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Wayfinding with Rebekah Bastian

Way Finding is OwnTrail’s interview series where co-founder Kt McBratney has an authentic conversation with a guest about the detours, decisions and twists in their professional journey. In this episode of Way Finding, they discuss finding your way through change with none other than OwnTrail CEO and co-founder Rebekah Bastian.

Kt McBratney:
Hello, hello, welcome to another episode of Wayfinding, brought to you by OwnTrail. We will be joined in a second by our amazing guest who I will introduce to you but also needs no introduction, I’m still gonna give her one. If you are new, this is Wayfinding. What is Wayfinding exactly? It is a LinkedIn Live series where we go behind the resume, where we have the real talk that you wish you could have on here but aren’t having, (which is what we have over on OwnTrail). We’re going to talk about the detours the decisions, and the things along our journeys, personal and professional, that bring us to where we are today.

I’m Kt McBratney. I am the co-founder of OwnTrail. And I’m excited to be here with you today. If you haven’t heard about OwnTrail, you should absolutely check us out, we are, really what we do is help you blaze your own trail to lead a more fulfilling life. And so much of that is often connected to how we spend at least a third of our life, which is at work. And what we’ve learned over at OwnTrail in the past two years and over 26,000 individual milestones people have shared on there is that often kind of some of the first changes that we make towards a fulfilling life or towards a more fulfilling life, a life led by our values, our goals, our definition of success, those first steps often involve our career. So what better place to bring those things together than bringing OwntTrail into LinkedIn. And going live where we can be real authentic, you can see my messy office, it is very hot outside, I’m not going to pretend that I’m a professional when it’s hot outside, I’m still a professional in a tank top. So we’re gonna go real, have real authentic talk.

And we’re going to have an amazing guest, because our topic today is finding your way through change. As we go, pop your questions in the comments. If you love what you hear, smash the emojis, invite friends. This is something that is interactive, and is really not just a dialogue between me and our guest, but a conversation that we want to open up to everyone here. So without further ado, I will invite our guest, who is a product expert, a tech executive for more than 15 years, she’s a founder and an entrepreneur, an angel investor, an aerial acrobat, an author, a parent, a great friend, and so much more. Her trail, which we’ll share with you, involves lots of different changes. And today we’re going to talk to her about how she found her way through all of those things. I’d like to welcome to Wayfinding, my amazing co-founder and the CEO of OwnTrail Rebekah Bastian. Hello.

Rebekah Bastian: Best intro ever. Thanks, Kt.

Kt: You’re welcome. It was easy to do. It’s easy to do a good intro when someone is as authentic and embraces their ‘ands’ like you do. And it’s one of the things that actually — fun fact — made me say I need to be her friend. When we met at a networking event, out of all the people there I was like, she’s she’s she’s the one. And here we are today. So Rebekah has been watching Wayfinding, since we launched it a few a few weeks back and was so gracious to accept the invitation to be on our own show. But it’s gonna be a little bit different than our usual co-founder conversations. And we’ve got some questions that we’ve gotten from our social audience as well, that we’ll be sharing along the way. And then live our amazing social manager will be making sure to, to pipe in anything that anyone is asking live, and continue to ask them in the comments because this will live on our LinkedIn page. As we get started Rebekah — and Liv if you can go ahead and pop in Rebekah’s trail so people can get to know her — I want to ask you, what does change mean to you?

Rebekah: Oooh. Also fun fact, we didn’t prepare for any of this.

Kt: Again, this is not scripted. We are going live and real, which you don’t usually see on this platform.

Rebekah: Yeah, no, it’s a good question because I feel like I wanted to answer it, like the same word but you can’t you don’t get to do when you’re doing definitions. Moving from one state or thing to a different one.

Kt: What has been a recent change that’s been hard for you? And how did you find your way to it? And through it? Because I think that those are different things, right? Especially thinking about how you just define change as a state of transition, right? It’s a movement, it’s a motion, it’s an action. And so how do you know that you arrived at change? And how did you move through it?

Rebekah: Gosh, I mean, you know, like, I just got my 11 year old his first iPhone, I tell you that it’s a little bit accidental, too. But like, I think the change of like, he’s becoming a a — this is my older kid. And he’s becoming a preteen and is looking for lots of independence and, and the the change, but it’s also kind of, you know, still a little bit of a baby too. And like, I think we’re both grappling with some changes there in that transition. So in terms of most recent, that was the first one that came to mind. But you know, we also had a pretty big OwnTrail launch last week. And the interesting thing about that, so last week, we rolled out memberships, and we expanded to all genders. And that was a really big change for us. We started as a women’s centered platform. And for a lot of reasons, and equally intentionally and with intersectionality in mind expanded to all genders. And the interesting thing is that I think I grappled with that change, when we first started working on it more, and by the time we actually launched it, I had really like, gone through all the different feelings around change. So there’s, which is another interesting thing about change is that it can, you know, the timeline can be different for different participants of that change. And for us, our timeline preceded the announcement by several months, as we’ve been, you know, working on our strategy, talking with our community members, researching all of that, and then it’s like, the launch moment is when others experience that change. And so, which fortunately, we you know, I feel like we’ve been hearing really good reception to it so far. And in terms of what that change means to the different people in our community.

Kt: Yeah, those are two really good examples. And I love that you brought in something personal and something professional, that were unfolding simultaneously, right, because so often, when we talk about what’s happening in our professional lives, it gets siloed away from the things that are also happening in our personal life. And the fact that change might be happening on multiple avenues, at the same time, is deserving of space and acknowledgement. And even though those were very different things, you were managing them at the same time in different ways. And that makes me think of one of the questions that we got asked from Isaiah on Twitter, and that was about making good decisions. Or no, it was actually about — who was that? That was one of the inventors NFT folks — was curious about how you did realize your vision for OwnTrail, how you found yourself ready to make that change. Because I think that that’s something that comes up a lot, or questioned a lot in any founder’s journey is how do you know that it’s time to make that change, and time to make the change to realize the vision. Everybody’s got great ideas, y’all think like, this could be the next big thing…if only. How did you get to that point where you were like, I’m going to realize this vision and make it happen?

Rebekah: Yeah, I would say there were two kinds of points of time. And then obviously, like the the act of the act of change can be a very drawn out thing without a definitive beginning or end. But I did there, I can name two aha moments that were points in time. One was when so you know, I’ve written my book, Blaze Your Own Trail. And that is a choose your own adventure kind of exploration of the different decisions and pathways that women take through our personal and professional lives. And so in the book it explores all these different paths, and I get signed with my publisher, Berrett Koehler, and I was kind of starting to think about, like, marketing, you know, which I don’t know that much about. But I was like, Oh, what if — so my version of marketing turns into a product, of course — and so I started thinking about, like, oh, this could be a really cool book launch platform where people could share their different trails, because there’s, like, you know, 19 different endings in the book, but that’s just obviously a finite subset of the infinite paths that we take in our lives.

And so I kept talking with people about it, and I, you know, that feeling where there’s, like this idea on the tip of your brain, and you need to like, it feels like you need a sneeze kind of thing. And it was just right there. And I kept having conversations with different people. And I was already at this point where I’m like yeah, people could see what their trail was, and it could be like, you know, cool, viral social kind of thing or whatever. And, and then there was one point where, just, you know, kind of a random guy that worked at my company and asked me for, to meet to talk about his career path. And you know, and I just say yes to all those meetings, and so, I was talking with him and he was talking about like, Yeah, I wish I just could see like different what different people’s paths to that. I think he was looking at going into product management or something. Those were — and then all of a sudden

I’m like, Wait, that’s it! And this poor guy, like, I wonder if he still remembers that meeting cuz I like kind of freaked out on him and like, had this idea bowling and I think I just put it together and I kind of got myself out of that meeting and call my husband. And I’m like, I know what that was. And that was kind of like that aha moment of like, oh, the power of seeing what other people’s journeys are as it relates to where you’re trying to go. And especially like to, when you’re able to see based on the different identities that you hold, or experiences you’ve had. So this idea of like people who look like me, seeing seeing their paths to this place that I aspire to as like, oh, that’s where there’s so much power here. It’s not just this individual, like share my trail, share my trail, but it’s like, how do they fit together? And how does seeing that real journey impact the what you see for yourself as being possible? And so that was kind of the that one aha moment.

And so I actually, that night stayed up all night thinking big ideas, as you know, I do. And I called, or I emailed Carolyn in the morning. So Carolyn, our VP of Engineering is one of my old friends. She and I actually used to commute to Microsoft together back in the day. And we hit been hanging out a few months before and I was telling her about this book, I was writing everything and she goes, Oh, cool. Well, you know, she’s Sse’s an engineer. And she was like, Well, if you want someone to make a website for your book, let me know. I’m happy to do it for you. So famous last words…

Kt: Little did she know…at the time. That’ll be that’ll be a follow up episode: Carolyn, did you realize what you’re signing up for?

Rebekah: So I called, I think I texted or emailed her that morning. And like, can you get lunch today? And so we went for lunch. And I was like, delirious friend who had been up all night with big ideas, and they think there’s a thing here. And she’s like, you know, try to try to follow along. She’s like, cool, let’s explore it. So, um, so that’s kind of how that idea was born and start playing with that, and I met you like, right around that time, shortly after. And I think I was somewhat more coherent by that point in terms of talking about what we’re thinking about there. But that was one moment of like, this is the thing that’s not just a book website, you know. Um, and then the other AHA point, I remember, this was when we’d already been building our OwnTrail for a while. And so this was like December of 2019. Right. And I think we’d started working on it in like, July, August of 2019. So we’ve been working on it for a while, I had been very transparent. I was at Zillow. Still, at the time, I was very transparent about, hey, working on the side project, it’s related to my book, I’m really excited about it. But like, it was very much this is happening on the side. And we talked about, like, you know, maybe someday we’ll put our to do this whole time. Let’s see how it goes after the launch, you know, and so we were going to wait and launch and see what happened and everything. And I think it was when I was in Mexico, for for vacation that December. And you’re just I remember sitting on the beach, I think I drew a picture of trails in the sand and send it to you. But I remember thinking

Kt: Oh, I remember, it was a drawing with a stick on the beach right around sunset…

Rebekah: Yeah, exactly. Like because, like the self-fulfilling prophecy, you know, like, if we wait and see how it goes, then it has a much likely a much less likelihood of really taking off. And if we like just go all in, you know. And so we, I know you and I and the rest of the team, we talked about that and kind of had that idea that I think it is time to, to decide now at least let our jobs know that we are planning to go all in. And so I went back to work after New Years of 2021 and gave my notice and the funny thing was that my manager is what I told him was like, oh, yeah, I knew you’re gonna do that. I saw that coming. I was like, Oh, really, I didn’t even see it. Apparently he could tell I was so excited about the side project. So…

Kt: What I hear and hearing you talk about this, and these aha moments that led to these big changes and into realizing this vision was that it was really about reflection and self-awareness and acts of authenticity that led you to realize the change. So change isn’t just the action, right? It’s also knowing, recognizing the opportunity, and recognizing what was right for you. And what excited you.

Rebekah: Yeah.

Kt: What I love about that is it feels like something that gets talked a lot about is how to practically navigate change, like how to tell your boss you’re leaving, how to incorporate your business and those are all really like necessary topics for navigating change. And also, none of that can happen without what you just described, which is this act of self-awareness, reflection and authenticity. Your you can’t actually make those powerful changes that then have all of these time practical steps.

