Jess Diamond (00:01.785)
Welcome back to another episode of How to 20 something with another special guest who is here to talk about taking the path less traveled. And by that, I mean following your own path and not just a path carved out by those in your environment or what society tells you is the quote unquote right way to go, but a path that feels good to you and makes sense to you. And this can be in regards to your career path, your familial choices.

and to even feeling like you have to buy a house to measure your adulting success. Because at the end of the day, we are all living different lives and achieve different milestones in different orders. And that’s what makes us human and unique. So I brought on a guest who exemplifies what living life by your own terms means and how you can make sure you’re following your heart and mind and not what others impose onto you.

But before I let her share her story and help you all out, I’m going to introduce her to the show. Jenna Heath is a talented communicator, educator, and professional connector of people. She received her master’s in education from the University of Nevada, Las Vegas in 2016, and her bachelor of arts in communication and political science from San Diego State University in 2013, where she switched her major six times before finally making a decision.

After graduating, she meandered many different career fields such as startups, fitness, nonprofit, fundraising, and food and beverage before landing in higher education. She started her career in higher education over a decade ago and rose through the ranks of large urban public university systems, serving in roles such as recruiter, assistant director of career and professional development, and director of student and community engagement. actively teaches leadership.

career and professional development courses at a large public university, a small public university, and a small private university. She has been teaching collegiate level courses since 2015 and has expertise in traditional college age students and non-traditional and adult learners. Jenna actively publishes research aligning with career and professional development. Her most recent research manuscript focuses on educating the educators, preparing faculty to teach career readiness. This article is openly available to readers.

Jess Diamond (02:19.659)
Jenna has served in many volunteer roles, primarily working with Gamma Phi Beta Sorority and the Crohn’s and Colitis Foundation. She has extensive experience in public speaking nationally and internationally and enjoys perfecting the art of networking and connecting with others. She also actively works in career development consulting and leadership coaching. Outside of her professional life, you can find Jenna enjoying spending time with her husband and for babies, enjoying health, fitness and sunshine. She will never pass up the opportunity to read a good book in the sun.

Jenna (02:29.934)
Thank

Jess Diamond (02:48.803)
Hi Jenna, and welcome to How to 20 something.

Jenna (02:51.736)
Thanks for having me, I’m so excited to hang out with you.

Jess Diamond (02:55.171)
Yeah, excited for our conversation we’re about to have. And I can’t wait for us to dive into all the insight you have for today’s 20 somethings. But first, I want to hear part of your story by having you answer the following question. And that is, how do you live your life on your own terms?

Jenna (03:15.126)
Yeah, that’s such a great question. I think that, you know, had you asked me this when I was in my early 20s, I would have said like a really different answer, but now kind of being in my early 30s and

as a kitten. So now being in my early 30s, I think I would answer this question really differently. I really feel like I’ve found the things that are most important to me and the things that I really want to focus on in my life. And I really honestly found that through just understanding my values and honestly, like what are my non-negotiables of life? I think that’s really what it all goes back to. I don’t know. mean, like, I feel like that’s such a

big concept to try to explain to someone, but when I really break it down, I was sitting in a college class and I had a leadership minor at the time and it’s so funny whenever people mention like you switched your major six times as if it’s like a badge of honor and I’m like, y’all, that was not the goal. I just couldn’t freaking make up my mind about what I wanted to do with my life and I still don’t know if I have the answer to that, but I was sitting in this college class and the professor introduced this idea of values and I was so awestruck by the idea that

You could understand yourself so well to know the things that matter to you and the things that you’re going to focus on every day and the things that you were going to commit to. And I never let go of that. Here we are like almost 15 years later and I continue to go back to like, okay, what are my values? How does this influence my life? How does this influence my future? And can I commit to this in a real way?

Jess Diamond (04:51.415)
All right. So I want you to give some examples because I know a bit about your story, but people listening, at least my listeners don’t, how do you live your own way? How did you find those values and step into living, taking action through what you believe to be the most important to you?

Jenna (05:11.916)
Yeah, so I’ll share a few, guess, there’s, I mean, the ones that I think people find the most interesting about me. So my husband and I, used to be child-free. We made that decision when we first started dating when we were in our early 20s, and we still live by that. And every now and then we get the person that’s like, you’ll change your mind. And I’m like, I’m I’m hitting the age where like, change my mind? I got problems. But I think that’s the most prominent one.

People have a lot of opinions about being child free. I was even on an organized event the other day and the person kind of went on this tangent about how child free people were gonna be like the end of society because we’re choosing not to repopulate. It’s just kind of funny to me how many opinions people have about something that doesn’t affect their life at all. Like it does not affect your life whether I choose to birth a baby from my body and that I would have to deal with the consequences of that. know, that’s babies are a lot of money. They’re a lot of time.

all things that my husband and I just decided we didn’t want to do. And yeah, I think people are just really like, honestly kind of hostile about it. But I think that him and I talk about this all the time. And we just remind ourselves that like, those people do not have to our bills. They do not have to live our life. They don’t have to suffer the consequences of our decision-making. We do. So that’s one area that like, I’m very, very firm in our decision to not have children. And I’m also very proud of it.

because I see way too many people having babies that honestly shouldn’t. And I think they know they shouldn’t too, but they feel so much pressure from their family or society to do it because that’s what you’re supposed to do. And I am very proud of myself and my husband for making the choice that is just purely unpopular and sticking to it. So I think that’s a really big one for us. I think another one that is maybe really relevant to your podcast is

I actually had applied to law school when I was a senior in undergrad and I had every intention of going to law school. That’s what my dad had always told me I should do. I apparently like talking, but I also am pretty decent in arguing with people and I think if you ask any boomer that they think that’s what a lawyer does is you just talk and argue, which there’s so much more to it. But he had really ingrained that in me and I think it was very all well-intentioned. He wanted me to pick a stable career

Jenna (07:34.06)
make a lot of money and be able to support myself. There’s nothing wrong with those things. But I was basically a few weeks away from graduating and I was on the beach in San Diego. Like you said, I went to undergrad in San Diego, so I had the honor and the luxury of getting that moment. But I was sitting on the beach and I just was bawling my eyes out. And my husband has this really precious picture of me staring out into the ocean. And from the backside, everything looks so beautiful.

