It’s very easy to imagine life as a straight line marked by milestones of school, career, family, and retirement. In practice, life is rarely linear. When talking with greatly successful people, I’m often surprised by how their story just fell into place over time. A chance encounter led to them joining a successful startup, or a random side project took off into a big company.
Realizing even the most successful people didn’t have a perfect plan when starting out made me feel two things: a bit of hopelessness in the reality that nothing in life can be guaranteed, and an excitement in the idea that by following your heart you can accomplish very great things even without having planned to.
Steve Jobs famously said that you can only connect the dots looking backwards, and I only find that to be more true with time. At the start of 2024 I could not have guessed where I’d be today, and at the start of 2023 I could not have guessed where I’d be by 2024. All the biggest changes in my life, like first learning about Ramp, largely came out of the blue.
If I had to summarize this idea, I’d say that life is not a continuous line you draw. It’s a series of dots you scatter on the board, connecting them in retrospect to plot the trajectory for future dots. These dots are work experiences, chance encounters, even books you read. It can be very hard to tell where they’re headed in the moment, but it’s important to pursue dots that have high potential to connect with other, even better dots.
It’s okay to not have a crystal clear vision for the future, because having one that plays out exactly how you intend is near-impossible. Instead, chase the most interesting and highly connectable dots, and when the time is right, they will string together to create something much bigger than themselves.