Dear EverMore

what career advice would you give your younger self? (career diaries with strangers at SXSW 2026)

Season 1 Episode 13

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0:00 | 27:34

Welcome back to Dear EverMore

A few weeks ago, we did something very special — Kelsey, Courtney, and Courtney's 10-year-old daughter (Henley) hit the streets of SXSW 2026 to interview people about their career. We heard how they got into their current job, the bobs and weaves they took to get there, advice they would give their younger self, and the movie (or genre) that would best describe their career story.

Here's what we took away from the conversations:

  • Be kind to yourself — some talked about how they put a lot of pressure on themselves when younger to be perfect and do it right the first time. They mentioned how this wasn’t realistic and didn’t make anything better.
  • Sometimes things don't work out the way you want it to — but ultimately, it always works out for the best in the long run.
  • Prioritize working for a company where you don't feel like a little fish in a big pond — one individual talked about being a new grad getting into the workforce and how important it was for them to work in an environment where she got coaching and was treated equally to everyone, no matter the role or level.
  • Figure out what you're good at and enjoy — how important it is to not listen to whatever everyone else tells you but listen to yourself first. Take the time and space to figure out who you are on your own without anyone else telling you what to do.
  • Life is supposed to be fun and we should play more — we couldn’t agree more! It’s important to see life (including work) as a way to build a craft, grow, and reflect on what gets our best energy.
  • You are never doing too much — being the most passionate person in the room is one of the most valuable skills you can have and it can inspire others to show up as their fullest self, too.

A huge THANK YOU to Henley for bringing her personality, talent, and curiosity to the Dear EverMore podcast. She did an incredible job, and we hope there will be more opportunities to highlight her perspective from the next generation. We hope this gave you all the chuckles and smiles it gave us, too! 💜

More things for you:

  • Feeling stuck or unsure about where to go next in your career? We’ve got you! We built EverMore so you can take ownership of your career story, track your impact and growth over time, and (coming soon) automatically update your resume + portfolio based on your reflections. Join the beta to try it out!
  • If you love a good career story, we have career diaries featured on our blog. If you want yours featured, reach out to us so we can get you scheduled on our blog + podcast.

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Have a burning question you'd like answered on the pod? We'd love to give you advice! Submit your anonymous question

SPEAKER_09

Welcome back to Dear Evermore. Today's episode is Us on the Street. We decided to use South Bayon Austin as a time to go out and chat with people. And to help us do it, we brought along my daughter Henley, who's 10 years old and was home on spring break to interview folks about their careers and what advice they have for their younger self. So we wanted to ask Henley about her overall experience. What did you think about meeting people on the street at South by?

SPEAKER_14

Well, it was really fun. Got to talk to a big variety of different people. They had a bunch of different jobs. They were from all over the world. And it was just like really fun to get to know a bunch of strangers.

SPEAKER_09

What was the coolest job you heard all afternoon?

SPEAKER_14

Okay, so there was like a South by Southwest like volunteer coordinator, and she said she worked a bunch of different music festivals, and I thought that was really cool. And there was also a data scientist and a journalist. And all those jobs I thought were really cool, and they're all very different.

SPEAKER_09

So yeah, we were just talking at home the other day about what was the point of math and how would you ever use it in real life? And the data scientist really helped us answer that question because she fell in love with math and didn't know how to use it in the real world until she found data science. What was the best advice you heard?

SPEAKER_14

So I learned that you can never do too much and you can never be too compassionate. And then some other things that I heard was that you don't have to listen to what other people say about you. Because I mean their opinions don't really matter. It's just how you view yourself. And um also I heard to never lose your inner child. And I just really liked that because you always have to have that like inner play and inner just like chill. Because when you're a child, you don't have as much you don't have adult responsibilities, so you can you can just have more time to chill and relax and play, and that lets you love yourself more.

SPEAKER_09

I love that. I think we heard a lot of people talking about kind of the stories that they inherited in childhood that they kind of told themselves about being too much or too different or too passionate or too dramatic, and how as an adult that they've learned that those things were written for them and weren't really a representation of them. And I love how so many people's advice to their younger self was to not listen to the stories and opinions other people have of you and like really get to know yourself and get to know what you love, get to know what you enjoy, and kind of follow that. Um okay, and one of the questions that we asked people is what movie their career was like. So, what movie do you want your career to be like?

