Kari Waldrep is a senior UX designer at Trulia (which you might know from finding your last apartment). Fun fact: Kari was my first friend - and repeat roommate - on We Roam. So going into this conversation, I thought I had a good idea of how she got to where she is now. But even the people you see every day can surprise you with the details of their journey, like hearing about her college art project combining 1950’s pin-up girls and lobsters, or stumbling on the adorable wedding invitation she designed for her college roommate. Our conversation has been edited for length and clarity.

When you were 17, what did you want to be?
 
I think early on, probably earlier than 16, 17, I wanted to be a fashion designer. I was really into art and drawing, and sketching a lot in my free time, clothes and dresses and things. I had a sense that I wanted to do something in the arts, whether it was something more like fashion design, or something like becoming a painter or a printmaker. I knew I wanted to do something creative, in line with the art that I had grown up doing and was really interested in.

Talking to Sari Abdo, co-founder and COO of a Toronto-based food delivery app, about his career trajectory made me think of an Edna St. Vincent Millay quotation I recently read. In a letter she wrote while studying at Vassar, she said, “Please give me some good advice in your next letter. I promise not to follow it.” In looking back, it’s easy to feel like maybe we should have done something differently. But when you’re so happy with where you’ve ended up, maybe that’s exactly what you were supposed to do. Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
I was really into computers, and I was a little bit into math in school, so I thought I wanted to go into computer science or computer engineering. I didn’t know [what that was], but it seemed to be a good career choice. I sort of arrived at it by deduction rather than by choice or by a real passion for it. I was basically like, “Not this, not this, not this, so this is what I’m left with.”

Andrew is a data engineer for Vesparum Capital in Melbourne, Australia. Although he’s still at the beginning of his career, Andrew’s current profession already represents a pretty significant left turn from his beginnings as an actuary. However he has been consistent in his love for a capella music, which I occasionally hear him recording in the exceptional acoustic setting of our stairwell here in Prague. Our conversation has been edited for length and clarity – but sadly, there was no way to convey Andrew’s charming Australian accent.
 
When you were 17, what did you want to be?
 
Yeah, I didn’t have any profession in mind; there wasn’t anyone whose job I thought, “Ooh, that would be good to do.” There were just a few things academically that I quite liked; so I quite liked maths, got good marks in science-type things, I also quite liked music, and in particular in maths, I quite liked statistics and probability. I liked the game Yahtzee if you’ve ever played that. I liked sitting down with a pen and paper trying to figure out what the odds were of getting the various Yahtzee rolls, and I spent a lot of time playing Rubik’s Cubes.

​Julia is a freelance researcher and fiction writer from my one-time home, Chicago. Julia and I have loads in common, from our unshakeable faith in the value of interdisciplinary learning to our years as Starbucks baristas. But our similar spirits have manifested in very different ways, and led us down divergent career paths. Read on to hear how Julia wound up discussing cults with me at Friends Coffee House in Prague. Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
Honestly I did not have a plan, which was not the intent of my high school. We had this program called Thumbprint, and it was meant to be a very individual, reflective exercise. It would ask you what you wanted to do in a year, in 5 years. I thought it was kind of ridiculous because I didn’t know what I wanted to do in a week, so asking me my five-year plan…(laughs).

Melissa Minucci is a freelance fashion designer from Montréal who specializes in swimwear, lingerie, and sleepwear. Talking to Melissa once again proved my hypothesis that everyone’s career path really is unique. Melissa’s journey to traveling and working remotely starts and ends in fashion (for now…), but also includes a stint cutting the leaves off of banana trees and owning and running an ice cream shop that got destroyed in a cyclone. Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
At 17, I had not a clue because, even as young as that, my lifestyle was more important than work or studies. I didn’t have to do much to get good grades, so I found a way to do as little as possible. I went [to school] maybe 50% of the time and then was just hanging out with my friends or doing other stuff. I did enough so that I still had good grades, but I found it very slow.