From Future Executive to Creative Entrepreneur: How Kendall Cherry Rewrote Her Own Story

In this episode of the Changeology podcast, I interview Kendall Cherry (yes, like the fruit!), who is the powerhouse behind the Candid Collective, a ghostwriting agency that delivers world-class storytelling services. Kendall has written for $100M+ startups, email empires with 750,000 subscribers, and thought leaders with 7 million followers, and also writes about the art and craft of telling stories that sell in her weekly newsletter, Wallflower Fridays. 

But before starting her ghostwriting business, Kendall was on the fast track to achieving executive status and corporate success at a Fortune 100 company.
Kendall shares how a panic attack during a high-stakes presentation caused her to reconsider her career path and what she wanted from her life, shifting focus from rapidly climbing the corporate ladder to pursuing her true desire to start her own business and reconnecting with her childhood love: writing. 

This episode is perfect inspiration for anyone considering a major career change, especially anyone who is thinking about leaving the stability of the corporate world for entrepreneurship. 

Kendall's story is inspiring and infuriating in parts, so be sure to listen to the end to hear why!

What You'll Learn in This Episode:

• How Kendall navigated a toxic corporate environment, including dealing with a narcissistic boss and exceeding unrealistic expectations
• The pivotal moments that led Kendall to leave her corporate job, and the transformative conversation that changed everything for her
• How Kendall repurposed her corporate communication skills to build a successful ghostwriting enterprise
• The importance of maintaining autonomy and connecting with childhood interests when choosing a new career path
• Practical advice for those considering a major career change, including seeking outside perspectives and trusting your instincts

Book a free 30-minute Clarity Call here to cut through the noise and bring next steps into focus: https://www.megtrucano.com/book-a-call

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For women who know something needs to change and are ready to stop circling the decision.

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Transcript

@4:42 - Meg Trucano  

All right, so on Hello, my guest today is Kendall cherry. Yes, like the fruit Uh, who is the one woman powerhouse behind candid collective, which is a ghost writing agency that delivers world-class storytelling

that sells your products and services. She is also writing a book set for lease in fall 2025, right?

@5:07 - Kendall Cherry

Yes, yes.

@5:09 - Meg Trucano  

Awesome. So today, she will be sharing a story of how she went from the hustle and go-go-go of a Fortune 100 company to a successful ghostwriter with lots of things in between, I'm sure.

But I promise that her story will both infuriate and inspire you.

@5:30 - Kendall Cherry

So I can't wait for our conversation. Welcome to Changeology Kindle. I am so excited to be here. This is a topic that is near and dear to my heart.

I actually don't know if you knew this here. My last role, it's all going to come full circle. I just have a feeling.

But my last role in corporate, I was working on a really big project. It's called an ERP transformation. It's basically like big IT implementation for a company.

But I worked in Change. management is what I was doing at the end, which I did, I just like clued into that.

like, Oh my God, I'm coming together. So I'm really excited about this because I've experienced much change, pretty much complete.

If you would have looked at me 10 years ago and like what I thought, you know, fresh out of college, what I thought my life was going to look like my dreams and my goals, my lifestyle, how I was making money, who my friends were, all the things like could not be more different and also could not be more grateful that it changed.

@6:33 - Meg Trucano  

Awesome. We can't wait to hear the story. So I'd love to hear about your former Kendall days.

@6:39 - Kendall Cherry

So tell us a little bit about your career at this Fortune 100 company. Yeah. So I, I tell people I had kind of a fluke of a first job out of college.

So I, for whatever reason, my roommate in college knew like had an internship at this Fortune 100 tech company and basically had an in and

to the company. So very abnormal path into the company, very abnormal first job where I somehow landed. I was 21 years old and ended up in the C suite working for the chief of staff for a senior vice president, which is like crazy that does not happen.

And I didn't know this at the time. I don't really talk about this that much, but you know, we'll talk about it here.

I also didn't realize until a couple of years ago that I had kind of been targeted as someone the boss that I was working for was major narcissist.

There's a lot of toxic corporate, like all of the stuff you read out in here, if you're into like therapy, all the like family systems and that structure that takes place in the family totally shows up in a corporate environment.

so I didn't really know that at the time. I'd kind of been targeted as your classic like perfectionist, people pleaser, super hungry, gonna hustle and

anything to like, you know, grow and and do whatever, especially being so close to the top, we were like gods, like we would literally walk the halls of this office.

It wasn't like in those movies in high school where like people are like, oh my god, the big pool is coming and they like hide up, you know, crush up next to the locker.

It's not, it was not quite like that, but it was definitely like, you saw the two of us coming in and people were like, oh my god, like they're here to work with an E and I didn't realize being so young and I have a lot of compassion for myself now, but I didn't realize like, one, my boss was a narcissist, two, there's like a really toxic culture kind of going on and not realizing that I'd basically been kind of targeted and groomed and groomed in the sense of like, I had someone kind of take me under their wing to, you know, show me the ropes, quote unquote, show me what I needed to learn, but also, you know, yes, great professional growth perspective, but also

so all the toxic parts of that as well. Like there would be moments looking back at myself, I'm like, oh my god, I used to trust like them.

Like I would sign my emails like they did. Like, what the was I doing? But I didn't really realize that that was going on.

But that first job, I basically got like a crash course in internal communications and I got a crash course in executive communications.

My boss was ghostwriting for the senior vice president. So when she was too busy, she would pass stuff over to me.

And that was what I was doing. It's very, again, it's interesting how things have kind of come full circle.

I was doing the ghostwriting thing, even in my early 20s, not knowing that's what it was. I was just thinking it was called executive communications.

I got my masters in PR at the time as well in executive communications, not realizing that that's ghostwriting. I didn't know.

anything about that world. It wasn't presented to me in that lens. so I had that skill set. I was doing it internally and I was just kind of your classic.

I mean, we've all seen, especially women, right? we want to grow, we want to climb the ladder, we want to have these big high-powered careers.

And I was like the yes person. I was like, give me any extra project. I'll work on the weekends, I'll work late nights.

I'm single, I can do it. I don't have kids like fly me anywhere, give me anything. I can handle it all.

