an opportunity for a comeback. I think it's an opportunity for you to gain clarity on who you really would be if you hadn't done with society, your family, et cetera, had said that you want to do. And so the book kind of walks you through those three phases. It's part one is curiosity. What is this feeling actually trying to tell me? And what can I learn from how I'm feeling in this moment? And then you go into part two, which is remembering who was I before I began to shape myself into what everyone else wanted me to be. And then part three is blank slate energy, where you begin to take what you've learned, that wisdom, that experience, and turn it into the fuel that helps you to go forward and be what you really want.
Travis
How do you. How do you reconnect with that younger version of yourself? Like, is there anything practically that we can do to think through that a little bit more effectively.
Yasmin Cheyenne
I have a lot of tips in the book and one of them that I'll share is here's something that's very interesting. If you I don't. If you don't have children, you won't
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Yasmin Cheyenne
you haven't been around children in a long time, but children rarely do anything that they do not want to do, even if it is something that is good for them.
Travis
Even if it's something that you tell them to do. 17 times in a row.
Yasmin Cheyenne
Yeah, 17 times in a row. It's every day it's the same thing. And it's because like they genuinely cannot do what they don't want to do or they're just incredibly defiant. But the part of that is incredibly, I think, helpful for them as they're growing because if they don't have that, then they begin to conform and they don't get the opportunity to explore, try new things, maybe even get hurt and learn the lesson like this. It's part of development and as we grow up, we stop allowing that to happen. We say, oh, I have to or well they would want me to or I should do it. And so I'd love to start with boundaries as an opportunity to connect with your younger self. Because you can ask your child like, hey, would you mind helping me with this really quick? And they'll like straight face, tell you no, like you could have your hands full. And they're like, I don't want to open the door, I want to climb that tree.
Travis
Yeah.
Yasmin Cheyenne
And although we can't be ridiculous in our lives, in every way. I think it's really an opportunity to get curious, because if you start to ask yourself, well, why won't I say no now? Why won't I do what I actually want to do in this moment? Why do I feel like I have to be this person in this relationship? Why do I always have to be the person at my work, in my work environment, who handles the project? Like, what are the reasons that I do the things that I do? And is it serving me? And a lot. You'll talk to people. I'm sure you talk to people all the time. So you hear people say, well, this is just who I am, or I'm better at it, or I'm just the person who gets it. And it's just, it's. It's something that you've developed and that you attached as part of your personality, not maybe necessarily who you actually are. And boundaries is a great way to begin to cut through that. And you wouldn't think that that's connecting with a younger version of you, but it's connecting with that version of you that wasn't so afraid to not necessarily be the person that makes everyone excited about your choices or your answers. You're. You're more willing to disappoint folks. And that's something that. That kids are definitely willing to do.
Travis
Yeah, it's one of those tough things, Yasmin, because, like, with my kids, too, it's like, I want them. I want them to. To think for themselves, to not necessarily, you know, be broken or. Or conform to everything. But also, I found it, and I'm curious what. What you think about this. I. I found it somewhat difficult because you also, like, we are social creatures and you have to be able to engage with people around. Like, it's really easy for us just to throw out the cliche or the trope of, like, I just don't care what people think about you. But it's like, we do to an extent. But also, like, you also have to care what people think about you.
Yasmin Cheyenne
We're.
Travis
We live in a society. We live like you want to have, belonging in a community. And if you just constantly are just changing the rules to the game because you can't win this one, I'm just going to go change the rules. I'm going to do this other thing, and I'm just going to do whatever I want. It's like, well, then we start moving into where this activity is not just a reflection of your. Of your inner child, but it's more of just a excuse to Be as selfish as you want to be whenever you want to be selfish. And that's only going to further alienate, alienate, alienate you and isolate you. How do you. How do you encourage people to navigate through this in a way that's healthy, that's a good version of reconnecting with that version of themselves, rather than just being like, I'm just going to do whatever I want because it's time for me to think about me.
Yasmin Cheyenne
This is such a good point. And I think it's important to mention because when you first start setting boundaries in your life, you do often swing that pendulum all the way to the other side and you just become, for lack of a better term, unreasonable.
Travis
Right.
