Jess Diamond (00:05.218)
That’s so that we have the audio version. Gotcha. All right. So I just asked, how did your parents scope your view of the working world? Three, two, one. So my parents are really different from each other and different from a lot of what I’ve learned. Other people’s parents are like kind of what you were mentioning and neither of them had a particularly linear career path.

My mom maybe slightly more so than my dad, but no matter what, when I was a kid, they always told me a lot about the life they had before I came into the world. So I knew a lot about my parents and I’m still always learning a lot about my parents life before I came around. And that meant I learned about their career choices. My mom, for example, was a model in LA and she just randomly decided to move from New York to LA when she was pretty young.

My dad was born and raised in California, but did everything from dig ditches, build bicycles, race in Baja and deep sea fish. So every time I heard about their life, whether it was together or separate, they were doing these really interesting things for either the short term or the long term. And that made me feel a little bit more comfortable just picking things up to try as a job instead of finding.

one set career at maybe one or two companies. Can you explain your career path a little bit? I know I did in the intro, what is it? How did your career path influence you picking your majors? And then I guess the other way around, like you picked your majors and then you had a career path and it’s still jumping around and I know it’s still about to change and it will probably continue to change over this next decade. So give us a little insight into all of those thought processes. Okay.

I think the kind of crux of the whole conversation rests on, don’t view my life as a career path. I view jobs that bolster the choices I make in my life. So when I want to try something new, I look at a way that I can either get paid to do it or something I’m already doing can make it possible for me to do that thing. So I think the prime example for this was the relationship with Harley Davidson. I randomly went into a Harley Davidson dealership.

Jess Diamond (02:25.248)
and wanted to see if, think my partner at the time was interested in a motorcycle. And we were talking about things that that office and station, I guess that rep needed. And they said, we’re so short on photos. I would love to show him a photo of this bike, but we don’t have any. And I said, well, do you need some? I have a camera and some free time. And it’s a…

way of responding when opportunity knocks. If you see something that you think there’s a niche you can fill or a skill you have or that one that you’re trying to develop and you step into that role, whether you feel qualified or not, whether you feel ready or not, some of those were very easy for me to step into because I had the credit, right? Applying to college made sense because I was graduating high school.

going into an English major made sense because I had applied for a writing scholarship and picking up additional majors happened really naturally. So the same thing was true with picking up odd jobs or starting new career paths, you might say. After I graduated, it was very similar. So I think that’s kind of a prime example of it, but when it comes to making those decisions and like,

jumping from one thing to another it can come across a little bit Truncated or like I’m making a left turn in the middle of my life and that’s what my life looks like My mom’s is less so she now runs a international private investigation an executive protection firm But she’s been in similar industries for 30 plus years So the industry carried her through Starting these new roles

and picking up something only slightly different than what she was doing before. I make 180s, the occasional 359 degree turn, and my mom has taken more of a, ooh, this is similar, but it cultivates a skill I’m interested in. I’m gonna take a step a little to the left. My dad, I’m a little bit more like my dad in this regard. He takes left turns, right turns, U turns all the time.

Jess Diamond (04:45.402)
Well, I think I relate to you in the complete left turn. And I think my mom was terrified when I made that decision because I during the pandemic, I was like, fuck the corporate world. I am never returning and I’m to be a personal trainer for the rest of my life. And my mom was like, uh, you need to go try this again and stick with it. And I know that’s a lot of it comes from a place of love. And you’re in you were in a position growing up.

and you still are where your parents are very supportive of these crazy left turns that you make. But I know not everyone in our immediate environments are going to be supportive. Again, coming from that place of love, they just, they want to see you thrive and succeed. So it’s like, hey, stick with something, like see it through to the end. But how do you deal with any outside voices say like, hey, maybe this isn’t a good idea. Or like, you should stick with what you’re doing right now and look for stability or.

different thoughts of people trying to almost project their own thought processes into your life to try to sway your decisions. How do you navigate that? This is very good question. I think it’s what my mom’s going to want me to answer the most. My mom absolutely had my back when it came to leaving my pharmaceutical job, but she definitely put up some resistance in the beginning to make sure I was making that decision with all of my brain cells. Right? Was I really invested in this choice?

I think having the confidence in yourself to sort through what those problems are going to be when you make that change. So in almost every situation I’ve been in, I’ve known what my next source of income was going to be. And that offers a level of security that then the choice seems a little bit less daunting. Then it’s just a pivot, right? It’s less so a…

my gosh, what am I gonna do? I wasn’t forced into this decision. I made this decision on my own and now I have this opportunity that I want to seek out. That would be the naysayers that I hear from usually come from a place of, what are you gonna do? Don’t you have bills, right? And yes, I have bills, I’m just like you. And a lot of that confidence from within helps, I would say, quell some of the concerns of other people once you…

Jess Diamond (07:08.046)
know in yourself what it is you want to do next. So sometimes the opportunities arise. I wasn’t expecting to leave Harley-Davidson with a job. I was definitely not expecting to, you know, move to North Carolina and then end up leaving my corporate safe, well-paying job with health insurance, Much like I’m sure during the pandemic, you just said, I’m done, right? Sometimes you just throw up your hands and you don’t know.