Only to kind of find out I was promoting very, very quickly. kind of what prompted the change was a lot of the pressure and we'll kind of talk more I'm sure about like what specifically was going on.

But keying into like, I'm doing all this work and all this effort for all these other people and I'm half satisfied.

And I think this is what have. I'm the first person in my family to go, you know, white color.

I was the first person in my family to have a six figure salary. So it was a huge deal that I had, like, you know, the epitome, whatever, you know, what every blue collar kid hopes to become once they get an education.

And I just remember sitting there and being like, okay, I should be happy. I should be fulfilled. I should be loving this.

I'm like 27 and I can't even imagine doing this for another three years, let alone, like, we'd had this really big retirement push as well.

And I was like seeing these people that have been there for 30 years. And I was like, that actually sounds terrible.

So I had all these really interesting moments and vignettes happening, but that's kind of like where I started. was doing, again, unbeknownst to me at the time, I think everything happens for a reason.

Doing and learning and honing those ghost writing skills and all the like toxic corporate structures around them, but really learning like what that can look like.

to then, you know, as I pivoted over the years, it was a really natural progression and kind of skill set.

didn't even know that I had because for me it was like breathing and so it means you do.

@12:13 - Meg Trucano  

So it sounds like you definitely started leaning into your zone of genius while you were being groomed in that way, but I'm interested to hear more about these vignettes that you talk about.

So for some people big change comes about after kind of a series of false starts almost like something will happen, right?

And then they, especially if your change is a career really change, you will get like and this happened to me as well, you will get a something will happen and then something positive will happen right after and you think, okay, so maybe actually I could stay.

Like maybe actually this isn't so good.

@12:57 - Kendall Cherry

Yeah, you know, hand press.

@12:58 - Meg Trucano  

Yep. Yep. And so I'm curious if you want to spill the tea, what were some of the cuts?

@13:04 - Kendall Cherry

Yeah, so I think for me I was so young at the time. I also like thinking back there, you know, trauma is an interesting thing.

We process it so many years later. There are so many times being as young as I was where, and it's interesting now my perspective has shed so for, you know, the people are saying I'm 32 now.

I was 21 at the time, but I've like managed people before. I've managed people. The real epiphany actually came for me.

When I started, I had an intern a couple of years ago who was the age that I was when I started.

That was mine, , because I remember when it happened being like me, and I was like, it was all the trauma just like, you know, coming up as soon as that happened.

I remember thinking like, huh, my boss at the time, I'd been in the job for like three months. She was constantly on the, like,

on a plane she was never around so I got like literally no onboarding. She'd be in like India and we were a team of two we had no no one else around us so I'm like quite literally floating with nothing to do where I'm like okay I'm like hanging out in this cubicle like what do I do all day so having to like kind of give myself stuff to do and I remember like at the time really kind of cluing into I'd gotten this really big job like the huge project they were doing this like a massive event it was like 1,500 people and my boss because they had such an ego instead of giving it to someone who'd been at the company longer who knew like the internal systems example how to book a conference room how to book catering like very basic things that you need to know how to do to run events my boss didn't like.

in our department to be like the hero, that she was like, well, you can figure it out. And like, we'll just connect you with the right people.

And I'm like, what the hell? So like, kind of that, that was a really one for me where looking back, I've managed people that were then the age that I was when the grooming was happening.

And it took that experience, I just, you know, buried it down, was like, that was just part of the story.

This was also probably six or seven. There's lot more content now on TikTok around like more of the corporate structures, things that can happen, know, for your worth, you know, whatever those things are, you know, that is a little bit more common of a topic.

I at the time had none of that. So I had, I was kind of like this pioneer in that.

I had no examples. I just thought like, this is how it is. This is how it's always been. So this is what's supposed to happen.

But it really took managing someone's was my age for me to be like, wait a minute, that was that was actually like very inappropriate that I was doing that.

Like, why didn't someone of authority push back and realizing like, especially when we get into these institutions that are laced in power and different types, not just money, but like ego, etc.

Realizing like, oh, this was like so much more about them and little baby Kendall at the time had no idea and like did her very best.

@16:28 - Meg Trucano  

crushed.

@16:30 - Kendall Cherry

It was like, people loved, people were like, this was the best event ever. So fresh, whatever. But that also then created the expectation of like, like me on my absolute best day, like, you know, days and days and days of like late nights and just, I mean, 12 hour days, just learning what I needed to learn, also kind of setting the expectation of like, oh, well, you can do it again.

Right? You can, that was easy for you. I'm like, like, I remember that next summer was like seven months later.

Someone came to me and they're like, you did such a good idea of that event. We're actually going to like gift you this opportunity.

It's, you know, I was ball and told is the phrase people love to use, but I was told that I was going to then for our Houston campus, I was going to execute a give back week where every day was a different on campus philanthropic opportunity on top of my day job, which I picked up on top of everything else that I was going on and doing, like managing the communications for this location.

I also then had this like very complex, basically someone got the idea of like, oh yeah, we're going to do this.

You can figure it out, right? I was like, can we have a little bit of logic here? Like this is, this is, I'm 22, like I was, I think I was 22 at that point.

So like that, that's one example of a vignette just kind of like looking back that is, you know, a little, it's interesting the things we kind of uncover once we look back.

after a really big big change and kind of what that looks like.

@18:04 - Meg Trucano  

Yeah, totally. And that, if anything, I have ever heard is a recipe for burnout, right? even, and I think there is, there is a misconception out there that if you are kind of young and hungry, that burnout won't happen to you.

And I think this is maybe like a generational thing, possibly. yeah, so did you end up, how long did you kind of go full throttle like that until you think?

@18:33 - Kendall Cherry

went full throttle until I was there five and half years. I'd had three promotions and five and a half years.

