Sydney – TikTok Travel and Tech Sales

Sydney – TikTok Travel and Tech Sales

 #59 – Many people know Sydney as the ‘TikTok travel sales girl’ where she’s gained a significant following (160k+) by telling stories about the crazy phone calls she received while helping people book their dream vacations. Does Sydney’s TikTok fame figure into the future of her career? No, Sydney is a realist and sees social media for what it is: a way for people to share funny stories, trends, and ultimately take a break from the pressures of their lives. 

Given that, what does Sydney want to do with her life, and what has been the path that’s led her to where she is today? Listen to her interview to hear how softball, travel sales, and a job that just wasn’t the right fit have all played a part in getting Sydney into a career she loves. Along the way, we hear how intentional planning and research can both help you find the perfect fit, but still, sometimes lead you into a job where there isn’t a cultural fit. 

Follow Sydney on TikTok @poorandhungry or on Instagram @poorandhungry_

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The below transcript is A.I generated with light editing and may not be 100% accurate.

Transcript
Jonathan Collaton:

Good morning, good afternoon or good evening, you're listening to career crossroads. And if you're new here, welcome. And if you're not new welcome back. I'm Jonathan Collaton. And this is the podcast where I talk to people about all the pivots, changes and life events that led them to their current career path. This week, I'm talking to Sydney about her path to working in sales, and all the different jobs she's had along the way. We're also going to talk about Sydney's TikTok account, because she is not an unknown commodity on the app with over 160,000 followers as of November 2021. We'll get into why people follow her pretty quickly. So let's get right to that conversation. And then afterwards, we'll talk about the lessons we can learn from Sydney's career path. Sydney, thank you for joining me today on the podcast.

Sydney:

I'm excited to be here.

Jonathan Collaton:

I'm really excited that you accepted this invitation. And I think that there are probably people listening to this, who, maybe not yet but eventually they'll start to recognize your voice. But they won't be able to put it to a name because most people who might know you and know your voice know you as poor and hungry or as I called you for the longest time to my wife, the travel sales girl from TikTok.

Sydney:

Yes, it's weird to hear that said out loud, that's for sure.

Jonathan Collaton:

Yeah, you have these like alternate names that people that don't know you are calling you in their homes. That's got to be odd.

Sydney:

Yeah, one of my favorites was I shared something on my personal social media from my TikTok. And I got an influx of messages saying, Oh, I know that girl I went to I went to college with that girl. And I was like, yeah, that that's me like that is that's how you know her because that is that is me. But yeah, it's definitely it's something I keep very separate, like the social media component and my like, actual professional, social life. But it's still funny to see that for some people. I see folks will say things like, Oh, I saw the travel sales girl post about this. So then I went and did it. And I'll come up on my page. And it's weird to see that I'm referred to period, let alone like, by people out it's, it's, it's funky. That's for sure.

Jonathan Collaton:

Yeah, well, now I I know your name. So I can refer to you by your name now. Alright, so today, we're going to talk about your career. That is what we do. In this podcast, we talk about all the changes that happened over time that were expected and unexpected, and sort of how you dealt with them and how they impacted you. And to start, I want to go back and tell me a little about your upbringing, and kind of at the point where you were a teenager, what were you like, what was influencing you? Generally? Where were you located in the world? Who were you at, say 16 years old?

Sydney:

Yeah, I grew up in the north shore of Massachusetts. So for anyone not from Massachusetts, that is basically anything 15 minutes or more north of Boston up to the Maine or New Hampshire border. So very urban area, city I grew up in and like High School Sydney was involved in every possible club, Class President, marching band, every sports team, like any picture, I'm the one like holding the sign for the clubs. And it was, I had a very I have like a shark tank approach to High School of everything I did was to build the resume for college, which I know is not necessarily you know, the normal approach. My mom likes to always describe it if I had this confidence, where I was frequently mistaken by substitute teachers as a teacher rather than a student, because I was just so squared away, you know, going about my high school self but part of that was I was just so desperate to go to high school I wanted I wanted to be in like in the world since I was probably eight years old. So high school me was you know, very impatient, always looking for the next thing. In terms of what that looked like. Specifically, I had no idea. But it wasn't until I went to join yet another club called DECA. I'm pretty sure it's a North American club. They might have chapter chapters of it in, in Canada, but I thought it was some type of like journalism club and then after I joined, I realized it was a a scholastic competition of business initiatives type model. So basically, what that is, is I was an individual competitor, in mock interviews and exams, all around the theme of marketing. And I had we didn't have that at my high school. We didn't have marketing as a course. So that was really my introduction to anything that was not you know, English, math, social studies, science, and I loved it. I absolutely loved it. I loved how competitive it was, I loved that I got a taste of the real world in it. And that was one I knew I what I wanted to do in college was how can I do you know, more of this? How can this be my major, and the fact that people actually do this for a living was was the coolest to me. So that's kind of my journey from how do I pack in as much as I can into a resume at the age of you know, 16 to, okay, like, here's what this could actually look like, as a life.

Jonathan Collaton:

So one it's kind of funny when two TikTok people meet, and we don't really know each other. You don't know this. But up until six months ago, I was the club coordinator at a university. And so I worked with DECA all the time

Sydney:

I saw the head nod. Now, I was like, I've never heard anyone know what DECA was before.

