The Cost of Hiding

Who This Episode is Perfect For

This conversation is for anyone who has ever:

✔ People navigating gender identity or expression
✔ Friends or family trying to understand a loved one
✔ Anyone struggling with shame, self-acceptance, or fear of judgment
✔ Listeners who grew up in rigid religious or cultural environments
✔ People who feel pressured to fit in or hide their true selves
✔ Those interested in authentic storytelling and human psychology
✔ Coaches, therapists, and leaders wanting deeper understanding

Episode Highlights + Timestamps

00:00 – The cost of avoiding honest conversations
01:30 – Ashton’s early memory of gender expression
03:00 – School, identity, and masking feminine traits
08:00 – Attraction, confusion, and internal duality
11:00 – How social pressure shaped self-denial
14:00 – The “masculine safety / feminine freedom” conflict
19:00 – The secrecy cycle: hiding, drinking, self-punishment
23:00 – The moment Ashton’s mom discovered the truth
27:00 – Depression, self-harm, and spiritual confusion
35:00 – Coming out: reactions from family and friends
40:00 – Religion, fear, projection, and “spiritual attack”
47:00 – Music as spiritual connection + emotional processing
53:00 – Why curiosity matters more than judgment
58:00 – Truth-telling and the universal human experience
1:04:00 – Advice for anyone hiding part of themselves
1:06:00 – Final reflections on nuance, compassion, and identity

Full Transcript of Episode:

Stacy Rich (00:00) Welcome back to Rich Connections, the show where we go beneath the surface to explore the real, raw, and sometimes uncomfortable parts of being human. My goal is to have conversations that are typically avoided so that we can bridge the gap in communicating with each other.

Today’s episode is about something like to shed light on. I’ve been thinking a lot about why people lie, not just to others, but to themselves. Why we hide parts of who we are thinking it keeps us safe, when really it’s what keeps us disconnected. I’ve seen how secrecy can impact lives and relationships. I’ve experienced the pain of loving someone who wasn’t living in truth.

And I’ve also learned that we all carry our own version of that, whether it’s hiding behind fear, shame, or expectation. But there’s another side to that story. What it looks like when someone stops hiding, when they discover their truth, and when they decide to live honestly and unapologetically, even when it changes everything. My guest today is someone walking that path with incredible courage. They’re a young adult in the process of transitioning.

Stepping into what feels true to them. And I wanted to have this conversation because it’s such a powerful example of what it means to live authentically. So I wanted to start by giving them the space to share their story in their own words. I want to introduce Ashton Kester. Thank you so much for being here and being willing to have this conversation with me. I know it takes courage to share your story.

Ashton Kester (01:42)

Yeah.

Stacy Rich (01:46)

Especially when it’s still being written, right?

So I want to start from the beginning and how we got here. So can you take us back to where your journey began? What was life like before you started this transition? And then what made you realize it was time to live your truth?

Ashton Kester (02:03)

Well, I would say I didn’t have the typical, and I guess this is it took me so long to live my authentic self, is the fact that I didn’t have the typical upbringing of someone that… I didn’t know that I was trans or whatever. You was like, you know, there’s a lot of people’s stories where it’s like, ⁓ I always knew that I wanted to be another gender when I was younger. I didn’t feel like that. I also just think I was a person that was kind of like…

living in the present a lot, I never thought like, well, this is what my future could look like or whatever. I was just going with whatever was going on, you know? And so I played with, you know, toys that I guess boys would play with, you know, it’s not like I played with dolls or whatever. So there was, I guess, nothing that my parents could really like pinpoint and say like, OK, well, this makes sense or, whatever. They didn’t see the signs, I guess.

Um, but I do remember that I like to play dress up a lot. And, um, so I, a lot of times I would wear my mom’s like clothes and like, they would kind of think that was like a joke. Um, but I guess at the time, like I didn’t, I didn’t read too much into it. It’s not like I thought, oh, well I’m doing this because I want to be a girl or whatever. Um, but I always had this like.

I don’t even know how to describe it. It’s like this like full body like feeling of like, it was like I felt like I could like breathe easier or like, you know, it was just this like relief of like, I’m wearing female clothing and I have some sort of reaction to that. And that’s all that I knew. And I remember when I was in

Stacy Rich (03:51)

Wow.

Ashton Kester (03:56)

I it was when I was in high school, is really when it started because I was in choir and, you know, lot of people in choir are like mostly girls. And so a lot of times I would just do the things that girls would do. And it kind of got to, I used to be in cross country and I remember there was one point where I used to have this like, I hated my body hair.

And so that was kind of another thing where I was like, okay, well, there’s gotta be something to this, you know? Because a lot of the other boys that I was around didn’t worry about that, you know? But I had this patch of hair on my leg that was darker than the rest of it. And so I remember one time I tried to shave that and I kind of made an excuse of like…

Oh, well, I messed up and now I have to shave my entire legs, you know, because, you know, it was just like a thing of like, I knew that I didn’t like, you know, I was like, okay, well, I could just have this like, you know, hair that’s not here and leave the rest of my legs, you know, but like, I had this like desire to want to shave my legs, it just felt good to me, you know, and I remember going into the locker room the next day, and everyone laughed at me.

And so then I think I learned really quickly to hide that part of myself. And I remember a lot of times like being in choir, like I would, know, because I was hanging out with women a lot, you know, they would want to do my makeup and stuff like that. And I was always like, yeah, like whatever. And like other guys were kind of like, well, like, why would you let them?

do your makeup. you know, it was just like this thing where they kind of started looking at me differently, you know, and a lot of people thought that I was gay, you know, so I knew that there was some something that was different, you know, and but I never, it wasn’t really until like, I think my maybe my freshman or sophomore year of high school, I, I remember my mom, my mom and dad would both like,

go to work at this time. Now my mom works from home, but like at the time I had like this cross-country camp thing and it was like summer conditioning or whatever and I would come home and I would get into my mom’s makeup and I would start wearing her makeup and I was awful at it, you know, but it was I still it was weird. I still didn’t have this feeling of like, well this is what that means or I didn’t I didn’t have

Stacy Rich (06:33)

Right Right

Ashton Kester (06:34)

the terminology to describe that, you know? But I just remember like, I started looking at myself when I would wear makeup and think, ⁓ I like how this looks, even though it was like a mess, you know? But I was like, I like the feeling of it. I liked the ritual of getting out the makeup and looking through everything, being like, what does this do? What does that do? You know? And so, I just…

Stacy Rich (06:58)

Yeah.

