Author’s Note: You know what’s crazy? This is my 50th blog. If my mentor saw this three years ago when I first proposed this blog project he would be like wow, that is 5x your original goal. Granted, I had three years to do this, but I think that’s crazy, yeah. Enjoy, this is gonna be a crazy story.

Do you want to take a guess how this blog became the way it is?

It is literally because the idea of spontaneity just popped into my head, spontaneously. I was like, okay, that is kind of crazy. I have been writing a lot of agentic AI technical stuff lately and I wanted to write something that could resonate with everyone, not just people in the AI crowd. Also AI is getting people less connected in this world and I want to change that.

So let’s talk about being spontaneous.

Originally, I was going to structure this nicely. You know, sections, headings, all that. Actually, fuck it. Fuck planning this blog. Let’s just go with the flow and write this in a spontaneous way too.

When Being Spontaneous Was Easy

When we are younger, it is very easy to be spontaneous.

In high school, you can just text your friend like, “Yo, you want to bike from Cupertino to San Jose just for fun?” Or “Hey do you want to climb up the stairs of one of the skyscrapers in SF” I have actually gone on some crazy spontaneous adventures a few times. As a high schooler, that feels insane. It is your first time leaving your little comfortable suburban bubble and going out into the world. Coincidentally it’s also the memories I cherish and remember the most.

One of the most spontaneous things I did back then was in ninth grade. At that time, pocket money was scarce. You would get 20 dollars and think, wow, that is so much, I can finally eat at Ippudo Ramen and get Cafe Lattea Popcorn Chicken.

One day, I got an email from Facebook about a research study. The email basically said, “Hey Jack, we think you qualify, and if you come do this study for about an hour, we will give you 100 dollars.”

Most people would brush this off and be like, “It’s a scam. Don’t take it.” But I am sitting there thinking, 100 dollars an hour? As a ninth grader, that is ridiculous. I have to try this.

So I grabbed my bike, which was a 40 dollar special from Walmart, and decided, completely randomly, to bike all the way to Facebook after class ended.

It was a crazy journey. I biked from Cupertino to Sunnyvale. I had never gone that far by myself before. I realized very quickly how unfriendly a lot of American suburbs are for bikes. Like the bike lane is one-third the narrowness of the sidewalk. Then I ended up on El Camino Real, which is basically an unofficial highway that stretches across the West Bay. I just kept going and going even when there’s like no bike lines and I have to bike with the cars. It was kind of scary at the time. Because the cars do not expect a fucking bike. But even more crazy: a bike with this high schooler. Trying to get to Facebook.

When I finally arrived at Facebook, I was stunned by the views overlooking the bay. Facebook’s headquarters is right next to the water, and you can see the East Bay, which was a crazy view. When I walked into the office, I walked into what felt like a different universe. Free food everywhere. Free snacks. Everything was gleaming. I realized how nice it would be if I were to be working at Facebook, and I decided to pursue software and computer science. You know, it sounds crazy, but that’s how I really started pushing myself to be better at coding.

As high schoolers, our intentions are simple: have fun, get free food, get free money. That is it. But because of these experiences, you grow as a person, and your world horizon, your perspectives become wider and more open.

Growing Up Makes Spontaneity Complicated

But as you get older, it becomes harder and harder to be spontaneous.

Every year, I notice people are just busier. Right now I am in my fourth year of college, and I find that even with my closest friends, I have to schedule time with at least half of them. They do not have the space to just pick up a spontaneous call or hang out with no warning.

Everyone is too busy trying to figure their shit out.

I do not think that is a bad thing. The alternative is you are doing nothing and drifting through life. But I do think there should still be space where people are free and open to explore, to be adventurous, to be a little unhinged in a good way. And I think corporate life and society in a sense is sucking the soul out of people. I’ve seen people from freshman year, amazing people, loved what they’re doing: world-class as Sudoku, people who loved outdoor hiking and backpacking, people who have done some really cool pop-up coffee matcha stores. And in the end, a large majority of them go into investment banking, consulting, and software engineering, and I’m treating them as dirty words. But it reflects what society is like for a lot of people. Though there’s still a lot of people who are doing really cool stuff. So I think we should celebrate that: for the people who are still pursuing what they really care about their passion and what is important to them.

