Believing

how the dots connect

“Again, you can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever — because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well-worn path, and that will make all the difference.” - Steve Jobs 2005 Stanford Commencement Address

---

In the spring of my senior year of high school I decided I would like to give a speech at my graduation. I honestly can’t tell you why anymore, but from digging through old facebook messenger history, it seems like I was just excited by the idea of getting to speak in front of thousands of people. I emailed my principal and was told this was impossible, as there were four speeches pre-designated as our Senior Class President, Student Council President, Valedictorian, and Salutatorian, none of which I had a shot at anymore. It turns out I was so motivated to try and give a speech that I started a petition to allow the student body to vote for who got to speak at graduation and got a bunch of my friends and teachers, including the eventual Salutatorian, to sign. I cringe when I read the petition now, but I’m honestly proud of this past version of myself. I actually really wanted something, tried hard to get it, and got a lot of support along the way. Unsurprisingly, my principal went on to ignore me, and I ended up going on a family vacation instead of graduation anyways. However, there were a couple of weeks where I really was thinking about how to write a graduation speech.

During my search for what such an address would look like, I watched many famous commencement speeches, including this 2005 Stanford Commencement Address by Steve Jobs. I’m not going to try to summarize it, because I won’t do it justice. The speech is only 15 minutes, so I’d recommend just watching it; it’s worth it. He told three stories, each with a point about life that he wanted to impart to the graduates. As a high schooler watching this, I think I was full of some nebulous, awe-inspired motivation but with very little understanding of what he was actually saying. More and more these days I feel this way about life wisdom. Right now, as I sit here and type this, I pretty strongly believe I don’t understand his last two life lessons. It’s almost as if without losing something I’ve loved deeply or facing my own mortality, I will never grasp what he truly means. It’s not that I don’t understand the words coming out of his mouth, but more that my intuition cannot internalize the wisdom being imparted because it simply hasn’t had the necessary life experience to know what is going on. Sometimes I wonder if that’s a feature rather than a bug. Maybe the life wisdom gained by having a certain experience actually shouldn’t apply prior to having said experience, because that experience is fundamentally changing who you are. Maybe until I confront my own mortality, I will never understand why it’s a “trap” to think I have something to lose, but maybe it simply isn’t a trap. Maybe the version of me that hasn’t confronted his own mortality is better off thinking he has something to lose, and the version of me that has confronted it can’t conceive of living life without unrestrainedly following his heart. I’m going to more clearly explain what I mean through the only example I believe I understand.

When I first left Jane Street, some days I was hit with a shockingly high amount of fear. There were times that I was simply terrified that I had made a huge mistake, and the journey I was embarking upon was not only pointless but maybe regressive in my life journey. A well-worn path that had very recently seemed full of thorny rosebushes now at times seemed less thorny than it had before. The lowest moments were when I felt lost, confused, and scared, but most importantly, unsafe. Trapped in a dark forest, wandering blindly with no light in sight. Thankfully, I had and have wonderful people around me to provide emotionally safe spaces to express these feelings, so these low points were never lasting. In the end, the truth was I needed to learn how to live with these feelings on my own. I needed to be okay with feeling lost, confused, and scared.

At the beginning of being unemployed, I was following my natural curiosity, and it decided I wanted to understand how different people from different walks of life think and behave. I still want to gain that deeper understanding today. Despite never having been religious growing up, I decided to tag along with a friend to church one day and sit through service. There were many things that struck me about this experience, too many to talk about today, but one thing I started to feel was the power of belief. Now I’ve read about this power in a religious context before and what it can do for people, but I hadn’t put together that this was a potential answer to my problem. Believing that there is a plan for me; that if I strive to be good and do good, then things will work out. This was a potential safe space that I’d been looking for. Despite not being anywhere close to adopting any new beliefs of my own, I could already glimpse the power that believing held. In those moments of listening to song and prayer, I took my first steps toward understanding where to derive the confidence to stay off the well-worn path.

I have mentioned this to some of you already, but hand in hand with my desire to learn more about humanity came a desire to have a greater capacity for empathy. I had a simple empathy exercise for myself every day. During my daily “just be outside the house for half an hour, please” walk, I had to 1) not use my phone at all, 2) give at least one compliment, and 3) do something helpful. It was like training a muscle I had neglected. The more I observed the people around me, wondered what they were thinking, and interacted with them, the easier the exercise became. I found myself showing more interest, care, and compassion for everyone around me, especially those I cared deeply about.

Here’s the thing I didn’t anticipate. A shocking number of the doors that have opened up for me in my journey so far started with empathy. Growing up, I never believed in the idea of karma. But through my lived experience this year, I’ve started to develop that intuitive belief. Having repeated moments over and over where someone talks to me about an opportunity they think I’d like, wants to set me up on a date, or confides in me about their inner self all because I attempted to connect with them on a deeply human level has reinforced the intuition that pursuing my natural interest in and empathy for the people around me will come back to benefit me in the long run. There’s the possibility that there’s an unluckier version of me out there who hasn’t had as great a time this year. That man maybe hasn’t developed an internal belief for his gut or karma or something I’m not sure I can put a name to yet. But I’ve seen it in action. I now have the lived experience to see how caring about people puts you in their lives in a meaningful way and brings the two of you closer together, which can come around to impact the story of your life. It’s not that all these moments will fit into the bigger picture. As Jobs said, you can’t connect the dots looking forward. “You have to trust in something … because believing that the dots will connect down the road will give you the confidence to follow your heart even when it leads you off the well-worn path, and that will make all the difference.”

This wisdom I understand. I’m not sure the version of me that never left Jane Street needs or even wants this wisdom. He might not be ready for it. But I need it. If there’s anything that’s changed about me this year, it’s this. This core belief in myself, in my intuition and curiosity, in karma and kindness. This is the belief that allows me to trust that the dots will connect when I look back. In some ways, they already have.

I honestly do not have any memories in my head, even after digging through old emails and facebook chats, of why I wanted to give this graduation speech that never was. All I remember to this day is being days from turning 18, sitting in my room, watching this commencement address by Steve Jobs. There’s no need for me to say this, but you all know that kid didn’t think when he was 25 he’d be sitting at his laptop writing a blog post about how that day fits into the story of his life.

---

Bye NYC! I’ll be back in September. I’m in the bay for the first week of August! Hit me up if you want to hang out.