Like you see the ocean and the waves and the sand and my hair and it’s just all so pretty. But if you saw it from the other side, I literally like makeup everywhere, tears streaming down my face, ugly crying, snot everywhere. And I was so confused and lost and frustrated. And the more I thought about actually enrolling in law school, which I had gotten into a few programs at that point too, I was so overwhelmed at that thought. And it just felt so incongruent with who I was as a human being and who I

what I wanted my life to look like. So I feel like that was a super pivotal moment for me. And honestly, it came with a slew of like what ifs, right? Like whenever you make up any big decision in life, I mean, I think about the leap of faith you took, right? Like leaving corporate and doing your whole entrepreneurial journey. And that is such a cool story on the flip side, right? Like when you’re into the point of success and you’re like, I’m doing it. This is awesome. I’m loving this. But when you’re on the front side of that, that’s freaking terrifying.

And that’s how I felt in that moment that I was like I had this path set up before me the one that I was supposed to go down the one that I worked so hard for and then once I got to that moment I was like I don’t want this and I remember like having that conversation with my dad and I could tell that he was Maybe not disappointed. I don’t think he would ever use that word but definitely like confused and even as I continued to like go through a slew of jobs and different industries not sure what I wanted to do

Like I could tell he just kept getting more and more confused. And it was like, he was living how my emotions felt. Like watching him, was like, yeah, that’s how I feel, okay. So I feel like because I’ve had all these like crazy experiences of doing things that are like not what everyone wanted me to do, it’s made me even more rooted in the decisions that I have made.

Jess Diamond (09:48.943)
Yeah, I think you said it best of you are picking the unpopular decision and you are sticking by I mean going back to deciding to be child free. I was actually having a conversation with a couple people from one of my gyms that about this because one of them is a mom. She is actually about to compete in a bodybuilding competition and looks amazing. So we were talking about her body because she’s in the end of her prep for it. And she’s like, Yeah, I had two kids. And so we got on to the conversation of having kids.

and my friend is 23 and she was like, oh yeah, no, I’m not having kids. I know I won’t. And her response, this woman’s response, not meaning anything insulting or projecting or anything was, you’ll change your mind. Like you’re young, you’ll change your mind. And just, I know that’s such a common reaction. I mean, when I was with my ex-boyfriend, he was very adamant on no kids, that it got me thinking of, do I even want kids? And…

For a while I was like, no, I don’t. I don’t want kids. But I kind of go back and forth with the do I or do I not. And I’m now in a place where I was able to think for myself, which is really where this all comes to is thinking for yourself about what I want. And for me, I’m actually indifferent about kids. I don’t have the burning desire to be a mother, but I also know like I could be and I’m not opposed to being. I’m not against it. The way I think about it is it.

I need to be with the love of my life and he needs to be all in. He needs to be 100%. We’re a team. We got this. It’s you and me. And then I will say yes. But if there’s even 1 % of doubt, it’s a no. And that’s my thought, which I think is also, it’s not as unconventional. think it’s that middle ground. But we grew up with our parents and our grandparents.

with this nuclear family idea of like, no, you get married, you have kids, like that’s the steps you take in life. There’s no other purpose for you to do besides recreate, like procreate and have another child and bring them into society. And it’s like, well, no, times are different. Times are a lot harder. School systems aren’t great. The government gives you no support. Like there’s, it’s a, it’s a bigger decision to have kids today than it was 30 plus years ago.

Jenna (11:51.789)
Yeah.

Jenna (12:10.126)
Absolutely. I think you hit the nail on the head is that you know most people are making decisions off of a Totally unrelatable system for young people these days. I mean people are not coming out of college making 50 60 70 thousand dollars when in reality in the United States right now research shows that poverty is considered fifty eight thousand dollars a year so most young people are living in poverty is essentially what we’re saying and that alone, know the

Research also shows that it used to be around $200,000 to raise a kid to 18. It’s now closer to $300,000. And I mean, that’s a ton of money. Like some people will not make that in 10 years. And you’re saying you’re gonna invest all that money into a kid? And I mean, like you said, if that is, I have my best friend, she was one of those people that growing up, she always knew she wanted to be a mom. And she went through some really crazy infertility issues and it was rough.

I mean, I would say that’s a topic within itself that people don’t talk about in your 20s, that if you’re in committed relationship, you wanna have babies, be prepared for someone in your friend group to suffer with some really rough infertility issues and be prepared to be the friend that needs to support them, because that’s a hard journey. But she went through this whole process, and she has this precious baby boy now who I love, and he calls me Auntie Jenna, and it is precious. But watching that whole thing, like,

She never wavered in her decision that like going through IVF, going through crazy amount of loans for IVF, you know, the challenges, all that, the emotion, she never wavered. She was like, this is what I was meant to do. The same way that when someone comes at me and they’re like, oh, well, when are you gonna have babies? Or why do you think you shouldn’t have, I mean, like the amount of times people ask me, well, but like, what are you gonna do with your life? Or like, what will your life be known for? Or, you know, who’s gonna take care of you when you’re older? And I’m like,

You know what, my mom and I do not have a great relationship. Lord knows I ain’t taking care of that woman when she gets old. I mean, she’s kind of already old and I’m not doing it. And that’s my own personal choice, right? So like, I don’t really understand that narrative. And I just hold firm to like, that’s not something I identify with. And like, if that’s something you identify with, amazing. Like we need people that want to be excellent parents. And I really hope that you’re that person. I do. Like the people that are responsible and

Jenna (14:31.93)
and have financial security. I hope you choose to raise babies and I hope they’re incredible adults and I hope they change our world. And I hope they sit in my college classes one day and I hope I get to interact with them. But that doesn’t have to be me.

