Cali O’Connor is a recovering corporate hustler. She didn’t realize it, but she was addicted to hard work and the praise that came along with it. The praise fueled the self-induced stress spiral which ultimately led to a breaking point.

Until this point she was distracted by her achievements within the company, but a day didn’t go by without wishing she was somewhere else. She couldn’t see herself continuing on this trajectory, she couldn’t see a position in this company where she’d be happy (despite 4 promotions in 3 years), she needed A BREAK.

So she left and pursued the ONLY thing she cared about. World travel. For 2.5 years. For the first time in her life she felt like she was doing what she was supposed to be doing. She will never forget the feeling that overcame her from her window seat on her flight to Nairobi…

So she started The Travel Shifters to help others do the same, to leave the corporate world, or at least their desks behind, and take the road less traveled, a life of adventure and loving what you do! We’re talking to her about starting her company, her world travels, and living in Mexico.

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Alice: Great. So, welcome Cali, we’re so excited to have you here.

Cali: Thank you. I’m so excited to be here.

Alice: Yes. Thank you for being on the podcast today.

Cali: Yeah.

Alice: So we kind of start off with some more fun questions or some quicker ones. What have you been up to in the pandemic? I guess that’s not as fun.

Cali: The first fun question. So, a quite a few different things. I actually was working a temporary job at the onset of the pandemic in International Education. And so, it was a crazy time because we had all these students from all over the world in my school in San Diego. And so, at the start of the pandemic, I was dealing with that. A lot of students leaving, trying to get back home to their countries. I get that it was a temporary job, it ended that June and I really needed some time to reflect and think, and I spent some time with family. I ended up going to Mexico at the end of 2020 for several months to gain some space. And yeah, during that year is actually when I birthed my business. And since then, I’m back in Mexico. I’m working on my business and I’m working remotely, staying safe but in a different environment.

Alice: That’s amazing. And for all of you who don’t know Cali, what she does is she started her business, the Travel Shifters. Can you talk a little bit about what that is?

Cali: Sure. So, it’s taken a number of iterations but right now we’re a community of burnt out professionals, people who kind of followed that social norm of going to college, getting a job, working till you retire, but really experience that burnout. We value travel, we value experience, but don’t really have the vacation time to make that happen on a deep level. So, Travel Shifters is really about breaking that social norm in order to travel more. So, whether that be taking a career break, so totally leaving the work force for a period of time, not retirement, or finding ways to work remotely or start your own business in order to travel and see more of the world on your own terms.

Alice: That’s amazing. And can you talk a little bit more about that? So, it’s been percolating in your mind who work for an international school, how did you break from the cubicle and decide to start this completely new business?

Cali: Yeah. So I’ll back it up a tiny bit. My background is in Chemical and Biomolecular Engineering which is not related to this at all. And I worked as an engineer in the oil field for a number of years, and it was really, really stressful, it was incredibly demanding. Some weeks I would work up to a hundred hours on call and get phone calls all night long, and I got to a point where I’m like, “This isn’t sustainable.” I can’t see myself in any position in this company because it’s a 24-hour business and I know that. I don’t want to get phone calls while I’m sleeping. And so, I just happened to be on vacation in Australia. I managed to finagle a few extra vacation days for my boss because I did a [inaudible] worked 30 consecutive on call days.

Alice: Wow.

Cali: And I was taking a scuba certification course, and every single person in that course was on a break. They were on vacation, they were traveling, and I was blown away. I didn’t know this was a thing people did, I didn’t know people traveled long term. I just thought I was destined to take a week or two off at a time, and then when I’m 65, I can go live it up. But once I found out it was possible, I couldn’t get it off my mind. I’m like, “I care about the world. I want to see the world for longer than a week or two at a time.” And so, from that point that I found out it was possible to the point that I made it a reality and actually quit my job was four months. And that’s the first time I did that, and it was the first time in my life that I just remember this feeling of being on a plane to Nairobi, Kenya and I’m like, “Oh my gosh, this is exactly what I meant to be doing.” And it is the most powerful feeling in the world and I wish it for everyone. It’s incredible.

