Reinventing Yourself with Heather Land

Jen: Okay. Good morning. Hello. Hello. We have a fun show today because my friend Heather Land is on, and we’re going to get to that in a second. She kind of made her splash on the internet with a series of videos called I Ain’t Doin’ It. 

So in the spirit of I Ain’t Doin’ It, which we’ll talk to her about shortly, let’s do one of our segments called Bless and Release. 

Okay. Bless and release. I’d like to hear you talk about your feelings on unsolicited advice. Oh, now, you may take that in any which direction you want. From whom it comes. What they want to tell you to do. Why you are releasing that from your life… Pick it. What do you want to?

Amy: I actually don’t mind it.

Jen: You don’t mind unsolicited advice?

Amy: No. Because if I’ve started a conversation with someone, it’s number one: someone I’m close to. And number two: I do take everything with a grain of salt. And how else do you find out about new stuff?

Jen: What if it’s stuff you don’t want to find out about?

Amy: Well then I’ll say I don’t. I’m not going to do that. Yeah, but I don’t take it personally if I’m actually sick, like, in the moment, sick in a flare. And then someone I don’t know very well gives me advice. Absolutely not.

Jen: Well, I’ll tell you what. They’ll regret saying that to you. And I mean that sincerely. Then I would be behind you like, Dude, don’t even start. You don’t even know the rabbit hole you’re about to fall down when it comes to, like, alternative health shit.

Amy: Yeah. I am not great at blessing and releasing that. 

Jen: I can see.

But they occasionally release your advice to me when it just gets a little too witchy and I’m like, I’ll think about that, although I won’t think about it.

Amy: I know.

Jen: I won’t.

Amy: The problem is, I remember sitting by the lake and, I know you didn’t ask. And this is unsolicited, but I think you would really benefit from just trying to be gluten free for a couple of years.

Jen: Autoimmune thing, all your family history.

Amy: And you’re like no. Yeah. And then five years later when you’re like, Internet, I’m gluten free! I feel so much better.

Jen: No, I’m sorry about it. You were too soon. 

Amy: I know.

Jen: And I can’t care about it all at once. So if I am already caring about some other categories, I only have so much room. But I will admit, here in 2024, the year of our Lord, that you were correct about the gluten.

Amy: Thank you.

Jen: And I mean, the gluten thing came with the perimenopause attempt to get my body back under control. And it is the singular factor, I think mostly, or at least the biggest factor that has kind of reconfigured my body in the last year. Just so.

Amy: Upsetting. It’s terrible. I’m so sorry.

Jen: Thank you. Thank you for at least being sorry that the advice was mean and consequential.

Amy: Yes. At the time I said this, it’s going to be awful.

Jen: Yeah. My favorite food is sandwiches.

Amy: I know.

Jen: So, Yeah. And I’ve been through the all the stages of grief, of course, already, but when I want the info, though, then I’m like, everybody on board? Yeah. Everybody on board. Everybody. When I was trying to figure out perimenopause last year, I couldn’t get enough information. And then I had to sift it, which is overwhelming.

Everybody tell me what your thing is like. Your your weird supplements and your whatever it is. Oh my gosh. This is also… perimenopause update: I think I conjured this and am mad at myself and I won’t do it again, but I was just having this recent conversation about perimenopause and what all my things are. And I was like, weirdly, though, I don’t have the hot flashes;  that’s just not been my thing. I’ve got all the other stuff, all the inflammation and the brain fog and the insomnia and just the delightful buffet.

Amy: It’s so amazing.

Jen: It’s amazing. But I haven’t had the hot flashes so deeply. 

This is a true story. Maybe about a week ago, it took me three nights to figure it out. Three nights. I’m in bed. I keep my house cold because I like it cold in the middle of the night. I mean, it’s too cold.

Like it’s too cold to have your body out of the covers. It’s immediately too cold. I got so hot. I kicked all the covers off from head to toe and I still couldn’t cool down. And then all of a sudden I was frozen. So then I got covered back up. Three nights in a row that happened. And I’m like, how could I be hot? I’ve got my temperature at like 60. How can I be hot? Day three I was like, oh, I think, I think I’m having a hot flash in the middle of the night and it waves over me like instantly. It runs down my back worse than my front.

I don’t know if that’s a real thing, but all of a sudden I’m like, I could just sweat through everything. 

Amy: I’m really sorry. I mean, I did have the like, this weird like medicine reaction a couple of years ago, and it was sort of like a seizure, but like, I was being electrocuted, sort of. And it went hand in hand with hot flashes, and my body sort of learned that trigger. I don’t know, it’s really weird, but every so often still I feel like I’m being electrocuted from the inside. But the more I talk about that, like I’ll hear like, oh, my mom had that. It’s not just me, but yes, I also have the problem.

Jen: It is we’re the first generation truly to talk about it, to talk about it, I know, or to even have medicine talking about it.

Amy: Right.

Jen: Like all of a sudden there are perimenopause experts and doctors and forums and books and I just don’t think it existed. I don’t remember my mom talking about this or her friends. And she says that she didn’t. When I go back and like mom, I do not remember this. She’s like, because we weren’t talking about it.

Amy: Yeah. Suffering in silence.

Jen: So all that to say, I lost the thread of whatever we were talking about there…

Amy: Well, we welcome advice when it’s solicited. If it’s unsolicited, it can feel intrusive and hurtful. And you don’t know me.

Jen: Yeah, like when somebody’s like, all you need to do is hot yoga. I’m like, all you need to do is sit down, ma’am. Yeah, like, thank you all pass.

Amy: Sorry, but I still haven’t perfected in the moment. If it’s a bad time to give me advice, I don’t bless it. 

Jen: Okay. Let’s do one more segment. Let’s do my favorite segment that we do which is GenXcellence.

Okay.

Amy: What is it today?

Jen: Oh boy. We’re going to have to just find a cut off space. We could probably talk about this for the solid hour of the show. Because one from one memory leads to the next memory, and then it opens up this whole thing, which is, did you have and if so, what was the telephone etiquette in your house growing up? Let’s just start there and we’ll just see where this takes us.

Did you have one phone, by the way?

Amy: One phone. And I still have incredible telephone etiquette. Oh, like listening to my children answer the phone still makes my eye twitch.

Jen: They’re like garbage kids. Is that what you mean?

Amy: Like, their phone rings and they say, yep.

Jen: Okay.

Amy: The proper answer is like Hardin residence.

Jen: Oh, well, we’re in very different zip codes with our kids.

Amy: But I actually in my nuclear family, we did not have etiquette rules. When we answered the phone I just answered hello. But if I was at anyone else’s house, my grandparents, aunts and uncles or friends and I answered the phone, it was so-and-so residence, this is Amy. May I ask who’s speaking? 

Jen: What I am hoping for is that at least a handful of our listeners today are younger than us, because this is just a crazy conversation. They’re hearing everybody our age is like, oh, of course, like, this was how you spoke to somebody that didn’t live in your home. There was a whole gatekeeping situation called a landline, and so you just had a raw dog.

I mean, you just dialed your friend’s number, which you had to have memorized, right? Because you hit it with your fingers. Beep boop boop boop boop boop.

Amy: Except not always.

Jen: Did you put a little what, like a little thing on the wall?

Amy: Well, no. Before you beep beep beep boop. You did. Didn’t. Oh, look at the rotary dial. Yeah. Rotary.

Jen: I feel like I had those in my earliest years, but then we got fancy. I had touch buttons, but. So you had. I had all my friends’ numbers memorized. Yeah. So that’s how we did that. And then you just had to talk to whoever answered the phone. Can you imagine doing that now? Yeah.You’re gonna have to talk to their mom.

Amy: Or like their brother.

Jen: Or like their dad.

Amy: Come on. Please put her on the line.

Jen: Hi, Jennifer. How are you doing? Oh, how long do I have to make chit chat with your uncle? You know, or, like, with your brother? That was just a real grab bag.

Jen: Also, when you answer the phone, you don’t know.

Amy: You know now.

Jen: Like it was later in the phone journey that we got caller ID but much later. Yeah. Like much, much like I feel like I was in college before we had caller I.D., don’t you?

Amy: I think it was a little before that, maybe, but.

Jen: We don’t have any money for.

Amy: Most of our childhood. You did not know who was calling?

Jen: Absolutely. No way. If you’re trying to avoid somebody. Oh, and do you remember this? Like you don’t want to talk to somebody? You are doing an avoidance game. That’s my deal. You know, avoidance attachment and somebody calls and your sister answers and you’re like, I’m not here. And if if she was being a real bitch that day, she’s like, she’s right in front of me.

You know, she would just disobey. You’re like, frantic. I’m not here. Body language. Oh, my God, I just had such a bad memory thinking of it.

Amy: I have something. Oh, you. Oh, my gosh, it’s going to help your mood. You ready?

Jen: I don’t, I literally don’t know what this is. You’re reaching behind your chair…. you’re wobbling something around, like, did you hide that when you walked in the studio?

Amy:  I did. This is for you, Longhorn. The rotary phone that my father in law got from his parents. It was at the farm. The kids brought it home and had it in their room forever. And then they finally decided they were done with it. And I’m always the one saying like, get rid of your crap to everybody. Oh, but I could.

Jen: Not that. This is a treasure. Oh my gosh. Everybody, you need to race to YouTube, if you don’t know what we’re doing right now. So you can see this.

Amy: But your parents came over for dinner a couple of weeks ago, and I put it in the middle of the table. And then after dinner, we all dialed our own phone numbers.

Jen: Do you remember your original phone number? Of course I think I do, too. It doesn’t matter. It’s gone now. Can you tell me?

Amy: Oh, what?

Jen: My phone number is your original phone number?

Amy: 6909546.

Jen: That’s so good.

Amy: And we didn’t have to do area codes, so it was only seven numbers. But Brad’s. Let’s see – the kid phone number ended in. Oh no. It’s the home phone number ended in 0098. So it was like oh.

Jen: You had the longest of all the numbers to get around. The youngest won’t know what we’re saying.

Amy: But.

Jen: But zero takes the longest work. And then nine and then eight. I think this is my phone number. I’m going to fact check this myself. I think it was 6861958. Oh, it’s so in my bones and I can’t be wrong.

Amy: Anyway.

Jen: That is a real good time. Also when you just have the one phone. Okay, I can’t talk about all the phone. There’s so many things I want to say about the phone. This is the last thing I’m going to say.

Amy: But I’m not bringing the prop again.

Jen: That is amazing. Never get rid of that.

Amy: I’m not.

Jen: Okay. In. When I was in high school, so probably the girls were in middle school. Drew’s in elementary. All four of us lived on the top floor of our house. We got, my parents got us a kids line.

Amy: So fancy.

Jen: Oh, my gosh, are you kidding? It was like a rebirth. Our own phone number on our own dedicated phone, which was upstairs in the little landing between our bedrooms. Now, unfortunately, it was just the one phone for the four kids. And so there’s still like, a lot of fighting over the phone. Remember the phone fights like get.

Amy: Off my little sister.

Jen: And it’s my turn.

Amy: My sister’s 11 years younger than I am so we didn’t have any. True, we had no overlap. I mean, if my parents said get off the phone, I got off the phone.

Jen: Well, well.

Amy: That’s my version.

Jen: I was just going to say.

Amy: They have a different version.

Jen: My parents would say, get off the phone. I’d be like five more minutes. And then it was never, it was always more than that. I want talk about busy signals. There’s just so many things, so many things that we endured. But I just do want to say that the number I just rattled off 6861958 I’m pretty sure that was the kid’s phone. I’m going to fact check it with Drew, Courtney, Lindsay.

Amy: Okay.

Jen: But I worked really hard at stretching the cord over the course of months. Yeah, so that it could go under my door, which then I could shut and stretch it all the way to my bed. And, I mean, it was practically like having a cell phone.

Amy: Practically. Except you destroyed the cord for everybody else. Destroyed like this one still has. You know, when it grabs the coils, the wrong way because it’s been overstretched? 

Jen: Oh, I see now I got it.

Amy: Anyway for a child with OCD to have it coiled the wrong way….if you hadn’t overstretched it, it wouldn’t have.

Jen: Well, if the kids would get off the phone and I didn’t have to learn how to stretch it to my room, I’m not going to talk in the landing where they can listen to me.

Amy: I lied in the middle of the kitchen floor all the time. Like I I’d sit down and lean against the fridge and then I would end up laying down. And then I put my feet up.

Jen: But isn’t that insane that we just sat there and talked on the phone with our friends in the shared living space of our home?

Amy: What would you do if you walked into your kitchen and one of your children was just laying in the middle of the floor.

Jen: Talking nonsense.

Amy: Talking on the phone with a friend for 47 minutes.

Jen: Okay, now, I’m very delighted that you brought that phone. That is a gem.

Amy: Yes.

Jen: Okay, let’s segue in. Somehow it won’t be seamless, but let’s segue into our guest because we have a delight on the show today. She could have absolutely had this phone conversation with us. She’s our age. We’ve got Heather Land today you guys. So this is just a friend of mine that is so dear and so marvelous in a million ways.

So she didn’t ever plan on becoming a comedian. She had actually quite a road up until the year she went viral, which was 2017, which we’ll talk about a little bit. But she was raised in Tennessee. She was actually pursuing a career in music. She was in worship. She was married to a pastor. It was just a whole, like scripted life that I know well.

And then somewhere between all of her childhood trauma, which she mentions a pretty not just a tough marriage, but then a tough divorce, I don’t know, she just dug deep and discovered that she’s hilarious. And in 2017, she started going viral with these like I would say this to her face dumb, hilarious nonsense videos that she did with the Snapchat filter called I Ain’t Doin’ It.

She’d just pick a thing. And then with this just outrageous filter on her face with these huge eyes and the big mouth, it altered her voice too. So it was high and squeaky and she’d just pick a thing. What she wasn’t going to do? Yeah. Shave her legs. It didn’t matter. She was making them in her car. And they just. I think she told us that in two months she had 2 million followers. Yeah. So it was like that. And that parlayed into this career in comedy. And she started touring and doing standup shows and, and she’s transitioning even further now, which we’ll discuss. 

And she’s got a brand new podcast called Dear Heathers that she does with her other friend Heather (Lenard).

Life has been like in some ways for Heather, hard and a lot of ways, unexpected. And then in so many ways, beautiful and new. And I think that’s what everyone’s story is. I relate on every single level. So our history is that we worked with the same tour team, and that’s how she and I met, so that at one point she and I went on tour together.

It was called, Hot Summer Nights, But Not That Hot. And it was so much fun. We had a whole separate tour. It was a blast. And last year we went. We hosted a cruise together, the Jen Hatmaker cruise. And Heather came and, and we did, like, a whole fun trip. And we’re doing it again this next January (2025). 

And I’ve known her fabulous husband Stephen, even longer than I’ve known Heather, which we’ll talk about him, too. And so you’ll love her. I already know that you love her. I think you’re gonna love this conversation, because this is Heather right now. This is this next iteration of Heather and what she’s learned and where she’s going and how she’s growing.

And, I love watching it. I love watching her story continue to unfold like all of ours do. And so we are delighted to bring you this conversation with fan favorite Heather Land.

I’m just delighted to see your pretty face on that camera over there.

Heather: I know, I’m so happy to be here with you.

Amy: You’re looking so cute. Thank you.

Jen: You are just looking so cute. I’m so happy that you’re meeting my friend Amy.

Amy: Hi, Amy. Nice to meet you.

Jen: We’re going to get into having a friend do a podcast in a minute with you. This is something you can speak about. First let’s start here, though. Let’s start with that darling brown man who kept popping his face into the camera.

Heather: Come on.

Jen: Your husband Stephen. I knew Stephen before I knew you. And he was the production manager on my tour with Nicole Nordeman, Moxie matters. That was the longest tour I’ve ever done. We did three rounds of it, so it was a year and a half. Stephen was on all of it from the job, and it was pretty ragtag. That was a tour bus tour. Like that was that was ten grown adults sleeping in a moving vehicle together. Right. And some shenanigans. And so, I know the story, of course. And I’ve made you tell it before in my world. So maybe it was when you were on the show or maybe it was Instagram Live, I cannot remember, but I would love for you to tell both Amy and whoever is listening again about how you and Stephen met, and I have some commentary as you go.

Heather: And, I would gladly retell the story as many times as necessary. I love to revisit this. Stephen was also the production manager on my first tour. Also on a bus.

Jen: That’s right.

Heather: And I actually met him the first time at your Moxie Matters tour.

Jen: Yes.

Heather: And I thought, oh, what a cute. What a cute little guy. What a cute young man.

And then when I was a little more up close and personal with him on my tour bus, you know, on the bus we were. And, I was like, Okay. He’s really cute. I see some some salt and pepper in that hair. So he’s got to be, you know, at least mid 30s, you know, and I was like maybe 41 at the time. And we just got to chit chatting like, really early on into the tour for the first couple nights and after about three nights in, we were like, this is a thing.

And I was like, hey, how old are you, though?

Jen: Like, I’m just curious.

Heather: Yeah. If someone wanted to know. Yeah. Looking for a friend. And it was like 29.

Amy: Yeah.

Jen: And there was a two. The first number was a two.

Heather: The first number was a two. Yeah. It was. Yeah. And he may as well have been two. Yeah. Big jump I’m like okay I was like 13 when you were like coming out of the womb. Sure, sure. That’s a big gap. But yeah, we just fell in love. We lived on a bus together for four months, thinking we were hiding it from everybody. And like the last night of the tour, we were like, guess what, guys?

We’re a thing. And they were like, no, you’re kidding.

Jen: Oh, really?

Heather: Also.

Jen: Just thought the two of you like to stay up late every night.

Heather: Every single night.

Jen: It’s just you have the same sleep patterns.

Heather: I guess, right? Yeah. We thought we were being, you know, so inconspicuous. 

Jen: Yeah.

Heather: We got together on that tour and we’ve been together ever since. Got married in 2020, and it’s been a really great ride. It’s amazing. Best decision I’ve ever made.

Jen: Wow. Yeah. The two of you are literally meant to be married. And it’s a real toss up. Which one of you I love most? And I guess the answer is just the two of you together.

Heather: We are, we are. You are. Truly.

Jen: Yeah. It’s one unit for me. I’d like to just remind the listeners also that when Heather says she thought that she was hiding it on the tour, we all have a bunch of the same partners, so we have a lot of the same players when we are out in the world doing a lot of our work.

If you’ve ever seen a tour bus, the whole middle section on both sides are three bunk beds stacked one, two, three, one, two, three, and then another side one, two, three, one, two, three. It’s 12 beds. Yeah. Like little coffins is what I call them. And nobody likes that. But that is how it feels. And so, what these two real sneaky folks did was just because of their backs or they had some sort of reason they needed to be on the bottom bunks right across from each other.

And when I say bottom bunk, it’s on the floor. So it’s like just you get down there and you just roll out, you roll out, roll in. Exactly. And they’re like, it’s just the way that I sleep. Best, of course, is on the bottom bunk of the both of us. It’s weird. And then as that bus starts humming and it just puts you to sleep like you’re like a baby in a rocking chair. One of the two of you would just roll right across the hallway. It’s a real wonder nobody caught on.

Heather: I mean, it’s right.

Jen: Anyways. It’s fine. It worked out. You’re married now. You’re respectable.

Heather: Thank you. He definitely made an honest woman out of me. Finally, gosh, you know, the guy never wanted to get married, bless his heart or have kids. Sure. Of course. That came with two. So he really bit off a lot there, but, man, he’s just killing it. He’s a great dad. Great husband. I know, he’s amazing. I love that guy. Nothing but good things to say. Everybody loves him.

Jen: He’s the life of the party.

Heather: He really is.

Jen: It took me about five seconds to fall in love with him.

Heather: I know, just a perpetual optimist. And then here I am, you know, just like. I mean, he kisses me, hugs me every morning, and I’m like, you know, if you could just turn off all the overhead lights like, this is a lot for me. You’re just you’re just a lot.

Amy: I know, but I’ll take it.

Jen: I know you will.

Amy: So, as you’ve mentioned, you’ve toured all over the country a lot. So many people discovered you through your I Ain’t Doin’ It videos, of course. How on earth did that get started?

Jen: How did that get started? I don’t even know if I know how that got started.

Heather: How long do you have? So how long is this podcast? Let me tell you. Let me try to give you the short version here. So I went to Bible college because I was a good girl, and all I ever wanted to do was be a worship leader, be a pastor’s wife. I just want to be a preacher.

Even from kindergarten, it’s written in my little kindergarten book, What do you want to be when you grow up? Pastor’s wife? Like, I don’t know why. It’s how I was raised. And so, that’s what I did for about 18 years. And after about 14 years of a really toxic, horrific marriage experience, I finally divorced, and after I did that, I was just, you know, a typical single mom.

I’m like, broke is a joke. Waiting on that child support check to come in. You know, I mean, just the typical experience, moving back home with my children. Literally moved in with my parents for a bit in Tennessee. And finally, you know, I was renting this little crappy farmhouse and just kind of barely making it, living back in my hometown, which I swore I’d never go back to.

And a buddy of mine gave me a job because, you know, I’ve been in ministry for so long, it’s hard to be a worship leader when you cry all the time. They don’t go together.

Jen: It breaks the spell.

Heather: Yeah. It was a tough gig to keep up. So I started working in sort of like refinance, and, I mean, I had no idea what I was doing, but I figured it out. And so as I’m working, Noah, my son, my oldest child, showed me Snapchat, and I found the ugliest filter I could find. And I started making really stupid videos and just sending them to like two of my girlfriends. And they would send them back to me. And, I mean, it could be about anything, right? And so I would go sit out in my car during my lunch break, make a stupid video, be in the school drop off line, make a stupid video, and on a dare, one of the girls dared me to put it on social media and I was like, what do I have to lose except my dignity? Who cares about that anymore? So I posted one on social media and people started watching it and they started saying, I love your I Ain’t Doin’ It video. And I looked at one of my girlfriends and I’m like, what are they talking about? And she said, I think maybe you said I ain’t doin’ it in the video. So I went back and watched it and I was like, oh, sure enough, I did. And so people said, can you make more? And I was like, okay, let’s think, I live in rural West Tennessee where there’s material on every corner. I bet I could pump out a couple million more. So yeah, I made some more.

And then a blogger, Susanna Lewis of Whoa, Susanna!, she got hold of one of them and reached out, said, hey, can I, can I post this? And I’m like, yeah, girl, I got a real job. You do whatever you want, I don’t care. And she convinced me somehow to start a fan page. And I very reluctantly did because I never wanted, you know, being a comedian was not in my portfolio. I never wanted to do that. So I very reluctantly started a fan page. And these videos just started going viral. And, before the end of two months, I had over 2 million followers.

Jen: That’s bonkers. I don’t think I’ve ever heard you tell this story, to be honest.

Heather: And I’m just like, I’m just going to work every day, like being a normal human. But then my boss would come in and I’m, like, refreshing my page on my phone, and he’s like, hey, can you…. I’m like, hey, I’m busy. I got two jobs now, okay? 

But I have no clue what to do with all of this. First of all, people wanted t-shirts and I’m like, do I look like a t-shirt maker? I got a big girl job, but I figured out how to make t-shirts and I made enough money selling it shirts in a week to allow me to quit my job for seven months.

I had it down to the pin. It’s. I can make it for seven months. What? And people were asking me to come do events and I’m like, what? Do what? And they’re like, well, comedy, of course you’re a comedian. I’m like, I’m so not. But, yeah, I took a risk. I looked at one of my best friends who ended up being my road manager because, you know, she was a homeschool mom.

And I’m like, hey, do you want a job? Do you want to get away from your kids? And she was like, I’d love to.

Jen: You’re unqualified and have no experience? You’re hired.

Heather: Yeah. Yes. Because nor do I. That’s the point. So yeah, I was talking to her and I’m like, hey, I don’t, I don’t think I can do this. And she said, do it afraid and that changed my life and that’s what I did.

I quit my job and I went on the road and I cried every night after every show for about six months until I figured it out.

Amy: Yeah.

Heather: And that’s the story. 

Jen: I’m glad you asked that. 

Amy: So before this, you were a worship leader? Melancholy, funny in between songs like where? Where did you hone this?

Heather: I had a childhood trauma. It’s where it came from, and I guess I just let it out on my friends at, you know, at dinner. I don’t know, like, maybe my kids got the brunt of some bad humor here and there. Yeah. And but you know what.

Jen: Really stand-up is maybe the hardest form of comedy. Like, it’s not scripted. You don’t have cameras, directors and writers. It’s. You’re working on it. It is a hot seat. It’s live. It’s sink or swim like you picked the hardest way to be funny.

Heather: I did not pick it. I did not. I’m grateful for it. But yeah, you know, when you’re leading worship, you just close your eyes. And if people think you suck, you don’t know about it. You just walk off the stage. But you have. I mean, you need instant gratification from a comedy stage, and it is scary. Yeah.

Jen: I can relate as much as I understand what it’s like to stand live in front of people and say words. Right. And they either need to work or they don’t. And a live crowd doesn’t lie like, you know, right away.

Heather: Learned the hard way.

Jen: This is working or this room is dead. Yeah. And I hate this day.

Heather: I hate it too. But let me ask you, after a while, you know, when you when you kind of do the same set, you know, and like, you go to the same show after a while sometimes, aren’t you like, okay, this is you, not me, because that’s funny. This is on.

Jen: You, this worked in Cincinnati. I’ll let you know. So. Yeah. Right. Yeah. It’s so true. So let me ask you this, because you and I have worked together in some marvelous ways that I love. We went on tour together. And last year we went on a cruise together. And I loved a moment that we had on that cruise.

We have these women who came with us. They were sort of our people on the ship. And we were in an ice skating rink. And that’s a real story. That’s real. That’s the real truth. That’s what was free that day for our group session. So it was just really cold. Real cold. And you stood in front of these women and said out loud that you were feeling ready to pursue a new dream, that you had something stirring in you to move away from comedy and toward life coaching and this was still in its infancy.

I mean, it wasn’t even realized yet. It was an idea. And you said it out loud. And the women, of course, were just like, let’s go. And we called you our life coach the rest of the trip, if you remember. And we kept coming to you like, what would a life coach say to this? 

Heather: Like, I haven’t been through training yet. I don’t know.

Jen: Who would that matter to? Not on that particular cruise. And so I think I’d like to hear about this a little bit. This, this what was stirring in you. What was some sort of knowing that you were having and, and with a pull to a pretty different space.

Heather: Yeah.

Jen: And then the courage to kind of say it out loud and move in that direction.

Heather: Yeah. It was really interesting. I had been feeling just some different things coming for me for a while at that point. And I mean, now that I’ve kind of shed some light on the fact that I didn’t grow up wanting to be a comedian, you know, it probably makes a little more sense that I had other things kind of, you know, under the surface of what I wanted to, to do with my life.

But I think I had come to such a head with my own childhood trauma. And, you know, I’m 48 years old. I did not want to go back to school. I mean, I’ve been to three colleges and still don’t have a degree, so I’m like, this is not going to go well if I go with it.

Jen: I know you’re saying it’s not where you flourish.

Heather: If I go back to school to be a therapist, I’m going to be 100 and still not have a degree. So I’m like, what can I do to give back to help women? I just love women. Yeah, I love Uncle Sam. And I just didn’t know, you know, how can I merge all that I’ve gone through in my own healing?

And the encouragement that I bring from the comedy stage. How can I bring those together, but in a different way? Because, you know, and I know we’ll probably get into this, but, comedy was kind of running its course. I was getting a little worn out and so I just wanted to switch gears. I really wanted to lean into my melancholy side.

I wanted to cry again, more often because I enjoy it for some reason. And so I felt like this was a good avenue. And so when we got on the cruise and by the way, super excited for the next one to come. Cannot wait.

Jen: Tyler’s coming this time at the insistence of your husband, who was like, how dare you?

Amy: Wait, what?

Heather: Right. Yeah. He was really upset last year. Yeah, well, this is.

Jen: Be the only dude this time it’ll be our guys and Pepper.

Heather: I mean, Pepper’s always got to be there. It’s not a party. Yeah. So on the cruise, I was like, I don’t know what I was thinking, honestly, I think I just thought, okay, this is safe here. You know, there’s like, yes, there’s hundreds of women, but they’re Jen’s women. So I think I trusted them. You know, they’re trustworthy. So I think I just wanted to test the waters and throw it to the wall, see if it stuck, you know and the response was, oh, man, I cried, which is exactly what I wanted to do. And it was lovely. They really embraced it with me.

And for me, I was just so grateful. It really gave me the courage to lean into it and I went to school after that – well, school, you know, a course.

Jen: It’s schoolish.

Heather: It’s schoolish. It’s the most I could give. It’s been amazing. I love it, I love it.

Amy: You’ve spoken openly about burnout and the struggle with that which so many of us have. What did that look like for you? And do you think the burnout you were having sort of propelled you into this new space?

Heather: Well, 100%. It propelled me into the space. Yeah. The burnout was so real, but I was so I had been burnout for a couple of years. I mean, you know, when you’re in the real world and you’re making funny videos about everyday life, that’s one thing. But then when you get on the road you live on a bus, you’re not really living everyday life. And so I got to a point where I felt like I was a little out of touch with humanity. And so I’m like, I don’t know what to make videos about. And if I have to make one more, I Ain’t Doin’ It video, I’m literally gonna throw up in my mouth. You cannot keep doing it. And I just knew something’s got to give.

But I felt so guilty, y’all. So I’ll watch Only Murders in the Building, as we do. And a couple of weeks ago, there was a scene where a guy said, my success is my prison. And I was like, oh, my God, I have never resonated more but I felt so guilty that this gift I had been given in comedy had now I felt trapped by it.

And then I didn’t know, like, okay, well, what am I going to do? How do I make this transition? And I felt like because so many people love the videos and love my comedy, which I’m so grateful for, I felt like I was failing in front of 3 million people. I mean, it was just so scary.

And then there’s all the fear. What am I going to do? Is it going to work? You know, how am I going to make money? Is everybody going to reject me? You know, even, like my sweet husband who’s never once made me feel this way. But I was like, you know, I was so driven when he met me. Is he going to think I’m a loser? You know, all of these daunting, fearful thoughts came. But I was at such a place in my career where I just knew if I don’t do something different, I’m going to die. I cannot keep doing this. I was dragging this thing out as long as it could go, and I was miserable.

And I think probably everybody around me was to trying to squeeze the blood out of a turnip, as I always say, you know, people like more videos, more of this. And I’m like, I just don’t have anything left. And so I had to switch gears. I had to do something. I had to reinvent myself.

Jen: I’m proud of you for that. That’s hard. Because comedy had given you a different life. And it is when you are in full integrity when you make a change like that, when something is still working, because outwardly, it was still working.

Heather: Yeah.

Jen: But you were still succeeding. So, that is a move that is just in full alignment. Yeah. Which is something to be really proud of. And I would love to hear you talk about your particular coaching style, because undoubtedly you have a lot to pull from.

If you’re comfortable talking about it, you’ve got a childhood to pull from that. You turned in some ways into joke gold, but it’s not funny.

Heather: Right.

Jen: And then also, if you’re comfortable, you’ve even recently gone through this sort of hair journey, which is a deal that’s not small. It’s not a small deal. And so I’m positive these and your divorce, your toxic marriage, everything is probably informing the way in which you coach women. So I, I don’t really know what the question is, but if you can find it.

Heather: Yeah, yeah. Well, first of all, I think that, you know, it’s interesting when you go through, like, life coaching courses, the goal is you become such an intense listener, which is hard for a talker like I am. And you learn how to lean in and ask the right questions. And that has been an amazing process for me and just invaluable to me in my personal life as well.

But I had to really design my own way, because I know that when women know me as a comedian and then they come to me, they want to hear my stories. They want me to pull from my own experience. And so I’ve had to really find a balance in that because their sessions are not about me, they’re about them.

But I do find when I say, you know, hey, I have a similar story. Would it help you if I share a piece of this? And kind of what I went through, and I found that it really does help them because look, Jen, you know this. So when, when you go through something in your life, when the minute I walked out the door of my first marriage, the only people I cared to talk to were divorce me, right?

That’s all I needed. Like the rest of you, I don’t want to hear it. You haven’t been here, so tell me you’ve been through this. Talk to me so I know that the majority of us have been through some kind of trauma. We’ve been through a divorce. We’ve been through, you know, I mean, menopause. How many of us are going through that?

Which is, you know, while also my hair? How can I take these situations, turn them around and use them to help women and, and I really think just having somebody else that’s gone through it is such an encouragement, even if you still don’t know how to walk through it yourself, knowing you have somebody Lincoln arms with you that’s been there has been amazing.

And on that note, let me just say my mother, you know, she’s been an addict since I was a kid, and we’ve had stints of her sobriety and, you know, a few years on and then off and just more stories than, you know, you can shake a stick at. But she’s been clean for four years, and I actually had to separate from my family for three years and not talk to them, which is really difficult.

But, so much good has come out of that in my life coaching as well. But she is doing so wonderfully well that we’ve actually spoken together this year. And that has also been, man, just a great place to give back as well. And so I think pulling from all of these live situations is what I’m finding to be so vital, in a coaching scenario.

Jen: It gives me goosebumps.

Before we ask you about your podcast, which I’m excited to hear about, I would just like to know how you are finding life coaching. I mean, that is a whole new lane. It is a whole deal. Yeah. I mean, you’re not refinancing, you’re not doing stand up comedy, you’re not leading, you’re not singing Oceans at church. This is a big departure. And so what do you think?

Amy: That’s a great question. Yeah.

Heather: You know what? I want to say this, I hope this lines up with the question even. But, I think when you’re a kid, we’re all so well-meaning. Whenever we see a child and we don’t know what to say, we’re like, what do you want to be when you grow up? You know, and I think that question really gets, subconsciously, it just gets in your craw, your whole life and you’re like, okay, what do I want to be when I grow up? And I don’t think a lot of us leave room for what do I want to be next? Or what do I want to be when I’m 40, or when I’m 50 or when I’m 60? And so this idea of reinventing ourselves is foreign.

It was to me, luckily I had jumped on the comedy train and taken that big risk. So I was like, okay, I know how to take a risk in a career. But how do I transition all this? I think that just, taking the next step, whatever age you are, it really can be so scary.

I think right now, as it sits, I’m just so grateful to be able to work with women one on one and in really in any setting, and be more authentically myself. That I’m just kind of embracing it right now and just trying to hold it loosely and see where it goes. And then, hey, maybe on to the next thing you know, if comedy has taught me anything, it’s that, hey, you know, nothing’s forever.

Take a risk. It’s taught me so much, you know? So, yeah, right now I’m taking a risk with the life coaching phase and we’ll see what it transpires into hopefully more and bigger and better. And you know, I actually I don’t maybe I don’t know if I should say this out loud, but I have this visual of me standing on a stage and really being able to, to do both to be funny, but also really tell the story, like, talk about addiction, talk about, you know, a crappy marriage and now talk about a great one and give women hope, you know?

Yeah. So that’s hopefully the next transition. But good grief, who really knows? I don’t know. I could be dead for menopause tomorrow.

Jen: Nobody knows. Amy is a podcaster now. She was just minding her business just a few months ago.

Heather: Oh, my gosh, I feel like I should interview you. Yeah. So she knows.

Jen: She’s 52, 53.

Amy: 53.

Heather: We have to think about it, don’t we?

Amy: Yeah.

Jen: But exactly to your point. What’s next?

Heather: What’s next?

Amy: I know I love that I’m not going to, I mean, I don’t ask my kids all the time, but I think there’s a huge difference. And what do you want to be and what do you want to do next? Yeah.

Heather: Like because we change, right? Yeah. You’re not the same at 53 as you were 33 now.

Amy: Gosh.

Jen: What do you want to be is a grave question because that’s can we lighten that up a little.

Heather: Like yeah.

Jen: How about next to the pressure off. Yeah I like that.

Amy: And speaking of next steps, your hilarious podcast. Oh with your co-host Heather, you talk about hysterical mundane things but also some really heavy things. How has opening up this space, of being vulnerable and transparent on your podcast, helped you in your own life?

Heather: Man, I think it’s just, you know, they always say like, if you can get paid to do what you love, like what a gift. Although let’s be clear, I have not made one dime from that podcast.

Jen: But okay. Thank you for sharing. That comes later some two seconds later.

Heather: But being able to be on a phone call with my best friend, which I do anyway, and be my fully authentic self and people actually listen and gain anything from it, is such a joy to me and to not have to fit it in any kind of box. You know, I can, we can have a conversation where I’m crying and then the next, the next sentence, I can be funny.

That is such freedom for me. And, I love it so much. Yeah. I didn’t, you know, everybody for years have been like, do a podcast. And I’m like, yeah, it’s just not in me. And then all of a sudden, Heather and I were just like, should we do a podcast? And, I absolutely love it. I literally think this is the cheesiest thing on Living Earth.

Literally had a sweatshirt made for me and her just with our logo. I’m just like, I’m just so proud. Oh, I would never wear an I Ain’ t Doin’ It shirt. But this is what I like, this is my podcast. Yeah. It just feels very liberating. Yeah. To just get on there and talk crap and it’s good, it’s great.

And if it’s nonsense, so be it. Yeah. But I think what we’re hearing overall is women are saying, I just feel like I’m in the room having coffee with you. And I told Heather, I said, for me that is the pay off. That is the point. I want women to feel like they like we are their friends because we are.

We’re all going through the same thing, some version of it. And I just want women to feel heard and seen. And if they can walk into work after listen, our podcast, you know, on the way in and feel like they’ve just been with their buddies that morning. Man, what a gift. I’m happy to give that gift. It’s easy.

Jen: So we have two things to say about that one. I’ve been asking for a co-host for probably three years. And, wanting that dynamic. And Amy and I’ve been friends for 15 years, so we have this deep well of history and memories, and our kids grew up together, and anyway that’s what we do half the time. We’re talking about cell phones, and the other time we’re talking about our bodies like it’s all over the place. But it’s so fun to do that with a friend. Yeah. And that brings it down into this real, authentic space where you’re just talking. She’s always asking. This is just like, is this it? Like, is this the job? Is the job like that? We just this is what we talk about and that’s what it is. 

Heather: We talk about the same thing we always talk about. We just have a microphone.

Jen: In front literally.

Amy: I’m starting to believe it but it’s ridiculous.

Jen: Just like will somebody tell me if it’s wrong? I’m like, this is what it’s supposed to be.

And the other thing I want to tell you is this show did not make a penny in its first year. It cost a lot of pennies. It costs a lot of pennies, right? Didn’t make any pennies. So just, you know, just keep on as I’m saying.

Heather: I’m glad to hear that, honestly. And, you know, luckily, I have a really hot producer who works for free.

Jen: That is a great point.

Amy: Yeah.

Heather: So we’re doing all right right now. But yeah. Yeah, I would love for it to be like a, dare I say it, a job.

Jen: Oh, but listen, just believe in your dreams.

Amy: Well keep going. I was enthralled for ten minutes about whether men should take baths or not. Stop listening to them discuss whether or not it’s okay for one of them to take a bath every day. That’s good content.

Heather: The gift of that is I think it’s being with somebody like Heather Lenard has walked with me through everything, this girl, she’s the first person, the only person, who ever looked at me and said, you have a horribly toxic marriage and, you know, you don’t have to live in it right now. And this girl has walked with me through so many things and I’ve walked with her. So having somebody who knows you to the depths and can pull out the funny and the sad and all the things like that, that’s where it’s at. That is like, you and Jen have known each other for so long. Like, that’s that’s the gift. It just is.