Rebekah: Totally. And I think, you know, I mean, well, while there’s like, there was a point in time aha moment, and those stories I shared. And there’s obviously a point in time, like the day that I went from, you know, well, they, the day that I gave my notice was a point in time, the day that I actually stop working two jobs and move to only working one startup job was a point in time, right. But I think there’s, but there’s a lot you can do to pave the path for those. And it doesn’t have to be sudden and uninformed either, right. So like, definitely OwnTrail, like, we’ve been working on OwnTrail for six months before I gave my notice, or five months or something. And then I did a four month transition out of Zillow, where I was like, really planning my exit. So really, there was a, you know, a total nine months there where I started working on OwnTrail I still had a corporate paycheck, right, um, but also not just the paycheck part, but also like building the team and fleshing out the idea and doing the research and working on it. Right. So like, you know, the the transition from kind of side thing to full time thing, I think, like, that’s a really important part of the transition process, too. And like, this is an extreme example.

But even within Zillow, like I had spent years doing side projects relating to like culture, and social impact, and equity and belonging, like I’ve been doing that for years. And then I made a big pivot from Vice President of Product to Vice President of community and culture, after having laid the groundwork both to prove to myself that this is a new area I wanted to go into, but also to prove to others that I could really lead in that space. And I’ve done similar things with like starting our mobile apps on the side for a year before moving fully into that space. So like, I think there’s so much power in trying trying things out. I also like, those are some great examples of things I did on the side before making a big change. There’s also examples of things I’ve done on the side and definitely that like, I’ve been doing aerial acrobatics for 13 years, I don’t, I don’t think there’s going to be a point in time where I quit everything and go join the circus full time, right? Like, I think that will continue to be a side thing of mine. And I love that. Or like, you know, I’m a writer, I’m not going to be I don’t think I’ll ever become a full-time writer. I don’t think I want to do that all day. But I love having that be a side thing. So not, you know, it also gives you the time to decide which are the things that belong in different places and different kinds of commitment levels in your life.

Kt: That that — Oh, sounds like we’re having a little bit of LinkedIn glitching out. So the folks that are bearing with us, I’m so sorry, I can’t control that. I absolutely would, I would say our team would look into it, but it’s not our team. So please bear with us

Rebekah: We’re recording in a way that we’ll be able to share.

Kt: Yeah, this is also being recorded so we’ll be able to repost it to our LinkedIn and also on our blog. So if you’re having some issues, let us know. We’ll pause for a second, not because this conversation isn’t great, but just to let LinkedIn maybe catch up with the fire that is happening here.

Rebekah: We burned them with our chatter, right?

Kt: We’re hitting it. We’re having such a good conversation that they don’t know what to do with it. So just bear with us while we let LinkedIn catch up. If I had a what do I have music? Maybe I can find music to play. Just play a little song. I will.

Rebekah: Do — is this going to fix it? This is this is a new solution. Instead of the hit restart, you just hit hit play on the music. No. Kathleen says she got a message that the live ended and restarted.

Kt: LinkedIn stopped our stream. Just one moment while we figure out what’s going on. I’m going to continue the conversation. I think we’re in a great conversation, we are recording it—

Rebekah: — for afterwards. That sounds good.

Kt: We can go back to it after after the fact. And we’ll just upload it and make sure it’s captioned and everything. So again, thank you for the folks who were joining us in real time. And we experienced some plot- product glitches which do come when you change your product, and we know that and thoughts and prayers for the LinkedIn team because that’s never fun. Nobody wants to get that that bug report.

Rebekah, what you were just talking about though, in transition being a period of change that is a lot like can be extended small changes and experiments and experiences that made me think of Isaiah’s question, which was around what’s maybe been a counterintuitive moment in your journey. And maybe that’s around change. Maybe that’s been a decision that you’ve made. But yeah, what’s been the most counterintuitive, counterintuitive thing that you’ve learned along the way and all the changes that you’ve navigated within your profession, general roles and responsibilities, but also in your personal life, becoming a parent, becoming a writer, and exploring all of your ‘ands’.

Rebekah: Yeah, I love that question. I mean, there’s a few, but actually, it’s since you just mentioned the parent thing, I’ll leave that as one of the counter- the bigger counterintuitive things is that, for so long, I had this idea, which didn’t come out of nowhere. It’s an idea that has definitely been been passed on to us from from a lot of different systems. But this idea that I had to get to wherever I wanted to get in my career, before I had kids. I knew I wanted kids, but I had to get to whatever point because then once I had kids, then it was all just kind of dead from there, and there was no more advancement. And, and I was trying to have kids for a while. And that didn’t happen, I was trying to get promoted for even longer. And that happened. And, as it turned out, I ended up getting pregnant and then getting promoted into people management when I was eight months pregnant with my first one. Um, and so I literally, like went into labor at the office. And one other story, and then came back to, you know, a team of several people I’ve never met, before my first time really managing people, we were a newly public company, we were in a new building, so big change there. And, and, and I couldn’t have been further from the truth in terms of like, what it would be like to be a parent and be in this new leadership role. Like, I feel like becoming a mom made me such a better leader than I would have been otherwise, like, in terms of the empathy and the, and also just the time management and efficiency of being able to work smarter, not harder, you know, and I was very, like, I, as soon as I had kids, I was very clear, like, I will be leaving by five every day to go get my kid from daycare on the way home. And that’s just what I’m doing. Right. And I think that was actually really good for the teams that I ended up growing from, like, you know, starting off managing a few people to having a pretty large order within the company. And, you know, I got moved into vice president and had, you know, leader of leaders and stuff. And I always set that precendent of like, you know, it’s not about face time, it’s about working smart while you’re here. And I think that ended up being good for, for my teams as well.

But, you know, then after my second baby, and shortly after that, I got promoted into my vice president role. And so like, I had been wrong about my career stalling once I had kids. And it wasn’t because I unfortunately, I was at a good company where I was able to grow without that need for like, over face time, or hustle culture, which helped, of course, but um, you know, I think that was that was counter to what I had thought would happen. And so that, I think that’s a really great example, because it’s one that I hear a lot of people worry about is like, how do these pieces fit together, and I think you can make it what you want. And, you know, for those that aren’t as lucky as I was to be in the company, where you are able to set those boundaries, then maybe it requires a bigger change of moving to a company or you know, creating something where you are able to those boundaries.

And along those lines, another really counterintuitive thing for me was I had for a long time felt very entrepreneurial, you know, I think I probably am just at my core, I you know, I wanted to be an inventor when I grew up. So but for so long, I think this was after, like having gone through the early startup days at Zillow were were just working around the clock, but it was fun, because that was like that was good for where I was in my life at that time. But then it was like, I could never start my own company because I can’t handle that kind of startup hustle. You know, I have a family now. I don’t want to be working 24/7. And this should be intuitive. But it wasn’t me a while to realize this that like, oh, when you start your own company, you can set the culture, right, you get to decide if it’s also culture. And Kt, you and I decided before we even like, when we were deciding are we going to do this that was one of the things we talked about is like, No, we don’t want to create that hustle, we want, wee believe that we can both build something powerful and impactful and successful and take care of our and our team’s mental health and life life balance or integration along the way. And that was something that was really important. And and, you know, so interestingly, in both of those examples, I think the counterintuitive part was what society has had told me versus what I discovered in myself. And that’s a that’s a beautiful thing to discover and turn out that you were wrong about in that sense.

Kt: I love so much of that. And I love that question, right? Because we’re so often told that like, what we learned will be what we expected or will be will be obvious and I think that there’s a lot to be gained, obviously from as you just share it from looking at like what we didn’t expect. That’s kind of the beauty of change, right? It’s like what’s on the other side of that change might be what we expected and it might be something completely different and it’s that learning and that finding out that’s really the constant. There’s a great reflection going on, an OwnTrail reflection conversation about change. And we’ll drop that in the comments as well so that you can follow along and join in if you’re an OwnTrail member, but really about how change is one of the only constants. And what you’ve talked about both from like navigating longer transitions, having those aha moments, and then the counterintuitive learnings really kind of tie that together, right? That theme that we’re always navigating some kind of change.