Jonathan Collaton:

Yeah, yeah, that was me. I was the guy that clubs came to for help with pretty much anything they were doing. So I am familiar with deca, we haven't in high schools here to actually. So yeah, you as a teenager, you were very much a go getter for a while without really knowing where you were going. It was just sort of get out of the thing that you're in until you find this one particular interest, deca, and that gives you some direction, obviously. So the practical next step was something like higher education always in the picture, or was it when you found deca, where you thought, like, Okay, I need to go and get a degree to do something like this?

Sydney:

Yeah, Higher Ed was always in the picture. Both of my parents were in the military, that was how they got their higher education. So for them, it was very important that I had something established beneath me that I could, you know, on merit get into college. So that was something that was instilled from a very young age. So I never saw it as not an option. So I knew I was going to go to college. Did I know I was going to go to grad school I went to I also have my MBA did I know that was part of the picture over achiever me probably did, but I it wasn't part of my plan, necessarily. So I sports was a huge part of my life. I'm a bit of a side note. So I was on top of being very involved. I also was very gifted athletically. And I was on track, I was getting tons of looks from what's called D one schools. So the big schools that you see on ESPN, those types of schools, were very interested in me because I could make it on merit. And I also had the talent to get there. My senior year, I got very, very sick. So health is super important in D one athletics so with my lack of being healthy, that kind of took that option off the table. So then it became more of okay, what can I actually do now that I'm not in athletics now that I actually have to re evaluate what's going to be my life for the next four years if sports might not be part of that equation. I was very lucky. And I found a school that did take me it was an amazing athletic and academic experience. But during that time, I wasn't able to play softball, which was, oh my gosh, how to how to stop the world from spinning is take the tip of the glove off my hand. And during that time, one of my first real commitments, was professional softball coaching. So I was the assistant to former D one baseball player, and we took a team that there they were in shambles. Their coach had recently been fired, it wasn't going well they hadn't won a game yet. We took over I then poured all of the things I couldn't be doing physically into helping young athletes it was a junior Olympic team. So if I can't be the one physically out there doing it, how can I help you as much as you can and it was incredible. They ended up qualifying for the World Series and it was such a such a special season. And I did that for several more years into college. It wasn't something that I knew I wanted to do as a full time job but as a as a college kind of gig. It was absolutely incredible. And honestly, most of the the big nuggets that I've taken personally and professionally came out of those four years of coaching because the highs are so much higher when you get to help others be part of it. But the lows are so much lower as a coach than as a player because it's ultimately it feels like it's your fault like this didn't go well because I didn't I should have done more so that these girls were more prepared. But that's that's really what my first introduction into any type of like Job style commitment was through coaching. And it was marrying athletics was something that challenged me so much. Was was an amazing place. To be as I started, you know, my 20s and looked forward to, you know, actually a professional career.

Jonathan Collaton:

Yeah, so timeline wise, was that something you started right around the time you started university?

Sydney:

Yeah, it was the summer. Gosh, I think yeah, the summer right before so right between end of high school into university. That's when my commitment started. And then I I coached for four years, I was an assistant for two and a head coach for two.

Jonathan Collaton:

Gotcha. The D one school then when you're getting recruited for something like athletics, I would say that it's more likely for a lot of people then that you'll be moving away from home because those schools are where they are. It's not like you can go to the school nearest you and they just happen to be a D one school, or is that what happened for you? Were you going to school close to home for either way.

Sydney:

It was a it was a bit of a mix, I would say the furthest that I was seriously considering I think was either Penn, which is the University of Pennsylvania, or brown is also in Rhode Island. So only like an hour and a half from where I was from. I toured, I got seen by like schools down south schools in Florida, things like that. I went and I visited and I was just, it didn't feel like a place that I would thrive in. And one of the things being from Massachusetts is we're so spoiled. We have a million universities all, you know, on the same land as one another. So in terms of just sheer volume, there were so many things that happened to be closer to home, that that were great opportunities. So I ended up within school, like less than 45 minutes away from where I grew up.

Jonathan Collaton:

Oh, that's pretty good. Yeah. All right. So what was the major? What was the name of the degree that you were going there for

Sydney:

a marketing marketing degree, there were a couple of schools that I looked at that had something similar, but the one that ended up fitting was I call it my Goldilocks school, if it wasn't too big, wasn't too small, wasn't too elitely competitive, but also wasn't too, like, this isn't going to be too hard athletically. So it had the Goldilocks of kind of all of those things being right in the middle. And it was a marketing degree was what I pursued and what I got

Jonathan Collaton:

perfect. So that time in DECA made you think that that was gonna be the degree that would get you a job you wanted, even if you didn't have a very specific one in mind, it sounds like it was just you want to do what these people do. So as you advance through university, you're coaching on the side, to the academics feel like, Yeah, this is the right decision, I'm going to just power through this, get my degree, and then move on and get a job in this field. And life is great.

Sydney:

I mean, I, we all like to think that that's the way that it goes, mine ended up being this is, gosh, this is gonna sound so ugly out loud. But I wasn't necessarily challenged academically at my at my university. So I ended up graduating an entire year early. But for sports, you have four years of eligibility, so there was no way I was going to let my final season go by. So that's when I enrolled in an MBA program, which is, you know, Masters of Business Administration Program at my university. Luckily, the, you know, the master's program was, is considered an elite program. So it's still respectable, but I was able to earn another degree, get my master's, and also finish out my athletic eligibility as well.