SPEAKER_14

So this is really hard. I do not know. I want to be an actress. I can't really name that many movies about actresses. Um but the first thing that popped into mind was like legally blonde. I don't want to be a lawyer. I just like how she tried and she tried and she eventually did it just by working really hard. And I don't know, it's just very inspirational in girl power. And um yeah, but it doesn't necessarily resonate with my dream career. But um I guess the only one I can really think of.

SPEAKER_09

I mean, I think you hit on like the spirit of it of someone like having a goal and then trying really hard because I think sometimes from afar it can look like people's careers are an overnight success or they weren't hard, but they always are hard, and I think a lot goes into achieving your goals and your dreams. And I think legally bond was a good example of someone who was working really hard and putting things aside that they might have otherwise wanted to do to pursue their dreams. So I think that makes a lot of sense. You're very dogged about becoming an actress, so I think it fits perfect.

SPEAKER_14

Yeah, I mean she wanted to be a fashion designer or like something like that. I mean, we could hear her. She got like a major in like polka dots or something like that.

SPEAKER_09

But um I think she did take like a history of polka dots class. That sounds that sounds right. You can always change, I guess that's the thing. You can always change your mind about the path that you're on. Any final thoughts? Thank you for having me on Dear Evermore.

SPEAKER_14

I loved being your host and taking over. Without further ado, I hope you enjoy my interviews. What's some career advice you would give to a younger version of yourself?

SPEAKER_08

Follow your dream, I think. Uh, and uh don't um be nice to people, uh be nice to uh everyone who you meet on the way up because who knows you might need them uh in a couple of years.

SPEAKER_14

Everyone deserves respect and everyone deserves a chance.

SPEAKER_08

Yeah, definitely. Definitely.

SPEAKER_14

What type of job are you in right now?

SPEAKER_08

I'm a journalist, uh a news editor, so I work with uh local media in Sweden.

SPEAKER_14

I've been interested in journalism. Oh really?

SPEAKER_08

Yeah. What makes you interested in it?

SPEAKER_14

I don't know, I just like it.

SPEAKER_08

I think it's a very important uh job, and if you're into it you should check it out. Basically, I was uh reading a lot of uh Tintin and I wanted to see uh the world uh and I thought uh what better way? But I was also interested in uh becoming a teacher, uh but then I thought that journalism is basically teaching but at a larger level. So uh I pivoted. Uh I was going to go into finances, but I uh so I studied finance, but I thought that was really boring and it didn't speak to my heart, so I changed career paths.

SPEAKER_14

It's good to know what you like and don't like.

SPEAKER_08

Yeah, it is. You should definitely try to figure that out. And I mean, uh your life is very long, so it's um uh there's always time to uh change your mind about what you want to do.

SPEAKER_14

Well, thanks for talking to us today. I hope you have a good rest of your day.

SPEAKER_08

Yeah, you too. Thank you.

SPEAKER_14

So, what are you working in right now? What's your job?

SPEAKER_07

In uh university.

SPEAKER_14

How'd you get into that?

SPEAKER_07

I was uh working in a consultancy firm back in Brazil and uh I was wondering how to help people to change, uh to find out how they they learn about what they really want want to do, what they really like, what they really love. And then uh I saw that uh consultancy was about education, and then I changed my career to education path.

SPEAKER_14

What's some career advice you have for your younger self?

SPEAKER_07

Never let your brain take over uh absolutely. Uh listen to the the small signs, listen to your consciousness, uh don't forget what you love, don't forget what you you really care. Uh because we always try to rationalize all, uh but we need to feel more and uh follow what you feel is best than what your brain tells you.

SPEAKER_14

So, what's your job?

SPEAKER_00

So I do all the national media and performance advertising at Carnival Cruise Line.

SPEAKER_14

Um, how did you like get into that?

SPEAKER_00

So uh I started off in an ad agency in Fort Lauderdale, um, and I was doing TV, radio, and print for a Chevy account, and I really didn't know what I was getting myself into and worked long hours and paid a lot of attention to detail. That brought me to a digital ad agency because I realized like I grew up with a computer already that had Froger and color, and I was growing up as AOL was created, so I moved to a digital ad agency where I got like my foundation there. Um, and from there I got recruited to a um professional soccer team in uh startup in Miami, and I played soccer my whole life, so I thought I was like set and done, and I found my happy place. I think it was a good lesson that like some things don't work out, and it didn't end up being the best thing for me. So I left to Carnival, and that was actually the best thing that I've done in my career, and I've been there for nine years now, and uh the things I wish I knew, um the things I know now I wish I knew when I was in that startup, and um I guess my what I came to say was like sometimes things don't work out, but they work out for the best in the long run.

SPEAKER_14

That makes a lot of sense. What career advice do you have for your younger self?

SPEAKER_00

Give really g giving back to the community and and to other people around you will help make you grow stronger than you ever realized.

SPEAKER_14

Uh what job do you have? Like what j what's my job?

SPEAKER_04

Yeah. Like my job title?

SPEAKER_14

Yeah. Okay. Like what is yeah.

SPEAKER_04

I design customer service.

SPEAKER_14

That's cool.

SPEAKER_04

For Chase Bank.

SPEAKER_14

How'd you get into that?

SPEAKER_04

Drawing.

SPEAKER_14

I like drawing.

SPEAKER_04

Yeah, you do? What do you draw?

SPEAKER_14

Uh I don't know. I draw people, I draw houses, I draw clothes because I want to be a fashion designer. So maybe. Um, and then I draw, uh what are some other oh I draw dogs. Oh, very cool.

SPEAKER_04

Very cool. Yeah, I started drawing. How old are you?

SPEAKER_14

Ten. Ten? I'm 43. I'm Cecilia. Nice to meet you. Nice to meet you.

SPEAKER_04

What's your name? Henley. Henley. Okay, cool.

SPEAKER_14

So what some career advice you would give to a young to your younger self?

SPEAKER_04

To how old younger self? Like it my 10-year-old self? Or like my 26-year-old self?

SPEAKER_14

Like a like a young adult orchid, anyway.

SPEAKER_04

Okay. I would tell her that life is supposed to be fun and we should play more. And draw a lot. Keep drawing. That's what I would say.

SPEAKER_14

I like that. If your career was a movie, what movie would it be?

SPEAKER_04

Oh, that's such a great question. So definitely Julia Roberts is gonna be in it, um, as me. Maybe her character name is Vivian. The movie Erin Brockovich. That's the movie. I would love to do something of that impact. I've never seen that, but Okay, maybe your mom could show it to you at some point. It's a good movie. Okay, the other one would be Encanto. Have you seen that? Yeah, I have. Okay. So that she like saves the world and gets everybody to like um feel more and remember and be more alive and be c more connected with people in all like people that have passed and people that are still here. That would be another film.

SPEAKER_14

I like Encanto. Yeah. Was great talking about.

SPEAKER_04

What do you want to be when you grow up?

SPEAKER_14

Um, I want to be like either a fashion designer, I want to be an actress, definitely. Um I want to be an author.

SPEAKER_04

I'll kind of be like a gosh, you're gonna have a bright career. Yeah. Do all of those things.

SPEAKER_14

I'll be a different version of a triple threat. What's your job?

SPEAKER_06

Uh I'm event staffing assistant for South by Southwest.

SPEAKER_14

That's that's very that's very cool.

SPEAKER_06

I've always I've South by Southwest sounds fun. It's it's an adventure for sure. It's my first South by ever, so I'm getting to learn everything about what South By is about.

SPEAKER_14

Sounds kinda chaotic though.

SPEAKER_06

Absolutely. I've been running straight for what is this, day 13? No breaks. Just making sure everybody has what they need, making sure our volunteers feel safe, seen, and heard. It's a lot of work.

SPEAKER_14

It sounds very hard, but you're probably good at it. Oh stop, thank you. Okay, how'd you like get into doing that?

SPEAKER_06

Um I started working music festivals about six months ago. Um I went to school for audio engineering and music industry, but I couldn't really find a good spot for me and recorded music. So I realized that live events had a lot of girls working in music and I liked that a lot. So I was like, how do I get in with the girls? And um so through working festivals, girls help girls out, and they're like, Do you want to work this event? Do you want to work that event? And I kind of just got to use all of my skills in every aspect, like from school and from making friends in a festival context.

SPEAKER_14

I love music festivals. I'm a big music girly.

SPEAKER_06

Who's your favorite artist?

SPEAKER_14

Um, right now I really I'm really into Olivia Rodrigo and I also like TLC.

SPEAKER_06

No way. You have taste, yes.

SPEAKER_14

Um, if you uh what career advice do you have for your younger self?

SPEAKER_06

You are never doing too much. Being the most passionate person in a room is like the most valuable skill you can have. So don't let anybody tell you you're too much, and when you feel like you're doing a lot, know that that's your superpower.

SPEAKER_14

I really like that. Um, if your career was a movie, what a movie would it be?

SPEAKER_06

Oh my goodness. 13 going on 30. Yeah.

SPEAKER_14

Oh, I've seen that. It's good. I like it.

SPEAKER_06

Yeah, definitely feel like a kid thrown into the midst of adulthood, and I'm just figuring it out with each moment.

SPEAKER_14

Yeah.

SPEAKER_13

What's your job? I'm a data scientist.

SPEAKER_14

I really like science.

SPEAKER_13

Me too. It's currently my dream job.

SPEAKER_14

Um, so you kind of already answered this before, but what made you get into being a data scientist?

SPEAKER_13

Yeah, when I was younger, I always enjoyed science and math. I've always enjoyed solving problems. I've always been really good at math. I just didn't understand how I could actually apply it to a career until I got to college. I tried to go into these things called hackathons and it opened my world of knowing what's actually out there and what's possible.

SPEAKER_14

That's really cool. Um, what career advice do you have for your younger self?

SPEAKER_13

Prioritize working for a company where you don't feel like a little fish in the big pond. I think as a new grad, it's very easy to be in a space where you're kind of lost, confused on what's going on, you're not really involved in the day-to-day of the company. But I'm really lucky to work for a company called Mindstream where I get to work with everybody and collaborate and be trained by everyone, so it's really amazing.

SPEAKER_14

That's really cool. It's not, it's not very fun feeling like there's bigger fish than you. Exactly.

SPEAKER_13

Like everyone's equal. Exactly, and no one ever makes me feel small in the company. I am the youngest, but everyone's always willing to coach me, walk me through anything, and they're genuinely investing in me, and that feels great at this point in my career.

SPEAKER_14

That sounds great. Of course. Um, if your career was a movie, what movie do you think it would be?

SPEAKER_13

Okay, that's a good question. I need to think about this. Hmm. Have you seen the movie Soul on Pixar?

SPEAKER_14

Yes, not in a while, but I have seen it before.

SPEAKER_13

Okay, uh that's actually one of my favorite movies, and I say that because I feel like I kind of got in my career on accident. I was actually able to combine two of my passions unknowingly. I kind of got there without even knowing it. So I think Seoul is definitely a good representation of where I am today.

SPEAKER_14

And I'd love to know more about your career.

SPEAKER_12

Yeah, I just graduated from college early in December, and right now I'm doing some research at Harvard Law School through their Nuremberg Trials project, and I'm hoping to apply to law school um next cycles.

SPEAKER_14

I know like you're not very far along in your career, but if you had to describe your career as a movie, what movie would it be?

SPEAKER_12

Ooh, that's a good question. Um this is probably a very basic answer, but definitely somewhere towards like a legally blonde, I guess, because I will be going into law in the future.

SPEAKER_14

I love legally blonde. My middle name is Reese after Reese Witherspoon. Oh, that's so cute. So what's your job right now?

SPEAKER_05

Uh my job right now is I'm a creative strategist. So what I do is I have a lot of conversations with people and I help them um understand what they need to do in their business to grow. So I work with a lot of startups that are pre-revenue that are that kind of need a hand in figuring out what they need to do next. And so I come in with all my smarts and I tell them when they're very on track with their purpose, I let them know what all the surrounding things they need to do to get up to speed, get where they want to go.

SPEAKER_14

That's really cool. Um, why did you pick this or how did you get there?

SPEAKER_05

Well, when I grew up, um, neither of my parents went to college, they were all in trades. Um, and all I knew is I wanted to be important and I wanted to work in a really tall building. And the first 10 years of my career, I did that. I worked at PayPal and Expedia Group. Um, I had a lot of fun, but then I decided to become a mother. I realized I couldn't give away eight or nine hours of my day, that my time became invaluable to a company. So I left and I spent a couple of years hanging out with my kid and figuring out what I was good at outside of just clocking in and out. Um I met up with a lot of my friends that I had met through business and they were all going in their own direction too, and AI kicked off, and I kind of just decided to figure out what my strengths were and to kind of just go from there.

SPEAKER_14

I love that. I love that you decided to prioritize your kid rather than what you were doing before that.

SPEAKER_05

Yeah, motherhood is the most important job in the world. It we're raising the next generation.

SPEAKER_14

What career advice do you have for your younger self?

SPEAKER_05

Figure out what it is that you're good at, but you enjoy. Not something, don't listen to what everybody else tells you you are. Like growing up, my parents told me I was dramatic, I was too much, I was this, I was that, and those were the badges that I wore growing up, and it wasn't until I became a mother that I started to wonder if I was that person or if that person was implanted on me. And so I took some time and space, did a ton of journaling, um, listened to a lot of podcasts, a lot of older, smarter women than I am, um, and kind of just yeah, took the time and effort to just figure out who I am on my own without anybody else telling me what to do for a while.

SPEAKER_14

I like how you said you should find something that you're good at but you also enjoy. Because there's I know that there's a lot of things that I'm very like good at, but I don't and I don't want to spend my time doing I don't want to dedicate my life to those. Exactly. Um, if your career was a movie, what movie do you think it would be?

SPEAKER_05

Um I don't know. Devil Wars Prada pops in my mind, but I think that was just because I I wasn't necessarily the Andy Saxon where I was kind of getting dumped on by my bosses. So I'm not quite sure because I've been lucky enough to have a lot of leaders, male and female, who have seen that something special spark in me and who have basically told me just follow your curiosity and let me know where it leads you. And they've I've I've just been really lucky in that way that a lot of people have trusted my judgment, and um my career has been built on a lot of intuition following. So I'm not I'm not quite sure there's been a movie yet. Maybe there has been, but I just haven't seen it.

SPEAKER_14

Maybe one will be made.

SPEAKER_05

Oh, I definitely plan on writing a book.

SPEAKER_14

So what's your job?

SPEAKER_11

Um, I work in public relations.

SPEAKER_14

That's cool. Uh, how'd you get into that?

SPEAKER_11

Um, kind of on accident. It was just the first job I got out of college, but um I liked communication just because I like to talk to people, so I like talking to people too.

SPEAKER_14

What's some ad career advice you would give to a younger version of yourself? Oh your younger self?

SPEAKER_11

That's a really good question. Um I think I would just say to stay true to who I am as a person and really hone in on my passions and not be afraid to um put myself out there even if I don't think uh I have the skill set to do something. I totally get that.

SPEAKER_14

I hate when people try to like shape you into a person. We get we should be able to shape ourselves. Yes, exactly. Um if your career was a movie, what movie do you think it would be?

SPEAKER_11

Oh, wow. I feel like there's not a lot of public relations movies. Um yeah, I I'm like a really big horror movie fan, but I feel like that's not the vibe for what I would for what it would be.

SPEAKER_02

What's your job? I am a chief of staff, so that means that I do a lot of different things across the company. And we work in the accounting and consulting space, helping farmers. That's cool. How'd you get into that? I fell into it by doing lots of other things during my career. So starting off doing anything from sales to doing operations to doing customer service, doing strategy, innovation, and that's why a chief of staff role does a lot of different things. And that's why my background is perfect for what I do today.

SPEAKER_14

It seems perfect.

SPEAKER_02

Thank you.

SPEAKER_14

Um, what career advice would you give to your younger self?

SPEAKER_02

I would say if you want to become a DJ, go be a DJ. Is that what you wanted to be when you were younger? I think when you're younger, there are lots of things that you want to be and you have an opportunity to be. And if you think outside of the school system, like you're doing today, that you can realize any of those different paths that are non traditional and you can make something out of it. Which is different than when your mom and I grew up. So you have an opportunity to take something that you're passionate about, go after it, and then find the next thing you're passionate about, and then go after it.

SPEAKER_14

If your career was a movie, what movie do you think it would be?

SPEAKER_02

It would be a futuristic movie. Dystopia.

SPEAKER_14

I I don't think I've ever seen that one.

SPEAKER_02

Because it hasn't been made yet.

SPEAKER_14

Nice to meet you. I'm ten years old and I would like to get to know a little bit more about your career.