Some Of The Crazy Things I Have Done

Over the past few years, I have actually stayed pretty spontaneous and done some genuinely crazy stuff. Let me share a few of those moments.

The Cave That Did Not Exist On Maps

A friend once told me there was a cave in the mountains near Santa Cruz and asked if I wanted to check it out. This cave does not have a location on Google Maps. People who have gone there keep it secret, and there are rumors that people have died inside.

This is not the kind of cave you visit with a tour guide and a gift shop at the end. It is a pretty intense cave.

I was not exactly thrilled at the idea of squeezing myself into some underground death tube. I am not naturally a “crawl through a crack in the earth for fun” kind of person. But at that point in my life, I felt like I needed some deliberate discomfort, something that would shake me out of my usual patterns.

So I said, screw it, let us do it.

We hiked through the woods for about an hour trying to find it. There were no proper directions, so we had to approximate using satellite images and vague descriptions people had left online. Eventually we found what looked like the entrance.

The opening was tiny, basically a slit in the rock. The rumor was simple: if you cannot fit through the slit, you cannot fit through the cave. Brutal, but effective.

We crawled in.

Inside, the cave was muddy and tight. You are not strolling upright like in a movie. You are on your hands and knees or your stomach most of the time. Easily more than 90 percent of it is crawling, not standing.

As we went deeper, I remember realizing just how far we were from normal life. No sky, no phone signal, no sunlight. Just rock, mud, and your own breath.

When we finally reached the “party room” at the end, there was this strange sense of tranquility that washed over me. I had never really felt what a true cave is like from the inside, not one of those touristy caves, not sanitized. Just raw space under the earth. It was peaceful in a way that is hard to describe. You hear your voice echo, you hear the silence, and you feel how small you are. It quietly stretched what I thought I was willing to do, and what counted as a “normal” hobby. Because of this, I have a knack for all things crazy like riding electric unicycles, or urbex (urban exploration). I’ve went into abandoned plants, secret tunnels under university campuses, and rode the EUC across a mountain. Crazy looking back.

The San Diego Flight That Should Not Have Happened

Then there was San Diego.

I knew about this conference, but I originally did not commit. My thinking was very straightforward: why fly all the way out to a conference when I could just stay at home, be comfortable with Youtube or video games, and catch up online later. It felt like extra friction for no guaranteed payoff.

Then my friend texted me from the conference. He talked about the people he was meeting there, the energy of the place, and casually dropped that there was nitrogen ice cream.

Something about that combination, serious conversations plus this little absurd detail, flipped a switch in my head. I realized I was about to skip something I would probably enjoy, just because it was slightly inconvenient. What if I keep skipping things because I “don’t feel like it”

He sent the text at around 2:40. Within roughly 50 minutes, I had bought a ticket, called an Uber, checked in from the car, sprinted through the airport, and ended up on the plane. I went from sitting at home to flying to another city in under an hour because of a single message and a gut feeling. I don’t even think the guys doing the Jet Lag Game Show went as fast as this.

That trip ended up being one of the most memorable conference experiences I have had. This is the first time I was really exposed to startup culture and met some really interesting people: people who’ve dropped out to create DAOs, people obsessed with bioluminescent lights and dancing, and that Nitrogen ice cream burnt the shit out of my tougue because it is so cold. :/ would not recommend.

San Diego kind of unlocked something for me. After that, I started going to conferences like CES and NVIDIA GTC. Each one came with its own stories: wandering the floor, talking to founders at tiny booths no one else cared about, stumbling into side dinners where somehow you are suddenly at the table with people who have been building in the industry for decades.