Ashton Kester (07:00)

I don’t know, but there was a lot of moments where I was made fun of in school. mean, I remember like, I always used to sit with my back straighter or like my legs crossed a certain way and people would be like, why do you sit like that? You know, and so it was just, and there was like one point in choir where we kind of had this like guys group. And we would, you know, have like, cause we would go to competitions like on the weekends. And so we would.

sometimes have like sleepovers at like, one of the guys house and then get up that next morning and go to the competition. Well, I had a group of girls that I love hanging out with them. And I realized it was like, I like doing the things that girls do. And so then that’s when it started occurring to me. But I think like, I saw a lot of family members that, and I don’t think they meant to, I don’t think they knew, I mean, obviously no one like,

They started questioning it because I didn’t have a girlfriend. You know, like that wasn’t a thing that I thought about. And I think it was because I looked at girls not in the way that other guys looked at girls, but I want to embody that. Like I want to be that.

Stacy Rich (08:06)

⁓

you wanted to embody it. That’s beautiful. Did you ever find that you were like attracted to them, to women, or did you find yourself like more appealed to the men or did you have any thoughts towards that?

Ashton Kester (08:08)

Yeah, yeah, and

I think that I’ve always kind of felt both ways, you know? And so I think that was kind of, but yeah, like, I don’t know. just, never looked at women. Like I was definitely attracted to women and my first relationship was with a woman. But I always looked at them in a way of like, I want to do what they do or I want to like look like them, you know?

long hair and like you know all of this different stuff that I associated with women having you know so I think that was kind of you know I just never really put an emphasis on like well if a relationship doesn’t happen then it is what it is and I think you know being like a typical guy like a lot of guys and they’re like that that’s what they think about like they they chase the girls and they chase you know and it’s like I just didn’t do that.

And so a lot of my family, that’s when they kind of started to like question me or like they used to think that I was gay because they think that like, well, like you’re not bringing anyone home or you’re not, whatever. And so, yeah.

Stacy Rich (09:33)

So how much of do you think everybody saying those things to you and your family, know, because they say that your inner circle is the most influential people, the top five people that you’re around, right? So you have all these people that are kind of saying these things to you. How much impact do you think that that had on your decision to transition or your decision to ⁓ change some of your lifestyle?

Ashton Kester (09:58)

I guess that part is kind of conflicting because I think there’s two sides of it where one side, I was involved in choir and so there was a lot of people in my choir that were a part of the LGBT community and I felt very comfortable around that and I felt like that was also a place where people could express themselves freely. But on the other hand, there would be times where like

Some of my family members, I knew that they didn’t support that or they would make comments. Like I remember my grandpa specifically made a comment one time about there was like a commercial for like an AIDS medication. And of course they had like a gay couple on the TV and he goes, well, I’m about tired of seeing this. And you know, it’s just a lot of these like

comments that like or my grandma for example like every time she would refer to someone that was gay she’d be like is he the one who’s a little funny and You know, so there’s just like this negative connotation, you know about like someone being gay and so I always thought like Okay, if they feel this way about like gay people then they’re gonna be super shocked when I tell them that you know, I’m trans or whatever it is, you know, so I just felt like

Honestly, I feel like it would be easier to just tell people I’m gay even though that’s not true because I feel like at least it makes sense. think there’s a lot of like other people’s experiences that are trans where they they are gay and then they decide to transition and that was also never my experience either. Like I was attracted to women and I’m attracted to men too. I think it’s like a thing, you know, I’m open to anything.

But ⁓ when I was in school, think that was more of my attraction was women. And so I didn’t feel like that was my experience at all. And so I think that I was telling someone the other day, I think that it was hard for me to accept it and be truthful to myself because I didn’t feel like I met the criteria of someone who was supposed to be trans. I remember reading books about like,

Stacy Rich (12:05)

Almost.

Ashton Kester (12:11)

⁓ trans people that when they were younger they used to like have so much like gender dysphoria that they would literally want to like you know like cut their genitals off or like things like that you know and I was like well I didn’t like you know I could wear like boy clothes and not be bothered by it but there’s also this feminine part of me that I have that I don’t

Stacy Rich (12:22)

Right.

Ashton Kester (12:36)

know what to do with or I don’t you know I don’t know how to like express that or be honest about it to people but yeah so

Stacy Rich (12:42)

Yeah.

Interesting. you know, it’s like, I believe that, you know, we all have a feminine and a masculine side to us, you know, and sometimes it can be more dominant in one way versus another. But it’s, I find that very interesting that you kind of allowed yourself to just unfold what you felt was right for you. Like you were okay with being in the masculine.

Ashton Kester (12:54)

Mm-hmm.

Yeah.

Stacy Rich (13:12)

but you really enjoyed the feminine, the soft side, right? ⁓ So what is like, what made, you were okay with both, was it because feeling feminine was more freeing to you than masculine? Or like, was the, you know, what was the inner dialogue, I would say, like of what felt, what was right for you?

Ashton Kester (13:16)

huh.

Though I’m realizing that the reason that I’m okay with the masculine part of me is because there’s a safety aspect to it. Like there’s like a, can blend in. And I think that’s just like what I naturally did when I was a kid was that I had that part of me and I had that feminine part of me, but like there was also like,

guys are gonna interact with guys, you know, how they interact with each other, you know? And so it’s like, you just, I think I was always like, I just played along, you know? And it was just like a thing of like, okay, well, and I think once I started to kind of realize that I was feeling that way, I think that my first thought initially was, ⁓ crap, like it wasn’t excitement.

It wasn’t like, I’m going to embrace this. Like it was like, ⁓ crap. this is like, I can’t tell anybody about this. I’m.

Stacy Rich (14:34)

And why was

that? Why did you feel that you couldn’t tell anybody?