I was managing people by the time I was 25. and like, this is, again, corporate's interesting that the things that can fall through the cracks, I don't know if it's the same anymore, but I had a boss that like, again, kind of in it for themselves, ego,

25 never managed people before basically like ghosted our project and I had people on the team like I don't know what 's going on but I'm out here hustling learning like going on all these calls I'd never worked in IT I'd never worked in change management I'd never worked in HR I'd never worked in training but they gave me the job because they were like she can figure out anything so it's it's like don't you know be careful because you can type cast your person you're being the kind of person that is scrappy and I didn't know it at the time I was very entrepreneurial which serves me very well in my career path now at the time and know that that was a skill set that I was I was having and I stuck out I think like a sore thumb in a very bureaucratic environment where people are a lot slower so when you get someone who's scrappy and agile and you know I'll like I can you know have an idea build a program

All the programs, like, I can do that. That's running your own business, basically. Didn't know that that was a skill I had at the time.

But I just remember having like a bunch of like my losses and stuff like that where they I was basically like classically over functioning for people, not knowing.

That's what it's called, you know, now I know in hindsight, but not knowing that that was impacting, I mean, my mental health and kind of what was going on.

That was kind of the one of the things that kind of where things started slipping through the cracks, where I'm someone who has, you know, high functioning anxiety and depression.

I've had it my whole life, you know, I'm kind of raw dog in and out here. I'm in zero type of coaching.

I know nothing about mindset work. I'm just like, I'm pretty self aware, but I don't really know. Like, and I think I know more than most people around me.

But like, I don't, especially compared to now, like, I don't know a lot of those things. And I think

for me that kind of started tipping me off that something was off, wasn't necessarily like burnout, but it was more so I started having panic attacks.

And this was this was if you're someone that is listening and you have anxiety, this is something for me I have probably only had like two or three in my life all during like the same period.

Anxiety and it's more specifically panic attacks or your body signal that something is wrong. Something is off it's trying to save you in some way.

I didn't know this at the time. I wasn't therapy but I was just thinking I was like doing my thing and we'd had again I have this boss who's basically kind of ghosted us.

I'm getting zero like truly figure the out yourself like I'm getting no guidance. I'm getting no hitting every roadblock.

I'm like well like she's not around so I've got to just like push through all this like tape to still get done.

And so I'm like putting it in in the effort. And my boss at the time, we'd have like a pre-meeting.

We were supposed to do with all these like directors and senior executives talking about, you know, the status of a project, which is a show, quite literally.

Just for some perspective, you know, we have a weekly dashboard. It's red, red, red, red, red, red, all over the slide.

We have a pre-meeting before this big presentation. They want me to present because I'm really good at presenting, no, I'm the only one that knows what is going on and can speak about it.

So of course, they're going to put me in. Literally, I showed you not 30 minutes before this meeting. We have a pre-meeting and magically our dashboard goes from all red to yellow and green because we don't want to make it look like we don't have our together.

And in the green scheme, unquote, of the project and the problems that these executives have, it's not actually that big of a deal.

So that happens about 30 minutes before this project. object or before this presentation, then I'm forced to go have a present.

I have to talk through this slide and kind of talk through what's going on. And this just happened. to me, I'm one of my biggest values is I'm candid and kind is the huge part of my whole operating ecosystem.

I'm a direct person. I'm honest. don't like glossing over stuff. I'm going to tell you what I think, which in the end in hindsight really served me well because eventually all of these executives keyed into what was going on.

they would start having one-on-ones with me and being like, what's really going on? Like, what's happening here? Because they could clue into like the fuckery of our team dynamic.

They're like, this person's full of . They would like, I am maybe like, what's the real story? Truly. But basically the thing for me where I was like, okay, something's off.

So I'm That's the scenario. It's time for me to have this presentation. I'm supposed to like kick it off Like slide is getting shared.

Hi, everyone. My name is Kendall cherry and I'm the blah blah blah blah I swear to God. It's like I couldn't put air into my lungs.

It was like I'm literally sitting here like holy I can't breathe. I'm in a room virtual room with like 50 executives plus my team and my You know, whatever.

I can't put air into my lungs I have to fake it this entire time. This is like 10 minutes of my life longest 10 minutes ever.

I can't Catch my breath, but I have to keep going and it's more of I never I did have periods and burnout, but for me it was like the I have to keep going.

I have to keep faking it and I mean quite literally I'm here like struggling to put air into my lungs, but I You could not know that I was actively having a panic attack mid presentation Like if that's not for

I don't know what it is, but after the presentation, of course, you know, my teammate and my boss messaged me, great job, that was amazing.

And I asked one of my peers at the time, I was like, did I sound strange on the phone to you?

She was like, oh, you sounded totally fine. I was like, I literally just had a panic attack during that entire thing.

Like, I couldn't breathe.

@25:23 - Meg Trucano  

would have never known.

@25:26 - Kendall Cherry

But that was the thing for me where I was starting to pick up on. I could kind of, I was piecing together like, oh, I'm a high performer.

I am scrappy and agile, but in a way where in this environment, I am getting kind of typecast as this person that can push through anything and also get no support in the process.

So that is like, this is going to keep repeating itself. I need to set boundaries, which I didn't know at the time.

was just kind of, you know, again, I've been groomed since 21. This is It's just, you know, it's really easy to reinforce, I'll say like, I won't say bad behaviors, but unhealthy behaviors like that.

When you know no different, you're not in therapy at the time, no one else around you is setting boundaries and you're being, it's being reinforced that this is like quote unquote, good behavior.

@26:18 - Meg Trucano  

So I didn't know normal, right?

@26:20 - Kendall Cherry

normal.

@26:21 - Meg Trucano  

Yep. And so people, I find that all the time people will, you know, will, will start coaching and people will be like, is this like imagining things?

Is this weird? You know, and most times, no, that is, it may be normative in that culture, but it is not normal.

@26:40 - Kendall Cherry

It is not accepting any of those things.

@26:43 - Meg Trucano  

So, yeah, I having had several panic attacks before, I cannot imagine having like that many eyes on me while it's happening.

@26:52 - Kendall Cherry

It was crazy.

@26:54 - Meg Trucano  

You just want to die and like go into a ball.

@26:55 - Kendall Cherry

Well, it was, I will say it was interesting in that. I wasn't on video at the time, corporate thank God.

This was the time before the pandemic, so you could get away with, you would just have your profile pick.