Exactly what the path looks like but as soon as you start to make the choice and have the confidence in yourself to do that and move forward It is a lot less terrifying now. Is it still scary? Absolutely. It is still scary but when it comes to folks disagreeing with me or maybe disagreeing with my choices I then remember that all of these people in my life have taken very What would you say like non-traditional and risky paths

And they’re fine. They’re really, they’re doing really well. And in redefining what I thought success would be and in explaining to my parents what I now view success to be, I didn’t have the uphill battle with my parents so much as some people might, but I do have the uphill battle with some extended family and with some friends, even who, like you said, have my best interests at heart. And I remind them that, hey, I’m going to be okay.

because I think that’s where it comes from, is they’re worried I’m not gonna be okay. And additionally, I want this, right? Like my confidence comes from within because I chose this thing that I wanna do. And that keeps the kind of darker tone voices out of my head. Don’t get me wrong, I’ve woken up in the middle of the night and be like, did I just make a horrible choice? And that’s where the bravery kind of comes back and you have to lean on what you know about yourself and the confidence you have in what you wanna do next.

Well, I think a large part of the fear that comes with making a pivot or taking a risk in your career is the how. So a lot of people are like, I’m going to give an example. Like, let’s say you’re in your marketing and you’re like, all of a sudden I want to be a gym coach. How do you just make that transition? Like where do you, where for your, within your own experience, like where has that thought process come up? Like, okay, I want to change what I’m currently doing.

Jess Diamond (09:29.452)
this is the first step I’m going to take to try to get there or even from a connection standpoint of how do you get that next job if you don’t have any prior experience? think both of those go hand in hand. It’s like the fear of, don’t know what step to take. And then also how do I even make that transition in the first place? Even if I know the steps. Absolutely. I have a strong opinion on this. I will warn your listeners. Break your echo chamber. You need to get out of your echo chamber. There are a lot of people in your life that you’ve kept in your life.

because of one thing or another, go out and meet new people. Yes, I know that that is easier said than done, but I’ve struck up conversation with people at coffee shops and left with a $20,000 deal. I’ve had someone random walk into my life wearing the same shoes as me and then ended up getting a job offer for a friend of mine. So there are opportunities that disguise themselves as social interactions.

that you otherwise might not have had if you didn’t go out to coffee that day, if you didn’t make a choice to join that new gym or work with a new trainer and talk about the things that are actually happening in your life with those people. I think we shortchange ourselves a lot when I say, Hey Jess, how you doing? And you said, right? Hey, I’m really struggling with my mind muscle connection in my back, Jess, and Jess gave me a tip. Hey, stop, let go of your grip, calm down.

And now I implemented that today. That’s already going better for me. So the idea that you can bring what you’re worried about about your job or what you’re worried about in your personal life to other people, you know, maybe don’t overshare, maybe do. That’s your prerogative. But get to a point where you recognize that other people have as much to offer you as you do them and make a point to have those conversations because that’s honestly what’s gotten me almost every job.

Well, I love that you say that because it goes back to building connections, which is something that I stress for my listeners and with my clients. I even, the clients that I’m working with right now, I had my own connections that I’ve helped them. Like I had a guest on a podcast who runs her own editing business. And I am working with a client who is about to graduate college and wants to be an editor. So I was able to ask her how she did it and relay the information to him and start building up.

Jess Diamond (11:48.91)
the process for him to take those steps. And then similarly, I recorded with another guest whose husband is in the film industry. And I have another client who wants to break into the film industry. And I was like, even though the connections don’t help me directly, they I at least know how to connect them with other people. And it’s why you should always be wanting to connect with more and more people because you just never know. You never know who you can help. You never know how it’s going to help you. And it

does make these transitions easier. It’s the first thing I tell people they want to make that pivot is, or even if they got laid off and they just want a job, who do you know? That’s how you’re going to get it. You have to go through a person, especially with all this AI bullshit, built into these resumes and you’re not getting anywhere. You’re not even landing an interview. You need the real person. That real person comes with connections. That connection starts with stop putting up

walls all the time around people and actually talk to them and have conversations. Absolutely. I think the one thing that I’ve taken from my parents and the people around me and these other experiences I’ve accumulated, whether they be jobs or whatnot, is moving through life how you want to is pivotal. But when monkey wrenches get thrown in, you lose your job, somebody passes, you’re facing debt, you’re facing things that maybe you weren’t expecting to face.

that shouldn’t necessarily change your home base in the sense of how you move through your life. So for me, it’s the mantra move like water. If I am fighting for something and fighting for something and fighting for something and it’s not getting me anywhere, maybe that’s not meant to be for me. I’ve wanted jobs and not gotten them. I’ve applied for things and gotten nowhere, heard nothing back. And it was recognizing that that resistance was enough.

of the universe speaking to me to say, okay, we need to divert. We need to try something else. My best friend actually from college right now is saying today said, I am losing all of my friends here. People are leaving the company. People are leaving the area. And I said, I think that it’s time for you to go too. And he was like, well, the universe didn’t have to be so heavy handed. And I said, well, maybe you weren’t listening before. Right. So part of that is the serendipity of meeting someone who could get you that job.