Jonathan Collaton:

Okay, great. So one of the things I've been curious about the timeline of when some of these jobs popped up, because you know, we were talking about your Tiktok. And one of your your recent series of stories is all of these food service stories, the ridiculous encounters you've had with people in sounds like a lot of different restaurants, with these jobs that you had while you were in school, or did you take some time after university and working at restaurants or like, when did that all happen for you?

Sydney:

yeah, people tend to behave they're worst the second you put a menu in their hand. I've worked in anything food service from this started my my very first year of university, all the way up through the pandemic. So anything from like New England Patriots football games, to concerts to like rolling burritos to catering and a white glove Tea Party to working at a pizza place any like anything that involves food or beverage I've done other than like, I think food truck is the only thing I can't say that I've done. But that was always a part of my life. I love I still do. I love food service. I think everyone should have to do it for at least three months. You see you meet some of the most fantastic people. You see some bizarre things that no one will ever believe that you saw happen to you It's excellent in in having a big piece of humble pie of being spoken to in certain ways. But ultimately, I think food service is a fantastic experience. So I've seen a lot I've done a lot in terms of that. And that was something that I was I'll always hold on to my to my restaurant shift. Even after I got my degree and I had a full time job I still begged my restaurant to let me work one shift a week because I was like, I can't quit this is it so it's just something that I always just loved.

Jonathan Collaton:

It's crazy to hear the type of stuff that like some people are just so into, right? It's not like you were just doing it for the money. I'm sure working all through university was important or was beneficial to you financially, but then the fact that you keep doing it afterwards when you've already got a full time job you just like the job.

Sydney:

Yeah. Oh, there's the "eh" the Canadian eh, yeah, I just I loved it. I mean, I I got a really fantastic gig at a place that I was genuine friends and I still am I don't I don't work there anymore. A lot of us don't work there anymore. And we're still incredibly close. So I made some of my lifelong best friends working in restaurants. And it's just it's such a unique environment. The the money is is hit or miss there's days where you know, you'll have one table they won't have a good experience to walk out with $3 in your pocket. There's other days you know, you work New Year's Eve, have a 16 hour shift but feel good going home that night. So it's the money is so hit or miss but the the people and the experiences and it's just yeah, I was just great. I love I love it's so weird to love a job, especially one that's like, not glamorous or not fun of, you know, oh, yeah, cleaning, you know, the crud off of the back of the things in an Irish Pub doesn't sound fun. But it was, yeah, things you remember, it's, I don't have a better way to describe it than that.

Jonathan Collaton:

I get it, I had a job for five summers all through university. That was in many ways, it also taught me to work really hard so that I didn't have to do it forever. But I have stayed there for five years because I did enjoy the people I worked with. And if I was going to be working anyway, I might as well stay with these guys and move stuff into trucks and make deliveries all day. I got to work. Why not this this was it was fun. I get it. I understand that totally. So obviously, restaurants then are just a job a way to make money. There was never any thought of building a career in that field with your degree in marketing and an MBA, some people might want to go on and get into the branch of a restaurant like a big chain, and then work their way up. And that was never in your never in your I don't know what word I'm trying to say. But you were never thinking of that.

Sydney:

Yeah, it was never my roadmap. It was never something I wanted to do. Other than like working the floor, was the like the place that I would rather be true like full disclosure. Like when you're the the the ladder, right of working in a restaurant is maybe you're on the floor, maybe you move up to management, maybe inventory, maybe general management. And then unless you're looking to invest or open your own restaurant, that's pretty much it. And I've worked a lot of places and restaurants are scary. They're not a reliable business to start. So to, for me to spend. I mean, frankly, in the US, it's it's expensive to go to school to spend all that money to do something that I could easily do without any type of degree didn't seem like the right the right fit for me. It wasn't what I wanted. Yeah. And I mean, I know, times where I was working full time at a restaurant, I knew I was making more than the manager. So that's also like, why why would I Why would I make any changes to that?

Jonathan Collaton:

Yeah, that makes sense. You have a good rationale for why that that's what I always want to find out. I want to find out what's the rationale for one thing over something else. So that makes a lot of sense. I'm curious about the MBA then. And looking at the fact that you went back to school you mentioned because of your eligibility, you wanted to go back because you wanted to play again. And I work at a university and we're probably not too different in age you and I and I see people that will out of undergrad just go into grad programs because they don't know what else to do. And they view that as just sort of not quite a delay tactic. But it's it's got two purposes. It gives you more time but it also gets you more educated and more qualified and many, many jobs these days are saying like masters minimum, so I'm not trying to discount the value of it. But was the primary reason you did it was to get your eligibility or to to use your eligibility and play for one more year. Or was it also something that you you were beginning to get more of a clearer picture of what you might want to do when you graduated? And that was something that was necessary for what you wanted to do?

Sydney:

Yeah, that's a good question. It was definitely a combination of a few things. Number one being eligibility. I did not know, starting off school that I would finish it so quickly. So eligibility and being able to finish out softball was a nearly non negotiable of, okay, how, like, how can I say stay here for another year. So that was the first component. The second component was the job market at the time wasn't great. And this isn't necessarily tied to a recession or the pandemic or anything like that. So of course, you can compare it then to now and say, I was better than it was, you know, the last 18 months. But it wasn't great for what I wanted to do. And because I just knew I was going to go to grad school, I had the luxury of narrowing down particular industries, in particular roles that I would want with an organization's. And I just wasn't finding that. And when I was interviewing, I was interviewing with companies that just weren't the right fit. And I was looking at, I was truthfully, I was looking at microbreweries, that was where I was like, this is where I'm going to thrive. I have incredible beer knowledge, I love again, I love food and beverage, like how can I find a corporate spin to stay in this world? And what I was finding was that what I wanted to do was probably at least like eight to 10 years out of what I would need to do to get there. And that was not attractive to me. There. It's an industry where you have to what was the expression stand your teeth, grit your teeth?