So I just had to control my voice, and I knew that the level of, I mean, resilience to be able to do that is still insane, but I knew I had to stay calm.

I knew I had to do my best with what I was given.

@27:26 - Meg Trucano  

That experience though was kind of the first time when I was like, okay, something's off.

@27:33 - Kendall Cherry

I don't know what it is. I think I was kind of seeing the, not the golden handcuffs, but I was kind of seeing what was happening a little bit clearer, where I was like, oh, we're gonna, and honesty and integrity is huge for me.

It's the same thing that happens with clients. It shows up in my sales process. I'm not gonna sell you something that you don't need if you ask me question.

I'm gonna be honest with you. Like, I just don't. But like I'm not out here to just like make a quick buck basically.

Yeah, it's something that I've always kind of been like this to the point where it's sometimes challenging and like friendships or relationships from like I'm not going to just tell you I've had friends before be like, why can't you just be happy that she like loves her boyfriend and I'm like, because I think he's an .

I'm not going to like sugarcoat this because I just couldn't live with myself. think if someone, you know, they get divorced and they break up one day, I don't want to be the friend that's like, oh, I didn't like him the whole time.

Like, you know, I'm going to tell you that to me is the candid and kind thing to do. But it was a really tough thing where I felt like a lot of my foundations of this life that I, you know, broken my back really to try and build for myself.

was doing everything that on paper. Everyone told me was going to feel good and feel like success. And it all just really started crumbling around me where I was like, this is, you know, I don't even know.

I was questioning like, is this right for me? It was just like, okay, this isn't like what I was told and promise was going to be this great, you know, you and keep in mind, I was a communications major.

So I was like doing good to make 45k a year. So the fact that I was like advancing this quickly, I made it quote unquote, incorporate like that doesn't happen to people who have more like liberal arts degree.

So I was like, you should be grateful. Like, like most people don't have this. Like, they were also, I mean verbally telling me and grooming me, like, you're, we want to make you the VP of comms.

So they had already also reinforced from like other organizations. I'd had executives kind of like, you know, saying like, if you ever want to join my team, I was getting every, like all these kind of empty promises of like, this is what your, your world can look like.

think something I talk about a lot is like vision casting. So I had all these other people telling me the stories of what.

my future could look like, and somewhere along the way, I think for a long time I was kind of a sleep and I was like, oh, yeah, that's what I want.

And then there was just this moment, like, as soon as I had that kind of wake up and the panic attacks really, it was almost like then anytime that someone would tell me this like vision of what they had for my future, I was like, but that's actually not what, like, I don't know why, but I don't think that that's what I want, or like, if it's more of this, like, I don't really think this is what I want.

And so it was just this weird kind of out-of-body experience where people would tell me what I should be wanting for my life and then, like, more and more and more and more over time, just like this, like, rubber band that just kept stretching and stretching and stretching, like, okay, going to try and, you know, contain it, contain it, contain it as best you can.

So not even really burn out, it was more of just, like, keep it going. then it was like one day the rubber band just snapped, it was like, I can't, this, this.

It's like, I know it's not this, and so it's got to be something else.

@31:05 - Meg Trucano  

Yeah. Did you confide in anybody?

@31:08 - Kendall Cherry

Did you talk to anybody about that? I mean, not really. I mean, I think my family was pretty much reinforcing, like, you should be grateful.

you have to complain about basically, and, you know, everyone at my job, same thing. I was, you have to keep in mind, like, even to paint the picture, when I started, at the time, they have, like, hiring kind of classes, like, you would kind of come into the company with a group of people, usually.

I was an early career hire, so it was a lot of people around my same age. And like, again, I didn't really realize something was off until around this time, where I started with all these kids, and I very quickly was, like, othered.

So I was very much, because we were gods, we were in the C-suite. I would, you know, people can look in.

There's a way to look at your org chart and who you report to and people are like, holy .

You're all the way up there. I'm still making what you're making, but it's just some lines on a piece of paper, but I also didn't even have peers around me that were my age that I could confine in or other people because I'd been from the very beginning and it happened so quickly where it just got reinforced that I was kind of already on this quote unquote other level so I didn't have people that didn't already see me as like higher up than I was and so once I got to around this time and like the panic attack started happening, I, all the people that I started with at the same time or around the same age, they're the ones messaging me like, hey, you know what the raffle prize is for this thing?

Is there anything you can do to like, you know, asking me for like favors or whatever else and so I didn't really have people to lean on.

and I also felt like I couldn't share a lot of this stuff because I was so high up that there's a level of like it's almost it's giving like glass house again it it's if you're listening to this like so much of the corporate or I'll just say workplace environment if you can key into it very much mirrors family systems if you do any kind of internal family systems work like it's the same stuff it's just a bigger family yeah and you I didn't realize any of this at the time but like looking back like I didn't really have anyone I could confide in and if I did I would usually go back to the narcissistic first boss because we quote unquote understood each other it was like I mean it was like having an older sister and a mom at the same time but yeah I didn't have all the trauma of like having a narcissistic mother just like reinforced basically but so it was like I would go back there

which was one of the brain reasons things were going on. I would go back to the abuser essentially without realizing like that's what was going on.

Because I didn't have other safe spaces. I didn't have other people that were that high up at the top that knew all of the like, I mean, the nitty gritty, I mean, the realty of what's going on in the organization, not the like shiny internal demo that we, you know, it our way through.

Like we know the that's going on. And I didn't have anyone that either understood it or, you know, whatever else.

So I just kind of I stuck to the places that felt quote unquote safe. They weren't necessarily in hindsight, actually all that safe, but I stuck to like what I knew because I didn't know any better.

@34:50 - Meg Trucano  

Yeah. So tell us about the moment. Tell us about the moment that you decided you wanted to make a change and.

How that all went down.

@35:01 - Kendall Cherry

Yeah, so I had been I'm on this like very big stress project the one where the panic attack happens I'm still like crushing it and basically This project in particular.

There's like all of its IT implementation. So there's go lives essentially Just like basically the the system turns on everything like and my job was doing and making sure that the employees were trained and prepared and so Basically, they're they're a complete show for this if you ever know anyone that works in ERP implementation Like it is a hot mess.