And I’m gonna throw you a different kind of question. And we’re getting close to time. And again, thanks for everybody who hung out for the live. And for those of you who are joining us from the replay, we’re figuring this out as we go, platforms are changing, technology changes. And we just learn as we go.

What have you learned — there are, there are 1000s of people OwnTrail. And as we’ve said, there are 10s of 1000s of unique milestones and about 1500 unique trails, right? You’ve looked at every single one of them. I know that for a fact. And also, if you’ve ever seen Rebekah or I appreciate your trail on OwnTrail, that is not a bot, that is not an automation, that is literally us being like, oh, like. So it is very real. What have you learned about change? Or what is maybe your biggest takeaway from change in witnessing how so many people like you and completely not like you have navigated it? Or have experienced it?

Rebekah: Yeah. I mean, I think that what one thing that’s been really interesting is like the way we think about change, oftentimes, in terms of like, the current state, I’m in changing to the next state that like that I’m working towards or that I’m moving into. And that’s certainly a very real kind of change. But two things that I’ve seen changing on OwnTrail, through what people share and then update on their trails, that’s really interesting is like, we can also like, what’s happened in the past can change too, because it’s a perception based thing, right? So like, there can be milestones in our past that, you know, maybe felt really bad in the moment. And then as we reflect further, we realized that that was actually a really positive thing. There can be milestones in the past that seem like they were exactly what we wanted. And it turns out that it’s not serving us. So like the change in our perception of past milestones and our stories around what our journey has been. And then there’s also change in what our aspirations are. So when you look at the aspirational milestones, like, I mean, oftentimes, and I’m a case of this myself, oftentimes there’s there’s ones that we’ve been reciting for so long is like this is, this is my next goal, this is the logical next step, and where I’m going, and that’s my aspiration. And then as you start to dig in, and reflect and get to know yourself more, which is definitely what happens on OwnTrail, then you you realize, maybe that’s not what I want to be working towards, maybe that’s not even directionally, where I truly want to be. And, you know, we talk a lot on trail about, you know, blazing a trail towards a more fulfilling life. And sometimes, like, where we thought we were headed, or where you’re supposed to be headed, isn’t necessarily what’s going to make us the most fulfilled and so changing our aspirations, also. And so like, to me, that’s really powerful. There’s like the act of of like, making that transition or change in the moments. And certainly I’ve seen people getting incredible help from the community on doing that. But also changing your perspective on where they’ve been and where they’re going is, which then, of course, leads to tactical changes as well.

Kt: So powerful, and that act of, of having the permission and giving yourself the space and the grace to change your aspirations is huge. I think of it almost as like a quiet change that is internal, that with massive, external outcomes. And that’s where so many of these powerful shifts happen. And I’m so grateful that you’ve actually talked about it, because again, we’re very conditioned, and especially in career culture, to talk about the outcomes, the problems, how did you overcome this challenge? What is one of your biggest strengths? We talk about the outcomes, when we’re really trying to get at the heart of the how and the why

And that’s one of the reasons that, technology glitches aside, we felt that LinkedIn was the right place to have these conversations. Because it’s where we’re craving them. And where it’s not happening. We’re seeing a void for it. And that’s also what what’s happening on OwnTrail, really to bring it full circle. I mean, that’s, that’s at the heart of why we founded what we founded. And what we’re building today and continuing to build on is creating a space and tools to navigate this change because it’s not going to stop. What what what new change is coming next week? We don’t know, we did not know when we started OwnTrail that three weeks later a global pandemic would happen and the absolute world would change. We had no idea any of that, and that’s a big example of a change. But also the little changes are all around us too. And I really appreciate what you shared that —I didn’t hear — all this, this is all, some of this is new to me too. And thinking about how we think about change, not just what we do with it, and what the metric is, or the outcome, but how we get to that point.

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