Jonathan Collaton:

Bear down

Sydney:

Yeah, you have to earn your stripes in a way that I was like to get my degree and then go do this, again, is not a good use of this investment. So there was that that was a particular industry, there wasn't a good fit for what I was looking for with the experience that I had. And then looking at what marketing roles looked like in Boston, I went on many interviews prior to committing to grad school, where I was in one I made a video about it, where the it was a lot of social media, a lot of how can we use millennials to help us understand Millennials for a lot of what the marketing roles were at the time. And entering an organization that's very transparent about not knowing what they're doing also wasn't super attractive in that sense. So finally, the third component was just like timing, finances, things like that. So all of it made sense to kind of stay in school for for an extra year for those kinds of things. And then once I was finishing up my program, again, I still stayed with that same level of pickiness. But I, I instead of going with such a literal, vertical or horizontal route, I looked at what are some of the best places to work, because if I'm in a place that I enjoy, I enjoy what I'm doing, I enjoy the people, I support the mission. That's something I can be happy with. And what that is isn't necessarily very important to me. But I can, I can enjoy where I am. Let me start there. So I started with all of the, you know, best place to work 2017. That's what I started, I started working back from there. Of Where are people Best Place to Work for millennials Best Place to Work For women, I started with those. And I narrowed down okay, let me only hyper apply to these type of companies, which are getting the most traffic. And ultimately, that's where I landed my first job was it from pulling one of those lists and narrowing it down. Like, here's all the reasons why this would be a good place to work. What I'm actually doing is not as relevant. And that that was a that was the birth of travel sales.

Jonathan Collaton:

Wow, that is that is a lot of effort you put into figuring out very specifically where you wanted to work. I I sometimes wonder about this when I think is it just me that's not putting in that kind of effort? Or is it like some people do and some people don't and, and I asked that because I just had to, I read a book by somebody else I just recently interviewed, and they're a career coach. And they had very specific steps in their book. And I was thinking, I've sort of fallen into the things that I wanted, like, I can't remember the I can't remember putting in crazy amounts of research. I sort of just ended up there. And I've been happy with that. And they're the things I want to do. But so I guess I'm saying is it's good to hear that kind of perspective, the whole other side of the coin for young people who might be listening to this to hear that, like there are these resources out there that you can look into and you can analyze and cross reference and start to really narrow down where the best fit for you might be so I'm glad that you're able to I'm glad you told us that so All right, travel sales. This is the reason why we're even really talking because travel sales are where the TikTok videos started. We'll get to Tiktok later and figure out how it started. But okay, travel sales. What was it about travel sales in particular that really, of all that research you did travel sales was the place where like, this is what I'm going to do. And did you still want to be on the marketing side of things? Or after doing the MBA? Had you started to consider other areas of that business?

Sydney:

Yeah, what really attracted me to that opportunity were two things, one was the the things that I would learn in that role. In that role, it was marketed as, and I very much did, I learned so much about so many different aspects of business. So, of course, it was a sales position. But in the grand scheme of things, it was a very unsupported sales position. So what I got to learn, negotiation, I got to learn inside sales, outside sales, I got to understand more accounting, I learned more about, oh, gosh, every possible type of marketing, you can think of direct mail, digital, social media, everything, things that in a traditional organization would have departments supporting, were just another thing I had to do with every single sale I closed. So the first thing that was attractive was, yeah, you're you're flying, you're flying your own plane here. But you, you get to learn so much that now now that I'm no longer in that position. It's one thing I've heard in every interview I've had. And also in roles I've had, since travel sales was just the sheer things I can do in my in my toolbox, that if I hadn't had that type of role, I wouldn't have those skills. So that was one thing that was that was really attractive about it was, it's going to be hard. But I'm going to learn so much that if I stay here, or if I go somewhere else, I'm going to be a very attractive candidate. And the second thing was, is what you didn't get in your pay stub you got in travel. So that was another thing that was incredible was I got to travel the entire world for free in that position. But you know, tagging yourself in Instagram photos in front of the Eiffel Tower doesn't help you pay the rent that much. So it's great for young people where that is travel is a currency. But again, it gets to a point where you're like, I'm putting in all this effort, I'm doing all these things. And then the pandemic was a was a huge component of well travel ain't happening anymore. And it's not being made up for elsewhere. So that was, you know, one of the many things that had me take the next step of my career.

Jonathan Collaton:

I like to hear that you were really thinking even beyond that job, when you were going into that field, in that you looked at what it would get you and not just the valuable skills that you're going to learn today. But like really how that will impact you in the long run and how it's going to help you get the next job and the next job in the next job. So you've done a lot of strategic movements, it seems like up to this point where you've really, you're putting a lot of thought and time and energy into making sure things will be the right fit. And did you feel like you needed to love the job, or the fact that you were getting so many skills out of it, overrode the fact that you might have crappy days, it was just so valuable of an experience that it didn't matter if you didn't love the work. Does that make sense?