It is insane. They're a global company all the things It was rough but we had been having a go live in the Latin America region and Wouldn't you know it training You know my director is MIA truly like I hadn't heard

from her in a few months, which is super strange. And so they decided that they were going to have me go to Mexico.

I think I was there for six weeks in total, but I would do two weeks on, one week off, two weeks on, week off, just to talk to the employees and try to smooth things out on the ground versus trying to do it virtually.

Think like war room vibes, but for training, essentially. And I was there, at the time I'd had a couple of people that I could trust that were in that office that we'd kind of clued into like, hey, this is kind of up.

And so I did end up having someone I could confide in there that kind of started waking me up and then actually at the time started, it was kind of their mentorship was kind of the first person that was like, think you're great at anything you want to do.

It was just this really profound moment of not realizing that I could have dreams outside of corporate. where she's like, I want you to write 10 goals, 10 years from now.

So I'm writing all the ones, I'm married, I have kids, all the ones that, you know, I think are like more common.

And then near the bottom, there is one that was like, I own my own business. And I was like, what the is that?

Like, I'd, I'd had like entrepreneurial nudges and stuff. And I'd, I'd watch a lot of other people, you know, do that on an Instagram.

I would like get so obsessed with watching people who are around my age that I'd started doing it. This was also before, you know, 2020.

So it wasn't, it was still pretty uncommon for people to kind of take that path. And yeah, I like looked at that and I like, okay, what the ?

Like that is, I just remember being like, no, no, no, no, no, this is not what we do. No girls like me, don't start businesses.

We have really great healthcare. We have like subsidized their we have great pay time off like no no no we're not doing like I remember just being like no not me no no I'm not doing this and so I'd actually shared it with the person at the company at the time because Guadalajara is amazing where the people are I just like they're so hospitable they're so warm and so they're always especially for you know when the Americans come they it's very common for them to like you go out to dinner they like really and truly make sure you feel at home and I'm also like 26-year-old white girl in a foreign country so I'm like I am either going to eat in the hotel or like I have I have no way to experience things and so me and this other person you know and kind of shared with them like hey this this happened like this is kind of weird and we talked about like it was it was kind of like my island of like oh this is like there's life in a world

outside of this fuckery, basically, and I shared like, hey, this thing came up, like, I don't know what to do, and they were actually the first person that were like, well, you've made it so far, and this is true.

I really, when I first thought about starting a business, I didn't have people that believed in me at all, which we can get to, but I didn't have people saying like, hell yeah, you can do anything.

I had people only reinforcing more. No, like, why would you ever want anything else? You've got XYZ gold and handcuffs, and this person was like just like the perfect person at the perfect time to be like, you know, I know everyone else in the planet is saying like, this is what you could have and that's true, but like, I think they were like older, they were in their 40s, and they just had more perspective.

They've been there longer, and they're like, I've seen you present, I've seen you run this program, like, you're doing, like, if you can do it this,

at this level, at this age, like you can do it anywhere kind of thing. so I'm just so grateful for that, because I think if I wouldn't have had someone like that at that time, especially like, I mean, I've got family reinforcing, I've got corporate family reinforcing, like, I've got everyone telling me, like, no, like, you're the golden girl, like, you should stay here.

really think, honestly, like, that person not been there at that time, I don't know what would have happened. And so, yeah, from there, I kind of started thinking like, okay, what can I do to start a business?

And I, my first thought was like, I'd started having, for perspective, that last project, because I was crushing, I was the youngest person on the project by about 15 years.

And so I had started having all of these, like, you know, manager, or stretchers reaching out to me on the side being like, hey, how did you promote so quickly?

@41:58 - Meg Trucano  

what are you doing?

@42:00 - Kendall Cherry

not knowing now, like, you know, even at the time, like, oh, I'm like, I'm good at packaging things, I'm good at selling things, I'm good at talking about my ideas, and I'm confident I speak with conviction, and not knowing that that was actually the secret of what was going on, but I started having people, like, I would probably have three career conversations with people I would just meet from God knows where, mean, hundreds of people reaching out and asking to just get coffee with me to quote unquote pick my brain.

I thought I was gonna do, I was like, I'm already doing these coffee chats, why don't I just get paid for it?

So I thought I was gonna build this, like, career coaching thing to help people navigate their next, like, career move, and then that, course, like flops, because I didn't know anything about anything.

A little, little kennel that didn't go to business school, did not know about , but I, I remember there's just this like key moment of being like, oh, well, I don't actually want to help someone find their next corporate role.

@43:06 - Meg Trucano  

I want to help someone like get the out of here.

@43:08 - Kendall Cherry

Like, was it a big thing? I know that was kind of like a big thing where I like, oh .

Well, am I going to do now? Um, so, but, and I'm doing all of this. Keep in mind, like, I'm learning as much as I can.

I'm doing every rabbit hole. I'm taking the free courses. I'm doing the paid courses that like promise the world and under deliver.

Like, I'm just doing that and I'm, and I'm doing it while working a highly demanding job where I'm like, I, I'm literally, I remember I had to fly to Germany for a 10 minute presentation.

So stupid, 10 minute presentation flying halfway across the world. Um, I am writing the blog posts for this business that I think I'm doing on the airplane in the

Hotel yeah, I'm doing this and I'm just like like whatever I can do this presentation in my sleep Like y'all and I remember the two that there's this one girl on our team same vibes Okay Let's have a pre-meeting.

Let's rehearse what we're gonna say Yeah, is the pitch blah blah blah and I deviate during the presentation No, gonna tell them what the is going on like She was so mad at me after but that but that is like kind of where I'm I'm starting to get I Won't say toxically rebellious, but I'm getting to this point where I'm getting like pretty fiery and pretty pissed But so I want to hear about the conversation Yeah, I know what I'm trying to get out of Yes, yes someone says something to you That is the most emotionally abusive hearing

that hurt in a really long time. Oh, wow. Well, I didn't see better at the time.

@45:04 - Meg Trucano  

I want to hear about it.