Jess Diamond (14:47.255)
Yeah, well, it’s because it’s you’re finding your purpose through other means through the work that you do and the impact you’re making in the world. And for some people, that’s not what a purpose is for them. For others, it is. And for others, it’s both. And I think like you can have a both and situation. But for the people who don’t have that drive to make an impact, to have a podcast, to speak on stages, to teach younger generations on how to exist in the world.

their purpose does lie in being a parent and there’s nothing wrong with that. It’s just different from what yours is, which is also nothing wrong with the way that you view your life. So I think it’s being more accepting in how people live their lives. And I think my generation and even Gen Z is doing a really good job on changing that narrative. But I want to know, because I know this comes up in different forms for everyone of their doing something that is against the norm is like you said,

My example is quitting my corporate job on my 25th birthday, handing in the keys. Like that’s not normal. That’s not what everyone does or the vast majority of people do. So when people in a sense question or doubt what it is you’re doing with your life, how do you respond to them or how do you internalize it? How do you react? What is, give me the both the ins and outs of that kind of situation.

Jenna (16:15.63)
Yeah, so I think that I think I used to have a really different perspective on this. I think when I was younger, was, I mean, I’m still really stubborn, but I think I was really, really stubborn when I was in my early twenties. And I think that it’s true as you get older, I think you gain some wisdom and I think some maturity just from lived experiences. And not to say that young people can’t be mature, because I think I was way more mature as a 22 year old than most people are in their fifties. But I think as I got older and I interact,

I guess with this question more often. I learned that it was much more fruitful to be curious than to be judgmental or rude or even defensive. And I think this is true in like pretty much any question someone could throw at you that you feel passionately about. And so I try really hard to lean into like, well, you know, why do you think women should have children? Or why do you think that no one’s gonna take care of me when I’m older? Or something that I’ve recently leaned into is

people like if they’re genuinely curious or are they trying to make a decision on their own life and they need support with that. Especially working with young people I find more often than not they kind of delve into my personal life because they want to understand how to make decisions in their own life and they’re looking at me to be an example which is an honor and a privilege but and also a heavy weight right and so I’ve had to learn how to ask more questions so that I’m not always giving them the answer and I’m more so like helping them to think for themselves.

And so I think I do that by asking a lot of questions. And to the point that I think sometimes people probably get frustrated because they’re like, just give me the answer woman. And I’m like, that’s not gonna help you though. And so I’ve tried really hard to lean into like genuine curiosity when people ask me things. I think on the flip side, I think when people really push and maybe they’re like, yeah, like I’m just curious. And they’re like, you I really believe.

about how women should behave or I believe in trad wives or I believe in blah blah blah. So that’s their prerogative. They’re allowed to believe things that are different than what I believe, but that doesn’t mean that I have to listen to them. And so I choose to exit a lot of conversations. Like if people are pushy on a belief system that is not congruent with what I believe, then I’ll just walk away. So I’ll literally say to someone like, well hey, like good for you. That’s awesome. It sounds like you feel really passionate about that.

Jenna (18:34.51)
That’s not something I really care to discuss and I gotta run and I walk away and I mean obviously I can’t do that in all situations, you know if this is you know, I don’t know a superior person at my workplace or it’s you know Somebody that I have to interact with for you know, my podcast or something like that Then you know, maybe I need to find a way to be a little bit more Soft and kind with what I’m saying and that can look like just switching the topic, you know, I I

often like to remind people that my choice is to have babies is not their business. It really isn’t. And if it’s someone I like know or even like kind of sorta know, I’ll straight up ask them. I’ll be like, my gosh, like, it’s really nice of you to ask about my sex life. How’s yours going? And usually that turns people off pretty quickly because they’re like, this is uncomfortable. And I’m like, no kidding, it’s uncomfortable. You just asked about my ovaries. Like that is uncomfortable. And that is truly none of your business.

Like it is no one else’s business what I’m doing with my body except for me, maybe my husband question mark. Like, and I genuinely mean that and I think he would echo that point. So I think if I’m trying to be on a good day, kind, conscientious, I just ask a lot of questions. I try to be thoughtful in the questions I ask. But if someone’s really pushing me, I have no issues pushing back and just being like, I appreciate your concern, but this is really none of your business.

Jess Diamond (19:57.327)
Were you always headstrong on not having kids or was it an opinion and then a belief in existence for you, a reality that you grew into?

Jenna (20:08.654)
That’s a good question. I honestly think I always knew. I was raised in a really interesting household growing up. My dad is my best friend. I spend a lot of time with him. I think he’s the best dad in the entire world. But I had a really mom that was not around. And when she was, it was not a healthy dynamic at all. And I think that after a lot of therapy, I think I realized that…

Going through that experience growing up made me realize how important parents are and how vital, honestly, I mean, if you have the luxury of giving a child a parent set, a mom and a dad or a mom and a mom and a dad and a dad, whatever that might be, if you have the opportunity to a child a parent set, that makes a really big difference in how they’re raised, their belief system about themselves. And not growing up with that, like I obviously had a lot of trauma I had to work through and I just realized that that’s not.

that wasn’t something I wanted to duplicate. I didn’t wanna pass that generational trauma down to another kid. even after going through years of therapy, I still don’t think that I could, I don’t know if I would be able to separate that stuff from a child. Cause even I see it like with how I interact with my students or my nieces and nephews. Like I see like how my own personal belief systems and how I was raised, how that interacts with all those other relationships. And that’s after doing a lot of.

hard work and therapy. So I can’t imagine what it would have been like had I chosen not to do that. So I think I knew a long time ago that I wasn’t interested in kids. I think it really solidified when I met my husband because similar to what you said, he also didn’t really want kids. I think he could have gone either way depending on how I felt. But when I was like, this isn’t really something I’m interested in, he was like, okay, cool. And so I think that really solidified for me and I think that’s always the…

If people ask for advice in this area of life, this is the one piece of advice I give them, is that if you’re going to commit to a partner for life, then I suggest you two are on the same page. So although there are a lot of things in life that can change and there’s a lot of things you can change your mind on, there’s a couple that I really suggest is like a unit you maybe not change your mind on, and one of them is kids, because that’s kind of a make or break. So like if you’re in a committed relationship with someone, you should really know where they land on that.