Ashton Kester (14:38)

I don’t know. honestly don’t know. I think I’ve been judged a lot for certain things that I’ve done in my life. I’ve always been a more sensitive person. And a lot of times I’ve always heard, well, you’re too sensitive, or you overthink about everything. But I think I associated being sensitive and being in touch with my emotions

with femininity and that was always not encouraged. You was like, ⁓ you’re too, you just stop, just stop being so sensitive or like, you know, I was told like when I was younger, if I would hurt myself and cry, don’t cry, you know, you’re, and so it was just like those things of like, I think it’s just ingrained in you at a young age and you don’t realize it. But it’s really hard to unlearn that like as you get older, you know.

and feel like it’s okay to have this feminine side and it’s okay to, you know, and, but yeah, I don’t know. And there’s just a lot of like, just, I honestly, I think I felt when I would see people that were trans or whatever, and I think a lot of trans people go through this, I’ve realized that this is kind of maybe a universal experience, but like, I had some sort of level of like uncomfortability around it.

Stacy Rich (15:27)

Yeah.

Hmm.

Ashton Kester (15:55)

But

it wasn’t from like hatred or it wasn’t from it was from I think jealousy maybe and feeling like, well they get to express themselves this way, but I can’t. And I think I just, don’t know what it was, but some somewhere along the line, I just convinced myself that like, that’s not like you’re not supposed to do that or men, men aren’t supposed to do this or whatever. You know? And so was like, I just didn’t do it. And I think a lot of like,

Stacy Rich (16:07)

⁓

Ashton Kester (16:23)

It’s weird because I was in choir and so I was surrounded by the feminine part of like, you know, I was surrounded by women a lot. But then I was also like in cross country where like it was, you know, more masculine and like people, know, the men would like fight each other in the locker room for fun and like, you know, these things that like guys do, you know, or whatever. And so it’s just like, I don’t know. I think I always felt like I’m in the middle.

Stacy Rich (16:41)

Yeah.

Ashton Kester (16:49)

You know, and that’s why it was hard for me to like come to terms with like, well, I want to present a feminine because there’s always this like I was always like toeing this line, you know, and so I don’t know if that makes sense.

Stacy Rich (16:59)

It does

absolutely and so to the part of like realizing that this wasn’t what you wanted to live and that you wanted to Kind of embrace the femininity in yourself At that point what did the secrecy feel like in your body or or your daily life like now, you know what? What was the moment of like?

breaking free from, first tell me about the secrecy part, but then tell me about the breaking free moment, you know?

Ashton Kester (17:33)

Yeah, so the secrecy part, ⁓ a lot of that was a… So this is, think, the turning point was when I was in college, I think my sophomore year, my junior year, I lived on my own. And like, I really, had like one of those like studio dorms. So I had like my own bathroom and kitchen. It was like really nice. But I felt really, I’m not a person who likes being alone, you know? So like…

Stacy Rich (17:51)

uh huh.

Ashton Kester (17:58)

I was really lonely there and I think I was already going through this phase of like, know, just feeling like I didn’t know what I wanted or I didn’t know why I was there, you know, like I was doing this major, you know, that I thought I liked, but maybe I didn’t like it as much as I thought, you know, and so I just went through a period of like really, really struggling. But that was also the moment where I remember I had a lot of female clothing that I had like bought over time.

And I remember throwing it all away because in my mind I was like, I can’t do this. Like I have to shut this part of myself down. ⁓ And when I was in college, I remember I didn’t have a car. So I would literally take the bus. I would figure out the bus schedule and I would take the bus to Walmart and go buy more female clothing. And that’s when I think I realized, okay, you can’t ignore this.

Stacy Rich (18:33)

Yeah.

Hmm.

Ashton Kester (18:53)

because

you’re wanting, like you have an urge to buy more. And it was just this thing of every time I would like pass through the women’s section of like the clothing section or whatever, it was always like, I was so drawn to it. And I was so like, oh, this looks really nice or this looks like something I would want to wear. And I remember just like grabbing random stuff because I was so scared of like people thinking that it was like, I was shopping for me. And so I would just like,

hurry up and grab everything that I could and then go back to my dorm room. And I remember one time I ran into somebody that I knew at the store and I had like, and I was like, my God, I hope they don’t recognize what I have in my hands. And luckily they didn’t notice it or whatever, but I was like, my gosh, it just scared the crap out of me. But I remember I started going back to my room by myself and

sophomore year I didn’t have a lot of classes, so I had a lot of free time and I would explore that femininity. I would dress up in female clothing and I remember I got to the point where it was like at the time also I was involved in a youth group and so the religion aspect kind of played into it a little bit of like I felt like because of the things that I might have been hearing there

I felt wrong for feeling that way. And so I remember drinking in my room a lot and just getting drunk by myself. And it just was a kind of a slippery slope of like, you know, I, what was weird is like, I almost felt like I had to do that in order to accept that like I could dress that way. It was like it lowered my, yeah.

Stacy Rich (20:38)

You had to drink. Yeah.

Ashton Kester (20:41)

Yeah, so it lowered my guard enough to feel like, okay, you can do this and it feels good to you, which it felt good either way, whether I was drunk or not. But there was this part of me that was so in denial about it that I was like, just can’t, I can’t even bring myself to dress this way and not be drunk.

Stacy Rich (21:05)

Hmm.

Ashton Kester (21:08)

Then that kind of continued after college. You know, I had a lot of struggles with that. But then the other turning point was my mom came into my room one time and she found a bunch of empty bottles under my bed. And she also found all of my female clothing. And so right then and there, she was like, I need you to tell me about this.

Stacy Rich (21:23)

Mm.

Hmm.

Ashton Kester (21:34)

because I had been lying to her and saying that they were, because at the time, like me and my ex were kind of still communicating. And so I was like, well, it’s her. Yeah, yeah. And so she had clothes at one point that she would keep over, you know, and so I was lying and saying that they were hers. But then I started to get so many clothes built up that my mom was like, these can’t be all her clothes, you know.

Stacy Rich (21:42)

Your ex was was was it a girl or a guy?

Ashton Kester (22:00)

And so she was like, need to tell me like what’s going on like right here. And then I was like, my gosh, like I literally like my heart sank because I thought like, and what’s weird is I never thought that my parents would like not be okay with it. But it was just this thing that I had convinced myself that nobody’s gonna be okay with this. So.

Stacy Rich (22:21)

Yeah. So do you think

hiding your truth protects you in the moment or does it do you think it quietly hurt you over time? I mean with the with the drinking and stuff like, you know, so.