Alice: That’s amazing. How do you talk to people about taking that leap of faith, taking that jump into the unknown?

Cali: Yeah. It’s really scary. And quite frankly, it isn’t for everyone, but certain people think about it. They dream about it. It’s on their mind. It’s on their heart. And when that happens, that feeling isn’t going to go away. And then what we do is come up with excuses as to why we can’t do it. And usually it’s like logistics. “Oh, I’m going to get promoted next year. I don’t have enough money or like this, that and the other thing.” And when you start making excuses like that, it’s fear holding you back. So really, it’s about paying attention to what is actually limiting you. This is what you want because you think about it all the time. And why are you so set on staying the same, following that path that everyone follows when what you truly want in your one life is to take this leap? So, it’s not easy. And we are creatures of habit, and it feels more comfortable to just continue and keep the inertia going. But in reality, the most amazing things in life happen when we do step outside our comfort zone.

Alice: That’s amazing, Cali. And can you talk a little bit about being in Mexico and starting and kicking off this business?

Cali: Sure. So, I’ve always wanted to work for myself. And I had this limiting belief that I needed to have this grandiose invention and that I would need to go on Shark Tank and pair up with an investor and all of these things. And I didn’t realize, quite frankly, to start your own thing, the barrier of entry is low. Anyone can start a service-based business. Everyone has skills to share with the world. And it took me time away from the workforce. It took my temporary job ending and me kind of being like, “What’s next, what’s next?”, to figure out that it was possible for me. So, during that time I listen to a lot of podcasts, I did what a lot of people do. We’re kind of scared as humans to do nothing. So instead we try to do everything. I took a bunch of classes online to try to figure out. I’m like, “I have to be passionate about something. What is it? What is it?” I’m looking and searching, and then I went to Mexico because I finally realized that I was doing too much and what I needed to do is nothing. I needed to stay it in the silence, that I needed to let ideas blow to me, I needed to just take the space to see what happened. And when I finally did that and I slowed down and I stopped with all that I was doing, it came to me and I’m like, you care about travel, you’ve said this your whole life. If you want to do something you love, it needs to involve travel. And then I’m like, I want to bring it in a community aspect. It’s really important to have like-minded people. And slowly, it started as travel and personal growth. But what I realized and what I had already done myself with these career breaks which incorporates all that I wanted to accomplish, it’s just that. It’s taking time away from the workforce to really explore yourself, get to know yourself better. And yeah, for me, because I was so dedicated to my job, because I work so much, I truly didn’t know what I liked, or cared about, or valued. And it sounds silly to some people, but for me, when people are like, “What are your hobbies?” I would freak out and like, ” I don’t know. I work, and then when I’m not working, I try to sleep. And sometimes I watch Netflix. Is Netflix a hobby? I don’t know.” So, I got to a point I hated that question. I’m like, “You know what? That’s silly.” I don’t want to hate that question, but the
reality was like I didn’t know myself, and that’s why I hated the question so much. So, sometimes you need that space to really dig into self-discovery, and travel can do that for you very easily.

Alice: That’s amazing, Cali. And where has been your favorite place that you’ve ever been? Is it Mexico, where you are now?

Cali: I love Mexico so much. Is it my fate? Well, it’s different. I’m sort of living here now. It’s a different vibe than when you’re traveling. A country that really stands out in my mind is just having everything that I could possibly want. It’s Oman. It’s a little bit not your typical tourist destination, but it is the friendliest country. The people are so generous and accommodating. It has all of the nature you could ever want. There’s desert, there’s beaches, there’s mountains. It’s just incredible. The food is good. And just for me though, traveling and having experiences with people and the fact that they care about you as a tourist and a traveler, it makes a difference for me. It was incredible there. And not to mention, you can camp all across the whole country. There’s no rules on that. You just bring your tents, end it up wherever you want as long as it’s not in someone’s house vicinity or a mosque. And so, that’s a cool experience as well.