Yasmin Cheyenne
And no one wants to deal with boundaries aren't ultimatums. It's not, you do this or else. It's, this is what's important to me. This is what I need to feel safe in this relationship. And then the other person gets to say what they need and you come to a sense of a compromise. And I think it's important. I think that's the part that we've lost in reconnecting with ourselves or reconnecting with boundaries or reconnecting with what we really want is that if you want to be in relationships that are healthy, if you want to have your business grow, if you want to be in community with people, you have to also be that village member. You have to also be that person that's going to show up and be there and do all of the things. And so boundaries, yes, but also. But the caveat that you're also going to have to honor other people's boundaries as well. You're also going to have to do what other people want. Sometimes it's a relations, and it's something that allows you to learn not only how to respect yourself, but respect others.
Travis
Yeah, absolutely. Absolutely. What are some of the. I assume now you've been doing this work for a long time. Do you have any specific examples or stories of people who you've watched go through this type of a transformation in their life?
Yasmin Cheyenne
Absolutely. I think about one person, or I can't even just talk about myself, but I'll talk about one person in particular. People who are recovering people pleasers, I call them in recovery because we always struggle. I'm a recovering perfectionist. But it's hard to shift because you got so much validation for being what everyone needs for you or being the person that's like, I'll do whatever you need. Yes, yes, yes. And that when that dopamine hit shifts when that validation shifts. And you have to learn how to validate yourself. You have to learn how to be there for yourself. You have to learn how to be in relationships where it's not always necessarily getting love bombed or so not always incredibly grandiose. That can be really hard for people to let go of because they don't feel that sense of love and connection that they've gotten used to, but they don't realize that it was very conditional. It was only based on you doing what people wanted you to do. And I think the hardest part of boundaries, and it's particularly this situation I'm talking about, was that once they realized that people were only in relationship with them because they did not have boundaries, that's when the shift began to happen.
Travis
Yeah.
Yasmin Cheyenne
And that's where you saw them start to make connections in relationships and friendships and at work that were reciprocal, rather than just them having to show up in this particular way.
Travis
Have you ever read the book Give and Take or heard of the book Give and Take?
Yasmin Cheyenne
No, I haven't.
Travis
By a guy named Adam Grant, who's one of my favorite favorite authors. But he talks about this concept that what you're exactly you're talking about because he, he talks about the three reciprocity styles of givers, takers, matchers. And then he sort of posits this question at the beginning that says, where on the success ladder do you think givers, takers, matchers end up on? And as you're reading the book, it's kind of like, oh, well, I assume because you're asking that question, that givers are at the top and takers are at the bottom. I assume that that's probably the case. What they found was that givers are both at the top and the bottom, and they're the. The difference between the givers at the top versus the givers at the bottom is the givers at the top are ones who were willing to set those boundaries at some point because they. They were not willing to be somebody else's door. They were willing to give and be as generous as possible and help as many people as they can, but with the caveat that they're going to protect their personal boundaries, their personal space, that they're not going to allow people to take advantage of them just for the sake of feeling useful or feeling like they should. Which goes directly into the point that you just made, which is that it is. It is possible to do both of those things, to be. To be both generous and caring and giving and and, and have that be your ethos in life. But at some point you also cannot allow other people who are inherently takers to just constantly take advantage of you and rake you over the coals with no consequences in the interpersonal relationship that they have with you. So I appreciate you being willing to share that a little bit as well. How have you found the book tour? Have you, have you enjoyed that?
Yasmin Cheyenne
I will tell you, a book tour is. It's stressful, it's grueling. Yeah, it's grueling. But it's the best part of the book tour is getting to actually see people. Have your book, getting to actually meet people who. I'm a three time author. I'm humbled by the experience of getting to do that. So I get to meet people who have read other books and getting to connect with people. It's the best part, but it is the most grueling process. I don't know how musicians do it a different night every night.
Travis
Yeah, yeah, no kidding. No kidding. Well, yes, I appreciate you taking the time to come on the show and share a little bit more with us. Where can people go to get more from you?
Yasmin Cheyenne
Yeah, you can follow me on Instagram. Yasmin, Cheyenne, and then all of my books are available everywhere books are sold, but the newest one, the Comeback Era, is available now.