Jenna (22:30.312)
and if they’re really committed to that belief system.

Jess Diamond (22:33.915)
My boyfriend asked me on our second date, what my thoughts were on kids. And I gave the answer I gave you. It’s the way I’ve thought about it for the last couple years, pretty much since I ended my last relationship when I was like, it’s, it is a possibility. Do I want them? And he asked me because he is all in he wants to be a dad. And I was like, you’re all in that gives me my answer. If we are in it for for life, but it’s a very new relationship. We’re just

Jenna (23:01.72)
So we’ll see, we’ll see.

Jess Diamond (23:02.679)
Yeah, so we’ll see, but it was a conversation we had right off the bat. And we even had it around having pets and his response around pets is the way I feel around kids. And I was like, okay, well I’m all in for having pets. so we have our.

Jenna (23:17.394)
That would be my answer to that too. Like I have four fur babies and I’m like my answer is like I would have 25 dogs if my husband allowed that but I think he knows that would drive us both insane. I think he’s protecting me actually.

Jess Diamond (23:31.503)
Yeah, I think where a lot of people, I don’t want to say go wrong, but like, I’m going to be opinionated as my podcast and I can say what I want. It’s a lot of people go wrong with seeking for that end goal of they just want kids and it doesn’t matter with whom and they’ll have it with anybody. And that’s different from a sperm donor or anything like that, but just like marrying to have kids, not marrying to be with someone. And then later on it

Jenna (23:38.798)
Hell yeah, girl.

Jess Diamond (23:59.375)
as a result of being so in love and like having that stability and that foundation to raise a healthy family into. I like also I understand where you’re coming from, not through your lens per se, but I have a good friend who has the similar reaction of she does not have a good relationship with her mom. And she is in a committed relationship where she has to think about these things now is and she’s like,

do I want kids? And I know it’s a fear for her because she doesn’t want to pass down that generational trauma, which you don’t have to. You can end it with yourself, but you also have to do a lot of work as you were saying to make sure you’re not passing it along and being able to catch yourself with what that looks like while also knowing that it’s probably not just going to exist in your kids. It’s going to exist in any of your relationships. You’re going to have those moments where it comes up and you have to take a step back and be like, whoa.

This is my trauma. I’m sorry that this just got projected onto you. I need to go deal with this for a second, but you got caught in that crossfire of my own brain and the actions that came out as a result.

Jenna (25:09.548)
Yeah, totally. And I think that’s true of anything in life, right? Like I tell my students all the time that like you need to get like really in touch with your version of trauma, small T or big T, because it does affect everything in life. And some people choose not to go through therapy or traditional therapy. And you know, who am I to tell them that that’s what they have to do? That just really helped me. But I do think that you have to recognize your triggers. What are your traumas?

so that you understand when they are popping up in your life. I see this pretty frequently in my students when they graduate and I mean, graduating from college within itself is like honestly a traumatizing time for most people because no one prepares for you what happens after you graduate from college. It is so overwhelming in a beautiful way but also on a really scary way. So no one prepares you for that. But then no one also prepares you for your first job out.

and let alone like trying to launch into your career or maybe having your first toxic boss or your first toxic work environment and but more often than not what I see is that students like their their belief system around how it should be is so deeply rooted in not what it is anymore and so when they enter into those environments

their own beliefs and their own traumas are popping up and they’re like, well, why isn’t my boss doing this? Or why aren’t my coworkers doing this? And I’m like, well, they shouldn’t be expected to do that. They are not your mom. I don’t give a hoot that you were out until four in the morning partying. Show up at 8 a.m. at your desk. That’s the job. That’s what people pay you to do. If you don’t like that, find a different experience.

So I think in general, I think understanding your traumas, understanding how it impacts you and how it’s gonna show up in your life is honestly vital to success because it’s not anyone else’s job to walk around your trauma. It’s your job to heal yourself, work around it, and then figure out how to move forward.

Jess Diamond (27:09.135)
Yeah, exactly. That’s exactly what I say as well. So I’m glad you brought that point up. And it’s true. I mean, it’s why I became an adulting coach because nobody teaches you how to do any of this. It’s why I have this podcast and it’s why I bring guests on like you to talk to them because you interact with 20 somethings regularly with the work that you do as a professor, like working on colleges and then within your coaching business as well. But I want to talk about something that’s more conventional and kind of on the lines of starting your first job.

And for you, you hopped into different industries throughout your twenties. Can you talk about how changing your mind and going from one thing to the next helped shape your perspective on making other big life decisions or on how you viewed your relationship to your careers, like anything of the sort?

Jenna (27:59.084)
Yeah, yeah, that’s it. I literally feel like my brain is like flashing back right now. So I think that you asked the question earlier, you know, have I always like kind of known about kids? So I don’t think I always knew about kids, but I have always been a very strong-willed person. And I think that was primarily from being raised predominantly by my dad. He raised me to be a very hyper independent woman who can think for myself, make my own decisions. And so I was always looking for work environments that allowed me to do that.