Ashton Kester (22:33)

Yeah,

yeah, I think it was hurting me a lot. honestly wish that I could have admitted that to people when I was in college so that I felt like I could express myself that way when I was in college, because I think that maybe I would have made the decision to transition sooner and all that. But but yeah, I just I know, like you’re your own worst enemy a lot of times. So I just was convincing myself that like

people aren’t gonna like, and also I think I had a lot of experiences where like, especially in the youth group that I was a part of where they knew that I was struggling with things like drinking and whatever, and they were very judgmental about it. And so I think that like just a lot of my experiences of like, I was going through a lot of depression. I remember I was self-harming at one point.

Stacy Rich (23:15)

Mm.

Mm-hmm.

Ashton Kester (23:26)

And I think people were so scared of it that they didn’t know how to deal with it. they like, they, in a way I felt abandoned by them. Like they would turn their back on me in a way of like.

Stacy Rich (23:35)

⁓

Like they knew

that you were self harming and then you felt abandoned from that experience.

Ashton Kester (23:42)

Yeah,

yeah, they, they, cause I remember I had one point where I ended up in the hospital. that was the closest to like campus. And it was like, for like my therapist, I had like told him that I was experiencing like, you know, suicidal thoughts and he actually called the police on me. And because he was like concerned for my safety. And so they escorted me to the hospital and

It was just like an awful experience because like I was left in a room like all day and no one really came and talked to me. And then when they did come and talk to me, they only like wanted to get the answer that they needed and then they would move on to the next question. And so I just like a lot of my experiences in my life had made it seem like people don’t care about you as much as you think they do. And and now, you know, realizing that that’s not

Stacy Rich (24:31)

Mmm.

Ashton Kester (24:36)

true, I just was around their own people. But at the time, I was like, what else am I supposed to think? you know, it’s like, everyone is, and I don’t think they knew, nobody knew that it was because of gender identity and struggling with that.

Stacy Rich (24:51)

So you were having those moments of wanting to off yourself because of not wanting to bring to surface your true identity of your gender. And how was it because of your own personal self-infliction? Or I know you mentioned it was also the people around you, do you think that their judgments impacted your thoughts on wanting to do that?

Ashton Kester (25:04)

Yeah, yeah.

Um, yeah, I definitely think that like, there was a point where, I don’t know, I just felt like no matter who I was around, I didn’t really feel like I was accepted fully for who I was. And it’s also when you’re struggling with something like that and you’re keeping it to yourself, like, and you don’t tell people, you’re always going to feel like there’s a part of you that is not being accepted because you’re not bringing it to the surface, you know? And so like,

I struggled with that a lot, like, yeah, I don’t know. just, I really felt like for some reason I had this thing of like, and it’s also, think everyone in some way is hurt by gender norms, you know? And I think that mine was feeling like, you know, being around men a lot because…

It was weird, it was the opposite. When I was in high school, I was surrounded by women more, but then in college I was surrounded by men more. And so there was a lot of men that just didn’t talk about their feelings. And I got to the point where I was like, I would rather like, it’s almost like you still have this kind of like, well, I’ll just handle it on my own. Like I’ll just deal with this and I’ll just push it down and I’ll just keep going and I’ll just, you know, and I remember I wasn’t eating. Like I stopped eating. I stopped like,

you there be times where if I didn’t have class I wasn’t showering you know and I wasn’t taking care of myself but I was still like well I’ll just handle this on my own you know and it just and that’s why I was drinking you know it was like it started to get to a point I was like okay I have to accept that I can’t handle this on my own and I have to tell someone because I’m literally going to you know die before before this comes to the surface you know so

Stacy Rich (26:43)

Yeah. ⁓

Yeah. So who was the

first person you admitted it to or, or, well, let’s get before we get to that, like when was the realization for yourself of, and what was the hardest part? What was the hardest truth you had to admit to yourself during the process of realizing I can’t live like this anymore? Like give me that moment internally of what made you shift and decide this is no longer for me, the way I’m living.

Ashton Kester (27:20)

you

There was a moment where I’m not proud of this, even thinking back to it, really almost makes me like just really sad to think about this. But I remember my grandma a lot of times when she would, because my cousin, his kids are younger, so she goes over there and he’s like a single parent. So she goes over there and that kind of helps take care of his kids and stuff when he’s at work and all this.

And so a lot of times when she was over there, she’d be like, well, you can stay at my place if you just need a place to like get away and all this. Well, obviously I would, and I told her this so she knows, but like I would wear her clothes, you know, and I would, you know, it was just no matter, like I, whatever, you know, female clothing I can get my hands on, would, I would wear that. But I remember I bought like a,

thing of alcohol, was like a, it was like strong alcohol, like the 8 % cans. And there were like, I don’t even know how many, they were like 10 of them maybe. And I drank, I started drinking to the point where I would throw up and then I would drink again. And I remember my, I was like, okay, well, I’m going to sit down and watch TV. Well, I passed out.

with a drink next to me. And I guess my parents were calling me over and over and I had no idea. And the time had passed. It was like noon or something when I like sat down to, you at this point I was like super drunk. And then it was like nighttime. I woke up to my parents walking in and seeing me passed out. And my dad was like, come on, let’s go.

Like, we gotta go and take you home. And I was still drunk. Like, I was still out of it. And that was when I was like, I can’t do this anymore. Like, have to have some sort of, like, acceptance that this is what’s happening and this is what I’m going through, you know? But I don’t know. I don’t know why it took me so long. I think it was just, you know, the gender norms of like, well,

This is what men are supposed to do and this is what, know, and I was telling myself that nobody, don’t think a lot of other people were telling me that, but it was just the thing of, you know, but I remember like I went to a Halloween party at college one time and I dressed as a female character from something. And I remember like nobody could recognize me when I walked in and they really thought I was a woman and that really made me feel good.

Stacy Rich (29:48)

All right.

Ashton Kester (30:07)

And so that was kind of the point where I was like, okay, well, I know that this is how I want to feel all the time. And so that’s really when I kind of like knew. But then it still took me however many months of drinking myself, you know, to death or whatever, to like realize that, you know, that that’s really what I was going through. It’s not a phase. It’s not a, you know, because I would tell myself that too. Well, maybe this is a phase or whatever.

So yeah, that was really when I was like, this has to end. Like I’m going to like, like I’m slowly killing myself.

Stacy Rich (30:41)

Yeah,

and did being honest with yourself come before being honest with others when you decided that this was it and was it more of I don’t care what anybody thinks anymore? You know, did it come down to that?