Sydney:

It didn't, it didn't know why. And I, while I had a very sophisticated approach as to how I got there, I my position of how I look at new opportunities is very different than how it was when I was you know, fresh out of school and not having that corporate experience. So it at the time, it was super important that I was working at a flashy, cool place, it was super important that this is where Millennials thrive. And we have you know, we have a we have a snack bar. We have ping pong tables, those things were super important to me at the time. And it checked a lot of those flashy boxes that were being told that millennials love to check. So and having people who are all your co workers were pretty much the same age as you and you all have a very similar background and their diversity in the workplace is important for a lot of reasons. But what wasn't there that I didn't know at the time to necessarily look for were things that got me on board very quickly got me very excited about things very quickly. But again, work from home and the pandemic shift a lot of what was important. So with those things, kind of, you know, the flashy office, those kind of things stripped away. It had me put me in a place to reevaluate what I really wanted in the you know, the ping pong tables weren't as weren't as important anymore.

Jonathan Collaton:

Yeah, that's a great point, right? All these amazing offices that have been built for companies that probably don't need to be in the office anymore, maybe ever in a lot of cases. So all those ping pong tables being unused, sad, I think. So. So how did you decide then, where you want to do next? Because the pandemic, it's messed with so many people's individual jobs, so many people's career path, their planning? Like how do you then decide, okay, travel sales is not, it's not working anymore for these reasons? What will work for me moving forward?

Sydney:

Yeah, and actually, it wasn't even the pandemic that that led me to, to leave travel. Um, I really did. I really did love the organization. And I bought and part of that was, I love my coworkers, I still talk to my co workers from that job every single day. So I initially I really wanted to grow within the organization. And I'm sure everyone's heard the story of everyone who's gone up for multiple promotion after promotion, it keeps not working out. And of course, you have your own sentiments of folks that got positions over you. And that's, that's universal, everyone feels that way. But what really was my eye opening experience as to it's time, it's time to move on was, again, this, I'm not making the progressions that I want to internally. So I met with a couple of leaders. And I was like, look like, here's, here's kind of how the last handful of months have gone. For me in terms of progression. Here's where I want to be, I don't know how many how many years or what that looks like, I want to be in this this seat. I want to be in this on this team. So I know that there are steps and positions that I need to get in order to be in that seat. Walk me through that path. How long is that path? What are my what is my next step in that path? If I want to be in this position at this company, I guess the the candor was much appreciated, I was told, Hey, that path doesn't exist, there is no one that has been from the seat that you're in to the seat you want to get that doesn't that's never happens. And to put it frankly, like it's most likely not gonna happen. And that will of course, some people would say like, Oh, what do you mean, I heard that, and I heard, great, it's not going to happen here. Like, I need to now put all of my efforts into finding somewhere that it can. So that was I actually I made a I made a Tiktok the other day about like, because I kept getting asked the same question and a handful of my comments. And it was, if you there was there's two things I evaluated based on my last couple of positions. And number one is if you look at the seat that you want to be in, and there's no path that gets you there, get out. And number two is if you look at if you're you know want to stay in an organization you look at if I were to get promoted once who and I work with twice what I work with. And as I climb this ladder, those people that I would be working with alongside? Do I like those people? Do I want to share an elevator with those kinds of people? And if the answer is no, if I don't want to work with my boss's boss, get out. So that was that was pretty much how how I felt my last couple of positions have just, if there's no clear path that I want to be on. It's okay to move on. And for some folks, that's really hard. And it was really hard for me for a really long time. But then once I made that step, and I and I made that no first step in the right direction, even though it was over here, it felt so good.

Jonathan Collaton:

Okay, yeah, that's, that's a great analysis of your you've really put a lot of thought into why you did those things, which I love. And maybe just because I read this career book, and it was like, literally mapped out how to make these changes. And it feels like you read that book too. That's kind of what it feels like right now with the way you were thinking about these things. Alright, so then, what next? How do you how do you decide okay, or I should say, once you've decided there is no path here anymore? Is there a similar type of job you want to get to but in other areas of business and other areas of sales? Or do you have to go and do like a whole big search again and try to figure out what the skills I have and where I want to get to what is the next job for me to get and will I be happy with that job immediately? Or is it one of those things where I will start here and then climb this ladder over in this place?

Sydney:

Yeah, how I've built myself to be so poised and calculated is about to go right out the window. Wonderful. Everything I've all the credibility I've built is now about to just gone. So once I once I read I tried to use the same strategic approach that I'd used years past now that I was a great, let's start this up, let's, you know, review the resume, I even partnered with a recruiting firm of like helped me get placed. And I applied to probably, oh god, I had to be definitely more than 350, but probably a little less than 500 jobs. And like, for for the position I was in, I had a fantastic resume and the what I what I what I had was, it's competitive, it was great. And I out of those, let's just conservatively say 400 applications. I went through maybe six interviews, like first round interviews, I got maybe six. And I was even getting referred, you know, when your friend works somewhere, and they're like, oh, yeah, interview my friend, even that wasn't working was not even getting those and I was like geez this is bad. But there were a couple of companies that I was super interested in, I knew I wanted to stay in sales and in New England, you know, where I'm from in Massachusetts, like the best of the best salespeople either work in pharma sales, pharmaceutical sales, or you work in tech sales. And like, that's where that's where it's the hardest, that's where people are the most cutthroat. But like, that's where a lot of the money is. So I was like, I've come from this whole, let me make your dreams come true at the Eiffel Tower to like this kind of cutthroat environment, like this is gonna be the big change for me. So I finally found a company I was super excited about. They had amazing growth, they were super well rated, in terms of like great places to work, great benefits, like all all the things you look for it checked every box, and it had everything, you know, competitive pay all of those things. And I started and I was like, great, like, I've always been again, so calculated, and poised, here we go. And it was, I was not a good fit. I was not a good culture fit. It was, it was just bad. It was just bad. It's like if you've ever seen one of those pictures of like, oh, we said it was a dress up party, and everyone's wearing dresses, and one person's dress like spider man. I was I was the Spider Man of every room, I walked into there. And that's fine. But it was it was tough to go from spending, you know, building building my career up to one point at one company, ultimately, burning quite a few bridges when I left, and then kind of starting all over to then sit in that seat and and think Oh, no, did I just make a huge mistake? Like this is not? This is not good? Um,