Jess Diamond (14:14.83)
And you might already know that person and not realize it because you never made the point to have those conversations. So I would say connections and acknowledging that those don’t always look like a boardroom conversation, right? They almost never do. They rarely do. They rarely do. And I would say if that seems really foreign to you, if that seems like something too difficult to take on today, take a minute.

work on the relationship you have with yourself and Acknowledge that where you are is not forever if you don’t want it to be you absolutely can make those changes in your life so long as You work on your relationship with yourself You look at what you’re good at and what you like Even in the jobs that I’ve had that I did not like they had some really negative things going on I found the components of my life of myself and of my job that I liked the most and I focused on those things

Okay, I’m gonna find a job that lets me do those things. Now, I’m not one to preach, hey, you know, I don’t wanna work just so that I can live on the weekend. I’m not a weekender, I’m a live every dayer. And being able to make the choices one job at a time, one career move at a time to get to where I wanna do that. And I mean, you said it originally, I would be nowhere near that without my parents’ influence. Yeah, I mean, it’s hard. You’re gonna fight yourself, you’re gonna fight.

the people around you who are gonna question you. it’s not like, we’re not saying taking a career risk is easy. It’s not, it’s absolutely terrifying. But it goes back to what Summer was saying is like, you have to come back to yourself. It’s like, what do you want? What is important to you right now? And what career is going to support that? And I think a lot of it, a lot of what I see online and through conversations that people are like, I don’t like my career, but I have no idea.

what else is out there? And you know, they can’t just up and quit their job with nothing lined up. And I would not recommend that, I would like to say. I would not recommend just up and quitting your job. But how can someone even just start to explore what else is out there? I mean, it’s 2025. You can make money doing anything if you wanted to, but you have to know what that initial direction is going to look like. Like, what do you like to do? Yes. So how has that influenced some of your decisions to change paths and try something new?

Jess Diamond (16:41.44)
Absolutely. I think one of the things is opportunities always knocking you just have to be a lot more aware of what that looks like so acknowledging what we said before about connections and realizing that you could walk into a coffee shop and have way more in common with a stranger next to you than you ever realized or if You know what you’re good at and you want and you know what you want to pursue if you have a level of confidence in the desire but not in the actions someone has come before you and They might not have done it how you want to do it

but they might’ve started in a way that you can then emulate. You can talk to that person. You can go meet that person. And beyond their advice, you can see how you would do it differently. The thing is, if you have something you wanna do, there is somebody out there doing that thing probably way worse than how you would do it. And even if it’s not worse, let’s just say it’s different. The thing that makes you

do the thing you want to do, that desire within you is what’s going to make your approach to that thing unique. And it’s going to make it like you can monetize it that way. You can sell it, brand it that way and give other people a chance to partake in the thing that you have to contribute to the world. And part of that is knowing what you want to do. But for me, I’ve known what I’ve wanted to do for a year at a time, two years at a time, five years at a time, and accepting that when it’s done, it’s done.

So if you’re at the point where you know it’s done and you want to move forward, look at yourself, look at your career, look at your daily life. What are you good at? What do you like? And is there a job that does that? And I think much like what you just said, Jess, there’s probably a job that does that. It’s just a matter of talking to the right people and getting to a point where you acknowledge what that day to day looks like and how to execute from there. I couldn’t agree more. So I want to ask more about you and your story.

And just to give the audience a perspective on some of these scary leaps and maybe challenges you’ve encountered. So what would you say is the scariest career leap you’ve taken and what pushed you to do it, to go after it? Yeah, was, desperation is what pushed me. I had been in a long-term relationship and it just ended and we were sharing an apartment, a two-bedroom apartment. I moved into the other bedroom.

Jess Diamond (19:05.626)
And it was a family business I had been working for, that ag retainment farm. And I loved it. I thought I was going to spend the rest of my life there. And obviously I didn’t, but I was forced to find some type of job, anything. And this was a job I actually did get by applying online and went in for an interview, got an offer on the spot and it was just cold calling. And I said, well, I have bills, right? Back to the bills. I’m going to take whatever job I get.

that allows me to make what I need to make so that when I have to make a decision about leaving, I can do so freely. And I got this job and it was awful. And I hope somebody at that job hears this or somebody who’s in a similar position hears this because I worked my butt off at that job. I knew that there was a way to get out of there and into something that I wanted to be doing so long as I focused on being my best self at that job.

Now, that’s something that I harp on is bring yourself, bring the you to it, much like if you had a job you wanted to start or a business you wanted to start, the thing that makes it important is the you that you bring to it. Your podcast wouldn’t be just this podcast if Justin knows the podcast. So for me, I brought my whole self to this job every day and it only took two months before someone saw my work ethic, my attitude and said, what are you doing here?

