Caitlyn Lubas and I first crossed paths at NYU Stern back in 2018. Though she was a year ahead of me, she was hard to miss —a kind and generous campus fixture who always made time to share career advice between stamps in a rapidly filling passport. Not much has changed. Although her country count (over 100!) and career achievements have only expanded. After following her journey from afar, I reached out to feature her in the oyster x Career Crush series, and she graciously agreed.
If you know Caitlyn, you know she has lived multiple incredible and successful professional lives. Her resume spans big tech, a concert livestreaming startup and a book publishing venture, before she took the leap into solopreneurship running a successful group travel planning business and writing her incredible coming-of-age book documenting her travels around the world: You Are Where You Go, which you can also get a peak at on her Substack. Most recently, she has pivoted back into the technology space at an established company.
Caitlyn’s trajectory is a brilliant reminder that careers are rarely linear – they change as we do. Our priorities evolve, what fulfills us shifts, and sometimes we surprise ourselves by circling back to a familiar industry despite having changed as individuals. The beautiful thing about building a career in 2026 is that there are no rules.
Without further ado, let’s dive into the conversation…
THE CAREER JOURNEY
Makena (me!): Let’s talk about your career thus far, and the different stops along your journey. What triggered each pivot?
Caitlyn: My career journey has really been dictated by the place and time of my life.
After a year at a big tech company after college, I wanted to try working at a startup to experience a smaller environment with greater autonomy and impact. In a startup, more so than in a large company, I feel like you tend to be uniquely positioned for the role you are stepping into, and you are able to see the direct results of your work.
I worked at a concert livestreaming startup and then a book publishing startup – both connected to my passions for music and books. I intentionally chose startups where either my interests aligned or I gravitated towards the mission.
Alongside my full-time positions in Big Tech and at the startups, I was working on passion projects. I began writing and later published my coming-of-age book about my travels around the world You Are Where You Go. I also started casually running small group travel trips where I preplanned itineraries. I was already doing them in a recurring fashion with friends, but then I decided to pursue group travel planning full-time as a solopreneur.
^Pic of Caitlyn on the first group trip she planned and led in Oaxaca, Mexico for Day of the Dead!
After a while, I found that operating a business entirely solo was a bit heavier of a lift than I wanted. I decided to take a career break to prioritize a major personal life goal: visiting as many countries as possible because I figured when else can I do this except in my 20s?!
Post-career break, I prioritized low stress and long-term stability in my job search, so I’ve ended up back in technology in a role that gives me a stable income and ample time to focus on my personal life.
I’ve come to the conclusion that I don’t need to get all of my fulfillment out of work. I don’t need to feel tied to my professional identity, which I find gives me more time and energy to focus on friendship, family, travel, and other things I care about. I feel like I did a complete 180 back to where I started in technology, but at the same time, I have tried all these different passion projects and paths, so I have deep peace in that because I would have always wondered if I never gave it a try.
Makena: Do you have any career mantras you live by that guide your decisions?
Caitlyn: The overarching theme of my career has been trying different things. For me, it’s about maintaining an “experimentation” mindset. If something is not working out, it’s okay to pivot again. It’s not going backwards; it’s more of an evolution.
My perspective on careers too has completely realigned – I no longer want to climb the corporate ladder. I don’t dream about being the head of product. Instead, I focus on what I can gain in terms of stability, and ensuring the work environment allows for a healthy work-life balance. In the past, I might have valued passion or remote flexibility above all else, but now my priorities have shifted.
THE DAY-TO-DAY REALITY
Makena: Let’s talk about skill sets because I’m curious how you have been able to adapt to so many different roles whether it’s big tech or leading a group trip in Latin America. What skill sets have proved to be transferable “superpowers” across those different career pivots?
Caitlyn: Empathy and communication are the two foundational skills that have crossed over into everything I do. Whether I am thinking about how people are interacting with a digital product, knowing what readers will want to read, or navigating interactions in foreign countries – these two skills are essential. Running real-life experiences as well like group trips or public events in New York City (which I do in my free time for fun) especially requires being able to read a person and understand them. Empathy and communication have proven to be huge, invaluable skill sets.
Makena: Any unexpected skill sets you’ve added to your toolbox?
Caitlyn: Adaptability. I’m a natural planner, but things inevitably go wrong when you travel or run events. That means figuring out a Plan C, Plan D, and Plan E on the fly. Having worked five or six completely different jobs, I can honestly say I have learned how to adapt quickly to different situations.
Makena: What’s the best thing about solopreneurship, and conversely, what do you think is its greatest challenge? (Can you do some exercise for the corporate 9-5).
Caitlyn: Solopreneurship can be very isolating. I like to talk through decisions and bounce ideas off someone else. Unless you are building with a team that is equally invested, it’s a completely different and at times difficult experience. Solopreneurship brings a tremendous amount of pressure because everything falls entirely on your shoulders.