And I think, you know, here I am 15 years into my career, I have a lot of opportunities to critically think and be creative and do whatever I want. But I’ve really earned that through, you know, over a decade in my current career. And so I think in the early days when I was bouncing around, I was looking for that. I was looking for an environment where I could think out loud, I could be creative, I could teach other people, I could help others, but that I was also getting paid what I felt like I was worth at that time.

Which I would say, that number back then was pretty small. Like I knew I wasn’t worth, you know, $100,000 when I was straight out of undergrad. Now that number’s really different, I would say. But I think that that was a big piece for me. So like when I was working in fitness, like I went through a really rough journey getting diagnosed with Crohn’s disease when I was a senior in college. So I became infatuated with fitness and health and.

diets and workouts and all these things and I was like, this would be so cool to do for a career and you know, because you work in fitness, that it’s kind of a brutal industry. It really is. Like it’s not for the faint of heart. It’s not all like sunshine and rainbows and helping people. can be very competitive. There’s, you know, it also, you really have to know your stuff. It’s really easy to hurt someone. And so I learned really quickly in that environment that this woman that I was working for

she did not have good intentions. She said she did and she wanted to help people, quote unquote, but her avenue of doing so really wasn’t in alignment with my values and how I believe you should help people, especially from the health and fitness realm. So once I knew that, I was like, I’m out of here. You are not gonna take me down this rabbit hole of quote unquote helping people in a way that is not actually helping people. So I’m out. So then I…

Jenna (30:17.294)
From there, I went and worked and I did a lot of work in fundraising, which is a really interesting arena, I would say in general, right? It’s like sales, but for good reason is what I have still people. And I was actually really good at it. Like I loved working in fundraising and I was so good at it. The challenge I had is that, you I graduated from college, not during a recession, but it was pretty quickly after. And so people were still getting their feet on their ground. You know, there wasn’t a lot of money moving through the economy.

And so there were a lot of kind people who are willing to donate money, but once I like saw I was like, ooh, you really shouldn’t be though. Like you don’t have enough money to put food on your own table. You shouldn’t care about what other people need. And so I had a really, I had a moral dilemma with it to be honest with you is that like I really thought about this idea that like you need to learn to take care of yourself before you can take care of others. And I think that really embedded into me is that like I had to learn how to make sure that I was good, that I had enough.

money and savings that I had enough to take care of myself, that I had a backup plan if something went wrong with my career. I learned all of that through fundraising because watching these people who cared so deeply about the world and other problems that they were willing to give so much, but then they didn’t have enough left themselves. And just again, in my opinion, but if you are giving so much money that you cannot buy shoes for your kids, you’re making the wrong choice with your money. And so

I really learned that through that experience. And so I realized I was like, again, like I wanted to help people, but in a way that I felt was ethical and it wasn’t hurting people along the way. And so I think that really was one of the big outcomes of me job hopping for lack of better words, is that I knew I wanted a boss that cared about me as a person, which transparently I don’t think I found that until like well into my thirties. So that was a challenge within itself is just that there’s not a lot of leaders who have.

to care for the people that work for them. I don’t think they’re bad people, they just don’t have the capacity. Or they haven’t been taught how, right? Which is why I’m so passionate now about teaching people leadership and career development. I think I learned a lot about wanting that area of kind of creative freedom so that I could like, I don’t think I’m like a true creative, like I don’t know how to paint, I don’t write poetry or anything like that, but I like the idea of building programs in a way that works for people. I like to think outside the box, I like writing things in a way that is gonna help people to understand them.

Jenna (32:37.71)
So that was a big area for me and then ultimately, yeah, just being able to help people in a way that I felt like was morally and ethically sound and the more I looked into different industries, the more I realized that a lot of industries were struggling with that concept is that they said they were helping people but it was at risk of something else and I just couldn’t get behind that.

Jess Diamond (32:57.325)
Yeah, my coach, if she, she listened to this podcast, she’s probably ready to like slap you silly with not saying you’re creative because she just released her own podcast episode on if you’re creating things, it’s yes, it’s not in the literal sense of artwork and of that nature, but you’re making programs, you’re creating content for people to better understand or better improve their life or the way they think about things. So yes, you are a creator because I.

I’m a creator. create a lot of content and it’s I’m not sitting on the floor like on an easel like painting something. But I very much relate to what you said of wanting to be in charge of your own creativity and like your own flexibility in that nature. I mean, I remember growing up when everyone would ask you, I think I’ve said this on this podcast several episodes, but people would ask, what do want to be when you grow up? And my

little bratty self would be like, want to be a six figure CEO because at the time six figures was the number and it was mainly because I didn’t even fully know what CEO was like, I just knew they were the top dog. And being a little sister, I wanted to be the boss of me. was like, I don’t want anyone to be the boss of me. I want to be the boss of me. And

Jenna (34:01.08)
lot of money. Yeah.

Jess Diamond (34:18.709)
It even translates now. I mean, yes, I’m self-employed, but I am actually at the time of this episode. It’ll be long gone by the time this comes out. I’m getting ready to quit one of my part-time jobs where I do have a manager and it’s because it is a toxic environment. And I’ve had toxic people at work when I had a full-time job, but I never was in a full toxic environment where I felt so anxious or so

heaved around anything that was going on between my interaction with the owner of this gym. And it’s to your point of she doesn’t know how to manage people. She doesn’t know how to be a leader. She is only in it for the money. Yes, in theory, she’s in the fitness industry. She’s there to help people, but she’s not. The trainers are there to help people. She’s there for the money. And if you’re not helping her do that,

or in her way, in her mind, if you’re not helping her to what she wants you to be doing, then it’s not good enough and she’s gonna make your life hell. And that’s kind of the situation I’m at, even though I have consistently been their best trainer and performing great and signing on members, it doesn’t matter because I’m not doing the very nitty gritty things that she wants me to do because they go against my own health and my own boundaries and my own values. So that’s why I’m leaving.

