Singapore - Inventor & Explorer
Sabbaticals tend to get overlooked or reprioritized in order to accommodate more immediate demands – The major reports due at work, entrepreneurial aspirations, birthdays, they all present decent reason to stay the course for a little while longer. But in this interview with Cara Thomas, it’s evident that a sabbatical is not a nice to have, it’s a need to have. Cara deviated from the established course, and along the way unlocked more about herself, her personal trajectory and the world around her than she could’ve ever imagined. While traveling, she challenged her friends and family to give her 90 challenges to complete in 90 days, which put her on a collision course with the unfamiliar, unexpected and unbound. While we’re all on our own unique road to Somewhere, Cara’s interview shows us that if we’re controlled by fear we’ll only see what we want to see; but, if we’re guided by it, we’ll see what we need to see.
– Let’s get there.
TSP: Can you please share a little bit about your past? Where you’ve been? What you’ve done?
CT: I grew up in NYC, which gave me an innate sense of curiosity, and an at-times-overwrought sensitivity and what some might say was a tough shell to protect myself. Much of my personal and professional journey has been related to softening that tough shell, opening my heart and the minds of others in harsh environments, whether personal, physical or professional.
I studied international relations, specifically culture and identity, and thought the most prestigious way to live out the degree was to go into the foreign service. I started on a path towards the political world, and through a turn of events and a boyfriend moving across the country, I ended up where I am now: in the world of innovation consulting.
So what does that mean? Basically, I help big companies better understand their consumers and develop new products, brands and businesses that meet their needs. I also help these companies skill up their employees to be able to launch these ideas and start their own creative revolutions at work. I get to travel the world, develop new ideas, and empower people to make them happen – I love it!
TSP: You’re an NYC native? Can you describe for us what it’s like growing up in a city like New York City?
CT: I was born in Australia, but grew up in Manhattan from age five, so I guess that technically makes me a “native.”
I guess the best way I can describe it is through a story my mom tells. I think my family had been in New York a few years, and one day, walking home from school, she asked me what I thought of living here. Apparently, I responded with: “Well, I think if we didn’t live in New York, I wouldn’t want so much.”
And that feeling I think comes from being confronted with extremes in a big city at an early age – massive wealth and incredible poverty; and, huge successes and plummeting failures. Nothing feels average or mediocre, and it’s all on your doorstep. And when you’re constantly exploring the curiosities of social, economic, political and environmental extremes, you’re constantly unlocking new wonders hidden within yourself and your community – you’re honing as much as you’re broadening yourself.
No different than any other teenager, I went through a lot of “phases”. But there are so many neighborhoods and types of people that even if you don’t fit in in your vicinity; there’s always somewhere that you can explore to find an aspect of yourself.
Ironically, my dream was to grow up on a farm in the middle of Iowa, running through corn fields. I think I even tried to get my mother to bang a pan to call me into dinner once…
TSP: What are you up to now?
CT: I’ve just moved halfway around the world solo, after a sabbatical which took me through India and Southeast Asia. I was nervous about taking time off and losing steam in my career, but I needed a creative reboot. Looking back, I have a whole new creative path emerging and renewed inspiration in my current career, and so much personal growth that a promotion or pay jump couldn’t make up for.
During this trip, I asked friends and family to give me 90 challenges to complete in 90 days. I was asking strangers for mantras, finding old couples in love and getting the secret to relationships, killing parts of myself that didn’t serve me anymore, and generally saying yes to everything in my path.
It’s made me more openhearted and trusting, and optimistic. Every person in my path is someone with a story and a lesson. Everything put in my path, whether it seems painful at the time, is something I can grow through. It’s made me discover that behavior change doesn’t have to be calculated and painful, but it can actually be achieved through play. It made me want to launch a new product.
TSP: What inspired you to ask your friends and family to offer up challenges to complete while you were traveling?
CT: As I was planning my sabbatical, what I really wanted was freedom to explore, and the opportunity to meet new people and have random experiences. I started playing with the idea of “travel roulette” where I would create a list of friends around the world I could visit, and every few weeks, randomly choose a spot on the globe where I could go visit someone. Logistically and economically, not the most realistic choice!
So I started talking to friends about this desire for spontaneity and adventure, and one friend casually joked, “you should just have people give you random challenges to do while you travel.” That seemed the perfect way to get at the spontaneity I was trying to achieve – so I started building that idea and it took off. I emailed 100 of my friends, set up an email address and I took off!