Jen: It just is. Yeah, I know there’s just so much to pull from. Been through every manner of thing, every manner of thing. So, I love it. I love this for you. I love your what’s next? The show, the, the coaching. I’m just thrilled for you. I was having lunch with a friend yesterday, she’s in her mid-fifties, and we were talking about, you know, I just turned 50, and I’m like, I’m now convinced. I don’t think I’m having some special experience like that. I got divorced and then had to recreate a life that was better than the one I had. I don’t think I’m special. I think we just get better when we get older. Like I am better, that I’m better at 50 than I was at 40. Yeah, I’m a better partner to Tyler than I was a wife to Brandon. I am a better mom. I am so now, like when people ahead of us go, oh, honey, wait till you hit sixty. Oh, I’m like, I believe you. Yeah, I literally believe you. I think you’re right. 

I think we are just getting better and more interesting. I think we’re wiser. I think we’re less distracted by bullshit and more interested in what is true and what matters.

Heather: Absolutely.

Jen: And so I’m here for it. I like this aging journey. Oh, I mean, it’s the body part.

Heather: The body part, yes. Let’s be clear. All this having to get Botox and whatnot, like I’m going to keep doing it, but it’s exhausting. I’m not quitting. It’s tiring and it’s expensive, so could someone please sponsor my podcast?

Jen: Yes, I see, that’s right. They don’t. She needs Botox money. All right.

Heather: Advertising is silly.

Jen: Okay, we’re letting you go. Currently, where is the best places for my listening crew to follow you, to find you. Whatever they’re interested in… life coaching? Are you on the road? 

Heather: I am still doing some comedy one offs, so I’m still out on the road. Just so that I’m not poor. Tired of being poor. I lived that life. So I am still on the road, and I do still enjoy it. I’m just not touring because you know, my knees hurt and things like that. But for life coaching, for, booking me in any sort of way, you can always go to HeatherLandOfficial.com. There are links to all the things, and I have a chic like kind of bougie looking like new website, fancy fancy. It’s very fancy. But on Instagram, I’m still @HeatherLand_IAintDoinIt. Although recently in my bio it has changed to formerly the I Ain’t Doin’ It Lady, currently just me and I’m like really into that right now and Facebook @HeatherLand.

Jen: Okay we’ll round all those up. Everybody.

Amy: Thanks guys. Thank you.

Heather: Lovely to talk to you. Of course. And we’re going to throw down in a couple months.

Jen: That’s exactly right. I’ll see you in the ocean.

Heather: I’ll see you there. Amy, will I see you there?

Amy: Absolutely not.

Jen: You listen, we have our differences, okay. There isn’t a scenario that I can think of. Her going in an enclosed space with strangers. Absolutely not.

Amy: Well, the open ocean is fine for me personally, right?

Heather: Yeah. Hey, Amy. Do it. Afraid.

Jen: Oh, God. She just turned it on you. Do it.

Amy: I’m sorry. I’ve not hired you as a life coach. 

Jen: That’s free. If I can just drop right to the floor.

Amy: Yeah, exactly. I can handle that. About 450,000 people in a music festival. But for one day.

Jen: That’s right. But you don’t have to speak to them or be in front of them.

Amy: Right? I think the cruise is more than one day?

Heather: You’re trapped.

Jen: Yeah. You are.

Heather: I’ll just come. I’ll just come to Austin and see you.

Jen: That’s best. That’s best.

Amy: All right.

Heather: Love. Yes. Y’all are wonderful.

Jen: Love. Yeah.

Amy: Nice to meet you.

Heather: Nice to meet you.

Jen: Okay. So that is the fabulous Heather Land. If you didn’t know her before, you’ll see why we love her so much. Also, if you missed it, her new podcast with her friend Heather (Lendard) is called Dear Heathers. And you can listen to that wherever you listen to podcasts. And I can assure you it is the perfect mix of hilarious and heartfelt.

So you’ll get all of it in there. Everything that we’re going through, kind of this stage of life and also all the websites that she, her website, her social handles, we’ll round all those up for you and you can find them at JenHatmaker.com under the podcast tab. So we’ll have this whole show. We’ll have link to our YouTube channel. Because frankly, at this point it’s fun to watch these podcasts because look at Amy. She’s adorable. Wow. Look at this studio. It’s a beaut. And then we get to see our guest. And anyway, it’s kind of fun to watch.

Amy: And I bring in random props.

Jen: Oh my god. And props. Amy brought in a bright orange phone today, and you just can’t hear that through your AirPods. You know, you got to see that. You’re right. I didn’t get that right. You can’t see that through your AirPods, right? Also like, for example, last week or two weeks ago when we interviewed Stephen Colbert and his lovely wife, you brought cookies from their cookbook.

So you can’t see that through your AirPods. There it is. Found it again. Anyway, let’s just pop over to YouTube should you ever want to just check out this incredible show. Obviously. Thanks for joining us, you guys. We have a really great rest of 2024 planned for you. It is charted out. It is high level. It is as you know, we’ve been the guest on the show lately, and have just been fire.

And that’s going to continue. And so we can’t wait to bring them out here. So all right I’ll see you next week.

Amy: See you then.

Jen: And we’ll see you guys next week.

Amy: Thanks for listening.

 

 

Resources Mentioned in This Episode:

 

Heather’s I Ain’t Doin’ It Playlist

Dear Heathers Podcast

Heather Lenard

Life Coaching with Heather Land

Nichole Nordeman

Susannah Lewis (Whoa Susannah)

Jen Hatmaker Book Club Cruise

Only Murders in the Building

Should men take baths? – Dear Heathers: Ep. 3 Bath Time with the Swon Brothers