Ashton Kester (30:54)

No, I still did. I’ve always cared what people think about me and I wish I didn’t, but I just knew that I had to be honest with my mom at the one point where she found all the alcohol under my bed. And so I told her, but I still kind of told her in a way of like, well, you know, like I was like trying to almost like minimize it or trying to, know, but at least they knew.

And I remember my dad hugging me and being like, we love you no matter what. So then I think there was some level of like, okay, well then I’m just telling myself all of these false narratives. That went better than I expected, even when my mom was crying too. And so I was like, I’m hurting other people by not being, not only am I hurting myself, I’m hurting other people because of what I’m doing.

and the fact that I’m not being truthful to myself. So, yeah.

Stacy Rich (31:49)

Yeah, absolutely.

that brings up a good point is the impact on your relationships and the impact on the people that are at that time around you. So how have your relationships changed both positively and negatively since you began living authentically?

Ashton Kester (32:07)

⁓ I, I definitely, you know, the funny part is the more I would tell people, the more I would realize that they had someone who was dealing with the same thing. I remember, telling my, well, the first person I told was I used to hang around, ⁓ this gay couple at college and they were, so one of them was in my acapella group that I was in and, they, him, him and his boyfriend lived together and I would go over there and they would have parties all the time.

And so I would go over there a lot and hang out with them. And so he was the first person I told. And he kind of was just like, was like, ⁓ okay, like who cares? And then I told my friend Maddie because she is around a lot. Like she has a lot of friends that are from the LGBT community. And I told her and she was like, she was scared at first, cause I was like, I have something to tell you. And like, I didn’t say anything else. And then she’s obviously like, my gosh, like, what are you going to say? You know?

I told her and she goes, okay. And so I started realizing that like no one really cares as much as I cared about it for whatever reason. But the next person I told was my supervisor at work. I used to work at the post office. And I said, okay, I have something to tell you. I don’t know how this is gonna go over, but like for one, I had to tell them because I was going to the gender clinic at

Eskenazi and I’m like, if I have to be out for an appointment, I’m going to have to tell them like what that appointment is for, you know, like, you know, because it’s hard to take off for the post office. You work like six, seven days a week sometimes. So it’s like, I was like, okay, if they’re, you know, it has to be something that like, I can’t just keep making up excuses. Like I have to be like, okay, well, this is for like me transitioning. And so I told her and she goes,

Stacy Rich (33:37)

Yeah.

Ashton Kester (33:57)

my daughter’s trans. And I was like, ⁓ okay. And so I just started to realize that like, the more I told people, the more that they had had people in their lives that were going through the same thing, or they had a daughter or a son that was transitioning or whatever it was. So yeah.

Stacy Rich (34:16)

Wow.

So have you experienced people projecting their fears onto you or have you had any negative reactions towards first the ones you are closest to and love the most and then also like your grandparents that you mentioned, but then also society?

Ashton Kester (34:35)

Well, the surprising part is I didn’t think anyone, all the people that I thought were going to respond negatively to it were the complete opposite. Like my grandpa, my dad told him and he goes, he’s a good kid. you know, I, that doesn’t, like I love him no matter what. And I was like, what? Like I did not expect that to come from him.

And then my grandma, my mom told my grandma, and she was the other person where I was really worried about. And she was more worried about the fact that I was hiding it because of how that would affect me. And so it didn’t even cross her mind that like, oh, she was like, whatever. And so everyone was kind of, and then there are some people I told, like my other grandma, told her and she goes.

I kind of suspected something or whatever and then my cousin said the same thing. So it was just kind of funny. what I did have kind of, I guess the one experience that I’m kind of going through right now that’s kind of hard is I have two friends that are pretty into religion and I’m not knocking people’s religion at all in any way, but

they have it in there. Like I remember I told one of them, cause they’re brothers and one of them was very like, cause we had a conversation at one point and we were joking about something and we were driving. I was driving in my car and he was in the passenger seat and we were talking about, somehow it came up about like, you know, like if, if I was gay or something.

If you were gay, then my blah, blah. And he kind of like said it in a negative way, like of like not not accepting that. I was kind of like, well, what if I was gay? And he was like, well, are you? And I was like, and I like pulled over and like parked and I was like, I have to talk to you about this. And I could tell that he didn’t really know how to talk about it. But he kind of was like,

well, as long as they’re like the same person and whatever, like, then that’s okay. Like I’m not gonna just abandon you or whatever. And so I had that experience with him, but then with his brother, his brother is the one that’s kind of more into religion a little bit, I would say. And so I remember talking to him about it and I couldn’t get the words out because I was so scared of what he was gonna say. And I was like choking up almost and.

⁓ I finally told him, because he was like, come on, like can tell me anything, which made it worse because then I’m like, what if I can’t? What if it’s like this one thing that you like, you know, and so, but I remember telling him and he, this is where it kind of hurt my feelings. He said that he thinks I’m spiritually under attack and I don’t know how to defend myself.

Stacy Rich (37:17)

Right.

Ashton Kester (37:33)

And that really just hurt my feelings because it almost made it seem like I was like cursed or something or like the devil is like in me or whatever and like trying to get to me. I recently have switched from I was taking the oral pills for like the hormone replacement therapy and now I’m doing injections. Well, I guess injections for like a small percentage of people cause like really violent dreams.

And I had no idea about that until I’ve had however many violent dreams in a row. And I’m like, am I going crazy? I don’t know what’s happening here. Yeah. But I looked it up and I’m like, OK, that’s just a side effect of that. But then my friend texted and was like, well, if you feel like your dreams are affecting you anyway, I would just pray about it. That’s the devil trying to get to you through your dreams and all this. I’m like,

Stacy Rich (38:09)

What is happening?

Ashton Kester (38:29)

I think it’s just a side effect of the medication. Like I don’t think that has anything to do with that, you know? And so they keep sending me stuff that’s like, you know, about religion and they keep sending me Bible verses and I’m like trying not to take it personal and like a way of like, are they sending me this stuff because they think that like that’s what I need and they want me to live, get away from this lifestyle and that lifestyle and like.

Stacy Rich (38:47)

We.

Ashton Kester (38:56)

You know, and so I think I’m just really struggling with that. And it’s getting really hard to like talk to them about anything. Cause like, like I told them I was doing this podcast today and they were like, all right, well good luck. We’ll be praying over you. And I’m like, why? Like it’s not like a bad thing. Like I don’t need it. You know? And so I, I’m starting to kind of feel like it’s one thing for them to say that they’re accepting of it or that they won’t, you know, but it’s another, like they’ve never seen me look like this.

