Third Pivot’s the Charm

In the three years since I graduated from college in 2020, I’ve had three different careers. Almost none of them were what I had initially pictured for myself, but all have made me realize just how many opportunities could be available to us when we approach our careers with curiosity and the open mind of an entrepreneur.

From where I started — a Peace & Justice Studies major deep in denial about the wave of school closings radiating out from the center of Boston — a career in venture capital was the last thing I expected to be doing. To an outsider, VC seemed too cold, clinical, and profit-focused to be of any interest to a Peace & Justice major like me.

But the start of the pandemic was a time of upheaval and rapid change, forcing us to rethink the way we approached education and work, two areas that can have the largest effect on the trajectory of our lives — and two areas that are still rife with inequalities and inefficiencies. We found ourselves relying on technology to finish out our school year and usher us into our first jobs. And in places that didn’t have access to those tailored resources, things got a lot harder.

Knowing that I was eking out my career in an unusual time, I took a lot of risks. Adaptability, courage, and curiosity are lauded in brand storytelling and personal narratives, but it’s harder to understand how it plays out in practice. Real life comes with a lot of blind corners.

I’ll chart my unusual path to venture capital and Roble Ventures, and how an entrepreneurial mindset helped me to find purpose in the unlikeliest of places.

Career #1: Nonprofit Community Engagement

Education Doesn’t End With the Diploma

2020 wasn’t a great year to graduate from college.

When our campus closure was first announced that March, all I could think about was the darkroom photography workshop I had planned for the weekend — that it couldn’t possibly be canceled since I had done so much to prepare for it. I came to mourn the friends and professors I thought I would have more time with, and I rushed through all of our senior-year rituals in a matter of days.

But it wasn’t until months later that I realized there was another crucial component of the college experience that the pandemic had taken from us: guidance for what to do after it ended.

Undergraduate study was a time of discovery and reflection, but not so much of integration.

After graduation, it took me eight months to find my first full-time job, a remote one; I became a communications and network engagement associate for a D.C.-based nonprofit focused on executive leadership development. We would hold bootcamps for government-appointed leaders stepping into new roles, or figure out the best way to help the finance division of another major nonprofit gel better together. Our flagship program united high-level women leaders from across a variety of industries to build a new model of empathetic and values-based leadership.

Instead of learning a new commute or how to run team meetings, I was finding my way around Asana, Mailchimp, and Airtable. My day began and ended in Google Drive. I didn’t mind the solitude; if anything, the flexibility that the role allowed meant that I could spend more time on other pursuits.

What was crucial to my ability to finally land this role, however, was learning how to construct my own professional narrative based on the skills and experiences I had accumulated up until that point. Due to my writing skills and communications internships, I was able to make a case for corresponding nonprofit positions. Once I made the conscious decision to pivot from entry-level roles that were directly related to my college major (of which there were very few), the world of communications and marketing opened up to me.

One of the most important skills I learned during my time in nonprofit communications and engagement was the ability to self-educate. Because I had never studied marketing, I found opportunities to fill in the gaps with free online courses and resources — anything I could get my hands on.

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Career #2: Global English Teacher

The Unexpected Benefits of Risk-Taking

Several months into that fresh-out-of-college role, I was faced with a terrible decision: leave my newfound stability in the dust, or forever wonder how I could have risen to a once-in-a-lifetime challenge.

Everyone I had asked told me that there was no wrong answer, but I knew that wasn’t true.

I had won a Fulbright fellowship to go to Kosovo — a small but proud country in Eastern Europe — and teach English and photography there for a year. I was torn. Why would I put my career on hold for something I had applied to on a whim, a year prior, that now had nothing to do with the plan I’d laid out for myself?

After much agonizing, I decided to accept, and I moved my life to the small and smoggy city of Prishtina. What followed was a journey where “say yes to everything”  — within reason, of course — became my mantra. Because of it, I made the Fulbright worth the upheaval it had caused in my career.

I taught six classes: some English, some photography, even some language skills for professors. I gave lessons on verb tenses to the young women at a human trafficking shelter, and led yoga and chess for teenage girls at the Afghan refugee camp in Ferizaj. I ate countless, countless jars of ajvar. I helped paint the new design for the iconic NEWBORN sculpture, which changes each year. I took a perilous cliffside bus ride to Albania’s riviera, where I hiked along shepherds’ paths, danced to wild music, and got soaked attempting to do paddleboard yoga with one of my co-teachers, Yllka. Her family invited me to their New Year’s party, where I was welcomed with some of the most heartwarming hospitality I had ever known.

What started as a blind risk ended up becoming one of the best experiences of my life.