Jonathan Collaton:

how long did it take for you to think like, what have I done?

Sydney:

Ah, it took about 30 days.

Jonathan Collaton:

30 days?

Sydney:

Yeah, it was about 30 days. And I was like, Oh, no. And I kept it to myself for a very long time, because everyone was so supportive. And when you're interviewing, and you have to use all of your old managers and like coworkers as references, and then my, my poor, my poor, two of my friends were my references for like, several jobs, and they kept being like, yeah, she's great. You should hire her. And I feel like I didn't get the job again. I need to use you again. I'm so sorry. So I was like, I can't I can't do this again. Like I just

Jonathan Collaton:

was just the prospect of job searching was so yeah, I mean, after what? 400 jobs almost. That's, I get it. I get it. Okay. All right.

Sydney:

So unfortunate.

Jonathan Collaton:

Wow. So that's a tough spot to be in. Right. You've you put like, That's

Sydney:

right. We're in a pandemic. It could not it could not feel any worse. Yeah.

Jonathan Collaton:

Wow. Okay. Did another question, I guess. And without getting into too specifics. You mentioned you've said Boston, you've said New England area, were you having to move any real distance for these jobs? Because sometimes I think that locks people in if they are moving to a place where their family is or if they have to leave a city for a job well now like just practically if you have at lease somewhere you're kind of you feel you can feel trapped there like you have to go through with it all. Did you have any of those things that were sort of making you feel tied to it?

Sydney:

I was lucky enough that distance was not a factor. I mean, don't get me wrong. I've been very lucky for my entire adult life in terms of like my proximity to things I haven't had a car since I was in high school. So I've been able to walk to work walk to like, to anything walk to school, I've been able to just walk for you know, I walked around for nearly 10 years. I got my first car since high school last month. But um, yeah, so I walked everywhere. So when I was going through my job search, it was a it was a hard pill to swallow of like I might need just started playing playing to places that I need to take the train for. But yeah, proximity, I was lucky enough, that wasn't a factor.

Jonathan Collaton:

Okay? All right, 30 days in, then you realize, oh, and you have to use and abuse your friends for references all over again. So knowing that what you had gone into was the wrong fit. Did you just start like ticking things off a list and saying, Okay, this is like that. So that's not going to be a good fit. Did it feel like it was the individual company? Or like that whole industry? That was the problem for you?

Sydney:

It was, it was just the company. No, not not every place is going to be the right place for every single person. And it just, it just wasn't the right was the right place. For me, it wasn't the right place for me to grow. It wasn't the right place for me to collaborate, to learn it just it was not a good fit. And I really don't think that there could have been anything done in the the interview process on either side for it to to be identified. But it was, it was it was very quick when I was like, oh, no, oh, no, I'm the one thing that and again, I don't regret making that choice. Because the one thing I will say is it was a very, you know, good and established company, like I wanted to work there for a reason. And once I updated my, like my LinkedIn, once I started to update, like kind of my professional network with like, Hey, I'm working here, now things are going well, and they were on paper I was performing very well, like so if you didn't know me, and you only you know, saw my name in passing you like girls crushing it. Um, so with that, I was able to kind of broadcast that to my network. And the nice part I did spoiler I did, I did not last at that company for very long. But because of you know, kind of the the work I had put into it, I was lucky enough that I did have other companies in the space kind of knocking on my door of, Hey, I saw that you're doing great over there, like won't take an interview with us. So it went from, you know, six months of sending out dozens of resumes and applications every single day to now being in a place where I'm so unhappy. And I have you know, two to three recruiters begging to talk to me every day. So very, very much a flipped on its head. But I had a recruiter at another company that is very well respected who reached out was like, Hey, I'd like things are looking like they're going well, are you interested? And I was like, absolutely. And then I've been there for you know, a few months now. And I'm happy as a clam.

Jonathan Collaton:

Perfect. Wow. Okay, so all that discomfort and, and not regret, but but just that feeling of like, Oh, no. And in the end, that ends up helping you bypass 400 job applications, because the position you've put yourself in, even if it didn't pan out and that you liked the job, you're in a better spot in terms of your resume and how you look as a potential candidate. And now you're having people knock on your door. So that's fantastic. So you like the job? It's, is it still a sort of tech software sales type thing?

Sydney:

Yep. Yep. So still sales? I don't know if they'll ever be a Thanks for calling tech sales. I don't know if we'll get there. But, um, yeah, it's so so in the sales round, but yeah, much more of a strategic sale than like transactional.

