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Further Forward
Honest conversations on the art of becoming.
Through solo reflections and conversations with soulful, sharp, and courageous guests, Ashley creates room for the stories that don’t always get told—the pivots, the struggles, the magic, and the mess. Part spiritual, part practical, always human—Further Forward is a space for women invested in their becoming, who know growth is both messy and worth embracing.
Further Forward
Her Dream Job Didn’t Exist—So She Made It with Kate of Bucket List Boston
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In this episode of Further Forward, I’m joined by Kate Bergman, founder of Bucket List Boston, for a conversation about building a career that didn’t exist until she created it.
We talk about rejection, persistence, social media, entrepreneurship, and what it means to build something meaningful without waiting for permission. From getting rejected three times early on to turning a college passion project into a full-time business, Kate shares what it looks like to trust your instincts, stay true to your values, and create your own lane.
If you’ve ever wondered whether the work you want is out there, or whether you might have to build it yourself, this episode is for you.
About Kate:
Kate is the founder and creative force behind Bucket List Boston, a lifestyle platform dedicated to discovering the best experiences in Boston and beyond. She started the brand as a passion project as a freshman at Boston University and spent the past decade growing it into a full-time business and trusted guide for locals and visitors alike.
Through her content, Kate highlights hidden gems, supports small businesses, and inspires people to explore their city with fresh eyes. In addition to creating content, she works with hospitality brands and tourism destinations and runs Bucket List Consulting, where she helps businesses refine their brand storytelling and social media strategy.
Kate is passionate about building community, championing local businesses, and showing that a creative idea — when nurtured with consistency and heart — can grow into a meaningful entrepreneurial career.
Further Forward: Honest Conversations on the Art of Becoming, is hosted by Ashley Mitchell.
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Kate, welcome to the Further Forward Podcast. Thank you, Ashley. I'm thrilled to be here. I'm thrilled to have you, and I just I love that this moment is coming together because you were such a like kind and joyful presence in my classes a few years ago, and I knew I wanted to stay connected to you other than purely on the internet. So I'm glad that we have this opportunity to spend a little bit of time together. So thank you.
SPEAKER_02Oh my God, I'm so honored. And I felt the same way. I took your classes for you, not for the workout.
SPEAKER_00Thank you. That is probably the best compliment that any instructor will ever receive. So I appreciate it. It's so true. Thank you. So I always ask every guest the same first question, and you can answer it however makes sense for you as you are coming to our work together today. But who are you and how are you? Thanks for asking.
SPEAKER_02I'll start with the first question and then I'll go to the second. I'm Kate. I'm the founder and creator of Bucketlist Boston, which started as an Instagram page and has since grown into my full-time job and really a platform all about discovering Boston and supporting local businesses all around the greater Boston area. And I would say that I'm doing well today. I feel like there's finally some glimmer of hope that spring is actually coming. I'm going to a friend's wedding in Florida this weekend. So I'm going to get some sunshine. And I feel like almost waking up this morning, it feels like we're entering like a new section of the year that will be much more hopefully positive. And I'm feeling optimistic.
SPEAKER_00Yeah, you know what? I definitely feel that too. There is just like this energy of awakening. And um I noticed it last Thursday on my drive into the studio. I got to see the sun coming up over the city as I was driving on the highway. And I was just like, this is everything. This I needed something, I needed something to go forward. And like, yeah, it changed a lot.
SPEAKER_02We needed a sign.
SPEAKER_00We needed a sign. Amen. Um, outside of Bucketless Boston, what else is there to Kate? Do you have pets, siblings? I know you have a husband, so I'll just say that. Um, but what else comprises your life?
SPEAKER_02Yeah, I'm an older sister. I have younger twin sisters, so I am not a twin, but my sisters are twins. Oh my gosh. So fun.
SPEAKER_00Really? Is it fun?
SPEAKER_02Yeah, it's fun now. Uh when we were growing up, they ganged up on me a little bit, but it's okay. I grew a thick skin from it.
SPEAKER_00How much younger?
SPEAKER_02They're three and a half years younger than me.
SPEAKER_00Okay, okay. So you're kind of close in age.
SPEAKER_02Yeah, I would say so. Definitely.
SPEAKER_00Okay. All right. What else? Give me the tip.
SPEAKER_02What else? Ooh, um, I always loved photography and food growing up. So I feel like now what I'm doing makes a lot of sense because those were passions of mine from a very, very early age. I'm from New York, which is definitely part of my story because I came to Boston for college with a very New Yorker mindset in that I was like, Boston will be cute for a few years, but obviously one goes back to New York because it's the ultimate city. And quickly, when I got to Boston, I fell in love with every part of it: the architecture, the walkability, the cleanliness, the people. And I realized that I maybe was not going back to New York. And that's kind of what spurred my adventures, which ultimately led to me creating Bucketlist Boston.