I learned so much about myself, and the courage that comes from leaning into uncertainty. I also developed a passion for global education, now that I understood the major role that it played in the lives of my Kosovar students and their ability to tap into a global market that provided economic stability for them and their families. I saw so much potential in them that was stifled by an outdated, antiquated system, both in terms of the learning environment and the existing teaching pedagogy. I was told by my students at the public university that the weekly lesson plans I crafted, the extracurricular activities to help less-fluent learners catch up, and the points system I let students review on my Google Sheet were more than what most full-time professors did for their classes.

Putting myself in a situation where I was stepping outside of my comfort zone every time I stepped out of my apartment helped me grow exponentially. With each class I taught to a room full of students only a few years my junior, the easier it became to say yes to yet another unexpected opportunity. In hindsight, learning when to take a risk — and managing risk in general — is one of the most important qualities for VCs and entrepreneurs. I’ll always be grateful to everyone I met along my journey in Kosovo who helped me realize the potential that is latent in uncertainty.

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Career #3: Marketing for Vulture Capital

Helping Out by “Selling Out”

When I returned home from my time abroad, I knew I needed to get my career back on track. In addition to my teaching, I had been doing marketing professionally for nearly a year as both an employee and consultant, but still had never studied it in any formal capacity. My curiosity and habit of self-educating had saved me in my previous role, but now I had nowhere to hide. I had to learn it properly if I hoped to advance.

In came the Experience Lab, a virtual career launch program run through the University of Pennsylvania. The Experience Lab helps recent college graduates prepare for careers in the fields of business development, AI and data analytics, and digital marketing. Through workshops and connections with other fellows, I had the opportunity to articulate my goals for myself. I got to be creative again, both with my work and with my personal brand. Slowly, all the disparate experiences started to come together into a cohesive story of me. This tech-enabled educational pursuit allowed me to more fully bridge the gap between where I had been as a Peace & Justice graduate and where I wanted to be — a marketing and communications professional working on something big.

Their program was meticulously designed with a thought-out curriculum, highly choreographed workshops — on topics such as personal branding, networking, storytelling, etc. — and the opportunity to be matched with a startup company for 3 months of hands-on field experience.

Again, luck swooped in to guide me: instead of the typical product-led startup, the Experience Lab matched me with Roble Ventures.

I was excited about the opportunity, but my self-doubt almost won out: I didn’t know a thing about venture capital. How could I effectively market something that I thought required an MBA to understand?

But once I began talking with Roble’s founder about the history of the fund and its portfolio companies, the more invested I became. I started to see the potential in the story that we could tell about a human-enabled future, and what each of our companies was doing to get us there.

I hadn’t thought much about venture capital before that conversation (with most of my opinion having been formed by Twitter hot takes), but I could see that I had an opportunity to help Roble spearhead a movement to infuse more empathy and inclusion into the next generation of VC — or “venture capital with a heart,” as we like to call it. We would uplift our partnerships with underrepresented founders, and by doing so, paint a picture of the next step in the evolution of work and learning.

So, I found myself pivoting into marketing, but it was so much more than it was before: now I also had to grasp the world of startups, venture capital, and investing as a whole. It was overwhelming, but empowering. Each day was, and continues to be, a challenge to do better than the day before.

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Why Human Enablement Matters

From darkrooms in Kosovo to whiteboards at Stanford, I’ve spent the last few years learning how critical it is for our institutions to evolve, and how Human Enablement Technology is key to the future of work and learning.

Roble Ventures invests primarily in SaaS and data solutions that improve the experiences of education and the workplace in a way that will allow all humans to reach their potential. Roble is more than just a VC fund: our investments are risks that we take to bring about the future that we believe will be more empowering for everyone, not just the privileged few who are able to afford the best schools or leverage the densest network.

Socioeconomic empowerment requires not only an evolution of the structures through which people work and learn, but of societal expectations as well — and our culture is defined in part by the technology we use to mediate it. The more support we show for EdTech and HR Tech, the more we’re going to see a new status quo emerge that puts the student and the worker first, allowing for a true meritocracy.

I’ve never thought of myself as an entrepreneur, but when I look at Roble’s definition of the entrepreneurial mindset, I realize how many of its characteristics — adaptability, curiosity, empathy — I’ve come to embody over the course of my post-graduate life. I’ve made several pivots, and had the courage to take the leap into completely unfamiliar territory. Lifelong learning and my own latent desire to problem-solve helped me to learn the critical skills I needed to be confident in my work.

Through it all, this mindset continues to guide me as I figure out the best way to uplift and enable others to build a brighter future. Through a flexible, opportunistic mindset, I’ve been able to become the architect of my own life — without holding too tightly to the blueprint.