Jonathan Collaton:

Alright, so that brings us to where you are today in your career. And unlike everyone else I've ever spoken to on this podcast, I want to also explore this whole other thing that you do on the side which is TikTok because I don't know if you would call it like a side career. But I know that you have people buy you things like you are able to sort of make a I don't know not make money but like you there is a benefit to doing the work that you do on TikTok. Do you have this vision of like, I'm going to be a pro Tik Tok or just make content all day and that'd be my life.

Sydney:

Absolutely not. It's so it's so weird to me. Like it's something that I invest as much time into Tik Tok as I do, like Candy Crush, like it's not it's it's not something that I take incredibly seriously. It's not something I put a lot of effort or thought into. I just I when I made the transition from like, posting silly things to telling stories is when I saw like a huge boost in engagement. And yeah, it is weird. It's Oh, gosh, it feels almost dirty to hear you say like people buy you things. Um, it's weird. It's definitely a weird concept. The whole thing is weird to me. But the most important thing that I've always felt even you know, back in high school when social media or even middle school really when social media first came out, and I think you know, being in Our position we see it so much differently than, you know, younger generations do. But I always grew up with social media is not real, because I remember, one of the first times one of my friends got a Facebook, we had this big sleepover. And the sleepover was terrible. There were girls crying, people went home, it was not fun. But the Facebook album made it look like we did the you know, we had a great time everyone's smiling. And I remember my mom had like, seen it, oh, it looks like that was so much fun. That was like it was miserable. So that was one of my first introductions to just social media just being a total Sham. And I think that was like sixth grade sleepover. And so after that, I've always had that impression. So as an adult now having a somewhat like, footprint in it, it feels strange, but I've always just held this it's not real life, it can, you know, go in and instant with the new cancel culture or just like the app not being a thing anymore. It's, it's fun. It's, it's cool to see. But it's not something that like I hold with, like a ton of ego or anything like that.

Jonathan Collaton:

Yeah, social media is it's not real for predominantly, people are not putting all the bad stuff that happens in their life on social media, right? And what you said, like telling stories, I hadn't actually thought of it that way. But of course, that's what you're doing. You're telling these stories about these hilarious interactions you've had in the past with people in travel sales at restaurants. I feel like you've you've got some other stories you've put on there as well, but I travel sales. That's the one that kind of blew you up, right?

Sydney:

Yeah, that was that was the big one I had, like posted again, just like silly things of like, the little trends you'll see. And things like that. And then it wasn't until and I had like no followers, right? And then it wasn't until there was this trend of tell me your boyfriend will never cheat on you without telling me he'll never cheat on you. And I was like, Oh, I like I know one. And at the time, my boyfriend had just bought 55 packs of Pokemon cards that he was very excited about. So I was like, Oh, here's here's the winner winner chicken dinner and I made it and it it blew up it was unbelievable it within 24 hours had I think like what 10 14 million views Yahoo News was writing about us like it was bizarre. And then there was like nothing after that. But with that he saw you know a huge bump in like followers and views and stuff like that which just came from that one video and then it wasn't until Gosh six or seven months later that I made the first hey listened to this when I first worked in travel story and then it just blew up from from there.

Jonathan Collaton:

Wow. Okay, I've been curious about what the history is because I don't know at some point in the summer maybe I picked up on you know, gotta love that for you page when you're scrolling across my page and I have a long history and love of travel so I was like these stories are spectacular these entitled lunatics who think that you can change the food at the restaurants in Italy and turn off the rain oh my god these people are crazy. And I'm like I just I got to hear more about these so I I'm glad there are still more stories to come apparently from yeah,

Sydney:

there's never enough it's funny I put I got a text from one of my my old co workers and they sent the TikTok video along with it and they're like this just happened to me. Like this just happened someone is in Paris and they just called me to complain and then I see it on my see that I happened to you eight months ago and I was like yeah

Jonathan Collaton:

yeah, so it's great for nostalgia for you and your friends to bring up the old stories of what happened you and what still happens to them. Alright, so if anybody wants to follow along that isn't already you have what two accounts now because of course with TikTok you got to prepare for the ban hammer to come down at any point in time.

Sydney:

Yeah, I wasn't I wasn't ready for that one. But I mean not to be too overly dramatic. I've just been banned on and off for the last like three or four months to the point where like, fully banned and things like that. So I made a backup just to down just in case. But yeah, the main one is poor and hungry. There is no origin story to the name I wish I had a fun one. And then I was in I was in the live actually. And I was like I think I'm gonna get banned for real like what should I do and then everyone in the live was giving suggestions and by far the most boring one was still poor and hungry and that was by far the winner so that's what we went with.

Jonathan Collaton:

Perfect. Is that the that's the name of the backup account too?

Sydney:

Yes, the backup is still porn hungry.

Jonathan Collaton:

Oh, still porn hungry? Yeah, I didn't. It's like without seeing The @ symbol in front of it. I can't figure out which words are in it or not. So, all right, and then Instagram, same thing.

Sydney:

Yeah, Instagram. I don't does anyone still use Instagram? I have one. It's just poor and hungry, underscore. Nothing flashy. You're not gonna get any good stuff there, but it's still there.

Jonathan Collaton:

It's just all the TikTok stuff if you get fully banned from tick tock, yeah.

Sydney:

I don't know. It's it's all again, social medias just, it's not real. So it's like, sure you can go follow that we'll never meet in person. But yeah, how about it?