You know, I’ve always kind of, you know, I’ve always tried to hide that part of myself around them. So it’s like, I don’t know what would happen if they saw me like this. You know, I think that they would probably not know how to talk to me. You know, they probably think it was weird and a little strange, you know, and, but yeah, I guess their parents know and their parents are basically like,

Stacy Rich (39:38)

No.

Ashton Kester (39:51)

well we don’t support that, like, you know. It’s like this thing of like, okay, well we don’t support that, like, Ashton’s still welcome over or whatever. And I’m like, well like, you know, that just doesn’t make me feel very welcome, you know, like.

Stacy Rich (40:04)

Yeah, we

don’t support you, but you can be in our house.

Ashton Kester (40:07)

Well, yeah, pretty much.

And so that’s kind of how it feels sometimes. And like my friends have both said, like, you can make the decision on your own about like, whether you want to believe in God or not. But then they’ll keep sending me stuff. And it’s almost like they’re like hinting at the fact that this is what I need to be saved and live an abundant life and all this. And I’m like, no, like, I think that this is I don’t think that was I think that none of this is a mistake.

You know, like I think no matter what I would have ended up, even if I was religious and born into, you know, if I went to church every Sunday when I was younger, I still would have ended up like this. I still would have ended up this person. So like, I don’t think there’s any truth to that. I just don’t, you know, and that’s something that’s becoming really hard to feel like. It’s harder to hang around them or feel like I can talk to them about stuff, because if I do,

Stacy Rich (40:49)

Yeah.

Ashton Kester (41:02)

talk to them even about something I’m bothered about, then it goes back to like, well, the devil’s trying to get to you, you know, and so.

Stacy Rich (41:09)

Yeah,

well and it’s like, you know, I think that when when you’re met with things like that with that type of fear or concern or or judgment it comes from an internal place with them and It’s it’s they’re just projecting their own fears and concerns and judgments onto you So it comes down to you know, like it’s the collision of you

Ashton Kester (41:23)

Mm-hmm.

Stacy Rich (41:33)

trying to live authentically yourself and then people who are resisting something in their own lives and trying to merge worlds still. So it’s kind of interesting how they’re not supportive of it, but yet like they still obviously hold space for you, love you and all of the things. So it’s like they’re, you know, the inner inner dialogue that they’re probably having with themselves is is also probably conflicting for them.

Ashton Kester (41:58)

Yeah.

Stacy Rich (42:01)

you know, because they love you, but they don’t want to support your behaviors.

Ashton Kester (42:01)

Mm-hmm.

Well, what’s hard is like,

there’s, I’m, in my mind, the way I think about it is like, nobody thinks they’re wrong. Like, you know, like, whatever opinions they have about it, they don’t think they’re wrong. You know, so I feel like I have to be respectful to them and their religion. But at the same time, I’m like, it’s hard for me to be around people that like,

I’m always feeling like they’re pushing that on me because of the fact that I’m looking like this or whatever. It’s like they’re just, I don’t know. So that’s kind of where I’m conflicted with it.

Stacy Rich (42:42)

Yeah.

Yeah, and because you brought up religion, I want to know, like, I know you were part of your church and everything. How has that impacted your life? How do you feel spiritually now with yourself?

Ashton Kester (43:00)

I think that I’m definitely, I think I don’t know where I stand with it. And I think I’ve always kind of felt like that. I think there’s part of me that wants to feel like, it’s nice to like, like my friends, especially like, they’ll always say things like, well, God’s got a plan for me. Like when anything goes wrong, it’s like, God’s got a plan for me.

I’m like, I wish I could like have that mindset. Like I wish I could have that to fall back on because sometimes it would be nice to feel like, well, I’ll just go with the flow because this is God’s plan, you know, instead of going into panic mode or like, well, what do I do now? Why is this, you know, but honestly, like when it comes to gender identity, a lot of times I’ve had this feeling of like being angry at God because I’m like, why would you make me deal with this? You know, and that was my first thought was like,

when I was involved in that youth group and stuff and kind of drinking in my room, I was dressing up like a woman, but then going to this youth group every Wednesday or whatever it was. And so it just felt like so, I was like, why am I the one that has to take on this? And none of my other friends are dealing with this. Everyone else that I’m around is okay being the gender that they are.

Stacy Rich (44:13)

and

Ashton Kester (44:18)

And I’m the only one that’s struggling with this. And so a lot of times it just left me feeling angry towards God. And there’s a lot of times that I would pray when I was in my room. I would pray that God would not make me be dealing with this. But then I would also just pray for just a bunch of other things. But I never felt like

a lot of times my prayers were answered. And so that was the other thing. I told my friends, was like, sometimes I feel like, if this is God’s way of teaching me a lesson, it’s a pretty messed up way to teach me a lesson, like having me go through all this mental pain and suffering to finally get to this point.

And so I struggle with it. I think that there’s a part of me that is more of like a, I think that if God is real, he shows up. I’m a big music person and I think that God, I write music a lot. And I think that that’s my way of, if I was to communicate with God, that’s how I would do it is through my songs. But I actually made a song the other day.

that was kind of about that and being angry towards religion. I sent it to my friends that were really religious just to see what they would say. And they were like really sad that I felt that way. But at the same time, I’m like, I don’t think she should be sad. if God is real and this is the…

platform through who I can, how I can talk to him, I should be able to talk to him about the good parts and the bad parts. You know, and I don’t see anything wrong with that, you know, and I think that’s always kind of in my way of like communicating to a higher powers through writing stuff that I’m really feeling and being honest through like music. So I remember I did have like some kind of weird experiences at one point where I was, and this is why I say like,

Stacy Rich (46:08)

Yeah.

Yeah.