Seriously, what are you doing? You have four degrees and you’re making cold calls and I was like, there’s no job that I’m too good for. I’ll absolutely do my job. And that led to an immediate hiring for the parent company to the company that I originally got hired at. Didn’t even know that relationship existed, but it was completely out of my hands. It went from, hey, I’m gonna be at work 15 minutes early. I’m gonna stay late, make sure everything I need to do is done. Check in with everybody. I’m gonna do…

exactly what I would want my employee to do if I ran this firm and that led to the next job which was I interviewed and it was kind of a formality but I interviewed and started that next Tuesday and wound up getting another offer from that same company to move to Charlotte. I and that’s where we are now. So I

Jess Diamond (21:31.49)
I was terrified because at no point in this did I think anything was a given. And it was hard. I drove far to work every morning. I barely had time to take care of my dog and myself. The pay was not great. It was barely covering expenses. And I still made the conscious choice to bring myself to that job and give it what I had because I had to believe in whatever was coming after. And some people use faith. I believe in the universe. I believe in…

things just working out. And sometimes it doesn’t look how you want it to. Sometimes you’re barely scraping by and you’re eating peanut butter and jelly sandwiches for breakfast, lunch, and dinner. But when you get to the other side, it’s 100 % worth it because you find what that job was supposed to lead you to. And for me, that led to five years in pharmaceutical sales with tangible skills I never thought I was looking for and wound up really embracing. So.

The fear is, will I have enough money to pay my rent and pay for food? The fear is, will this really get me where I want to go? The fear is, am I going to use any of these skills ever again? The fear is, what if I’m wasting my time? The fear is, it’s large, it’s imposing, it wakes you up at night. it’s like we said earlier, changing careers, taking a risk, it’s not without pain. It’s not without fear.

So when you move through it, remember that the fear was part of the problems that you chose. So did I choose to end that relationship? No. Did I choose to find a job that I was going to give everything to? Yeah. And I’m a big proponent for the concept that you choose your problems. And some of them, not your choice, right? Like some medical things, some parts of your life you simply cannot change. Yeah, those are problems that you are quote unquote stuck with.

but the problems with your job and your career, those are problems that you’re choosing every day. So if there’s other problems that you think would fit your life better and the future that you want for yourself, your children, your friends better, go for it. Well, I want to highlight on something that you said a couple of minutes ago that I think is a very key component to taking any type of career risk or changing paths or whatever it may be. And that says, said,

Jess Diamond (23:53.55)
there is no job that you were too good for. So you took your ego and your pride and you shoved it in a box somewhere and you’re like, I’m gonna do the work that is not only expected of me, but what I would expect an employee of mine to be doing. So going, not even like overachieving above and beyond, but doing the work and doing it well, knowing that it is the bridge to get you to somewhere else. And you might not know what that somewhere else looks like. You had no idea that

doing that cold calling job is going to lead you to the next opportunity, to the next opportunity, to the next opportunity, you took that job and you’re like, I’m going to do this and I’m going to do it well. a lot of 20 somethings who have started their career path, maybe they’ve gotten a promotion or two, and then they’re like, wait, I don’t want to do this anymore. I want to change. A lot of times they misjudge that it’s not a lateral transition. You do have to take a step down and start

essentially from scratch of what it is that you want to do so that you can build the skills and the knowledge and the expertise to then work your way back up. But it’s thinking in that long term of if you don’t like what you’re doing right now, you’re the one that gets to decide to change it. Absolutely preach Jess. I think one of the things I see my friends do, unfortunately, is say that they don’t like their career, but that they’re not going to change it because they’re comfortable enough. And you know what?

I’m happy for them that they’re comfortable enough, but that wasn’t going to work for me. Timeline of your life can change at any moment. And yes, we hear, you could die tomorrow, right? But it sounds so hyperbolic that we don’t actually act on anything. So I like to look at the minutia of my life and acknowledge what can and cannot change under my control. when I wasn’t, my timeline was given to me, right? That relationship ended. I needed to leave. And

that created an opportunity for me. I could go wherever I wanted to go. Looking at that as an opportunity and reframing how I perceived my job and how I perceived myself in that job was what got me where I needed to go. So I think that kind of calls back to acknowledging when opportunity is knocking, even when it doesn’t sound or feel like one. And for those of you who are lucky enough to acknowledge that you don’t like where you are and you’re not being forced into a timeline,

Jess Diamond (26:16.312)
Take advantage of that. Look at your timeline and say, I get to make my timeline. I get to choose when I leave this job. I am going to search for something that truly fulfills me. Or maybe it’s just you don’t like your boss. You can do the same thing you want to do at another company. Go and rub elbows with those people. Go find folks who have done what you’ve done making that change. Find people who have left your company for the company you want to be with and rub elbows with them. But ultimately, if you’re in control of your timeline, you actually have a leg up.

because you can do it at your own pace and not be sort of under the metaphorical gun of time. Yeah, I can agree. I mean, when I left my corporate job, I didn’t hate it there. I mean, it felt soul sucking because I had already found what I wanted to be doing. But I wasn’t crying every single day. I wasn’t angry every single day. Like, I had the energy to go build my business outside of work hours. So it was fine. Like, I created my timeline. My timeline happened to coincide with my lease.

And that’s what created my end date of like, okay, I’m going to leave in March of, what was it? 2022. Fast forward to right now. I mean, by the time this episode comes out, it’ll probably be a month past this whole fiasco of the one of the gyms I worked at. And I’ve mentioned on several episodes now because it’s just, and I will continue to, because it’s so relevant of being in a toxic work environment that I, yes, it was still my own timeline to decide when to leave.