Travis
The Comeback Era. If you are in the middle of a phase in life where you're just not exactly sure where you're headed, you owe it to yourself to go pick up a copy of Yasmin's latest book, the Comeback Era. So please do that now before you forget. If you're driving, just pull over and do it safely. But do it now so you don't forget about it. Yasmin, thank you so much for taking the time to come on and share with us. I know you're a busy person. I don't take that for granted. Everybody else tuning in, remember, money always only solves your money problems. But it's a little bit easier to solve the rest of your problems when you got some money in the bank. So let's start there here on the Travis Makes Money podcast. Thanks for tuning in. Catch you next time. Peace.
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Release Date: May 12, 2026
Host: Travis Chappell
Guest: Yasmine Cheyenne
Main Theme: The importance of embracing risk, mindset shifts, boundaries, and intentional living when pursuing side hustles, entrepreneurship, and your own “comeback era.”
In this episode of the Travis Makes Money podcast, Travis Chappell sits down with wellness expert, author, and coach Yasmine Cheyenne to discuss her newest book, The Comeback Era. The conversation explores Yasmine’s unconventional journey from childhood hustles and military service to entrepreneurship and authorship. Together, Travis and Yasmine dig into how to make big life pivots, smartly transition from a 9-to-5, set meaningful boundaries, and reconnect with your true self—even (and especially) if you feel stuck or discontent in midlife. The episode is rich with actionable insights for anyone considering a career leap or personal reinvention.
Timestamp: 01:17–02:24
“They were really impressed with the way that we had turned it into something that people were interested in. We found a solution for what people wanted.” (Yasmine, 02:24)
Timestamp: 02:47–03:38
Parental role models:
A path to safety:
Timestamp: 03:41–05:21
Military service:
Economic reality check:
“If there’s so much of a risk here, then I might as well take the risk on myself.” (Yasmine, 04:28)
Timestamp: 05:32–06:32
The “side hustle decade”:
Key lesson:
“I didn’t want to have to depend on my business to pay my bills because it was just going to be too much stress.” (Yasmine, 06:02)
Timestamp: 06:36–07:20
“It’s the wildest story because I left my job on a Friday, and that Monday, the Today show reached out to me... Sometimes we need those winks from the universe to let us know that we’re kind of on the right path.” (Yasmine, 07:06)
Timestamp: 10:55–13:55
1. Consult a financial advisor:
“You need to see a financial advisor if you’re about to leave your nine to five… They’re going to actually look at your expenses and…. your retirement and let you know if you have enough money coming into your business.” (Yasmine, 11:31)
2. Consider emotional resilience:
“Some people really enjoy writing books and, or coaching or speaking, but don’t want their gift to be the thing that they have to rely on. It does change the way you show up with it.” (Yasmine, 12:17)
3. Be patient and don’t act out of scarcity:
Timestamp: 15:20–17:24
Purpose of The Comeback Era:
“To feel that discomfort is actually a gift, and it’s an opportunity to explore how you can make the changes that you want.” (Yasmine, 16:15)
Three steps for a comeback:
Timestamp: 17:34–20:40
Childhood wisdom:
“Boundaries is a great way to begin to cut through [conditioning]. … It’s connecting with that version of you that wasn’t so afraid to not necessarily be the person that makes everyone excited about your choices or your answers.” (Yasmine, 19:38)
Reflection questions:
Timestamp: 20:40–23:07
Important to balance self-care with social responsibility.
Boundaries shouldn’t become ultimatums or justifications for selfishness.
“Boundaries aren’t ultimatums. … It’s not, you do this or else. It’s, this is what’s important to me. This is what I need to feel safe in this relationship. … If you want to be in relationships that are healthy … you have to also be that village member.” (Yasmine, 22:13)
Timestamp: 23:07–24:33
“Once they realized that people were only in relationship with them because they did not have boundaries, that’s when the shift began to happen.” (Yasmine, 24:22)
Timestamp: 24:33–26:10
“The difference between the givers at the top versus the givers at the bottom is the givers at the top are ones who were willing to set those boundaries at some point.” (Travis, 25:04)
Timestamp: 26:10–26:53
On book touring:
Where to find Yasmine & her work:
Yasmine Cheyenne:
Travis Chappell:
This episode offers a refreshing, practical take on career pivots, entrepreneurship, and personal growth. Yasmine Cheyenne’s candid stories and advice invite listeners to rethink what “safety” means, how to make bold moves responsibly, and how reconnecting with your younger, boundary-setting self can unlock your next comeback. If you’re considering a major change—or just seeking inspiration—this episode is full of actionable wisdom and authentic encouragement.
Where to find more: