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The Anti-Career Path to Solopreneur Success: Finding Your Rhythm and Defining Success with Cara Laban
9 Plays2 days ago
NY Times featured Cara Laban sits down with us to share what it really looks like to build something from nothing and to do it on your own terms.
In this episode, we talk to Cara, a solopreneur and the founder of Travelreddi.com, a platform designed to take the stress out of international travel by curating personalized prep tasks and actions for travelers. But this isn’t just a founder story, it’s a story of evolution.
From aspiring actress to waitress, entertainer and now early-stage tech founder and author, Cara’s path is anything but linear. That’s exactly what makes it compelling. We love her and we know you will too.
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Transcript
Introduction and Podcast Purpose
00:00:10
Speaker
Welcome to Fractional Frequency, our take on talent, people trends, and the reality of building up businesses in an economy that keeps rewriting the rules. I'm Amy Crook, founder of Strativus.
00:00:21
Speaker
And I'm Erin Todis, Managing Director of Talent Delivery, which basically means I live in the universe of finding the right people to make an impact for our clients fast. Around here, talk about the real side of and talent, what works, what absolutely doesn't, and how to build teams that can carry a business, not drag it down.
00:00:40
Speaker
We'll break down trends, share the behind the scenes of scaling a consultancy from zero, and probably overshare a little because that's where the good lessons live. So whether you're building, hiring, leading, just trying to keep your company profitable, you're in the right place.
00:00:55
Speaker
This is Fractional Frequency. Let's get to it.
Introducing Kara Laban
00:01:00
Speaker
Hi Erin! Hi Amy, how are you? I'm good, how you doing today? I am great and even better, am so excited to welcome Laban, solopreneur who has recently launched TravelReady.com, a platform that curates customized travel prep actions and tasks for international travelers. And today we will dive into her path from an aspiring actress, waitress, entertainer, and even a simulated patient to now an early stage tech founder and author.
Kara's Journey from Actress to Tech Founder
00:01:33
Speaker
When we met Kara, we found ourselves just pulled into her story, laughing along the way, and most importantly, struck by her wisdom on topics like finding your passion, being true to yourself, and defining success at different phases of your journey. So I cannot wait to hear more. Welcome, Kara. Welcome.
00:01:53
Speaker
Thank you so much for having me. What an intro. can't let me try Your background is so impressive and i cannot wait for our listeners to hear more from you. So let's just get right into it. um I remember learning when we spoke last time, you initially chased a dream that led you to waitressing in New York City and then Australia Can you talk about those early professional experiences and how they shaped your understanding of work
00:02:25
Speaker
Yeah, for sure. I went to school. So I got um my degree, my bachelor's in applied psychology. And if you know anything about getting a bachelor's in psychology or is called a BS in psychology, it is exactly that because it does not qualify you to do anything in the real world without a master's except HR. So I got an internship so i got an internship my last year of college at doing HR and engineering firm. And within two months of being there, they offered me a job, but I was like over my dead body while I work in an environment like this. The fluorescent lights, like not being able to control the temperature, having no windows in in the office that we were in, like only being ah able to go outside for five minutes during my lunch break. i was like, this is not the life for me at all. I had dreams of becoming ah an actress, which is why I majored in psychology in the first place. But I was like, you know what I'm going to pursue it. So I moved into the city from Long Island, where I'm from.
00:03:34
Speaker
And as all actresses do, as you know, I became a waitress. And i was a damn good waitress. i was really, really good. My sales were always super high. And I was so good that they had me coming in all the time. i was one of the only people they trusted to close.
Travel Adventures and Diverse Experiences
00:03:51
Speaker
So on one of my days off I had a whole day planned. It was going to be lovely. I was going to walk across the Brooklyn Bridge. I had my sketch writing class and i was so looking forward to just being outside. And then I got a text from my boss while I was already out saying, can you come and close? So-and-so's dad had a heart attack and she can't close now. And I like, no.
00:04:16
Speaker
I'm such a people pleaser. So I can't say no, i can't say no Not when there's a heart attack in the equation. no not when there's heart attack. I was like, but there's really no one else. You asked everyone. please And she was like, yeah, so-and-so is out of town and you're the only other person I trust to close. And I was like, okay.
00:04:36
Speaker
Oh, she trusts me. They trust me. yeah So I went home cause I had to get my uniform, which was in the, the laundry because I hadn't had time to even do my laundry at that day. And it was like pit stained. It was a little white no little white shirts that go under a dirndl because I worked at a German beer house. yeah So it's a little white shirt. My dirndl stayed at work, but my the little white shirt that went underneath it, I had to take it out of laundry. It was like so gross. And I was like waiting for the subway to come. And I just remember standing there thinking like, I'm so miserable. I'm not following my dreams. I'm not, I'm barely going on auditions because I'm working so much. And I was like, maybe I don't go into work.
00:05:17
Speaker
Maybe I jump. Maybe I just jump instead. and then I was like, yeah. yes
00:05:27
Speaker
She's so honest. And then, you know, I'm too much of a people pleaser. I'm going to ruin people's days. What if they can't get their beer? Because of me.
00:05:37
Speaker
um The beer, the people on the train, all of them ruined. If I i don't. so ah I got on the train and I literally Googled how to move to the other side of the world. Yeah.
00:05:49
Speaker
And ah that's how I learned about the Australian working holiday visa. And six months later, I moved to Australia. And guess where I worked? A German beer hall in Melbourne. that but
00:06:05
Speaker
So that like that started me on my travel journey. And after I left Australia, like because the visa was for two years, then I continued to travel. And that's that's what led me to where I am now.
00:06:17
Speaker
And you worked a variety of different roles along the way. I mean, no variety in the beginning, right? One beer house, next beer house. But then there were some other things. and Tell us a little bit about that sort of phase of odd jobs, if you will. And and what did that, what did you learn from that in in that what you wanted or maybe what you didn't want?
00:06:39
Speaker
Yeah, so I went to the same restaurant essentially in Australia, which was so crazy. I really don't want to do that, but I was struggling to find a job. And then at that job, Australia, the pay system works quite differently than it does here.
00:06:55
Speaker
ah There's no tipping at restaurants. So your salary is much higher, which also means you get way less hours unless you're full-time. I did not want to be full-time because when you're full-time, they work you a lot.
00:07:07
Speaker
Yeah. so I thought, okay, I'm going to keep whatever hours I have at the restaurant, but I need other jobs. So I joined all of these like gigging platforms. There was side kicker. I was on the acting website there. I was also acting and,
00:07:24
Speaker
I started picking up these random side gigs all around. So it started mostly with like brand ambassador work and promo modeling, which are essentially the same thing. So, you know, a brand will have an activation at a mall or, you know, whatever store. So I just go, I wear the company shirt and I pass out flyers or I engage with people, whatever it is.
00:07:49
Speaker
And then through the acting site I was on, i got... a like children's entertainer gig. So I was an elf at Bunnings, which is like Home Depot over there.
00:08:00
Speaker
No. was an elf, had to run around and I was hiding from the kids and handing them cane. I did like some other Christmas stuff.
00:08:11
Speaker
I worked with like an Easter bunny. My favorite was Halloween. i wore this like mask thing that sat over my shoulder. So I was like probably six, seven wearing this. so Oh my goodness. Like a mask costume almost.
00:08:25
Speaker
Like a what costume? like a mascot kind of yeah and I was just scaring kids like there's like trick-or-treating area and I was just scaring these kids why am I breaking up or do you guys no you're good you're good okay um somebody paid you to just go around and scare children in a big mask like yeah going on in Australia and I was paid like 50 hour to do that
00:08:53
Speaker
um face Wow. Yeah. That was my favorite. The kids and the kids kept being like, us but I would scare them every time. Anyway. i would just not want ah I like delivered cheese in a truck for $40 an hour.
00:09:11
Speaker
that the jobs were crazy. And then i became a simulated patient. That one, I also got through the acting website, actually. um And I'd never heard of this before, but basically you go to the med schools,
00:09:25
Speaker
And you pretend to be a patient. So they give you a scenario before you get there that you have to memorize. So I had one where like I was suffering these migraines and I had to cry over and over again for each patient be like, I'm just so stressed and I can't sleep or whatever, whatever. And you're helping them learn bedside manner.
00:09:41
Speaker
And you're also... helping them with their exams. So I had one where I had to go and they gave it to me last minute. And they're like, you fell out a window at a party. You have a cut on your arm or your hand or something. We're going to wrap it up and you've lost nerve damage. So when they touch here, you can feel it. But when they touch here, you can't feel it. And that's really important because that's how they're going to like, and I was like, Oh my God, how that's so much pressure. Yeah. Sam. Um,
00:10:09
Speaker
that was That was a fun job And that also paid like $55 an hour or something. And this was 10 years ago almost. So and it pays more now. Wow. So those jobs were super fun. But what I realized in doing that is i love having a million things to do. And I hate sticking to one thing. And I hate having like a boss, like one single boss. Mm-hmm.
00:10:31
Speaker
And so all worth it to come to those conclusions. I think there are so many people who never allow themselves to realize or or maybe articulate those things, even just to themselves. and And then they just continue on whatever hamster wheel they happened on to um after their studies or or whatever.
00:10:50
Speaker
And so you are currently writing a memoir and it's called How to Do Anything Even if You're Lazy. What does that title mean? Tell us a little bit more about that. and And how does that mindset define your approach to entrepreneurship?
Productivity and Redefining Success
00:11:08
Speaker
So i i define myself as lazy. Other people probably wouldn't, right? Because they're like, you're you're traveling the world, you're a freelancer, you're doing this, you're doing that. But I've always done everything from my bed.
00:11:21
Speaker
So even my first year of university, I went away to school and I like never left my bed. i was studying in my bed. I was doing everything in my bed. My roommates would be like, Carrie, you've got to go eat dinner. Like you've got, please come. It's Halloween. Please come out with us. I'm like, I just love bed so much. and that's kind of always out been i don't work out.
00:11:40
Speaker
I like, I just love being comfy, cozy. I do as many things horizontally as I possibly can. Yeah. um And yet I've traveled the world. I started businesses. I've been freelancing and hustling and all ah all of that. So the book is really about how to not will yourself, but trick yourself, how to find systems that work with you and your brain.
00:12:10
Speaker
hmm. because our brains all work so differently. And we're, we think we're supposed to fit into this structure or the system of the world as it's been designed. And a lot of us don't fit into that, whether it's ADHD, whether it's depression or anxiety, because I i do struggle with depression, and anxiety, a bit of OCD type tendencies.
00:12:32
Speaker
So the book is like a combination of a memoir of all of these stories and how I figured out how to make life work, how to make it fun. how to, you know, not only wake up and get out of bed, but brush my teeth more regularly, vacuum or more regularly, to start a business. Like, you know, it's just, yeah it could apply to any of these, any of the small or big things, just figuring out how to identify the systems that will work for you.
00:13:05
Speaker
i think that's so powerful because it's it's kind of a false assumption that everyone's just got it figured out um and everybody's dealing with the same challenges, be it, you know, a laundry list of mental health concerns or just, you know, just don't know like where to start, you know, that they, so I think that's, it's a such a great concept. i I'm super excited to read it.
00:13:33
Speaker
um I'm curious, Cara, you're in the early stages of being a solo entrepreneur, how has your definition of success changed like over time?
00:13:47
Speaker
So interesting you ask because I just got off of therapy and I was saying, you know, sometimes I really struggle with Looking at myself and being like, I'm not as successful as other people in my life who make a lot more money than I do.
00:14:01
Speaker
my therapist was like, I would say you're very successful. You do so much that other people wish they did. Mm-hmm. Like you have a savings account, even if it's not a huge amount, you're not a debt.
00:14:15
Speaker
And all while doing that, you've been traveling the world. you can You've been doing whatever you want. I actually, this is very funny. Last week I was at like this schmoozy opening night party for a Broadway show. They had a party afterwards and I was with a friend of mine who's in the industry. Mm-hmm.
00:14:34
Speaker
And he introduced me to someone who's a producer and they were talking, talking, talking. and he looked at me and he was like, are you in the industry? And i was like, no. And he said, oh what industry are you in? What do you do? And I said, whatever I want. yeah He was like, that's the best answer I've ever gotten to that question.
00:14:55
Speaker
And i'm really, really trying to make that my definition of success is that I truly do whatever I want. And i know a lot of people are jealous of that. And while I'm not monetarily super successful at this point, I hope to be, i plan to be but I've really done so much of what a lot of people only dream of doing. yeah People say to me all the time, I want to be you when I grow up.
00:15:20
Speaker
My mom has said that to me. I mean, adventure is what it's all about. i think, you know, ah it's it's a brief moment in time that we get to experience life. And I just think you have to make the most of it. And if your definition of success is so entangled into things that are so subjective, and it's really difficult to like have a steady foundation. um So I completely relate to what you're saying and that, yeah, if you define success by giant bank accounts or fancy job titles, then no, I'm not going to meet your definition of success at this precise moment in time.
00:16:03
Speaker
But I'm so happy and I'm having so much fun. that I don't even care what you think. yeah it's And I think that's really powerful. So it's great to hear you say that. um You were accepted to the Web Summit Alpha program and you were recently featured in the New York Times. at Which of these milestones feels like um more powerful for you, more more critical for you?
00:16:33
Speaker
Oh, that's a good question. So they happened a few months apart from each other. They felt similar at the time of them happening because Web Summit happened first.
00:16:44
Speaker
And that was like the first thing, big thing that I had done with Travel Ready. i was like, I'm going to present this to somebody who's not a family member or friend. And getting accepted felt really validating.
00:16:56
Speaker
But getting featured in the New York Times was, that's like, Like, that's just a dream come true that like people are like, how'd you get in the New York Times? That's insane. So I think that they were both, they felt similar at the moment, but looking back on them now, the new York Times, just like, I don't know if I'll ever have success like that again. well I mean, you're starting big. So that the only way is up.
00:17:21
Speaker
yeah Hopefully. So when you look back on all of this journey, and honestly, i love your story. Not only are you like hilarious, but you're somebody who has never been afraid to try something different or just make a big move.
00:17:40
Speaker
What's the greatest lesson that you've learned about being true to yourself throughout all of those iterations of life?
Changing Paths and Entrepreneurial Mindset
00:17:50
Speaker
Something I have to remind myself and other people of a lot, it's okay to change your mind.
00:17:56
Speaker
and Okay to announce to the world that you're doing this and then doing something else. And I think a lot of people struggle with that. yeah um I still struggle with it. I judge myself often. I've had so many ideas, but that's kind of what an entrepreneur brain does. i have an idea. i announce it to the world. i do some market research and I'm like, maybe not the best idea. and then I have to pivot.
00:18:17
Speaker
Mm-hmm. And it could be embarrassing to be like that. But I think I'm judging myself more than others are judging me on that. I think other people are like, I wish I had ideas. Why do you have so many ideas? from So i I really think it's okay for at any stage in life. Like I went to school initially to do biomedical engineering and then I changed my mind.
00:18:39
Speaker
And then i ended up doing psychology, changed my mind. I didn't really want to do that. And then like, I just kind of keep changing my mind. I'm trying now to stick to some things, but I wouldn't have gotten here if I didn't allow myself to change my mind.
00:18:57
Speaker
that Always allowed to change your mind. i think that's, I think that not enough people believe that in so many contexts and it's empowering to hear you say that it's, it's not the end of the world. If you announce something even to a lot of people and then change your mind and do something different. And so I've got another question, Kara, that that's a little bit of a dovetail to this. Are there any myths about finding your passion or or finding your next passion, maybe, that um you would say you had to unlearn on your path to where you are today?
00:19:33
Speaker
think passion is such an interesting take where people say, like, follow your passion or, like work with your passion you'll never work a day in your life or something that's the saying or something like that all right yeah do what you love and you'll never work a day in your life yeah something like that right but I don't love working there's just no part of it that's ever gonna love working so if I did what I love it would be napping just money in napping there's not enough money it's enough um
00:20:09
Speaker
um Yeah. So, I mean, I'm passionate about a lot of things and I'm not trying to monetize any of them. Cause sometimes I do think trying to monetize your passions could damp, like tamper them, dampen, dampen.
00:20:26
Speaker
yeah Like there, now there's so much pressure on yourself to do the thing that you love and to make money from it. Whereas for me, like travel ready for the longest time, people are like, you should start a travel blog. You should do with this with travel. You should do with that with travel. And I didn't want to do it because it was going to ruin travel for me. I was like, I don't want to have to remember to take pictures, to write this down, to do this, to do that.
00:20:52
Speaker
But now I kind of just naturally let my talents lead me to travel ready because that's taking my systems brain, which is what I've been freelancing in is helping small businesses and people with their business and life systems.
00:21:08
Speaker
And travel ready kind of marries systems with travel because it is like onboarding almost. It's like client onboarding for international travel.
00:21:19
Speaker
So you know everything before you go. Whereas like I don't have to ruin my trip by writing down all of the restaurants I liked and all of the whatever. I mean, some people love doing that, but for me that that wasn't what I loved.
00:21:31
Speaker
So now it's just more the things that I'm naturally talented at, not so much a passion. so I think leave your passions, your passions, if you want to monetize it and it's not going to ruin it for you, do it.
00:21:47
Speaker
But don't feel pressure when people are like, you're so good at knitting, you should sell that. Don't feel pressure to do that because it might ruin knitting you. Yeah. Or and whatever it is. Yeah. Did that answer your question?
00:22:01
Speaker
It did. and um i I think that I've got a lot of curiosity about your next chapter because, you know maybe maybe it changes, right? I'm sure you've got visions and ideas about what comes next, but you'll pressure test and you'll tweak along the way. So maybe, you know, aside from kind of what the roadmap might look like today or tomorrow, would you share a little bit about your hopes for Travel Ready?
TravelReady's Vision and Kara's Unique Productivity
00:22:26
Speaker
And, um you know, what are you sort of excited about in this upcoming chapter?
00:22:31
Speaker
Yeah. My hopes and dreams, I'm dreaming dreaming big here, right? That it becomes a household name for travel, kind of like Expedia already is or Trivago, or I don't even know, maybe people don't even know these names of things in the travel space. They surely Yeah. think people in the who travel a lot. So it's like...
00:22:54
Speaker
anybody's like, oh, you got your trip booked. Did you do your travel ready? Like, did you get travel ready? but Did you do that? And everybody, it's just kind of the next step after you book your flight, you get travel ready. And that's my dream for it. And then the other side of it is also that it's integrated with existing businesses for like travel agents, for example, or certain airlines have this perk where they're like, we they have like their branded version of Travel Ready. So if you book a flight with them, you don't have to do anything. You're already getting nudges from the airline to remind you to do all of these things that Travel Ready reminds you. Like some airlines already will be like, you need to get your ETA, your ESTA, your visa, whatever. a lot of them don't.
00:23:37
Speaker
And I've had friends who've not been able to board their flights because- Yeah. They didn't know they needed an ESTA to come here because you don't need a visa, but you need something else. h Yeah. That's a bummer.
00:23:49
Speaker
Yeah. It's a huge bummer. And she was like, why didn't the airline tell me? I'm like, I don't know, but I'm going to tell you. Yeah. They bury it deep in there. Yeah. like Or it's like an ambiguous question of like, have you checked to see if you need anything? And you're like,
00:24:07
Speaker
Do I need something? Can't you just tell me? Yeah. I mean, there's a huge liability there because it changes so much. It's different from passport to passport. So that is going to be one of my biggest challenges with travel ready.
00:24:21
Speaker
um But there's some wording in there to be like, you probably need a visa. You probably don't need a visa, but you probably need this thing. Just so it's like, I'm not saying you definitely need it or not.
00:24:36
Speaker
Yeah, and but you do need to check. Yeah. But like we checked for you and this is information we found. Here's the official source. Yeah, that's way better. Here's the link to go do that now.
00:24:48
Speaker
So yeah, my my dreams are big for Travel Ready. It's like much bigger than a travel blog. And I think I can get there.
00:24:59
Speaker
I do too. I do too. um I'm just going to wrap this up with one final question here. So just taking us back to the, to the laziness ah comment, what is one belief that you hold about your ah laziness that actually became a powerful force in business growth?
00:25:23
Speaker
That is a really good question. Laziness to me kind of falls hand in hand with doing whatever I want. And I really have to listen to my own body at times of like, if I'm too tired to do something, if I'm too uninterested in doing something, picking what I'm most interested in right now and working on that actually gives me so much energy.
00:25:52
Speaker
hmm. So when I think I'm super tired, i think I'm feeling super lazy and don't want to do anything. It's a lot of times the one thing that I think I need to do right now that's making me feel that way. But I'm like, let me look at my to-do list.
00:26:05
Speaker
I'm like, actually, this one is giving me energy right now. who So let me work on that. And then... Three hours later, I'm like, I've i've been in it. I've been doing all the stuff and I i don't feel tired now. I feel energized.
00:26:20
Speaker
So it's like really just listening to my body and my brain. And also i schedule naps into my day. mom So if I need it, sometimes I don't need them, but if I need it, I have it scheduled into my day. So I could even just lay and like close my eyes for a little bit.
00:26:38
Speaker
And that's also part of listening to your body and giving yourself some rest time because rest is productive. That's always what I say too. And you're saying I'm not being productive enough.
00:26:48
Speaker
Rest is productive because you're going burn out otherwise. Yeah. Yeah. It's a marathon, not a sprint. Yeah. And you never know, it for me, you know, sometimes like the really tough problems sort of percolate in the back of your mind, maybe it's in your subconscious or, or somewhere in between conscious and subconscious that I find in listening to my own body and taking a step away. Sometimes that's when you come back and you have the idea you've been searching for. Does that happen to you?
00:27:17
Speaker
I literally dreamt about Travel Ready. That is how the idea came to me. And it's like my, it's somewhere between sleeping and being awake. There's like that little space that you have where you're like not fully awake yet.
00:27:31
Speaker
And I literally was laying there in my mind you're using an app that had all of the local apps for a place I was going. and And I woke up and I was like, did that really happen? Was that something I used?
00:27:45
Speaker
And then I looked into it. I was like, wait, that doesn't exist. I'm going to make it. awesome I love it. and so but yeah That happens from, from the funniest places, but yeah.
00:27:58
Speaker
Incredible. Thank you so much, Kara, for sharing your story with us. I know we're excited to follow the continued success of travel ready and just of you as a founder and solopreneur. I have ah a feeling that travel ready will be successful and also there will be more to come. beyond that platform in your career and in your life. And so we're just happy we've made the connection with you and look forward to following.
Inviting Engagement and Sharing Resources
00:28:23
Speaker
um Last sort of, I know Amy promised that was last question, but I'll tag a little bit If listeners are interested in learning more about you or just reading further about Travel Ready, where can they find information about that?
00:28:38
Speaker
Yeah. So if you want to check out Travel Ready, it's totally free to use. You just go and put your destination and then your passport country, not like details or anything like that. And that is TravelReady.com. And it's spelled R-E-D-D-I is ready.
00:28:54
Speaker
So go ahead and check it out. I would love if you did. If you would like to check out my book, the first chapter and introduction are available for free as well.
00:29:05
Speaker
ah You could go caralaben.com book and you'll be able to download that for free. And feel free to connect with me on LinkedIn and follow my journey. I would love if you did.
00:29:18
Speaker
Thank you so much, Cara. Thanks, Cara.