SPEAKER_00Oh my goodness. Wait, so are you from New York as in like the city or outside?
SPEAKER_02I'm from right outside the city in Westchester County. So like a 30-minute train ride. So I would go grow up going in all the time. I would go to Broadway shows. If there was a new cafe opening, like I would get on the train with my sister and go check it out. It was definitely part of my childhood.
SPEAKER_00I love how this is something that is just in every single episode. It doesn't matter what woman I'm speaking to, sort of like how her not necessarily like we're not unpacking anyone's childhood on this podcast, but our earliest I'm like underqualified to do that. But like, you know, your earliest memories and what you wanted to be when you grow up and all the how that all converges. And sometimes my in my like favorite iteration, because it mirrors my own, that we kind of find ourselves almost coming home to ourselves and finding a way to just be who maybe we most wanted to be or pursue the interests that we really loved, but didn't know if it could be a career or something like that. So I love that who you might have been as a little girl or a younger girl has made its way into your life as an entrepreneur, really.
SPEAKER_02That's so Definitely well said. I love that. And I ironically, my like childhood dream job, if you would ask me what I wanted to be when I grew up, was to be the president. I don't feel that way anymore. I don't know, but you know, the current, the current situation has made me say, I do not want that job anymore because I don't even want to be the successor to that.
SPEAKER_00I know. See, as I don't know why I said why, because as a kid, you should want to be president, and then you actually view politics and you're like, oh yeah, no, this would destroy everything that is good about my soul.
SPEAKER_02Absolutely. But I also on the same token, like I ran for school government for like any possible race. I loved that type of government, but that was more like planning prom than, you know, like geopolitics.
SPEAKER_00Yeah, a little bit more fun. A little bit more fun. Just a little bit. Okay. A couple of questions. I'm I always try not to get ahead of myself because my brain is moving at lightning speed because there's so much I want to know. So I always have to be like. Ashley, one question at a time. What was the moment after you started Bucketlist Boston where you were like, oh, this is a thing that not just matters to me, but matters to lots of other people. Maybe like you weren't blowing up just yet, but you were maybe like just seeing a lot of growth and you knew that it had the potential to blow up.
SPEAKER_02Yeah. The thing that comes to mind when you asked that question is just sitting in the dining hall as a freshman and having people who I would have considered to be peers or acquaintances approach me and tell me that what I was posting was inspiring them.
SPEAKER_00As a freshman. Yeah. What did it look like in the early days? Were you just wandering around and posting random photos of like, I like this, try this?
SPEAKER_02Yes, exactly that. Yeah. So I'll take you back a second just for like the origin story. I think it's important. So freshman cake gets to Boston University, pretty much new to Boston. I had been a couple times. Other than that, I hadn't spent much like longer periods of time really exploring. And so when I was here, I was like, oh, I want to get off campus. I would love to see the city because there's a city girl in me. And I would just start like between classes on the weekends, picking different neighborhoods and just like walking there and learning how the neighborhoods connected and like what each neighborhood felt like. And in those adventures, I would, of course, be capturing little moments on my iPhone. And by the end of my first semester, freshman year, my phone storage was full with all of these photos that I didn't really have a use for. And so I spent my winter break brainstorming what I could do with the pictures. And I ended up finding that there was an innovative photographer's community called IG Boston on Instagram that I could apply to become a member of. And long story short, I was rejected three times from this community. Yeah, we come from failure. It makes us stronger. Amen. Yes. And by the third rejection, I was like, you know what? I don't need them. I'm just gonna do my own thing. But I will credit them with having given me the idea because I first applied to the community on my personal Instagram page. And the feedback that I was given was that I didn't have enough Boston on my page, which I was like, of course, it's my personal Instagram page. But I took that piece of feedback and I said, I'll create a separate page that's solely about Boston so that when I reapply, they can't tell me the same thing. And so I sat down, spring of freshman year, right when I got back on campus and I went through the dictionary for words that began with BU in honor of Boston University. And that's how I found bucket list.
SPEAKER_01Wow.
SPEAKER_02And it was 2016, so the handle was available. And I grabbed it and yes, I just started randomly throwing photos up there.
SPEAKER_00No way. My I'm like mind-blown. That is so cool. Okay, so then I just because I have to complete the like picture of so you create bucket list Boston and then you apply again. And why was it a no the second time? Wow, no one's ever asked me that before.
SPEAKER_02And I tell this story all the time. I love that, Ashley. So the second, the second round, each time I applied, I made it a little bit further.
unknownOkay.
SPEAKER_02The second round, I believe they said I was on the right path, but I didn't have enough content for them to really know my scope of work and like what my talent was, and that they needed to just see more. And then the third rejection was the most interesting because at that point I made it like to the last step of their application process, if you will. And so the final challenge is that they assign you a challenge photo. And so mine was to capture Jamaica Plain in a way that was clearly Jamaica Plain without anything saying Jamaica Plain.