Jenna (35:43.672)
So I would say like, mad kudos to you, right? Because like, and I think maybe you could validate this, but I always tell folks that like, especially when I’m career coaching, that that is awesome. If you can get to that point where you know your values, your boundaries, what matters to you, and you’re willing to step away from employment opportunities because of those things, that is such a privileged place to be. And that is amazing.

however and but, that I think it’s so important to remember that that is a beautiful place that like you’ve worked hard so that you have the money and the time and the flexibility to be able to make that choice in a safe way that doesn’t make you feel like, my God, my whole life is gonna fall apart, right? Versus the people that like, so I call it the difference between fun employment and unemployment, right? So fun employment.

is when you are set up for success that you can take time off from working, whether part-time or full-time, because you have savings, you have other income streams, whatever it might be, right? Unemployment is where either you choose or someone chose for you that you are no longer employed and you’re not in a safe situation. And so I think that like you’ve just described this beautiful thing that I think everyone should aim for. I think everyone should aim for having enough money and savings that if you are in a bad situation, you can opt out of it. And I think that is

honestly, probably should be everyone’s like number one goal for their career because you just never know. mean like situations change, bosses change, environments change. You never know what things are going to happen and you need to be prepared to take care of yourself ultimately.

Jess Diamond (37:18.135)
Yeah, I mean, this has been ongoing for two months. And at first, it was like, Okay, no, I can, I can stick it out. Like, it’s fine. It’s fine. It just kept getting worse and worse. That it became more of the Okay, when am I leaving? It’s no longer okay, eventually, eventually, I started to put a date to it. And the date actually started to get closer because I was like, I can’t put up with it anymore. So what I like shortened it by about 10 days. It was like, I got to get out. It’s not it’s not happening. And it was more so thinking of I don’t want to

hurt anyone else and I also want my closure with the members that I care about because I know that this owner won’t let me have that the moment I send that email of I’m out. So it is, I love your description of fun employment versus unemployment because I have been in both. And when you said earlier in this episode, it’s like, oh, for me, when you’re talking about my story that it was probably scary to leave my full-time job and go and start my own thing.

And it was, but weirdly enough, when all of this started to go down, I felt way more fear. And I don’t know if it’s because I’m older, more things are on the line, but I felt so much more fear ending this chapter than I did ending my corporate chapter. The corporate one, I knew. I planned it for 11 months. It was ready to go. And this was just not something I forecasted for the beginning of 2025, but also knowing that

being there and continuing to be in that environment is actually holding me back from the real work I want to do, which is my business and it’s speaking engagements and it’s personal training. Like it’s the things that are mine that no one can take from me. And it’s getting that time back so I can put energy and time into those other things that matter more while also knowing that being in that environment is taking my energy. It’s not even keeping me at a neutral. was neutral slash sometimes maybe it’d be a gain, but

it’s actually taking away now. I think realizing that and being very fortunate to be in the position where I can step away, even if it scares the living shit out of me, because it is a good chunk of extra income that I was relying on for the last three years. It kept increasing. I’ve been at that gym for almost three years at this point. And that is scary. But you make plans. It’s not something I’m not just throwing my hands up being like, I’m out the moment something goes awry. It’s

Jess Diamond (39:43.831)
trying to stick it out, trying to improve the situation, doing what I can while also knowing if you have a toxic boss, there is nothing you can do besides make your plan and step away.

Jenna (39:55.266)
Yeah, absolutely. You’re spot on. think something else you’re describing is emotional regulation that I think most people are not familiar with and most people are not taught growing up. And I think that honestly, it’s a great career skill set that you’ll use in any career, whether it’s entrepreneurial or not, is that like everyone needs to have that moment where you’re like, I am so angry, they’re treating me like crap, like this isn’t right. And to be able to learn how to control your thoughts in your mind enough to be like,

This isn’t an appropriate place for me to blow up. I shouldn’t cuss my boss out. This is here. Here’s a fun story for you. So one of those many jobs when I was about to graduate undergrad, I had been working at this restaurant for like six years. I worked there in high school. I worked there in college. It’s actually where my husband and I worked together when we were in undergrad. And I had a horrible customer one night. I was so mad. And I like literally I knew not to take it out on the customer and I never would.

But I went to the back into the kitchen area and our general manager came out and he was pissed. He was like, you did everything wrong. This customer is so angry, blah, blah. And in my mind, I’m like, just comp their meal. Let these people leave. It’s like almost midnight. I want to go home. Like, come on, man. And he didn’t and he just berated me. So I literally like threw up the middle finger, both hands, and I was like, F you, I’m out of here. And I literally walked out. My poor husband.

we’re barely dating at the time and he was working at the same shift I was and he like called me and he was like, I have to close this place down by myself now, like are you insane? And I was like, I can’t do this. I was like, he’s bonkers, he yells all the time, like did I handle the situation with the customer perfectly? Looking back, no, I didn’t. Should I have like thrown up the middle finger, cussed him out and walked out? No, I shouldn’t. But.

I still like in that moment I was like this is so toxic and so ongoing like I gotta go. But I also was smart enough that like I had another like borderline full-time internship with a huge TV studio. Like I had a lot of other money coming in like I wasn’t gonna die and be homeless and not have food because I walked out of this food and bed place. So I think that in that moment like I and I go back to this all the time with my students because I was like I should have been more mature.

Jenna (42:18.146)
I should have been smarter, I should have regulated my emotions a little bit better and been like, you know what, this is a bad shift, this is a bad moment, like bite your tongue. And then like once you’ve like kind of come to an even keel moment, then decide if you no longer wanna work here. But I didn’t and you know, I choose to live my life with no regrets, but that is a moment that I look back on and I’m like, not my finest moment ever.