Ashton Kester (46:30)

I’m not completely like, I don’t know where I stand on it, because I have had some experiences that are pretty strange. I remember there was, at one point we used to have this like acoustic piano in the living room. I would, at nighttime, I would write a lot of songs and I would play on the piano. And I was writing a song about like God and stuff like that. And I remember I felt

hand or something like touch me and I was like what the heck and I like kind of looked back and I don’t know if it was like could have been a muscle twitching or something I don’t know like it could have been anything but that’s happened twice and so there’s there’s parts of me that are like okay there might be some truth to this and there is weird things that happen in the universe that can’t be explained you know and so but I just think that a lot of

I go through a lot of pain. I think there’s a darker part of my mind that I like to access, you know, because of writing music. And I think that sometimes like writing music that is about struggles is more important to me than like, cause like my other friend writes about God in a way that’s like very positive and which is good. But I, lot of times I write about my struggles with it. And I think sometimes like,

there’s a human element and like someone struggling, you know? And I think that’s like sometimes with like the religion thing, I think that was my problem was like, there would be people that I knew they were struggling like in that youth group and they were just very like, it was almost like that you could tell that they felt bad for bringing that up or there’s like all of these.

rules that they have to follow that make them feel like, well, I can’t do this or I can’t do this. And I think that there’s a part of me that’s like, I’m drawn to people that struggle. I’m drawn to people that struggle with addiction because I’ve gone through that and that’s real. know, and that’s, know, I, and I think that, you know, I guess I would be more spiritual because of that, because there’s just so many questions. so many, you know, and there’s a lot of times I’ve, I’ve

you know, ask questions about it and only got more questions, you know, and so I don’t know.

Stacy Rich (48:44)

That’s such an important point that you made there because I think, you know, I’m always in the mindset of leading with curiosity. And I think that in my very first episode of this podcast, I specifically talked about that because, you know, I think there’s an opportunity to rebel against societal norms and traditional thought processes and

Ashton Kester (48:53)

Mm-hmm.

Stacy Rich (49:09)

beliefs that were taught to us when we were younger. And all of it is just what’s taught to our parents, that was taught to their parents, you know? And so it’s like coming down to really being able to just be curious about what’s out there, what spiritually is out there, or when you’re talking to people, having curiosity instead of closed-mindedness, right? And I think in the spiritual world especially,

Ashton Kester (49:31)

Mm-hmm.

Stacy Rich (49:34)

⁓ You know, being able to continuously ask the big questions and allow things to unfold and just being open to it is like the true way of really getting to what is right for you, you know? ⁓ No, go ahead, yeah.

Ashton Kester (49:48)

Yeah, I’m sorry, go ahead. ⁓

I was going to say on the point of curiosity, I think that that’s kind of how I am too. I’m very curious about things and I question everything and I analyze things deeper than most people would. And I think that there’s when I was involved in that youth group, there was a part of that youth group that didn’t encourage curiosity. And especially like when I was, you know,

At that point, I was still dealing with coming to terms with my gender identity. so there was this part of that that I was almost being encouraged to stay confined within these walls of like, well, you have to do these things and you can’t hang out with people that drink or smoke or whatever it is. I was like, or you can’t hang out with, know, like there’s not a lot of people from the LGBT community there.

You know, and so like, I was just like, I didn’t want to get to a point where I stopped questioning things or I stopped feeling like wrong or I felt wrong for questioning things, you know, like, well, I have to like abide by like these things and anything outside of that. you know, I like my friends that I have that are really religious. I’ve heard them say before, well, this this person does this, this and this. They’re not godly enough.

And it’s like, kind of, it’s like, well, like we don’t hang out with these people because of that. And I’m like, for one, Jesus and God and whoever, that’s like the people that they were around, like the people that were like the thieves and like, you know, all these things, you know, because like, people have like just a human element to them. Like a lot of the people that like,

struggle with addiction, for example. Like I was around some friends where I was like, we were kind of using each other in a way to like smoke or drink at one point. But they’re some of the nicest people because they know how it feels to struggle. You know, and I think that there’s a lot of people that because they grew up religious, they’re told not to question these things and they’re told not to, you know, so they don’t, they don’t understand when someone’s struggling.

Stacy Rich (51:43)

Yeah.

Ashton Kester (52:02)

they are scared of it and they turn away from that person. And that’s not everyone, in my experience with that youth group, it kind of was. But yeah, so I think that, I don’t know, I like being able to be curious about, one of the things is too, is my friend Maddie, she reads a lot about, she has a book called, Religion Beyond the Binary or something like that. And it talks about, in a lot of these other cultures, their gods,

had multiple genders because they were almost respected in a way of like they were able to access both the masculine and feminine parts of themselves. And so they were these divine things. And so I think that there’s just so much more than like…

Stacy Rich (52:31)

Mm-hmm.

Thank

Ashton Kester (52:53)

a lot of times what my friends are telling me or like what you know it’s like I just think that I don’t know there’s so much more to look at you know and everything is nuanced and not everything’s black and white so

Stacy Rich (53:06)

I couldn’t agree more with that. Thank you for sharing that and you know and and bringing it back to like the human side of truth-telling and being authentically yourself and everything and even though your journey is unique right the feeling of hiding the shame or fear is universal I you know and I think that’s kind of what you’re talking about with

Ashton Kester (53:10)

Yeah.

Yeah.

Stacy Rich (53:30)

your music writing and tapping into the dark side, everybody has that. And what do you think people misunderstand most about truth telling within themselves?

Ashton Kester (53:41)

I I’ve always been someone that’s very self-aware, so I think it’s easier for me to tell the truth about things than a lot of other people. ⁓ I don’t know, I think it is because I’m more in touch with my emotions, you know? I think I’ve always known that like, even at a young age, like when I was just playing along with whatever gender roles were being assigned to me,

Stacy Rich (53:49)

Why do think you’re more self-aware?

Ashton Kester (54:06)

I still had this self-awareness of like, this is not what I like. I don’t like the fact that I can’t explore both sides or I feel like that’s not encouraged or whatever. I think that a lot of people don’t understand that it’s so much more freeing to just tell the truth, honestly. I think there’s a lot of people that will…

hide things to the day they die and just feel like, well, you just, you know, this isn’t a thing that you’re supposed to do, you know, and I’ve actually seen like, it was really sad. I saw a video the other day where some, it was a trans person, but they de-transitioned and they got really into like religion and they were like almost like saying these things about like, well, like,

Stacy Rich (54:35)

with you.

Ashton Kester (54:56)

You know, or they said something like, used to buy dresses for me, but now I buy dresses for my wife. And it was like, you could just tell that they were like, not like they were going backwards. Like it was like, no, that’s who you are. You know, and it’s like, you’re, it’s just like, I don’t know. It’s torturing, you’re torturing yourself. You know, and it’s just, yeah.