SPEAKER_01Okay.
SPEAKER_02So I went to Jamaica Pond and I got in a little paddle boat with my friend, and I got what I thought was like an epic photo of my friend rowing in this boat, the pond, and then a sign in the background that you could read, but that wasn't the focal point of the photo that showed you where you were. And I was like, this is it. I'm in. Like I accomplished what they asked for. And they wrote me back an essay, basically. It was a long email telling me that the panel went back and forth on whether or not I should be accepted. And ultimately they were like four to five, five in favor or five against my joining. And the reason was that the photo showed too much of my friend's hair and not enough of the scenery. I can't make that up.
SPEAKER_00Kate stop right now. I mean, okay, let me go back. I understand that photography is an art and a craft, and I understand that there are things that people look for and award-winning photos. Like, I'm not dissing the art form. But are you fucking kidding me right now? Thank you.
SPEAKER_02Yes, that was my reaction too. And I showed it to my parents, and they were also like, this is crazy.
SPEAKER_00Oh my goodness. Yeah. Okay. Wait, so at that time when for the third round, do you remember roughly how many followers you had had?
SPEAKER_02Wow, that's a great question. It had to have been a couple thousand, but I had not reached 10,000 yet.
SPEAKER_00Okay, okay. Something that I've noticed, here I am going off in a tangent. I'm going left. You ready? We're in the car. I'm ready. I'm on board. Um, something that I've been noticing more and more that's actually delightful to me was so when I first started posting, like you, there were certain things like a swipe up feature that you couldn't have unless you had 10,000 followers, right? Stupid stuff. So in your mind, 10,000 followers is this magical number that unlocks all of this fame and money and all this stuff. Yeah, truly. What I noticed as I started expanding out of just sort of straight fitness and started pursuing other things that I liked, I started seeing all these other people who are incredible, that are fantastic, that are like true craftspeople, and they'll have like a thousand followers. And and so I guess I'm I'm asking because I want people to hear that you can be successful without thousands or millions. You can also apply for things, you could show a point of view, you can have a whole brand that might be successful in one avenue or area or in a particular way, but not necessarily in the social media space. And that it seems like that's fine if that's what you want, right? Or am I mischaracterizing the whole influencer thing?
SPEAKER_02No, you're 100% correct. In fact, right before we got on this call, I was, I feel like my algorithm shows me a lot of like, this is what Instagram wants to see now type of content. And the post that I was just reading was that your follower account is essentially obsolete at this point. It really doesn't matter. It's about the quality of the content. You could have 5,000 followers and post a video that is just highly engaging and funny or interesting or educational. If it starts to get shared, it's gonna hit the algorithm and it's gonna continuously be fed to non-followers. And the same person with a hundred thousand followers could post that video and get the same results. So you don't need to have a following to have a really exceptional video, like hit the algorithm and succeed.
SPEAKER_00There you go. There you go. Do you think that people should it like right now in 2026? Do you think that anyone should be aiming to be an influencer or do you think that people should just do what they want to do?
SPEAKER_02I never think that someone should set out to become an influencer.
SPEAKER_00Wow, say more.
SPEAKER_02You can't just say, I want to be an influencer. You have to say what you would like to influence. And perhaps with that will come a community, but you need to start with a personal passion. Otherwise, this concept of it's essentially just wanting to be famous. Like what does that mean? You need to have a reason to be famous. You, your path could be that you want to be an actor or an actress or you want to get into politics and be the president. But anyone who asks me how they can become an influencer, I immediately tell them they need to reframe their thought process because if they're not passionate about something, that means they won't have a niche. And just like sharing about your life, once in a while, that may work for someone, but for the most part, that's not going to be a big enough hook to grow a community.
unknownYeah.
SPEAKER_00Yeah. If someone was like, My life is the most interesting thing about me, or I think my life is marketable because I have nine kids, or because I live on a farm and my day-to-day is the most interesting thing, whatever. How do they then like kind of niche that down? Is it still a matter of like I mean, I think of it as being of service. That's just my language for the world of does this help someone in some way? Does this give language to something that people feel like they're struggling to find language for? Or or somebody wants to feel seen and and something that I say makes them think, oh, me too. She gets it, right? So even if you're posting about your life, is that still the frame of reference of like it has to, it has to be something more meaningful than this is my avocado toast for breakfast?
SPEAKER_02I personally think so. Because to me, the question is what is the basis of the community that I would want to be a part of? And so, in your example of like, I have nine kids, is it that they love being a mother? And is that the community that they're trying to build towards? Because I just think the concept of wanting fame falls flat and never is fully authentically a reason to create a community. And I think that that's the the biggest way to build loyalty and actually have authentic followers.