Jess Diamond (42:43.395)
Yeah, and I help my clients if they’re unhappy with their job and are ready to quit. It’s like, hey, you can quit. We’re gonna make a plan for you to do so. And you have to go by my own mental model is it’s not forever, it’s for now. And for the next, at the time of us recording this episode, the next 12 days of my life, that will be on repeat in my head anytime I have to deal with this woman because it’s not forever. It’s happening right now and I’m gonna get through it.

And come April, my schedule is going to be so much nicer, so much more relaxing. My boyfriend isn’t going to hear me rant about how much I don’t like this place. And I’ll be able to get through it. But it is it is a part of emotional maturity, emotional regulation and time and place. You really have to know yourself and know your capabilities and know what’s next for you. Maybe you don’t know exactly what’s next, but know that there is a possibility to have a better experience somewhere else.

and then start making moves in that direction.

Jenna (43:43.382)
Yeah, yeah, I couldn’t agree more.

Jess Diamond (43:46.383)
All right, I want to talk about something else that I mentioned at the intro of this episode. And it was when I was talking about measuring success, because I think that’s we call it checking boxes. We call it like just different milestones. And it’s, again, what society or friends and family or social media has maybe intentionally or unintentionally imposed on us. How do you

personally measure success and how can 20-somethings redefine that measurement for themselves?

Jenna (44:20.046)
Yeah, I love this question because I think this is something I sucked at early in my career. I mean, it was so important to me to quote unquote be successful in the way that we probably measured in like, I don’t know, before I was alive, like in the 70s and 80s, you like you graduate from college, you get married, you buy a house, like you start a fancy career and

Yeah, it just doesn’t work that way for most people. So I would say I did hit a lot of those markers, but I will be fully transparent. Hitting those markers did not make me happy. It made me, I don’t like to use the D word, but it made me borderline depressed. It really did. So I graduated undergrad when I was 21 with a double major. After switching my major six times, say what you want. That’s pretty impressive, not to toot my own horn.

Jess Diamond (45:09.455)
Yes.

Jenna (45:11.054)
I had job offers when I graduated. I did a ton of internships. I did an internship with a senator. I did an internship with a really fancy TV studio. Like I did quote unquote impressive things. I moved to Las Vegas when I was 23. I got into graduate school. I started by the time I was 24. I bought a house when I was 24. I got married when I was 24. 24 was a big year for me.

Yeah, and then I graduated my master’s when I was 25. So I did it in like a year and a half, some change. It was right before my 26th birthday. And I just like, by the time I was 27, I became a director, which in higher education is pretty impressive. That doesn’t happen for most people at that age. And I was overseeing a large team of people, which I also didn’t have a ton of leadership experience at that time. And I remember it like it was around that timeframe, that same photo I told you about earlier when I was

standing on the sand and it was right after I graduated college. I had almost that same exact experience when I graduated with my masters. I was like, I was back in San Diego, I was there for a family trip and I was standing on the beach, I was in a different outfit, my hair was curly and sort of straight, but other than that, the picture looks almost identical and I was so sad and I mean like borderline depressed.

Like it was really unhealthy and really scary because I was so young and I had done everything everyone had told me I was supposed to and I was so unhappy and I think it Knowing what I know about myself now. I think it was because that goalpost was always moving for me So I was like, well, what am I gonna achieve next? And there’s only so much you can achieve when you’ve already bought a house and done all the things before your 30th birthday And so immediately I was like, I was like I should buy another

I should start my own business. should and like it just become these shoulds right like I should do all these things and When I really took a moment to step back and it was actually around the same time I think my husband would be okay me sharing this but he had gotten a huge so my husband works in television and film and he had gotten a huge TV contract and it was going so well and then one of his TV shows was canceled and overnight we made we went from making like $20,000 a month to nothing literally overnight and it was

Jenna (47:23.626)
I mean, like I remember I woke up one night and he was having a panic attack and neither of us knew what that meant and that he was having a panic attack, but knowing what I know now, that’s what was happening. And I literally like sat there in bed as we were both like freaking out and I was like, this is not working. Like this is not gonna work for us. Like, and I remember us having this really pretty rough conversation about just like what we wanted with our lives and what we wanted.

what was success for us and what were the goals we were trying to achieve. And I think it was the first moment that we really, after we had achieved so much success at a young age, that we took a step back and we were like, what do we actually want? Like not what is everyone else telling me we should want, what our parents want, what society wants, what social media tells us, what do we want?

And so we actually sat down and we did this like big goal setting session for ourselves of like, you know, how much money did we want to save so that if one of us wanted to leave our jobs or one of his TV contracts got canceled, that we were okay and it wasn’t going to be a panic. You know, how did we want to buy another house? Did we want to invest in real estate? What did that mean? Did I want to start my own business? Did I want to do coaching on the side? Did I want to teach for other universities? Did I want to go back to school and get my doctorate? Like we had all these big conversations and it really kind of all went back down to like,

what were the values of our life and what kind of life did we want to live? And I think the one commonality we came to and we together we decided we were going to write a family mission statement, which was so helpful to us. And the core of our family mission statement is that we’re going to help other people break generational curses and help them not live within the box that society encourages us to live within. And so our goal is to help other people do that.

But we also try to live in alignment with that because we believe in model of leadership. And so if we’re gonna encourage other people to live a life, then we’re hoping that we’re a good model of what that looks like. And so that’s the question we ask ourselves every day is like, are we breaking generational curses and are we living outside of that box that everyone says we’re supposed to live in? And that has helped us so much because even to this day, like we have been making a lot of big decisions this last year, we own an old home.

Jenna (49:31.694)
And so we’ve had to fix it up and do all this work. But at the same time, we’ve been trying to buy an investment property. And so we were like, we don’t have enough money to do both. We need to make one or the other. And so we paused and we were like, OK, which one of these breaks generational curses? And we were like, having a stable home is actually really important to both of us. And so we were like, that’s important. So investing in our current home that we live in is important. But then living in the box that people say outside of what you’re supposed to do. And I’m like, well, everyone says you’re supposed to invest in real estate.

