Ditch Using Google Maps for Your Career — Ask for Directions Instead
The Shortest Path to a Career Destination is Often Not a Straight Line
April 21, 2025 by Clint Chao, Moment Ventures
Most people fortunate enough to attend college followed a pretty prescriptive path to get there. It’s almost like having a childhood version of Google Maps — you (and your parents) could plug in a destination like “computer science major”, “Ivy League school”, or “schools that offer Division I Lacrosse” and get a fairly straightforward list of steps to follow: join the right clubs, take the right classes, ace the right tests, apply to the right schools.
But after college? Here is where that career Google Maps gets blurry. There’s no neat set of directions on how to become a venture capitalist, a chief revenue officer, a sports team executive, a startup founder — or really, any role that doesn’t follow a clear predetermined path (ie medical school).
Learn to Ask For Directions Instead
For the rest of us, we must get comfortable with the old-school way: by asking people for directions.
Some of the biggest turning points in my career came from what looked like small, random choices at the time. A chance on-campus interview at UC Berkeley where I bonded with a recruiter over sports that led to grabbing a beer with him at Henry’s at the end of day, which then led me to ditch the engineering opportunities and instead start my career in technical sales (and against my parents’ wishes!). And then years later, when having the desire to change careers completely when a group of friends and I decided to start angel investing, we found ourselves meeting an out of the box thinking institutional investor who had the balls to pluck two of us out of our group to encourage us to separately raise our own VC fund.
I doubt that anyone’s path to a successful career is like many others — as people get into an industry in the most unique ways. If you ask most seasoned professionals how they got to where they are, you’ll rarely hear “I planned it this way.” More often, it’s a story of unexpected detours, serendipitous encounters with people of influence, or other leaps of faith that became the paths that unfolded while finding their way.
And at the heart of those events? A handful of super interesting and serendipitous experiences — meeting the right person, saying yes to a surprising opportunity, opting for the less safe but more fun path, or pivoting to something that lit a new fire. Those are the stories that got us from there to here. And I bet if you asked everyone in the room that you’re currently standing in to give you directions on becoming whatever they are, they’d have these stories as milestone markers to tell you about.
Here are some examples of amazing career itineraries from people that I know:
- a finance student headed into a banking career switched “sports” after meeting an influential executive in class, and subsequently became the COO of a major baseball franchise
- a computer science major at UCLA dropped out to focus on dual passions: music and building apps. He’s now CTO & co-founder of a tech startup enabling musicians and creators to connect with their fans
- a magazine marketer who accepted a job at an industry trade rag changed his mind at the last minute to take a role as a new startup’s first advertising executive (which was Google)
- an aspiring young screenwriter rewrote his own career screenplay to become a logistics-tech startup CEO
The Path is Only Clear in Hindsight
For those of you about to enter into the working world or contemplating a change, success rarely comes from a perfect plan or set of directions. More often, it’s a mix of preparation, curiosity, luck, and the courage to keep going when the map isn’t making sense. Venture out and meet people in a space that you’re intrigued with, and ask them to tell you the stories that led them to the industry — you’ll be pleasantly surprised how crazy their path was! The path might be hard to replicate exactly, but that’s the point: no two paths are the same, so venture out and create your own!
And for those of you who’ve already gotten there, I’d love to hear the stories behind your career trajectory — was there a chance meeting with someone, or an out of the box job stint that helped get you to your ultimate destination? Let me know in the comments!
Clint Chao is a General Partner at Moment Ventures, an early-stage venture capital fund based in Palo Alto, CA. Moment looks to fund startups building the Future of Industries. He is also a board member for the Cal Alumni Association | UC Berkeley and the Diamante Scholars. You can reach/follow him on LinkedIn, Medium and X.