SPEAKER_00I feel like it's not worth it if it's like why would I want to spend precious time out of my life feeling hollow about what I'm putting out into the world? But you know, I'm like That's just you. No, that's just me.
SPEAKER_02No, I totally agree with that. And if I had started with the mindset of wanting, I mean, influencing was not a thing in 2016 at all.
SPEAKER_00Yeah.
SPEAKER_02And I started because I felt like my fellow classmates got stuck on campus. We called it the BU bubble. No one left. And I was like, what do you mean? We all chose to go to a city school and no one is actually experiencing the city we're in. I'm gonna go find the city and like go see what's cool, and I'll get back to you guys and tell you where you should go. And from there, I built a community around people, at first, BU students, who wanted to see Boston. And then it grew from there. That's so cool.
SPEAKER_00I mean, that's kind of like entrepreneurship 101, right? Is like identifying a problem or like seeing how maybe you specifically can solve something that other people are having a hard time with. You just kind of never think of it in terms of content creating, but you are kind of solving a problem. You're you're filling a gap in the space.
SPEAKER_02I definitely felt like I was, and I to this day I feel that I'm solving a problem. I hear all the time that Boston's not as fun as New York and there's nothing to do here, and we have no nightlife. And I see myself as like a detective in a way and a journalist investigating the scene and proving those people wrong.
SPEAKER_00I mean, I do like New York better. Sorry, I'm sorry. Sorry, you gotta just sometimes claim what you claim. I I mean I've been here, so like clearly I love it enough. But what I gotta kind of want to go like back to your family in this. You mentioned you're telling your parents that you didn't make it into the photography group. But I'm curious of like what they what they wanted for you for your life, and then how did how have they felt that you've kind of created this this whole business that, like you said, like couldn't have existed 10 years ago. Like, what do they think now versus what they originally saw for you?
SPEAKER_02Yeah, it was actually my mom who said after I got that last rejection, like, you don't need them. Like, go do, go do the thing without them. And my family's been just so supportive of everything I've done. And like, truly, when I was starting to think about leaving my regular full-time job to do this full-time, they were only the most supportive. Teddy, my husband in particular, was kind of like, What are you waiting for? I was thinking I was gonna do it like in nine months from when I first had the idea, and he pushed me to do it like within four months.
unknownWow.
SPEAKER_02Okay.
SPEAKER_00Well, one, incredible. And two, obviously, you you do this all throughout your four years of college.
SPEAKER_02Yeah.
SPEAKER_00What did you major in?
SPEAKER_02Public relations and journalism.
SPEAKER_00Okay, duh. As you should. That makes perfect sense. Okay.
SPEAKER_02It worked beautifully.
SPEAKER_00Yes. And then what was your first job out of school?
SPEAKER_02Yeah. So my first job out of school was the marketing manager for Life Alive Organic Cafes.
SPEAKER_00Okay.
SPEAKER_02And that was not an existing job that I found on a portal. Um, I had interned for them, kind of. I interned for a guy who was doing the PR for Life Alive, and I helped them open the Brookline location, which was perfectly located on BU's campus. Yep. And I loved the brand, I loved the food. And from doing that internship, I got a chance to have time with the managing partner, and I really appreciated him too. And so I remember senior spring, I wrote him an email and I was like, I think I should do your social, um, peer my qualifications. He already knew my work at that point. And I remember I didn't hear back from him for two weeks, and I was like, oh, I blew it. I should have done it differently. And then I got an email that had his cell phone number and it just said call me. And I called him and he was like, I want you to do some like sample Instagram posts. And if that goes well, like the job is yours.
SPEAKER_00So what I'm hearing behind your story is this level of persistence. Um one, just kind of in the world that we live in today, and this is no shade to anyone. Like, I know that we all have a hard time, but especially, you know, I feel exceptionally grateful that I didn't grow up with the internet, with a phone, with social media, all that kind of stuff. And so it's not any shade to anyone who's younger than me for sure. But working with kids, working with young people, I do see a level of people getting discouraged really quickly, um, being too anxious to start, uh, being really afraid of of Like being embarrassed, even if like none of their peers would know that they applied for something or whatever, but right just the thought of being rejected or the thought of having to apply for something three times and getting rejected all three times, it's something that you just see a lot of people not everyone, but I just see a lot of people give up faster than they should. Um, you don't see a lot of younger people who are like, you know, emailing the managing partner and being like, you should create a role for me, and like here's why, and I know I would be great at it. I think it takes guts to do that. I think it takes a lot of trust in yourself to do that. Where does that come from?
SPEAKER_01Hmm.