Alice: Wow, that’s so cool. Oh, that’s interesting. I’ve never made it there, but now I have to put that on my list.

Cali: Yeah, put it on there.

Alice: And Cali, can you tell us your craziest travel story? Whatever that encompasses.

Cali: Sure. There’s a few, different levels of crazy, but my story will be something that I’m still kind of dumbfounded that it even happened. But I was traveling through Uzbekistan, another a little off the beaten path. That one time in Uzbekistan. In the city of Samarkand, it’s famous for this complex called the Registan, and it’s beautiful. It’s just beautiful, and that’s the main attraction there. And so at night we’re eating dinner and then we hear the loudest music, really loud, what is going on? So we decided to just pop over to where it’s coming from, check it out, and are immediately ushered inside by security to the most opulent wedding I’ve ever seen in my life.

Alice: Wow.

Cali: Yeah. So they feed us at a table, they start pouring the vodka shots immediately. We’ve become quite the attraction as nobody spoke English, and it was like, who are these people? And so, it was just fun. Everyone was so kind, so welcoming, they’re trying really hard to communicate, and some of them even had flip phones and we’re trying to communicate on the flip phone as opposed to like Google translate on your iPhone. There was dancing. And then the main thing that sticks out in my mind was the wedding cake and it’s ridiculous. It was a five-tier cake, and it went cake, aquarium, literally a fish tank with goldfish swimming inside, cake, aquarium, cake.

Alice: Cake, aquarium, cake. There were two aquariums. There’s not just one.

Cali: Whether goldfish swimming in this cake. So, I mean, it was amazing to be brought into this wedding, but the cake isn’t…takes the cake in my mind really.

Alice: Yeah. Oh my gosh, that’s just amazing. That story of hearing some music and then being ushered in by security. VIPs right here.

Cali: Exactly. I’m like, “Okay, I hope the bride doesn’t mind but here we are.” It was the biggest wedding I’ve ever seen, so she probably didn’t notice.

Alice: Wow, that’s amazing. What a great story. Going to go visit Uzbekistan.

Cali: Yeah. Put that on the list, too.

Alice: It’s the places I’ve never thought to go. That sounds incredible.

Cali: Definitely.

Alice: Yeah. And can you talk about a favorite travel book? What should we be reading?

Cali: Yeah. So, for me, when I read travel books, I love to get inspired by stories. So, one that sticks out in my mind is called Wanderlust by a woman named Elizabeth Eaves. And it’s just her travel stories from when she was younger, and she’s gone to some pretty awesome off the beaten path places as well like Papua New Guinea. And to me, that’s exciting and I love to just read about places that people don’t typically travel. So, I like hers.

Alice: Wow, that’s so interesting. Okay, I’ll have to check that out. Amazing. And, what are you working on right now? So you’re in Mexico, you’re still growing your business, can you talk a little bit more about what you’re up to?

Cali: Sure. So, actually I’m in the midst of my first course on taking a career break. It’s called Career Break Bootcamp, and I have some amazing founding members and we’re going through it together live. So it’s a four-week course and we just finished week 3, and we’re covering all sorts of awesome material and I’m gathering feedback along the way. And so, things that have come up are definitely money mindset going into it. So, on the next iteration of the course, I’m really excited to expand on that topic. Also, definitely limiting beliefs and taking the leap, and overcoming those spheres. So, I’m going to expand on that, as well.

Alice: Yeah.

Cali: Yeah. And we talked a lot about just planning and saving and budgeting, and that’s a big piece as well, just the whole logistical component. So, we’re all learning a lot. It’s been amazing so far. These are all people who are planning on taking a career break within the next year. And so, that’s very exciting. And it’s just a great group of people. We love to talk travel, we love to talk about leaving those jobs that aren’t necessarily serving us anymore and doing what we want to do, highest priorities to see the world. So, it’s exciting.

