Reflections on starting a new journey
Friends,
It’s bittersweet to say, but my time at Guild Education has come to an end. I’ve accepted an opportunity to join the leadership team at Context Learning, a growing startup in the educational travel space. It’s an opportunity I’m really excited about, as it combines my passion for education with my love of hospitality and travel.
My new role as the VP of Business Development and Partnerships allows me to build on my Go-To-Market and strategy skill set while defining and growing a newly formed team. The thought of it has me energized, excited, and eager to get to work. This is my first public blog post (appreciate you bearing with me), and I hope to write many more about the things I will be working on at Context. For this one though, I’d like to reflect a bit on the personal journey that got me here.
I view closing the chapter on Guild really as the end of a phase of my career that started when I left investment banking. As I reflect on the years since, first at Entangled, then while launching Outset, and most recently at Guild, I feel an overwhelming sense of happiness and pride about a decision I struggled with while still in the Real Estate bullpen of Eleven Madison Avenue.
Up to that point, I felt I had received little guidance and had little clarity on what I actually wanted to do with my life. I knew that working in financial services for large institutions was not going to provide me with long term fulfillment. I entered investment banking hoping to learn about business and develop foundational professional skills, and I achieved exactly that. For the most part I also enjoyed my time on Wall Street, as I found the CS Real Estate team to be smart and fun, and I liked working on large transactions. But after a handful of years, my learning curve had drastically slowed and I had an overwhelming feeling of cognitive dissonance. How I thought I should be using my strengths and privileges to contribute to society, and how I actually was, were misaligned.
Over the course of the better half of a year, I spoke to a lot of people and heard a lot of advice. Some people were extremely helpful, others less so (maybe I’ll share the best tidbits and frameworks in another post). Ultimately, I triangulated around social impact entrepreneurship and found myself taking a leap — namely to focus my career on working with passionate people who seemed eager to build new things and make a positive impact on the world.
With some hindsight, I can now definitively say that choosing to work at mission-driven start-ups is one of the best decisions I’ve ever made. I found my footing in education technology. In the education landscape, there are so many important problems that need to be solved, affecting each and every one of us, from the toddler and their parent, to the underserved working adult lacking opportunity, to the grandparent looking to enjoy their hard earned free time well.
At Entangled, Outset, and Guild, I focused primarily on higher education and workforce development. Education plays a critical role in driving economic opportunity, particularly for underserved Americans, and there’s a lot of innovation to be done to make the system work for everyone. Guild for example, is on a mission to unlock opportunity for America’s workforce through education and upskilling in order to create a world where opportunity is as equally distributed as talent. It’s a mission I feel is tremendously important to a functioning democratic society and I believe Guild is uniquely positioned to achieve it. It’s that mission that continues to attract amazing people to Guild, and it’s in support of that mission and those people that I’ll continue to root for Guild to succeed.
At Context, education is used not for credentials or for skill building, but in support of something broader: inspiring “Learning as a Lifestyle”. This mission recognizes learning as a core part of the human experience, not just in support of economic productivity, but in support of discovering passions, connecting with others, and fostering a deeper appreciation for and understanding of our world.
It’s within this mission that two deep but important problems are addressed. First, by building a tech powered platform that connects people, place, history, and culture, Context promotes an expanded worldview where individuals can breakdown barriers and appreciate our shared humanity. It’s this platform that empowers Context’s global network of scholars to deliver online seminars and in person tours in 70+ cultural capitals around the world. And second, by building an inclusive community, Context combats loneliness and isolation, a problem that affects way too many of us and is often only exacerbated by technology. Some of my most meaningful relationships in life were formed within a learning community and I believe a learning community that leverages the transformative power of cultural travel can help create and strengthen the types of relationships that make life worth living. I’ve certainly found that to be the case.
There’s a lot still to be done to build Context into the company that I know it can be, but I’m eager to do the work. I’m also eager to join an amazing team of passionate and smart people. I hope to continue to share my reflections, mostly for the personal benefit of clarifying my thinking, but also for those of you who want to come along with me as I continue this journey.
For now though, let me just say thank you to the countless people who have made an impact on me over the past few years, both big and small, personally and professionally. And if any of you out there are reading this and think working at the intersection of educational travel, community building, and the passion economy sounds like a blast (I sure think so!), feel free to reach out — Context is actively hiring across our tech, operations, and go-to-market teams.
With wind in my sails,
Elon