SPEAKER_02I feel like I had a lot of support growing up, and that like family members and teachers just were always validating that I was like doing a good job, and that like I I feel like from an early age I was told that I was creative. And I I know some people have like mixed feelings on saying things like that to children, but it like it it stuck in my mind, and so I felt like everything that I did, I was allowed to do differently because I was told I was creative.
SPEAKER_00Ah, so good. If nothing else, you need to let your parents like listen to that clip of the podcast so that it will feel so warm and validating to them to know that you know, because we're uh there's gonna be like some way that, you know, you're gonna screw it up, right? Because no one's perfect. So as you're raising your kids, you're like, I don't know what I'm doing. But when something like that works, when the feedback that you give your kid and the validation you give your kid when they actually can bring it with them into adulthood, I think that's huge because then you actually believe it and then you go and live your dreams, like God forbid, like how everybody wants that. Yeah. So cool. Wow, I loved your reaction. That felt so good. I love it. Well, of course, I think about Zion and and I hope that I don't know, 20 or 30 years later, he can say, Yeah, my parents invested in me and it meant something. So yeah, I'm gonna have a reaction because your parents sound great. I love it. I love it, I love it.
SPEAKER_02Well, Zion will thank you in 20 or 30 years.
SPEAKER_00If he doesn't, you and I will have a conversation. I'll be like, you need to call this boy and tell him that his mom did all the things that she was supposed to do. Okay.
SPEAKER_02I'll call him and say that anyway.
SPEAKER_00Thank you. I appreciate it. I appreciate it. So life alive. What did you learn from that role that informs how you are moving forward? What informed the next phase of Bucketlist Boston? Because I think that's when you started to really blow up, right? The tens of thousands and beyonds.
SPEAKER_02Yeah, for sure. I mean, the first time that I was no longer a student and had like, you know, free time, truly free time, working full time, but also the rest of it being for me. Like I wasn't in clubs anymore. I didn't have class all the time. And I was able to start to figure out what it looked like to use my free time to continue to explore, but more as an adult and a graduate of college. Um, but then the pandemic hit like shortly thereafter. Um, so I was in my job only less than six months before COVID started. So that was a big pivot. Um, that was a lot of like, okay, now I can't go to restaurants and feature them, but the restaurants are asking me to come pick up takeout and to like create content around it in my kitchen at home. Um, so that also just stretched me. Um, of course, it stretched everyone, but that in particular was like the biggest way that I was stretched um during the pandemic, in addition to like, how else do I show the city and what's going on, but stay safe and like follow the guidelines. So, and not like encourage people to be going outside all the time, but also like we need to go on walks and like how do I represent that? And like just like you know, striking the right balance of you should still be outside exploring, but be safe. Um, so I mean, that wasn't exactly my job informing what I was doing, but that was like the time that I was living in. Yeah. Um, but I doing the Life Alive social media was my first time managing someone else's social page. So that's a lot of where I learned to focus on analytics and like what the numbers meant. Because before that it was really a passion project for me, but it changed once it became a job for Life Alive and like learning what the right ways to present it to non-social media experts on the team was like what what did they need to know? And like what stories was I telling them about what was working and what wasn't working? So I feel like that's when I like was able to put like my business cap on and apply it to social media.
SPEAKER_00That makes so much sense. So then when did you realize what was the moment where you were like, I'm going, I'm I'm going to quit this job. I'm going all in on myself.
SPEAKER_02Ooh, we have one job in between. So we do. Yeah. One more job. Did I know that? I don't know. Let me know.
SPEAKER_01Okay, go.
SPEAKER_02Okay, so so while I was at Life Live, I actually got approached by a startup and it's called Joyraft. It's part of the Boston calendar. Right, right, right, right. Yeah, yeah, yeah. And so I was actually consulting for them while I was at Life Live still. And I was doing social media and brand consulting for them. And I loved it. I loved how much there was overlap with what I was doing at Bucketless Boston with the Boston calendar. And so after a few months of consulting, they were kind of like, please join us full time. And I felt like a good time. I had been at Life Live for three years at that point to go try something new. And so I hopped from Life Live to Joy Raft and the Boston calendar, and I learned a lot there as well. I learned a lot about how to explore the city. We were very focused on what we called first to know content. So, how can you break the story? Like, we really took a journalistic approach to what we were doing, and I loved that. And I learned even more about like the analytics and the metrics and like what to look for, what to strive for. Um, but I would say like a a lot of overlap in what I was already doing and loving around exploring Boston and sharing that with a community is what I was doing over at the Boston Calendar.
SPEAKER_00If someone's listening to this and they're needing something to anchor on to because sometimes making content and being on social media can just feel like screaming into a void. When it comes to analytics and metrics, what's like the one or two things that people should know or that they should focus on if they're trying to grow an account?