Every morning I would stick my hand into the box of cards and pull out a challenge that my dear friend Anne put together for me. That was what I had to do each day – Something different, unexpected and illuminating.
TSP: Can you describe maybe one of the most odd challenges? And what did you learn from that challenge, specifically?
CT: One of the oddest challenges was to “find a pet that could travel with me for at least a week.” I had just gotten to India – Getting through US customs, let alone across the Bhutanese border with a living creature was steeped with issues.
We were traveling with an Indian fellow who had a strong meditation practice – we’d wake up each morning at 6 am and he’d teach us his school of meditation. “Your mind is very distracted,” he told me. In the spirit of the challenge, I asked for help: How does one harvest a less distracted mind?
Given the challenge that was on my plate, it came to me: What if instead of adopting a wild dog, I adopted my untamed mind? A year plus later, meditation and taking care of my mind have been behaviors I’ve continued to adopt (haha!), and have had really positive benefits. If you’d like to read more about it, here’s the challenge.
Another great challenge was asking a stranger for a mantra – I ended up crossing paths with Steven Tyler from Aerosmith that day in Bangkok. So I knew I had to ask him. Without this experiment, it merely would have had a celebrity sighting, not a hilarious encounter.
TSP: Wait. Steven Tyler?
CT: Yea. And he was awesome! I carry what he wrote down in my wallet with me as a reminder of the crazy things that can happen when I just say “yes.” I definitely posted that one on the blog!
TSP: Where do you hope to go next?
CT: I’m taking steps with two friends to build a new travel platform that connects adventure seekers around the world, based on this sabbatical. We’ve prototyped a set of cards that helps people to have more serendipitous travel and to get “unstuck.” They’re designed around the 5 emotions that get lost in day-to-day life – and done so in a playful and fun way. While the personal action of doing the adventures is great, community and connection are really important in making real change. If the idea starts to take off, our next step will be building a digital platform to connect these awesome adventurers, and to help people grow and change in different ways.
Our vision would be for this game to spread across the social-sphere and bring people joy, self-awareness and connection. I imagine people around the world doing these adventures, sharing their stories to our app, being uplifted by others’ adventures, and deeply connecting with others on a similar path. Being happy isn’t about being joyful all the time, but about being connected, purposeful and grateful, even if just for an hour a day. We can be happy every day, even in the most difficult of situations with the right tools and support.
TSP: Would you mind sharing an example card with us?
CT: Sure! One of my favorites is “Find the oldest or happiest couple you can find and ask them the secret to their relationship” – and another is “Explore what breaks your heart and what makes it sing. Take an action for both.” There are a good mix of ones that are more extroverted and physically adventurous, and ones that are more introverted and reflective to make sure there’s something for everyone.
TSP: What do you see as maybe the biggest challenge that you have ahead of you with regards to building this new travel platform?
CT: I think always using failure in a positive way – it’s easy to get discouraged if you get negative feedback, or overly excited by positive feedback, so the challenge is about taking that negative feedback and not quitting, but instead thinking, “how do I use this to improve?” It’s that balance of holding an idea loosely and being open to changing what feels sacred, but staying true to the vision.
TSP: How do you plan to step towards those goals?
CT: Well, we’re planning to realize these ambitions through doing a beta-launch on a site called Haystakt to get a sense of whether anyone else thinks that a new travel platform and these cards are a cool idea… If that’s successful, we’ll move forward, and incorporate learnings along the way, before we launch on Kickstarter in September. We’ll be selling the cards, tweaking the content and nature of the cards as we go, and raising funds to build the digital part of the offering to connect travelers.
TSP: Test. Learn. Test. Learn. That seems like a very smart approach. Do you have points you’re looking to learn more about, specifically?
CT: Yeah – we’re taking an adaptive approach to test and learn as we go. There are quite a few assumptions we want to test. First, is testing whether the content is right, whether it’s impactful and whether people will actually go on these adventures. Next, testing the product interface itself – it would be easy to create an app, but we have a hunch that people actually might want more tangible, handmade and personal things these days; especially on vacation, when the last thing a person wants is to feel tethered to their phone. So testing the hybrid model of actual, physical cards, and a supporting app that works to augment the cards themselves. And then, we’ll want to learn more about whether people want to share and be connected to others, and what the right incentives are.
TSP: And one last question: How can we, the TSP community, help you get to where you want to go?
CT: Check out the Serenflipity website – and our project on Haystakt, a fantastic crowdfunding site based out of Singapore. Share Serenflipity with your friends, family and peers. The beta product will be up for 14 days to test demand – and we’d love to get feedback from TSP community!