@45:06 - Kendall Cherry

OK, great. Yeah. So flash back to this is just to kind of like orient ourselves. This is me to paint the picture.

First boss and I are friends at this point. I don't work for her anymore, but I like go to her house on the weekends.

And like, you know, we drink wine together, all the things. This should not be happening. This is like very inappropriate, but it's just like, that's what was groomed into me.

And I kind of tell her, you know, I want to start a business. I want to do this thing.

Like, I'm basically going to break, not knowing what I know now. This person invested a lot of their social dollars, basically, to boost me up, not knowing what I know now about narcissists, but.

Um, groomed me, essentially, and so I'm like, standing in her kitchen, you know, drinking wine, whatever. I'm like, no, this like really feels like what's next for me.

I don't really know what's happening. And I'm confining in her very similar to, it's a perfect foil. We have like incredible, you know, Guadalajara teammate, who's just like, raw, raw, raw Kindle, good job.

I have that person reinforcing like, hell yeah. And then thinking like, okay, well, this person wants what's best for me.

So I'm going to tell them, like, I'm, I'm looking at for someone to be like, no, I believe in you, standing over a kitchen counter, why I'm the last in my hand.

And I tell her I'm like, this, this project, they're also grossly underpaying me because I figure out, because I don't know anything about paydans, I don't know anything about salaries, I don't know anything about like, negotiating.

I have another employee who's kind of keeping me and she like, hey, they're like really underpaying you for the value of what you're delivering.

person's also I had another person kind of being like you're good at what you're doing. Not realizing that they were underpaying me by basically two pay bands and I started getting pissed or I like this is dumb like I have this other person on my team who's not doing and is also telling like what the I had no idea and so I'm in this very fiery like I'm working my off, I'm not getting paid for it like every extra hour I put in over eight hours a day is just lowering my hourly rate like I'm starting to do all the math and I'm over like what the what the and so I just kind of start to realize like okay the math isn't mapping essentially and so I'm standing in the kitchen of this this person and I tell them I'm like I know this is going on like I've started building a case to advocate for my salary thank god I had and I had a couple people that were helping me key into like this like you're

only out like at least 30k a year. And so I'm like over here like building this case and also saying like that I want to leave the company.

And so she did this is my first boss. This is the narcissist who rooms me. This is the person who started this track at 21.

Keep in mind like and I'm here being like no like I want to do what's best for being and I start talking to her about like the compensation and like I just think there's a different world where I can make more money.

And like this isn't sustainable what I'm doing. Not knowing anything about projection and her own that's showing up. And she just goes I don't understand why you are such a money hungry millennial, full stop.

And I like look at her and I'm like I don't understand what you're talking about. This is I had been labeled internally as a job hopper.

I'd been labeled as someone like hard to work with quote unquote because I was pushing back. Yet all the executives are kind of coming to me for the truth because I had kind of gotten into this HR organization.

That was very soft, no offense to HR people, there is some there was I was around a lot of caddy women in HR and so I was I was starting to get around these like we'll say more masculine men in business.

And I was kind of putting together like, Oh, this is this is weird energy. And not realizing like there's so much in that statement around like being money hungry and I'm like, well, I deserve money and to be compensated for my time, effort and mental health better.

@49:42 - Meg Trucano  

Yeah, yeah, completely completely obliterated taking this role.

@49:48 - Kendall Cherry

Also feeling like I was the like, especially in this organization, like there is a lot of people that. Super ages to culture.

So people would love. saying, like, oh, you're so young, you're so new. And then expecting me to also perform in an output at, again, people that are at least 15 years above me, if not more.

We've been in the company for 20, 25, 30 years, unprecedented levels of influence and just understanding. And it was something about that statement.

It was completely heartbreaking at the time. I didn't really understand where it was coming from, now knowing what I know about all the stuff she was projecting to me, like from her own experience.

But it was that statement I think that kind of made me realize, like, OK, we're not going to please everybody.

And I remember when I left, she wanted to throw me a party. That was a really common thing. And this company in particular, the running joke was like, oh, everyone leaves.

This is the thing that was so up, too. Everyone leaves. And then they come. that entire time and so it can yeah like you said it's definitely a mind but I'd love to hear about the candid collective so how did that come into into being and how did you build such an empire you built it so quickly like from another entrepreneur to another entrepreneur like you're doing really well and I want to hear how you made that transition yeah so the business has definitely evolved through the years keep in mind when I first started I didn't know anything about business I didn't know anything about finances I didn't know anything about sales I knew a very very little bit so I'm learning it all on the fly um I also bootstrapped the entire business so full transparency I pretty much had like a personal credit card that evolved into the business credit card I had about 10k and savings and a dream like that's pretty much what what the business started with um and

You know, January of 2020, and then they'd say, oh, we're going to extend the project by three months by three months by three months.

So I could see, I could see like we didn't have it all together, but I could very clearly see by spring of 21, like I would either, like that job wouldn't exist anymore, and I would have to go find something else, not just was not an option.

So I really had like, I had, yes, like the startup phase, but there was like a very real, also like a loose state, give or take a month or two, but there was a very real cut off of like, if you don't figure this the out, you're going to have to go back there, or something else.

So that's kind of what I was up against. And so I mean, I tried everything. I literally, my first project ever, I was because I was doing software.

I don't know why this was a good idea. has a series of flops until they find their like bliss.

Absolutely. I first project, it took me eight months to close, like eight months to sign my first client. I built software for a gym and a website, which I don't do any of that stuff.

I didn't know anything about writing content or copy for a cheerleading gym. I cheered exactly like half a year at the age of five and there's a reason I stopped doing it.

Like I, that was my first project ever. I did it and I was like back to the drawing board, this is going to work and I started like kind of cluing into like batch working, efficiency, and writing content and it all is, you know, it all comes full circle, of course, again.

And so I started selling like almost like coaching, but more around content and about writing, didn't know anything really about sales content.

Yeah, I kind of, I worked with a coach that kind of clued me in just enough, like. I learned how to write a website because I like she kind of told me the basics and then I wrote my first website I'm like a three-day sprint and then come like she was like, I have no notes Not knowing what I know now.