SPEAKER_02Yeah, um, I love that you asked that because it's changed so much in the last couple of years. When I started, everything was about follows and likes. And now that pretty much doesn't matter at all. The things that matter are shares and saves because what that says to the algorithm is that either someone wants to talk about this with someone else and have discourse around it, or they're saving it for later so that they can hopefully come back to it and actually do something about it. So if it's a cooking recipe, are they then making that recipe, or if it's a place to go, are they actually going? Um, those are the metrics to look for now, um, which is it's so interesting because it's very different from when I started.
SPEAKER_00Do you remember when TikTok blew up during the pandemic and everybody was just trying to be a dancer or trying to be funny or like just trying to be whatever was working at the time, even when it clearly was not what they were interested in? Is that what we should be kind of going back to?
SPEAKER_02No, never. I mean, I'm a staunch believer that no matter what's going on and whatever metrics one should be striving for, there's a way to apply it to your niche or your brand in a way that is authentic. I mean, I was never dancing on TikTok, but that is not savable or shareable content. Unless it's like the most amazing dance in the world and someone's saving it so that they can like laugh at it or enjoy it later. It's uh a flash in the pan type of content versus if you create a recipe or a guide or something that's highly valuable that someone will either want to talk about with a friend or save to be able to refer back to later. That is just going to have much it's going to yield better results. And it's actually like it should, I think it should feel even better to create something like that because you're you're making the world around you better.
SPEAKER_00Good point.
SPEAKER_02Not that dancing isn't. I love dancing. I wish I could dance.
SPEAKER_00Same, same. But, you know, like you also have to be authentic. Like some people are dancers and we and we watch mesmerize because we could never, or some people are incredibly good at taking what's popular and teaching us how to do it. But it's still the principle that you spoke of is still applied. It just it's still serving, or it's still I'm saving this so I could do it later, or I'm saving this so I could share it, or whatever it is. Um, that makes so much sense. So now I get to go. When did you start working for yourself? How did you make that choice? What was was that scary? Oh yeah.
SPEAKER_02Did you ever question the scariest part? Was telling my current team that I was leaving. Oh, yeah, I I love them. I still love them. Um, and I feel like leaving is really hard for me. It was at Life Alive as well. Having those conversations feels like a death or a breakup, and those are just challenging and and sad, but also they set you free and allow you to take on that next challenge or that next exciting chapter.
SPEAKER_00What was the like, were you just feeling friction of like I just I know that I could do something more? Why couldn't Bucketless Boston have just stayed like this side thing that you made money from still? Like, why did it have to become your full-time job?
SPEAKER_02In the back of my mind, early on from when I started, it was always like a oh, I wonder if I could do this full-time. It was always a question in the back of my mind. And the longer I did it, the more, the more loud that question became. And then when my I got married in June of 2025. And so in the fall of 2024, in my mind, I was like, I will be working for myself by the time the wedding comes around because then I can take the honeymoon and like not be taking time off. And like it seems like a good moment. I'll be on Teddy's health insurance. Like, it just seemed like the right time to if I was going to try working for myself to do it. And once I voiced that to Teddy, I think I got actually first said it in the summer of 2024. Like, what if? And then I was like, I think I'll leave in May. And he was like, What are you waiting for? Like, why are you waiting until May? And so I ended up giving my notice in September. And I started working for myself in December of 2024.
SPEAKER_00So it's been a little over a full year.
SPEAKER_02Yeah, exactly.
SPEAKER_00Oh my goodness. Give me like the best and the worst, or like the most joyous and most scary.
SPEAKER_02Oh, it's been amazing. I love it. It's it's not scary to me. Wow. Why? Because I've spent 10 years doing it and I know that there's something there that speaks to people. And it's it's so powerful when I meet someone and when I tell them like what I do or who I am, that they say like they went to Providence because of me, or they went to Newport and went to the specific mansion I posted about because of my content. I get anecdotes like that, and they're just so impactful. And it tells me that I'm doing something right.
SPEAKER_00I love that so much because I'm also thinking of there's this organizational psychologist that I love Adam Grant. Yes, I love Adam Grant. Yes, love him, love him, love him. And he talks about like when you kind of feel I'm totally paraphrasing, those are not his words, but like when you kind of feel like icky or unsure about marketing yourself or selling your services or whatever, it's kind of like that's how you think about it. You think about the impact to people, you think about what you bring to people's life versus you and how you feel about it. It's moving all of the focus onto the work, not your brand and your ego and your whatever. And I think that's almost like what I'm hearing from you, which is like it's kind of not even a question because you are this conduit for something that's just helpful, but also joyful and fun and aesthetically pleasing. And you know, we're all really busy and flying all over the place. And, you know, it's literally truly helpful when we could go to a page and be like, okay, what do I do for date night? Okay, what do I do for girls night? Okay, I need a coffee shop in the South End. What are my options? And it's right there. Someone has already done that work, which especially as a mom, saves me. When I can just send my husband something from your page and like, please just look at take me somewhere from here. It is truly life-changing and time-saving.