But there does come a point where you have to acknowledge that you’ve been sitting comfortably in where you’re at. And it’s okay to acknowledge that. And it’s okay to acknowledge that it’s scary to step into the unknown by leaving something, but you have to put something behind. You have to close that door in order to open yourself up to a different opportunity. So if you’re not in the position where time is on your side, let’s say,

you are without a job and you’re like crap I have a thousand dollars left in my savings and I need something right now then it’s going on rover it’s babysitting it’s working at a coffee shop it’s doing something to help keep your head just a little bit above water so you don’t go into extreme debt but it’s also knowing that this rocky period in your life is leading you to something better as long as you don’t stay stuck with where you’re at as long as you don’t get comfortable

Jess Diamond (28:34.804)
in the in-between, knowing that you do have to keep pursuing, you have to keep rubbing elbows with people and keep networking, keep connecting so that you can get yourself to a better situation and know that the universe is on your side and that it wasn’t all for nothing and that it taught you some lessons and that it’s all going to be okay while also knowing that it probably damn well sucks right now.

I think you’re talking about something really important, which comes back for me in the choices that I’ve made with switching careers and left turns. And it’s that knowing yourself is important. Giving yourself the grace to change that is also important. And there’s a picture in your mind, three concentric circles. So a little circle, a bigger one than that, and then a third big circle. In the middle of that is your comfort zone.

That is things that you are educated on, that you have knowledge and experience on. You are in your home base. You’re good, right? That next circle is what I call the educational zone. That is where you learn a little bit more, right? Maybe you have a little bit of knowledge and now you’re looking to gain experience, or you have a little bit of experience and you’re looking to gain knowledge. Third circle is the danger zone, right? That is you have no knowledge. You have no experience. You are throwing caution to the wind with whatever choice you are making next.

I think as you grow those circles, mainly you’re growing your comfort zone as much as you can. But you want the biggest circle to always be your educational zone. Always having an opportunity to get into something new that you maybe know a little bit about, or hey, I know a guy that knows a guy about that. And that’s how I got into butchering, was I had never cut open an animal in my life, except maybe when we dissected frogs in high school.

or lamb’s brain or something. And my dad needed help. He said, hey, I am, my dad raises cattle as one of his many streams of income. And he said, hey, you know, I just don’t have any help. need you to come down and give me a hand. And I said, you know, dad, of course I’ll be there. He’s a couple hours away. And we butchered a cow together. Sorry listeners, for anybody who was unsuspecting. We butchered a cow together and I said, I could totally do this.

Jess Diamond (30:48.078)
And I looked at places that might be hiring. I checked out what they needed. Do I need licensure for this? Right. And so my educational, I was in the danger zone when my dad said, Hey, come down. We’re going to butcher a cow. I said, I have never done that. I don’t even know what the inside of a cow looks like. What are you talking about? What am I supposed to wear to that? Is my first question to everything. What am I supposed to wear to that? And I went down, dad brought me out of my danger zone into my educational zone, using a few experiences here and there to get

and knowledge, right? Googling. Googling has been my friend my whole life or most of my life. And getting to a point where more of my experiences are in my educational zone. And I’m able to expand on that to the point of monetizing it. And that is critical. If you’re looking at a way to expand what you want to do or change careers or stay in your career but go somewhere else, look at what’s in your educational zone.

acknowledge where your gaps actually are and be honest, right? Be honest with yourself and acknowledge what you can build up and then choose to build on those things however that looks, whether it’s in your free time or it’s at your job already and then it’ll make your comfort zone bigger, your educational zone bigger and you’ll be able to move into a different career or a different path more readily because you’ve had that experience and you’ve met the people that have done that experience with you.

or at the same time as you or before you. And that’s critical. Yeah. Well, I think even with these different zones, the, it’s easier said than done, but it’s easy to go from the danger zone into the experience and the knowledge zone. As long as you go in with that curious and open mind, which is something that you’ve exemplified with all your stories is like every opportunity you’re saying yes to is you’re going in with that openness of I’m ready to learn.

And as long as you’re going there, because the danger zone is really your brain’s way of protecting you of like, you have no idea what you’re doing, you’re going to die. That’s it. That’s all your brain is trying to tell you. Even if you’re not going to die. mean, butchering, that’s, that’s literally dangerous. Mamed or seriously injured, But it’s knowing it’s like, hey, brain, I’m not actually going to die by taking this new job that I have zero experience in, insert imposter syndrome. And

Jess Diamond (33:07.636)
go in instead of like just be ready to ask questions and take your pride, put it in that box that we talked about earlier, and know that yes, there’s probably going to be dumb questions. I know people say like no question is a dumb question. No, there’s, there are dumb questions, but if you don’t know the answer, like ask it anyways. You could even preface it with saying like, hey, this is probably a really dumb question. I have no idea how to tie my shoes. Yep. Can you help me? How do you tie your shoes? I can’t tie a bow that

isn’t lopsided. I’ve never in my life been able to tie a bow that isn’t lopsided. And I YouTube it. Yeah, Christmas bows and I learned how to do it on a shirt. Well, that’s just it is like, anything is searchable these days. Like, like, why are we pretending that you have no idea how to do something when you have a phone that can immediately bring you to Google and you get to search up a how to for it. This is a how to podcast, you can probably search up anything any episode I’ve done and get an answer about some aspect of your life. I’m sure I mean,