I was like, oh, you're always gonna be a coffee writer But so I had this like flooky launch basically Made like I think I had like a 20k month or something Which was like crazy and so like you guys.

I'm out of here like left in November before I Don't know if this is the right thing they do or not but like left before my big promise bonus salary was like I don't need the money.

The money would have been nice, but It's fine But so that business was doing well And then it was like all of sudden the plug got pulled out so like the coaching the consulting like I Had this like huge Rush and then like nothing.

I I'm not gonna live here. hate it here. So I moved back to Austin I was living with my parents for a little bit.

It's also like fully in the pandemic. This is like spring of 21 And I'd had a very very very small audience like very small.

I think email less had less than 50 people on it I think my Instagram account had Probably less than 500 and like 250 of them were like I'd converted my personal to business so these people are Like it they're just my friends like they're really supportive friends, but like yeah, they're not actual client like prospects And I was like I have to like get out of this house Like I don't want to live with my parents like I want to have my own place like I what do I do?

I need to pay money like make money. What are we gonna do? And so I like stood up I was like, what if I just write for clients like just to around for a little bit just to make some money And I ended up having the very first month It was like as soon as I told people I wasn't coaching and I was just gonna do done for you writing like the lights

turned on. I had a 10k month, the first month as a copywriter, which is crazy. First month of this business, I had a six figure year, the very first year, wild.

But a lot of it was, I tell people, I work with a lot of people that tend to have like referral based businesses.

And I'm generally kind of referral, mostly because my business never ran on referrals. I don't know what, you know, blip of the universe, you know, happened, but my business never ran like that.

It just wasn't how the money was getting made. And like, I would try to stand up for all programs, all the things, and it just, they wouldn't work for me.

It was just like, no, that's not for you. And I really and truly, and so much of the way that I write for clients now, where I'm telling stories that sell, I tell people, like, the reason I'm so good at it, I mean, I'll hit my four year anniversary.

This is actually crazy. 1st is four years, which wild. But like, part of The reason I got so good at selling in content was like, if your girl didn't close the sales, like I'm a single income household.

I didn't have a boyfriend. don't have roommates. I don't have a husband. Like, if your girl doesn't close the sales, she doesn't pay her rent.

She doesn't get the groceries. She doesn't go to therapy. Like, it's very much like self made over here. And so I think it's kind of a blessing in disguise knowing and it's kind of seeing everything now.

But so much of like the reason I'm so good at selling in content is because I had to learn how to sell.

And that was just like the reality of what was going on and showed up in my writing as well, especially the more I kind of keyed into.

I'm an introvert. I'm a highly sensitive person. I'm an empath. If you're in design, I'm a projector. I am all of the, like, get this girl off of the Internet.

Get her, like, I need to be in a cocoon, basically. And so I had to. all of those things where I was like, I have to figure out a very high leverage system for myself, and also I'm writer for God's sake.

Writers need big open chunks of space and time to just like fit deep into whatever they're writing. I knew that going on 15,000 sales clothes wasn't going to work for me.

And so I got better at the writing. I experimented grateful for all of the clients who have ever hired me over the last four years, because thank you for allowing me to experiment in your business and like kind of test and see what works.

But so where now it's just it's like this very, especially if you're on like LinkedIn, I get a lot of people right now that tell me they're like, Oh my God, your content's so great.

You stick out like a sore thumb and I'm like, I don't know, it's just like, you know, it's it's kind of my signature style that most people aren't writing with that has been like, truly, I'll say a clean three and a half years of R&D to get to where we are today.

So it definitely wasn't like an overnight success finding means, but It all it all makes sense kind of with the skills and what I was doing naturally in the full-time job.

just didn't know I mean, I just didn't know anything about business or entrepreneurship to know that those were skills that I'll say soft skills That would serve me in any career.

It would be true even if I went if I went back to corporate. I just Thrive the most and like highly independent and autonomous working environments And so that those skills like they're fine and corporate really great.

@1:01:32 - Meg Trucano  

So it helps me excel and promote so quickly But in my own thing, that's like where I'm truly like where I thrive Yeah, so this I think for for listeners just to kind of like encapsulate the experience for you You know, there is this sense of It can be really scary looking down the barrel of change, right?

And especially when you've started a new business and you don't know what's going on, you've had to learn every step of the way along your journey.

You were thrown into a corporate environment that you were like, hello, I need a little structure here and you made it work and you excelled.

And I think that there is an expectation or perhaps a hope that when people undergo a big change that they get it right, right?

Like they find the right thing to do or, you know, this job isn't working. hate it. know I should be doing something else, but the next thing has to be the right thing.

And your story really illustrates that no, actually, it can be the result of iterations and always improving. And that is the mindset, I think, that just differentiates people who successfully go from a Fortune 100 company and give it the middle

finger and come back on the other end and create something beautiful and unique and freakin' lucrative, right? So I want to ask you a couple of rapid care questions to wrap this up today.

@1:03:14 - Kendall Cherry

okay, ask me anything.

@1:03:15 - Meg Trucano  

What you gonna ask? so you, like in the early days of you have quit, you separated from your Fortune 100 job, Did you ever regret your decision?

@1:03:31 - Kendall Cherry

No, I will say in the darkest of dark nights of the soul, a darkest of dark nights of the soul.

I've like truly been through it. The one glimmer of hope was at least I'm not back there. And like sometimes that's like, I mean, there have been days where I'm like, okay, like I'm like asking friends, especially bootshopped, right?

I'm like literally asking friends to invent mommy money for groceries. Like I, I slept on a mattress on or for six months because I had to sell my furniture like definition of boots dropped over here.

But even when I had like lost all hope or it just like felt like things weren't working, there's part of me that there's like two parts of that.

like at least I'm not back there and at least I have the power and autonomy to choose what I want.

And if this isn't going to serve me more, I still get to say and what my life looks like and how it operates.

What I like, who I'm working with, how I spend my time, how much money I'm making, I there are parts of of course the sales process.

I don't get control over that, but I still get a say of what is aligned for me and that like I cannot read or write enough.