The pro and con of working in a larger company is you have a team but sometimes there are too many cooks in the kitchen. On the positive side, it’s nice that not every decision is my sole responsibility or my fault if things go right or wrong.
What is good about corporate is also what is bad about it, and the same paradox applies to solopreneurship.
Makena: Do you think it possible to juggle both at once: having your own business and still working in a 9-5 at a corporation?
Caitlyn: If you want to make a sustainable income from solopreneurship, I think you need to go all-in on it, unless you are dedicating a massive amount of time because context switching is hard.
However, there is a big caveat: I never wrote a book, led group trips, or created community events simply to make money. Those were side ventures and passion projects. When you have the immediate pressure of making money, you should go all-in, but passion projects operate under a different set of rules.
THE FUTURE & ADVICE
Makena: You’ve already brushed on this, but how has what you valued in a career evolved? What do you value most today?
Caitlyn: At the beginning of my career, I valued work-life balance a lot, and that is still true today, just for different reasons.
Today, I also care about whether a career choice is going to set me up for success in the future, not just in the immediate present. What I mean by that is at one point, working in a startup that let me work remotely was the most important factor. Now, in my late 20s, I think much more about sustainability: Is this something I could comfortably do for four to five years, rather than just right now? Finding a chill company that protects my work-life balance with stability in my income source is what truly sets me up for long-term success personally.
Makena: 72% of young adult workers start jobs and find they are nothing like we expect, leading to a sense of surprise or regret (CNBC). How do you mitigate that risk and make sure the job you are saying yes to is the right one?
Caitlyn: Before I accept an offer, I try to reach out to someone who previously worked at the company and left. I’ve done this for my past two or three jobs. Before saying ‘yes’ to my current job, I asked a person who previously worked there straight out about red flags or regrets. I find these conversations help you get an honest sense of the culture and day-to-day life. Glassdoor reviews are often too hot or cold to rely on entirely.
Makena: Of course, you have to take what people say with a grain of salt too because what someone loves about a job, you might hate and vice versa. Everything is subjective, but doing those coffee chats is a brilliant approach.
Any helpful tools, books, mentors, or communities that helped guide and navigate your journey along the way?
Caitlyn: The Pathless Path has been a really great book. The author also runs an online community around it too. It completely changes how you look at work. Even though I am working back in a corporate company now, I have an enlightened viewpoint. My core values are no longer tied to climbing a stressful corporate ladder.
Makena: Final question – thoughts on LinkedIn? Do you use it?
Caitlyn: I actually used it for that specific edge case of validating where I am going to work by speaking with someone who currently works there or ideally previously worked there. LinkedIn is generally good to see what is out there in terms of roles and organizations, but I have a strong opinion that the people doing the most interesting things don’t share them publicly.
Makena: Yup, they are not updating their LinkedIn!
Caitlyn: I haven’t updated my profile in a long time because I find people mostly use it for optics.
Makena: Yes, it’s become a very performative and ego-boosting environment. I also feel like it is too much of an echo chamber; it’s the same ten big companies and industries over and over again.
Caitlyn: 1000% because they are paying to promote. Small businesses don’t invest in that kind of promotion, so we don’t know they exist.
Makena: It kills me how the coolest companies, roles, and paths are hard to find! That is precisely what my company oyster is trying to solve.
Well, thank you so much, Caitlyn, for your time and this grounded and candid career advice. I feel like you’ve lived nine lives in just…how old are you?
Caitlyn: 28.
Makena: Wow! Well, I have no doubt people will resonate with your journey. Thank you Caitlyn for sharing so candidly and all of your advice!
^Pic of Caitlyn at Everest base camp during her career break - her 100th country Nepal!,
Hope you enjoyed the conversation with Caitlyn!
There is so much we can all take away from this chat. Caitlyn’s journey across tech, startups, solopreneurship, and authorship gives her a rare and invaluable mid-career perspective.
For me, the biggest takeaway was learning to normalize career pivots. It’s important to pursue a path aligned with your core values, and naturally those values will evolve from our early to late 20s. We must honor our values, and non-linear career journeys are proof of that. Another important takeaway: Life isn’t just about work! Side projects and hobbies can help us find passion well beyond the 9-to-5.
What were your takeaways?
P.S. Much of Caitlyn's approach to navigating a career journey actually embodies the ethos behind oyster, a career discovery and micro-community app I’m building.
On oyster, you can:
- Share your career experiences (and earn tips $$$ for doing so!)
- Chat directly with people in organizations and spaces you’re curious about to validate your next move
- Uncover niche organizations aligned with your unique skills and interests (filter by # of employees, location, top associated values, and more!)
- Showcase your 9-5, 5-9, hobbies, sabbaticals, and career breaks all in one profile
- Swap advice and resources with a trusted career community
- Find people to chat with by career pivot e.g. “consulting” to “film”
Join the waitlist here:
https://oyster.thekindsocialmediacompany.com/join-the-waitlist