This is episode 99. There’s probably 98 other ones that are going to help you with something, at least I hope. But it is going, knowing that you can easily transition from danger zone into, I’m going to accrue as much knowledge as I can. My question for you, Summer, is when you’ve gone to make these different career changes and risks, have you gone in with that pre-existing knowledge of, want to learn how to do X? Or is it, I want something different and then you’ve

gained knowledge and experience along the way. It’s been either and then also just necessity for new like when I had to move out or when like I graduated college and you know you need to start something new. You’re supposed to find a job. You’re supposed to do these things. I did not go into helping my dad thinking, this will get me a job, right? No. I went in and thought, okay he needs me so I’m going and

getting there and learning all of that opened my eyes to a type of work that I had never considered. And in learning from him, I knew I wanted to learn from other people who maybe actually did it as a full-time job or had a different way of doing it. And acknowledging that there’s a different way to do all the things we’re already doing is a really, I don’t know, it’s like a good place to live if you have an open mind. It’s a good

Jess Diamond (35:30.914)
home base to say, that’s how my dad does it. Let me go see how a butcher in the neighboring town does it. And can I apply any of the things I learned from my dad to the new butcher? Can I then bring that information back to my dad to make my dad’s life easier? And I think optimism is kind of a secret sauce with this, right? Like where I’m staying positive, I’m staying happy about these things I’m learning and trying.

But at no point in helping my dad or going down to help my dad did I think, I could totally monetize this. It took me, you know, experiencing another butcher and coming across a business that a business owner was more than willing to sell to me if I put in the time, put in the effort and was willing to learn butchering from that person. So while I do not own that butcher business, there was enough to learn from him and enough time spent that

that connection landed me where I really needed to be and learning about all kinds of components of beef and what he does versus what my dad does, what’s legal in North Carolina, what’s allowed. And in other situations when I’ve changed careers, it’s been, I need a job and I need it right now. And in another situation when I picked up random work as the Harley Davidson photographer,

It was happenstance. I wanted to get better at photography. I needed to grow some type of client base. And I saw the opportunity while I was out on a Saturday afternoon talking to a marketing person in in Harley-Davidson. So conversations definitely get me where I need to go. But realizing that when someone asks you for a favor, it could also be an opportunity in disguise.

And sometimes that means that you’re connecting people that need to know each other and you never know when that’ll come back for you. And maybe it never does, but I think I like to think that it does in its own way. Yeah. I mean, I would like to say I got started in group fitness kind of in the universe works its way out type of way of I lost my job at the start of the pandemic. I’m sure you guys have heard my story, but I’m going to say it anyways. Lost my job.

Jess Diamond (37:52.878)
And after a month into being unemployed, I was like, you know what? I was not in the danger zone. I was in the, gain some knowledge. How do I work out better? I like to work out. I want to learn how to be better. So I started a personal training certification. What, and then as of course, cause Facebook listens to all of your conversations, I got an ad for a group fitness company, outdoor group fitness company, which is perfect for a pandemic when you’re living in Florida and they were looking for trainers. The fun,

part of that story is January of that year, I was feeling settled in my adulting and I was like, I’m gonna go do something new. And I saw a Facebook post or something or an ad somewhere that was like, hey, free group fitness class. And I was like, sure, I’ll go, it’s right by my apartment, I’ll go on my way home. And I go, and it was a group fitness company called Camp Gladiator and that was the ad that popped up.

right when I started my personal training certification. So I had already done a workout. I’d already met these people. The coach, the trainer of that fitness class actually lived in my building on my floor across from the courtyard from me. So it was me deciding to go broaden my experiences just to try to meet people. That’s why I did the group fitness class. I was like, yeah, sure. I’ll meet people that are also working out. That’s fun. And it led to me discovering

group fitness and falling in love with helping people, which then led to coaching and personal training one-on-one. it’s like that one decision to go try and meet people in a new city that I lived in to broaden my like friend group. Honestly, I just wanted to make friends led to this whole career path that I now have five years later. You and serendipity have a wonderful relationship. I think acknowledging for people where that comes from internally.

Does the universe have your back? Yes, the universe has your back. Serendipity is your friend. Coincidences for me, yeah, they happen, but a lot of my life is serendipity. And believing in that is big deal for me. It’s that openness. It’s that positive attitude. It’s that curiosity. It’s the willing to not know and want to learn more. Capitalizing on just that exact thought. When I became a bartender, I actually became a server.

Jess Diamond (40:15.864)
first and was hired on the spot because I said, hey, you know, I’ve never done this before. I’ve never had a service industry job. I’ve worked sales. I’m fine with people yelling at me. I just really want to path forward to be able to become a bartender because I know that that’s where I’ll flourish. And he said, shake on it. Absolutely. We shook on it. And two months later I had my bartending certs and everything was in the clear. Two months more later, they were doing line dancing lessons where I bartend as a country bar. And the

scheduled person didn’t show up and My boss came up to me and said you’re the most country looking person here with your boots and your jeans and your belt buckle Can you get up on stage and teach somebody something anything? There was maybe five people there So don’t worry while my social anxiety spiked through the roof. I said, of course, I’m your girl You know why because one I love to be a problem solver, but two it’s that same thing of I would want to do the job that

I would want for myself. So when I executed it, it was a blast, right? I learned something about myself. I learned something about being on stage in front of random people and dancing. And I said, you know, I only know a few dances that well. Is that okay? And he said, just do two. I’ll pay you for that. And if you want, you can learn some more and we’ll just have you as a backup. And I said, that’s fine. I don’t.