SPEAKER_10

So I'm uh I'm a founder of Institute for Tomorrow. That's cool. I map out trends and insights to help people do cool stuff.

SPEAKER_14

That's very cool. How'd you how'd you like get into that?

SPEAKER_10

I started um to get into creative work, working on ad agencies, and then um I got out of communication, doing ads, and uh went to do cool stuff. So creativity is the thing.

SPEAKER_14

What advice, what career advice do you have for your younger self?

SPEAKER_10

Don't grow up. It's the best advice.

SPEAKER_14

I like being a kid.

SPEAKER_10

Yeah, yeah, me too, me too. I'm uh trying to write a book. It's called Growing Down. It's exactly the opposite because everybody told you you must behave, you must do this, you must do that, and it's the opposite. We need to be creative so can so we can help AI to do cool stuff.

SPEAKER_14

Yeah.

SPEAKER_10

So just like that.

SPEAKER_14

I love that. I'm a writer. I've yeah, you're working on a ton of different books.

SPEAKER_10

Uh that's really cool.

SPEAKER_14

Yeah.

SPEAKER_10

Do you wanna name one, please?

SPEAKER_14

Uh I don't really have titles.

SPEAKER_10

You have time, you have time, don't worry.

SPEAKER_14

But if your career was like a movie, what movie do you think it would be?

SPEAKER_10

Ah, that's that's a hard one. I don't know. Probably Toy Story. The first one? It's one of my favorites.

SPEAKER_14

I like Toy Story too.

SPEAKER_10

Yeah. Besides MD in the end gets sad, but yeah.

SPEAKER_14

So what's your job?

SPEAKER_03

My job is I work in social media and digital strategy and podcasting.

SPEAKER_14

That's very cool. Thank you. We're on a podcast right now.

SPEAKER_03

Wow.

SPEAKER_14

It's taking over our body.

SPEAKER_03

Everything comes full circle, doesn't it?

SPEAKER_14

Um how'd you get into all that?

SPEAKER_03

Well, it all started with technical and vocational education, which I'm very passionate about. I got my first job job because I had technical skills that I learned in high school, and nothing that I learned in college really um impacted that, but my technical skills from high school got me the job.

SPEAKER_14

I really like when people have jobs that it's not just something that they're good at, but it's something that they enjoy doing and they're passionate about.

SPEAKER_03

Absolutely, absolutely agree.

SPEAKER_14

Um, what's some career advice you would give to your younger self?

SPEAKER_03

I would say be kind to yourself. Uh, I think I put a lot of pressure on myself when I was younger to be perfect and do everything the right way the first time, and that's just not realistic, and it it only harmed myself. It it didn't make anything better. So I would say be kinder to yourself and take breaks and realize that what you're doing, unless you're a brain surgeon or a rocket science scientist, is you know, you're gonna be okay. It's not that serious, and um don't be hero, you know.

SPEAKER_14

Yeah. Um, I'm very much of a perfectionist, and it's not always the best because it's hard to stop that, but you just gotta kind of learn to um move past it.

SPEAKER_03

Yes, yes.

SPEAKER_14

Um, if your career was a movie, what movie would it be?

SPEAKER_03

Far scump. Absolutely. I like that. Because I've fallen into so many things by accident that turned out to be really good. And I think that's the way to be. I like that. And just generally a great movie to learn from.

unknown

Yeah.

SPEAKER_01

What a fun episode. Am I right? It was such a blast hanging out downtown during South By with Henley, and I'm so glad that she was game and eager to take over the Dear Evermore podcast. It was also really great seeing how many people, A, wanted to talk to a 10-year-old about their career, but B, how many also kind of enjoyed speaking about the lessons they've learned in their career and the things that they can tangibly take out of their story. And that's what makes owning and narrating and uh understanding your career story so impactful because then you can deliver those insights to other people who are earlier in their career or also want some advice. So to close us up for today, you can of course in the show notes find all the links to um join Evermore or request an invite to the beta. We have some exciting new features coming out in the coming weeks, including a mobile app to make it even easier to chat with your coach when you need it, as well as ways to tangibly tell your story through our portfolio. If you're looking for a way to do that and kind of keep all of your career info, attraction, accomplishments, feedback, story in one place, we'd love to have you in Evermore and get your feedback on what we're building.