I have been through it. That was always the like at least I'm not back there. Like at least I've chosen myself and like, I would much rather like.

live to die another day knowing I made that choice.

@1:05:03 - Meg Trucano  

That is, that is just a beautiful, beautiful kind of soundbites.

@1:05:10 - Kendall Cherry

Yes.

@1:05:12 - Meg Trucano  

Okay. Couple more quick questions. Do you have any advice for someone who is like in the former Kendall position?

Like one piece of advice for them if they're in a similar position that you were in.

@1:05:26 - Kendall Cherry

Yeah, I would say if you can, if it's possible, try to seek out someone outside of the system that you trust that can give you a fresh perspective and a gut tech.

So for me, it was technically like I was going to therapy and they would kind of keep me into it but they had kind of an old school approach, definitely not family systems.

It wasn't until I got a new therapist role like what the ? New therapist, she's hardcore. But find someone either

And the system that's outside of the, like that you trust, again, for me, was, I didn't have a lot of people for a long time until I found that one person who was kind of a safe haven for me to be like, Hey, this like makes me feel this way.

This is like, this feels off and that could be a friend that could be maybe someone in a different industry, like it could be a coach, it could be just someone who has your best neutral interests at heart.

I just, I would say like looking back, that would be the first thing is, especially in these toxic work cultures, it doesn't matter if it's corporate or a business, that someone who genuinely cares about what you want, that is huge, so I would say go there.

And then the second thing I would say is like, back to like, there's a lot of talk right now about like your inner child, go back and just look back at

Who you were when you were four or five six? What were you naturally doing? What was naturally giving you joy?

What were you doing that felt like breathing that I would say to you know, especially for high performing achieving types?

What would you have done all day if no one? Commended you or padded you on the back for doing it.

So for me, answer was always writing I was I actually not saying you need to do this, but I had a really interesting conversation last year when I re-picked up the book that I'm writing.

I actually got to have a conversation with my second-grade teacher ahead of the Zoom call. Oh, that's incredible. It was so cool.

She was like my Miss Honey from Matilda. And she was the person that really kind of keep me into a lot of things about myself.

When I do meditations and stuff, I do a lot of like to be magnetic. That membership like sometimes they take you to your safe space as a child like it's always.

her classroom and so I had a conversation with her and she told me this thing I didn't you you miss things when you're a kid you're just kind of like you know hearing you know whatever you know you're playing but I realized like for me she told me that she was like kindle when you were a kid like you know we would have writing prompts I'm like over here like I just remember I had to get glasses like I don't remember what we were doing in class I just remember I loved it in there and so she'd be like yeah we would you know we would have journaling you know I'd write a prompt on the on the board and she was like just like the thing about you I was probably six at the time maybe seven she's like the thing about you that was so different than other students like most kids would just be like tell me about your weekend you know they'd answer just like the thing about you is like your stories always had a plot they had characters they had dialogue like they were on a whole other level which those are things when you're kid you don't pick up on that it's any of that that different knowing what I know now and

what I naturally kind of move into. That was something that always gave me joy. My sister will even tell me she's like, she'll like, watch me when I'm talking and I get really excited.

I'm telling a story I'm doing right now. And she's like, you just look like how you, I just remember, she's like sparkling in her eyes.

like, this is, this is, I just remember like sitting on the bunk beds and like this is how you would tell stories to me when when I was little, like you would just get so excited.

And it's those things that you don't remember quite as much. We tune them out. We don't think they mean that much.

But that kind of storytelling, I mean, even think back to like, not just what I do today, but what feels the most natural for me.

Those things, having people that support you outside of a system, be it family or career, but also like keying into what you were doing when you were a child.

That was, that was so natural that. If you thought about it now, you probably already kind of intuitively know what that answer is, but those two things I would say are the biggest, biggest.

@1:10:11 - Meg Trucano  

That's amazing. And I give that advice all the time for my clients that I work with. I ask them to think back to the things that they did as a kid.

And before kind of social conditioning hammered the amount of us.

@1:10:27 - Kendall Cherry

Infrastructure, social conditioning, institutions, yeah. Power, money, pain, ego, yeah. Who would you be if you had nothing is the thing I like, what would you still be doing?

And that's the thing I always kind of think about.

@1:10:42 - Meg Trucano  

That's a really great way to kind of succinctly put a fine tip on that piece of advice. So thank you.

Well, Kendall, thank you so much for sharing your story today with us on Changeology. But before I let you go, I want to inform everybody in the

audience that Kendall's contact information can be found in the show notes, but where would you like people to connect with you?

@1:11:07 - Kendall Cherry

Yeah, so I am pretty active over on LinkedIn, so you can definitely check out there. But I do write a newsletter every week called Wallflower Fridays.

It's kind of my take on, it's very much in the name, you know, Wallflower. My take on how to tell stories that sell, but using, you know, real conversations that I have with clients, maybe I watched a movie, I've been really into opera lately, so like maybe I bring that in, you know, books, whatever movies, but really helping people not just learn about storytelling, not just, you know, learn about sales skills, but there's always usually, if you know what to look for or, you know, key into it, it's always kind of this reminder as well about how you can, you know, find your independence and remember and see your value and your worth, in whatever way.

That looks like, you know, whatever it is you're doing, whatever you're kind of going through. It's always like sprinkled in, and I don't think I'm less directive.

Like, that's actually what I'm doing over here.

@1:12:09 - Meg Trucano  

I wrote it back, but I know Meg is a long time reader, and that's kind of fact over there.

All-flower flight at Fridays. look forward to that newsletter, and I love the tone. It's very like, I just know I talk.

@1:12:27 - Kendall Cherry

Yeah, it's always on. So, you can write, talk, it's the secret to it all. Yeah, if you are interested in reading that, you can sign up at wallflowerfridays.com.

But yeah, that's kind of where to find me.

@1:12:43 - Meg Trucano  

That's my little love child over there. Oh, thank you so much for your time today, Kendall. I look forward to talking to you again, and thank you all for listening.

Oh, Phil, scratch that. And we'll see you, Kendall, it was great having you here. Thank you so much.