I don’t care. just want to make sure the night goes off without a hitch. I would teach the hoedown throwdown. You know what? Maybe you should come in and teach the hoedown throwdown. That’d be phenomenal. I think people need you. The people need you. No, I mean, it goes back to the risk isn’t as risky when you’re open to any outcome and going from there. It’s not saying like, hey, I’m going to make this decision and it has to turn out in this exact way.

It’s I’m making this decision because I want to leave the path I’m currently on for something new, whatever that something new is going to look like for me down the line and just be open to that. Again, knowing you can change your mind again and again and again. We’re in our 20s. We have a lot of life to keep changing our minds if that’s until you find something that sticks and that you enjoy and that you want to continue to pursue. And even then it could just be for a season and you can change your mind later on.

Jess Diamond (42:38.508)
I love that use the word seasoned. Like if you use a job as a season of your life instead of your career path for the rest of your life, sometimes it can be instead of, sometimes you can pick something up, love it so much and want to do it for the rest of your life. And maybe you change the context in which you do it. You love to write, but instead of being a journalist for the rest of your life, you start writing children’s books. There’s little shifts that you can make in your life that get you closer to where you want to be. And

that’s just as important as the left turns. So I don’t want anyone to hear this and think, well, I’m not going to quit my job tomorrow. Okay, you don’t have to, but you could also go to a new workout class. You could also go to a pottery class and try something new, whether it’s walking home a different way or getting coffee at a new restaurant. It can be any of those and many, many more things that open a door for you to the next thing that you can do in your life. Because for me, for example,

I, while bartending and serving, met somebody who got their paralegal license. And I heard all about her experience. We were paired together as bartenders. And I said, you you’re amazing for that. You are incredible, studying like this, working so hard. And she said, I just know it’s what I want to do. And sometimes you just know. And that’s great too.

I’m taking the opportunity to apply to law school as a result. She had such an impression on me that I thought, you know, this could really lead me somewhere. I’m going to take the risk and I’ll report back and let you know how that goes. Yeah, come back in a year. Yeah. But I think it goes back to what I was saying of you have the whole rest of your life ahead of you. It’s very hard to think in that way when you really haven’t lived that much of your life yet in the grand scheme of things. And

What I hear a lot is people are afraid to waste time in the wrong job. So yes, you’ll stay stuck at the job you’re currently at, but you’re afraid to waste time on that new endeavor, like with the thoughts of what if it goes nowhere? So what advice would you give to someone who feels like they’re going to waste time or they’re currently wasting time in the quote unquote wrong job? You are never wasting your time as long as you are learning something. I think

Jess Diamond (44:59.946)
There is always something to be learned, so you’re not wasting your time, as long as you’re actually approaching your job and your life that way. So the job might be the problem, yes, but your approach to your own job might also be making it harder on yourself because you’re not open to learning the things in that job. I’ve had bosses I didn’t like. I’ve had a lot of people I’ve disagreed with in professional and non-professional settings, but acknowledge when you do that, when you make the choice to say,

Well, I hate my job, my job’s the problem. Okay, are you learning anything at your job? And the answer should pretty much always be yes, because it might not be, well, I have this tangible skill I’ve learned. That’s all I know. Let’s take a… I have an example. I was gonna say welding. Okay. Right, so like you’re an expert welder, let’s say, and you’ve been welding for 15 years and you have pristine welds and everything you do, everyone says, I just hope that they do it because they do great welds.

You just don’t feel fulfilled because you’re not learning anything anymore But let’s say you have the opportunity to start your own firm. You can go be a welder solo or you can change The things that you weld on right it’s about looking at your job from other perspectives how people have accessed your job started your job Your role whatever it looks like to say, okay. I’m really good at this part of my job

there’s this other thing I don’t know how to do. I’m going to learn how to do that because it’s a lot closer to where I want to be. Now, I think we limit ourselves to and acknowledging like I, when I left corporate America, it was like, hi, I’m leaving corporate America, right? Same. Yeah. and it’s like, it’s like, I’ve, I’m going to go fight the good fight. And, what folks really shortchange themselves in is you can fight the good fight and stay in corporate America.

That’s okay. If there’s something within it that you’re helping yourself learn, I’m not saying you have to hit your job to leave, but a lot of the times people do. So ultimately, if you are learning something, you are not wasting your time. If you are learning something outside of your job and your job is helping you do that, that’s still not wasting your time.