Jonathan Collaton:

Exactly. But your career very real. And thanks for telling us the whole story of the intense decision making and how at some points, it led you to very good parts, or very good jobs and at some points, not so good jobs, but eventually leads you to where you are today. And it sounds like you're very happy if what you're doing right now, right?

Sydney:

Oh, yeah, absolutely. One, one thing I recommend for anyone that's either like very well established or like trying to orient themselves is Have you heard of the the Clifton Strengths Finder?

Jonathan Collaton:

Yeah, absolutely.

Sydney:

I was huge. And both my undergrad and my graduate studies was very much focused around that. And then in my professional life, every company I've worked at, has been very adamant on understanding everyone's strengths. And so futuristic, strategic, competitive learner, those are some of my top self assurance is up there, shockingly. So that's what I always recommend is like, understand your strengths. There's a million different resources that you can check out to learn more about, like, literally how your strengths, which seems crazy, but yeah, that's what we're a lot of my themes come from are my Clifton Strengths.

Jonathan Collaton:

I don't remember all five of mine, but I did it a few years ago at work. I have the odd combination, though, of having context and futurist, which means like, I love to hear how things were. And I also like to think about what they could be so yeah, I guess that's why I have a podcast where I talk about people's history. So make sense. Alright, Sydney, thank you again, so much. And I hope that a lot of people who know you as the travel sales girl are going to get to hear this, and hopefully learn something really valuable that they can use when thinking about their own career.

Sydney:

Awesome. Thank you.

Jonathan Collaton:

All right, that is Sydney's career path. I feel like in many ways, Sidney is a lot like many other people that I've talked to people who quite recently got a new job, and now they're willing to share some of their successes and their failures that got them to where they are now. Now, successes and failures kind of hint at the lessons that I think we can learn from Sydney. So let's dive right into that. I think there is nowhere better to start than with travel sales, because obviously that has been a huge part of Sydney's life. She told me all about how that job allowed her to travel the world. And there's the very obvious point that I can make that stories from that job or why she is well known on Tik Tok. It's a job that has given her a certain level of internet fame. And that's how I came across Sydney. We do not know each other. I just messaged her one day when she was on a tiktok live. And she was interested in my podcast. So here we are. Getting back to successes and failures though. The travel sales job was a massive success for Sydney. We heard her talk about all the things she was learning in that job, every different kind of sales, about marketing, about finance, about customer service. And now all those skill sets will benefit her for the rest of her working life. Even if she isn't in sales at some point. I think the really important thing to note is that she got to learn all of those skills at her very first job outside of post secondary education. Could it just be that Sydney is very lucky. Sure that could be true, but I don't think that's the case here. I think it's that Sydney was very, very intentional in the choices that she made. And I think we heard her clearly articulate the rationale for all those choices during our conversation. The decision to go back to school for the MBA after graduating early Yes, softball was the primary reason but her research had shown her how many jobs were looking for people with MBAs, and she recognized that she could get a useful degree and keep playing softball, which sounds like a pretty intentional decision to me. But really, once she graduated, things took on a whole new level of intentionality. Sydney looked at all the lists of best places to work and she narrowed it down and she did a ton of research. She probably put in more hours than most of us ever have when we've been searching for a job. And because of that, she was able to very confidently make decisions that were best for her. And that is exactly why she ended up and travel sales. She determined that that was the perfect fit for her at that stage of her life. And it stayed integrate fit for quite a while, which I think validates all the hard work she put into picking travel sales in the first place. The lesson we can learn from Sydney here is that the more intentional you are about the choices you make when it comes to finding your next job, the more likely it is that you'll find something that gives you the practical experience you're looking for. But also maybe gives you some practical skills you weren't expecting. Having said that, I also think what we can learn from Sydney is that preparation doesn't always lead to success. And there is no better proof of that than the job she took in tech sales that she left after only six months. Now, Sydney did nothing wrong during this job search. In fact, she went above and beyond and actually worked with a recruiting firm to help her find a good fit. At the end of the day, the job even looked great on paper competitive benefits and a company at the top of her field. But despite all that, all that planning just didn't end up helping because it just wasn't a good fit. And it took until she got there for her to really figure that out. Sydney illustrated that perfectly for us when she explained that she was like a spider man in a room full of suits and ties that really helped me visualize the situation she had ended up in. So I heard all that. And I'm thinking that if she put that much effort into her job search, only to end up in a job that she didn't love and it just wasn't the right fit. Isn't that proof that sometimes things just don't go to plan and there is nothing you can do about it. It's no one's fault. And you've just got to move on and try to find the next good fit because this one didn't work out. The good news is that all that hard work you've put in is probably put you in a better position than you were before. So dust off that LinkedIn profile and let the recruiter messages start rolling in just like they did for Sydney. And if they don't roll in, who cares? You have put in the hard work before and you can put it in again and get a job you're actually going to be happy with. Well, that is all for this week's episode of career crossroads. And if you want to go spend a whole Saturday afternoon hearing stories of travelers who don't like that there's too much pasta in Italy, go find Sydney on Tik Tok. I have linked to all her social media accounts in the show notes for this episode. And while you're there you can also find all the links for my social accounts including TikTok. If you enjoyed this episode of career crossroads, please share it with a friend. And if you want to hear more interviews like this, go to career crossroads podcast.com Or subscribe on whatever podcast player you're listening to this on right now. A quick reminder that you can support the show at our Kofi page in the show notes and also by leaving the show a five star review