SPEAKER_02I love to hear that. And that, like, I hear anecdotes like that, and I like it's so easy for me to keep doing what I'm doing and to do more because it it's fun for me, and I know the impact it has on people like you, but also on the businesses.
SPEAKER_00Yeah, yeah, that's so true. So now it's time for you to reveal what your full-time job now encompasses because you're not just taking pictures and giving recommendations. You've actually expanded uh how you work with people in businesses. So can you tell us what you do?
SPEAKER_02Yeah, so on top of running the Instagram and the TikTok bucket list Boston, and more recently, I just added YouTube. Um, I'm also working with brands, local businesses, on their social media and brand consulting. So I come in and I build brand pillars with them and I build a social strategy, and either I work with their existing social media manager to execute that strategy, or I bring in my own person to execute my strategy and almost work as like a conduit social media person under my bucket list consulting umbrella, but you know, doing social for that business. And that's um like new as of the last six months that I've been doing that, and it's been so fun to be able to give back to the community with what I've learned. And it's like a little bit of imposter syndrome, but I'm like, oh, everything that I did to build my page, like when I teach other people what I did and they do it, it it helps them grow too.
SPEAKER_00There you go. That makes sense. It does, but it's still really cool to see it. Yeah, yeah. And you've you've got to be so proud to see your work out there and working for other people.
SPEAKER_02Yeah.
SPEAKER_00Definitely. What do people not understand about being an influencer? Right? Some people, you even mention the word influencer, and people are like rolling their eyes, they're pissed, and it could have this, you know, like people could just think, well, all they do is, you know, take a picture and post it online. Like, why do they deserve XYZ? But what do people have wrong about what you do?
SPEAKER_02Yeah. Um, definitely what you're getting at. It it can look easy. And I walk the line of wanting my content to look effortless, but to have immense value and to be packed with information and to be something that's worth sharing or saving. That actually is the thing that pushes someone to maybe take that day trip to Marblehead, Massachusetts, or to try that new restaurant, or to not go to the same coffee shop they go to every Saturday and to try something different. So I it there's a lot of research and work and vetting and validating that goes into anything that I post.
SPEAKER_01Yeah.
SPEAKER_02Everything you see on my page is a genuine recommendation. I would go back there, I would tell you to go. I would be shocked if you didn't have a good experience at anything I posted. And that's because I take my recommendations very, very seriously. And I am all about building loyalty with my audience. The second I post something because someone told me to, or because I'm being paid to do it and I don't actually think it's good, I'm gonna start losing that credibility. And then what's the point?
SPEAKER_00Yeah, yeah. Have you ever had to turn down jobs because maybe you go to this restaurant or this coffee shop and it's like not as good, or the people are not nice, or how do you manage when it's not representative of who you are and what the page is?
SPEAKER_02Yeah, it depends. If it's like they're a local spot and they were gonna trade me a meal or a drink or something like that, and I don't have a great experience, I'm happy to talk to the owner and like give that feedback. Fortunately, this doesn't happen very often. I do a lot of vetting, like I mentioned, where I'll look on Google reviews and I'll talk to people and I'll just get the vibe of a place before I commit to going. But once in a while, things may require feedback and I'm happy to deliver that. And then the other piece is if I go to an experience or something that maybe didn't exist before is a one-time thing and it's not amazing, I'll give that feedback too, and I'll explain why I don't feel comfortable sharing it. And the times I've done that, I've been well received.
SPEAKER_00What about when people are um expecting you on your page to speak out about issues, anything from our own government politics to uh anything that's happening globally? Like, are you ever confronted with people saying that maybe you're not saying anything or you're not saying enough, or why aren't you posting about X, or I haven't heard you say anything about X? Do you encounter that? And how do you kind of uh manage what the brand is and what people may be expecting from you?
SPEAKER_02Yeah, I definitely encounter that. Not too much, which I think is good. Um, I think people who have followed me for at least a little bit of time, I hope understand. Like, I'm on the internet to be like a sunshiny corner of the internet and to give people something to inspire them or to smile about and feel good about. There's so much out there that's not meant to make us feel good. And I don't want to be that source of someone's stress or, you know, like upset that day. But given the platform I've built, it is my obligation, I feel, to use it when I need to to speak out around politics or movements happening, whether it's local or across the country. So I'm always try trying to strike the perfect balance of showing my community like where I stand and sharing resources more than just sharing where I stand, because I think just saying that I believe in something isn't enough anymore. And that if I am going to think about the most powerful way to use my platform, it's also to then give back in the sense of education, resources, support for the right groups and organizations around Boston. But it's a really delicate balance because you got to remember why people follow you in the first place. For me, they're not there to hear about politics, but it is also part of being a Bostonian. And so election times, I definitely speak out more around causes and policies than a non-election time. But things pop up and I'm constantly asking myself, is it my place to speak out? And and how do I do that properly?