Stacy Rich (55:09)

Yeah.

Yeah, absolutely.

Absolutely. And why do you think it’s so hard for people to just be honest, even with simple things?

Ashton Kester (55:25)

No.

Well, fear of judgment, for one. I think that nobody wants to be judged, you know, and I don’t know, there’s some people who definitely don’t care as much about like, you know, what people think about them. But I think there’s I don’t know, this, this element of like, yeah, people want to fit in somehow, you know, and I feel like sometimes it’s safer.

or at least people think it’s safer to not tell people things because, well, I’m fitting into this group. You know, it’s like that’s more important to them than not fitting in. that’s the point I got to as well, where I was like, I would rather not have any friends and be myself than to have friends and like be this person that’s just pretending every day. Because I’ve tried that.

And I almost drank myself to death. like, obviously that’s, you know, that can’t work, you know?

Stacy Rich (56:27)

Yeah.

And so through this whole experience, what has this experience taught you about compassion for yourself and for others and who might still be hiding something?

Ashton Kester (56:38)

I know, I’m definitely, I think I’m more, I’ve become more accepting and loving. I think there was a part of me that like, because I was hiding a part of myself, I became hateful and resentful, you know? And so through just being honest with myself, I’ve learned to, ⁓

Like honestly, probably before I started transitioning, I probably would have been uncomfortable around somebody that was trans just because of feeling like, well, you know, it’s like, I told myself all these things in my head already. so, but on one hand, it’s like, I’m telling myself this story, but then also looking at that person and wishing that I could be them, you know? And so it’s like, I think just…

It feels relieving to realize that you can let that hate and resentment go and just fully be accepting of everyone. And even with the religion thing, like I said, there’s people that they don’t think that they’re wrong in feeling the way they feel. And I understood that more as just feeling like trying not to knock anyone for… There’s things that…

Stacy Rich (57:36)

Yeah

Ashton Kester (57:52)

People are gonna say to me in the future that they’re gonna be hateful. But I think I’m able to handle that stuff more. It almost changes the way you handle situations. It changes the way you handle conflict because you feel… It comes from a place of like, now you’re not feeling like, ⁓ I hate that person. But you’re like, I feel sorry for that person. Because in some way they’re being hurt by whatever gender norms are being put on them or…

Stacy Rich (58:13)

Yeah.

Wow.

Ashton Kester (58:20)

whatever

society is putting on them. So I think it’s all around you just become more accepting.

Stacy Rich (58:23)

Yeah, wow.

Yeah, absolutely. I love that.

What’s one piece of advice you’d give to someone who feels trapped by who they think they should be?

Ashton Kester (58:37)

in my experience, if you’re not alone, you’re not the first person that’s gone through whatever you’re going through. So, and I can’t believe I told myself that for so long. I’m the only one going through this. I’m the only one that’s dealing with this. And it’s like, people are dealing with it. They just don’t talk about it. So that’s why you would never know. But like, you know, that’s the one thing I would say is like,

If you feel like you’re alone in it and you’re the only one dealing with it, you’re not. I guarantee you there’s probably five people that are close to you that have some sort of connection to whatever you’re dealing with. So, yeah.

Stacy Rich (59:13)

Yeah, wow. That’s so

true. And if you could, so if you could speak to your younger self, that the one who was scared of just telling the truth or didn’t know at the time, what would you say?

Ashton Kester (59:27)

I guess everything is going to be okay. And people aren’t going to care as much as you think they are. So, and that’s the thing I realized too, is like I went to a restaurant the other day with my grandma. And sometimes I like have a thing about like living in Indiana, because I know it’s not as the trans thing isn’t as accepted or understood maybe in like certain states, you know, and like,

but I went to the restaurant the other day and I could tell people were kind of looking at me. But for the most part, everyone’s more concerned about themselves than they are you, you know? And so, yeah.

Stacy Rich (1:00:00)

Yeah, absolutely. Well, I appreciate this conversation, Ashton, and I appreciate you being open. you know, this conversation reminds me that hiding who we are, whether it’s our identity, emotions or mistakes, it doesn’t protect us, right? ⁓ It isolates us. It can cause us to hit rock bottom. you know, and the courage to be seen, even when it’s uncomfortable, is what builds connection because

Ashton Kester (1:00:17)

Yeah.

Mm-hmm.

Stacy Rich (1:00:28)

you’re allowing people by being your true self and authentically living, you’re allowing other people to have the space to consider doing it for themselves. So I commend you for that. so I just appreciate this with you. I appreciate you taking the time to be on my ⁓ episode today and just ⁓ really, really enjoyed our conversation, learning more about your story.

Ashton Kester (1:00:50)

Yeah.

Stacy Rich (1:00:56)

and just the vulnerability. ⁓ So I really appreciate that. Is there anything else that you would like to make sure our viewers hear or anything else that you would like to mention?

Ashton Kester (1:01:07)

I guess, like, just reiterating, like, not everything is black and white. Like, if you see somebody who is trans and maybe they don’t pass as well as somebody else or whatever, I think a lot of people just assume, oh, that person’s weird or that person’s strange or that there’s so much more going on. Like, there’s so many layers beneath that, you know? And so I would just say to just not look at

things so black and white and see things as more nuanced, especially with the LGBT community.

Stacy Rich (1:01:43)

Yeah, absolutely.

Well, thank you so much. And ⁓

Ashton Kester (1:01:47)

Yeah, thank you.

Stacy Rich (1:01:47)

Before we wrap up, I want to give a big thank you to our sponsor Organic Olivia for supporting this mission of mind, body, and energy wellness. I personally love their Focus Juice and Mood Juice, literally changed my life. They’ve made such a difference in helping me stay clear, grounded, and balanced through conversations like these. You can find the link in the show notes. Also, you can get a discount by using discount code STACY. Along with today’s resources and ways to connect with our guests will be in the show notes.

If this episode spoke to you, I ask if you could share it with a friend, tag me on social media, and let me know what part resonated with you most. I love hearing your takeaways. You can find me on Instagram, TikTok, Facebook, all the socials, at Rich Connection Podcast, and follow along for more raw, real conversations about truth energy and transformation. I appreciate you being here for this episode.

Thanks for listening and remember, keep choosing honesty over comfort and always live richly.

🎤 Ready to Rebel, Root, and Rise? Tune in now and live richly!

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