Alyssa Allen is a senior paid social consultant, freelancing with Apiary Digital while traveling through Europe and Asia. After chatting with Alyssa, I could tell she really knew what she was doing. But my only thought after attending her recent workshop on social media advertising was, “Where do I sign up?” I found Alyssa’s story so inspiring because of her combination of focus and flexibility. She executes her work at the highest level, but she has the confidence to admit that she doesn’t know exactly how everything will turn out. Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
No joke, I thought I wanted to be a marketer for a toy company, or work for marketing for Neutrogena. I liked commercials. I thought it was really interesting how they could speak to me and get me to buy things. And I was obsessed with Neutrogena commercials. I really loved when Jennifer Love-Hewitt would wash her face. It was graceful. So I definitely wanted to do marketing.

​Logan Sears is a senior software developer at Brandfolder, which he explains far better than I could, while managing to reference Star Wars. Logan’s career path is full of more twists and turns than most (Craigslist plays a surprising role), but that in itself is a testament to his openness, curiosity, and willingness to say yes to things most people would turn down. Our conversation has been edited for length and clarity.

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​When you were 17, what did you want to be?
 
I always wanted to do something in the tech world. I wanted to make video games because I love playing them, I love game theory. And then I tried to teach myself programming and I thought I hated programming. I tried to pick it up throughout high school and I never could. I just didn't get it.

JessaElaine is the director of implementation and process improvement for Never Grow Up, a private child care company based in Tennessee. Jessa’s career path started with the goal of becoming a lawyer to support victims of child abuse and human trafficking. But she astutely realized that there are many different ways to change the world, and shifted her attention to social work. This year, she’s mastering the art of work-life balance, continuing to support Never Grow Up’s goal of delivering high-quality child care, while becoming a certified scuba diver and digital nomad.
 
When you were 17, what did you want to be?
 
I thought I was going to grow up to be a lawyer, potentially a judge. I was always really fascinated by the process of social justice. I wanted to be a lawyer for the Department of Health and Human Services and try to find healthy placements and prevent children from going back to abusive ones. That was the end goal; where that stems from I can't really pinpoint.

Brittany Dutra is a software engineer and – although it didn’t seem very helpful at the time – a living testament to the idea that you really can do anything with a degree in math. In the six years since she graduated college, she’s moved from financial analysis to project management to computer programming, following her instincts into projects that pushed her intellectually and professionally. And the best part is, as a fellow Bay Arean (Bay Area-ite?), I get a front-row seat as Brittany’s story continues to unfold. Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
I had no idea. I had always really loved animals, more so than an average person, so I thought maybe I would do something with that, be a vet or go into conservation or something like that. Actually, because I knew you would ask this, I asked [my boyfriend], Doug, if he remembered what I wanted to be in high school. He said that I wanted to be a math teacher because I had a math teacher my junior year of high school who had a really big impact on me. And my mom said when I was growing up, I always wanted to play teacher. So I guess that was something I thought about.