Jess Diamond (47:23.534)
And that’s a reframing of your brain, right? Like you kind of have to change your perspective on that. If it still feels like you can’t be your whole self because of the job that you have, I would cite what I said before. Get to know yourself, get to know what you like at your job and what you don’t, get to know what you like in your life and start to make a plan to pivot. Whether it’s by two degrees or 180, the plan to pivot is being open to those opportunities and being aware that

you’re not wasting your time if you are looking for opportunities and still learning. Well, I think when it comes to taking a risk in your career overall, any decision you make, any move that you want to make from where you’re at right now to just anywhere else in down the line is all reframe. It’s all the way that you think about it. It’s going to be scary regardless, but it’s been done before. It’s not going to kill you. You’re not going to end up homeless. I hope not.

please don’t quit your job tomorrow without a plan lined up. I’ve said this many times. It’s like, strategize. That strategy begins with how you’re looking at your life and who you want to be interacting with on a regular basis. I think the other kind of quote from my life or things that I’ve heard in my life for a long, time, probably about 20 years now, is they can’t eat you.

Right? It’s like very dark and scary. But the idea that the people that you’re upsetting, they’re not going to eat you. The job that you’re leading. cannibalism. Yeah. Let’s talk cannibalism. Maybe there’s a valid career there. I don’t know. Maybe you’re into that sort of thing. We talked about butcher. Yes. But the people that are upset with you, they’re not going to eat you. Right? Nobody’s going to force you to make a change that you can’t at least get ahead of in some way. Now, is it going to look conventional? Maybe not.

Is it going to be your dream job right off the bat? Probably not. making those small changes gets you to where you want to go, even if they seem non-traditional or risky. It’s more about bolstering your confidence and acknowledging that when you go to make that shift, you’re going to have to face some changes, whether it’s budget changes or timing changes, scheduling changes that allow you to get a little bit closer.

Jess Diamond (49:41.752)
to the life that you’re looking to lead. Yeah, knowing that sometimes getting a little closer doesn’t necessarily mean that as in you’re getting closer and you can see yourself getting closer, but it’s getting away from what was holding you back. Absolutely. And you don’t know where those opportunities are going to come from. Just like your friend that did the camp, right? Camp counseling. we talk about that off air. Yeah. I’m so sorry. This is off air. It was off air. But I really appreciated that. I think a lot of the things I’ve done have been almost happenstance.

as someone who’s been a camp counselor and gotten like a second job from that, there’s a way to do that. Yeah. For the audience. The story is I had a friend in college who went to try to apply for an internship going into his junior year and he didn’t get it. So what he did instead was he became a camp counselor at some random camp in California. And then the next year he applied for a different internship and he ended up getting that job because the guy interviewing him had some kind of connection to that camp or

They connected on some kind of life lesson that was developed from that camp or like from being a camp counselor. There was, there was a connection that happened from a very random job opportunity that my friend decided to take instead of trying to find a different internship in the business field. But I have one last question for you, Summer. And that is what do you think is one small risk someone can take today to get closer to a career that they love?

Do it scared is my number one, right? That’s really popular on socials right now. I think there are, it’s gonna depend on what they wanna do, right? Like if you’re making a full left turn or not, if you are able to quit your job or not. But go talk to a stranger in a chatty setting. Join a run club, talk to somebody new. Go to a coffee shop, talk to somebody new.

and really push yourself to keep that conversation going and see not just what they do, but what have they done to get to where they are. I strongly recommend talking to somebody who is noticeably older than you. My best conversations have been throughout my 20s with people in their 40s and 50s. And they’re usually a little more chatty. They’re willing to talk because they remember being 25 and confused and not ready for whatever came next.

Jess Diamond (52:04.524)
That is my number one advice is expand your network socially by talking to new people over the littlest things you may have in common and preferably with someone older than you. Yeah. The risk is changing it up. Get used to the change and try something different. Change your schedule a little bit next week. Talk to someone new at a coffee shop. Like do something different that without that expectation of this is going to lead me somewhere.

in the direction I want to go. Just go in it with, I’m going to do something different this week and name what that is and go and do it. Yeah. The follow through is epic. The not conditional behavior is essential. I’m only going to do this if it gets me a new job. Well, then you’re probably not going to end up with a new job. You’re going to just end up with a really like tunnel vision, blinders on focus. And while that does serve people in like longevity of a job.

It does not necessarily create new opportunities and keep you open to newness. So take the blinders off, talk about whatever’s relevant, get in deep conversation with someone, keep light conversation with someone, find out just what they do. But many, many times you’ll find if you bring your whole self to that conversation and really stay present, you’re going to learn something really cool. Yeah. Go in it with the, can I help you? And not the what’s in it for me mentality, but amazing.

Thank you so much, for being a guest on How to 20-something. Where can people find you if they want to follow your journey and all the changes that are about to happen or connect with you? If anybody wants to connect with me, you can definitely look to me up on LinkedIn at Summer Dice, S-O-M-E-R-D-I-C-E. And I am also on Instagram under the same app. All right, yeah. And her information will be linked in the show notes per usual. Otherwise, this does conclude another episode of How to 20-something.

If you liked what you heard, if you learned something new or know someone who needs to take some risks in their career, then please share this episode, post on social media, send it to a friend, give me a five star rating. Just help me help as many 20 somethings as I can because we all know we all need a little help navigating the most confusing decade of our lives. And as always, I can’t wait to be in your headphones again next week with another brand new episode. Episode 100.

Jess Diamond (54:23.63)
Okay, signing off now. You’re so cool! my god, that’s awesome!