Okay, well then I think our answer is clear. We need to invest in our current home, make this livable, fix all the stuff that needs to be broken, and we can decide if we want to invest in real estate next year. And it’s fine. So I think all of those things kind of helped us to realize that sometimes you gotta take a step back to take a step forward. You also have to know what you care about most. But also, in my lived experience, doing all the things that someone tells you you’re supposed to, that never works.

It never makes you happy. I mean, like, am I proud of myself that I did all those things at a young age? I am. I think I’m freaking amazing for doing all that and accomplishing all that. But it didn’t make me happy. It made me accomplished, but it didn’t make me happy.

Jess Diamond (50:46.421)
Ooh, that was a mic dropper. Made you accomplish but not happy. And there is a difference. And yeah, sense of accomplishment and happiness can go together, but I think when it comes to big life moments or what you think you should be doing as your big life moments, it’s not necessarily one and the same. I love the idea of a mission statement though, and that you mentioned that in goal setting and just coming back to that every time you’re at a crossroads of,

what do I want to do? Not what what should I do? What do I want to do next? And how does that decision act in alignment with my core and that core is that mission statement. So that was really good. The writer downer for anyone listening, write that one down. I do have one final question for you as we wrap up this episode, because I would love to end it on that mic drop of accomplished versus happiness. But what is one thing

Jenna (51:20.014)
I’m

Jess Diamond (51:43.585)
you wish someone told you when you were making the transition from college life to the real world.

Jenna (51:50.734)
change is the only constant. I think that I, yeah, I was just raised in a way that I found stability to be the number one most important thing, whether it’s financial stability, home life stability, relational stability, but in reality, stability does not exist. You can create it. Like I think that you can create a sense of stability. And I think that’s what I’ve done in my own life. You know, I have, I’ve really stable relationships. I have a really stable husband. have, you know, stable rock.

like people in my life, but it doesn’t create stability. They are stable people because they are healthy people. But at the end of the day, change is the only constant in life. Like, I don’t know if I’m gonna be employed tomorrow. I mean, God, I hope so, but I don’t know. You know, I don’t know if I’m gonna make the same amount of money. I don’t know if there’s gonna be some natural disaster that like takes my home away. I just don’t know. And I think that, you know, of course there’s the people that…

live with chronic anxiety and I really encourage people to seek out professional help if you are struggling with something like that. But I truly believe that in a general sense for most people that are not dealing with a diagnosed disease that anxiety is fear of the unknown which is not helping us. It really isn’t. So focus on what you do know. And I think the one thing that I do know is that change is constant and the more comfortable you can become with change the more successful you’re going to be.

However you define success, change will absolutely be a partner in success. so lean into that. That when things are changing, that’s a good thing. That means you’re on the right track. That’s exciting. And instead of getting anxious or nervous, get excited about those things. Feel the butterflies, lean into the butterflies, and be like, ooh, this is a good thing. I’m doing the right thing. I’m on the yellow brick road. The next big thing is coming. And I try really hard to remind myself of that. And I wish someone had told me that earlier in life.

not only that like the quote right the quotable moment that change is constant but you have to get comfortable change whatever that means for you.

Jess Diamond (53:54.893)
Yeah, I actually tell people you’re never going to be comfortable with change. It’s always going to feel uncomfortable, but you become familiar with that discomfort. So it’s you know how to handle it better. You are able to recognize it, but it’s always going to be uncomfortable. It’s no matter what, because it’s always going to be a different type of change. As you move through life, it’s going to be a different experience that is changing. So and with the stability, I agree like they’re

Jenna (54:03.694)
Yeah, yeah.

Jess Diamond (54:21.431)
you can create your stability. And the way I coach my clients around that is you need that solid foundation so that when other things in your life, all the other moving parts are happening, you have a place to come back to and reset yourself. And the things that you have control over, your health while you have is like, don’t take it for granted, but like feeding yourself while moving your body, getting sleep, like doing those things, having a routine. So

you know you have a place to come back to. That is your stability as well as people having the right people around you as well. But thank you Jenna. I feel like I could talk to you for another hour. So thank you so much for coming on How to 20 something. Where can people find you if they want to connect with you?

Jenna (55:04.332)
Yeah, absolutely. my Instagram is my most popular spot. It’s J Heath Moreno, M-O-R-E-N-O, or my LinkedIn. I’m very active and I love, love, love nothing more to help people figure out how to be productive on LinkedIn because especially most young people are taught like create a LinkedIn and then they just ignore it forever, which is not the answer. So LinkedIn and Instagram are my hotspots for now. and of course my podcast.

Jess Diamond (55:31.14)
It’s funny you say that. What’s your podcast? Play your podcast name.

Jenna (55:32.952)
Sorry, tearing up my heart. Yeah, tearing up my heart, it’s about emotional leadership lessons and we try to focus on self leadership before leadership of others. So I think it’s applicable to any age range or anything. Definitely a little bit more focuses on the career development side, but it’s a ton of fun. if you are, even if you’re not a 90s girlie, if you can appreciate NSYNC or Justin Timberlake, you will love the references.

Jess Diamond (56:01.739)
I love it. I’ll have to go give it a listen. And as for LinkedIn, I think the timing is the guest episode that gets released before yours is on LinkedIn. So we’re getting our bases covered. But all of Jenna’s information will be linked in the show notes per usual. So if you guys liked what you heard, if you learned something new, or if you know someone who needs to hear any of these golden nuggets from this episode, then please pass it along.

send it to a friend, give it a five star rating, share it on social media and tag me tag Jenna when you do. And as always, I can’t wait to be in your headphones again next week with another brand new episode.