Alice: Wow, that’s amazing. That’s so cool. That’s great that you could have just these conversations and kind of know where you want to take your next workshops, too. With all about finances and the logistics, and what have you, taking the leap.

Cali: Definitely, exactly. So the next version, it’s going to be recorded modules that we can go on at our own pace, but it’s been so great together, the live feedback like this.

Alice: Oh, yeah. Oh, very cool. Awesome. And something that we always ask on this podcast is, what is your definition of womanhood?

Cali: Yeah, great question. So, for me, it’s an interesting one for sure because, as I mentioned, as an engineer in the oil field, that’s a very male-dominated business. And quite frankly, I didn’t realize being a female and that industry was quite a superpower at the time that I was there, but I can look back and reflect on it and see that now. But to me, womanhood, the “hood” part really sticks out like a neighborhood, i’s the community, it’s the group. It’s the powerful resilient group who needs to come over. On an individual level, we face adversity, but together as a group of women, it’s a really powerful force. So, to me, that’s what I think about when I think of womanhood.

Alice: Oh, that’s wonderful. Yeah, I love that idea of the “hood.” I’d never thought about it that way. It’s really interesting and kind of ties back in with Travel Shifters and this idea of community.

Cali: Yes, definitely. Stronger together, and it definitely helps to have support from people who are on the same path as you or are in the destination, so to speak, because where you’re going.

Alice: Yeah, that’s awesome. And, what is next for the Travel Shifters? And where are you going to go next after the pandemic?

Cali: Great questions. So, next for Travels Shifters is really going to be focusing on this Career Break Bootcamp, hoping this pandemic can come to an end so everyone can travel freely and plan really awesome breaks. I know some people are in that position right now, or they might be being asked to go back to the office and that’s not align with what they want anymore, so a career break is a great way to kind of take time away, re-evaluate what you actually want, see some of the world if that’s your thing, and then make a decision based on your own needs. So, really focusing on that. And then for me, where I want to go next is, I mean, everywhere. For the longest time, I want to go to Sri Lanka really badly. It’s been on my mind for a long time. So I hope to be able to make it there in the next year or two.

Alice: Amazing. That’s awesome. And how can people find out more about Travel Shifters?

Cali: Yeah, awesome. So, you can find me on Instagram. It’s probably where I hang out the most, @TheTravelShifters. If you are interested in joining my Facebook group, you can also search the Travel Shifters on Facebook, so that’s where we kind of gather as a community. I feature a different member each Friday, sharing their story of when they ditch the nine-to-five to do something a little bit different. So, it’s super inspirational, I feel very inspired every week. If you love this career break topic, on Thursdays on Clubhouse, I talk about it at 4:00 p.m. Central Time. You can find me, Travel Shifters. And also my website,

Alice: Amazing. Thank you so much, Cali. It was great to get to talk to you today.

Cali: Thank you so much for having me, Alice. This is great, and I really appreciate it.

About the author

Alice Cash is the Marketing Manager for Jubilance by day and an award winning Theatre Director by night.  Leading the podcast Weekly Woman, she loves her candid conversations with women from all over the world about how they live and the amazing things they are doing to make a difference. Alice is also the editor of the bi-monthly newsletter the Jubilee, a blog dedicated to the power of female wellness especially concerning menstruation.  She’s worked in France creating theatre pieces and taught drama and filmmaking to women and children in Haiti.  She graduated from Georgetown University and holds two master degrees from NYU and The New School.  Alice has traveled to  40+ countries, including Tibet.  She is a New Yorker and can often be found in Central Park, searching out the best bubble tea, or directing a play, you never know where she’ll show up. @alicesadventuresinwonderworld
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