SPEAKER_00I I really appreciate that you're so thoughtful about it because we're we're we as in society, as in people who are deeply feeling and affected by what's happening to us, our rights, other people. You know, I think that like we feel powerless and uh hopeless. And that sometimes leads to feeling like you're out for blood, right? So it's like you look at somebody who has a big platform and you're like, you could be doing XYZ. Why aren't you doing XYZ? And I I think that. For me, especially now, I think that balance is important because life is not life is not all destruction and life is not all sunshine. I think that is what's to me hard about being on the internet is because you can't always capture everything in a carousel or in a 90-second video, and there's so much nuance that's lost, and there's so much that people do or don't do that you never see. And you're getting one slice of a person's time and their humanity, and it's you know, it's just it's just a tough balance. It's a tough balance. It is, yeah.
SPEAKER_02We're all trying to figure it out and do the right thing.
SPEAKER_00Yeah, for sure, for sure. Um, so I wanted to end with a little bit of rapid by ya. Yeah. Just like a couple of just a couple of things, a little bit of things. A place in Boston that you'll never get tired of.
SPEAKER_02Yeah, Athena. Same! Oh my god, I love it there. I love it there so much.
SPEAKER_00Uh, a place in Boston that changed your life. The public garden.
SPEAKER_02I got engaged there.
SPEAKER_00Very sweet. Shout out to Teddy. Shout out. Something that is still on your personal bucket list.
SPEAKER_02Ooh, okay. I most recently was saying I really want to go to Florentine in the North End because I heard that Assembly Designs did the basement, and I love everything she designs.
SPEAKER_00Okay. Hey. Anyone listening? Hello. A recent moment where you felt proud.
SPEAKER_02Oh, wow. I just celebrated 10 years from the day that I started Bucketless Boston. And in the same vein of pitching myself, because I love to do that as a PR person, I was planning to reach out to BU to be like, you guys, let's do a feature. Like, this is kind of cool. And before I had a chance to, a journalist from BU Today actually wrote to me and said, We know that you're coming up on your 10-year anniversary, and can we interview you?
SPEAKER_00That's awesome. Thank you. So I feel very proud of that. Yeah, that's really cool. Really, really cool. Is there anything that I have not asked you that you wanted to say?
SPEAKER_02Yeah, one thing. Yeah. Something that I'm focused on and working on this year is making like a Bible of Boston and having a guide that lives on my website. Because to your point, around like you may go on my page and look for a good date night spot with Mark and you find a post. Like sometimes it's really hard to find posts on Instagram. There's no way to search on someone's page. You could know that I posted like great date night spots in the South End a couple months ago, but look, go to look for it and you just won't find it unless you've saved it. And so I think it's really important that I take all the knowledge that I've garnered over the last 10 years and put it into one place that's very easily searchable and just like, you know, you can keep it on your phone and open it or whatever. Um, so that's something that I'm excited to be working on.
SPEAKER_00That's really exciting and so helpful. Thank you for continuing to serve the people. We need my job, of course. And as a closing, can you share with us one mantra or piece of advice or something that you live by that you can leave as a parting gift?
SPEAKER_02I would love to. Biggest piece of advice is that you don't need to find your dream job on LinkedIn or indeed or from your professor. If you know something that you're passionate about and that you can find the intersection of that with what you're good at, you can go create your dream job. It doesn't need to be pre-existing. And I think in school, we're often taught to like take the path of being a doctor or a lawyer or going to business school. And I didn't do that, but I took what I loved and what I was good at, and I was able to create multiple dream jobs. So go make your dream job happen. Don't think that you need to be confined to what society tells you.
SPEAKER_00Hey, man, thank you for that. I'm receiving that in real time. This was such a great conversation, and I'm I'm so grateful for just having this like picture of your journey and how persistent you've had to be. But it sounds like to me that you have this guiding light that you just sort of follow and that you seem to be pretty unyielding in your vision, and that has allowed you to clear your own path. And I admire that so much. And I love to see it in other women because I feel like if I can see it in you or if somebody listening can see it in you, then like we can see it in ourselves and do it for ourselves. So thank you for being such a great influence on all of us. My honor. Thank you for having me on your podcast. Thank you. Thank you, thank you. All right, so tell the people where they can find you, follow you, work with you, all of the things.
SPEAKER_02Bucketless Boston on Instagram, TikTok, now YouTube as of last week, and then bucketlessboston.com.
SPEAKER_00Yay! All right, you got it, people. Follow, reach out, do what you gotta do. Support Kate. Kate supports us. That is the ecosystem. That's the best of the internet. And we will see you next time. Thank you for having me. Thanks, girly.