What I started to notice is that if you simply show up, people often assume you belong there. It sounds obvious, but it is underrated. If you keep putting yourself into slightly absurd situations, there is this invisible line that you slowly cross. One day you stop feeling like the random kid who snuck in, and you start feeling like someone who has a legitimate reason to be in the room, even if it is just that you chose to be there. And perhaps, you become one of them, one day.

The Hacker House Texts And A Room Full Of Future Headlines

The last story starts with a hacker house in San Francisco.

I had just hosted a hacker house there two years ago. It was a crazy experience, and later I wanted to recreate a similar energy at MIT for HackMIT. So I started texting people, trying to see if we could spin up a little hacker house experience.

The house itself never happened. Most people decided it would be easier to just go with Airbnbs and keep things simple.

But I kept in touch with some of the people I had reached out to. I would occasionally check in, ask what they were working on, send updates on what I was doing. Not because I had some strategic networking plan, but because I genuinely wanted to know what they cared about, what they were trying to build.

One of those people eventually invited me to what became one of the craziest events I have ever attended.

Back then, the companies there were tiny or barely formed. Today, some of them are everywhere. Mercor, for example, is now a multibillion dollar company, but at that time it was just getting started. Same with others like Delve, Third Layer, Marc Industries. These were just teams of co-founders with slides and dreams, not glossy press cycles.

I went to that event spontaneously too. The flight ticket alone was about 400 dollars, which, for me at the time, felt very expensive. I remember debating it. Is this stupid? Am I overestimating how important this is?

I went anyway.

When I got there, I realized very quickly that I was in a room full of people who, objectively, had way more going on than I did. A lot of them already had startups. Many had raised millions. Some of them later ended up in TechCrunch, the New York Times, and so on.

I had none of that. I was just there, talking to people, asking questions, trying to learn.

In those moments you do not magically stop feeling out of place, but something else shows up alongside the discomfort. There is this quiet sense that saying yes to situations you feel underqualified for is its own form of confidence. You are telling yourself, “I might not fully belong on paper, but I am going anyway.”

And looking back, that 400 dollars paid off in a way no spreadsheet would have predicted. They covered my lodging, Uber rides, food, housing. More importantly, it gave me a mental reference point for what “being in the room” actually looks like when world changing companies are still just people at tables with laptops.

Why Any Of This Matters

So why am I telling you all this? What is the actual point of this blog, beyond me crawling through mud and sprinting through airports?

Part of it is that I really did write this thing somewhat spontaneously. But the bigger part is that I keep seeing the same pattern in people around me.

A lot of people are doing genuinely cool things. I am lucky to know people with great routines, solid habits, intense work ethic. They are building impressive careers, stacking achievements, and from the outside, it looks like life is on rails.

The problem is that kind of life has a hidden trap.

When your routine is amazing and you feel like you are on a good trajectory, it becomes very easy to stay inside that bubble forever. Same places, same people, same conversations. You tell yourself you are being responsible, stable, peaceful. You are told not to be controversial, not to rock the boat, just keep compounding quietly.

There is value in that. Stability is not the enemy. But if you never step outside that zone, your world slowly narrows without you realizing it.

Being spontaneous is one way to fight that.

Every time you say yes to something slightly chaotic that you would normally talk yourself out of, you run a new experiment on your life. Most of those experiments do not turn into some massive “career move” or “relationship win”. A lot of them are just good stories and mildly inconvenient logistics.

But together, they do something important.

They increase your surface area for luck. The more rooms you enter, the more people you talk to, the more odd situations you put yourself in, the more chances you create for luck to find you. The cave did not give me a job, but it rewired how I think about fear and discomfort. The San Diego sprint and the later conferences made it normal to show up in new cities for ideas and people. The hacker house texts and that event full of early stage founders showed me what it looks like to be around people who are swinging hard at the future.

Over time, that changes you as a character. You become the kind of person who can tolerate uncertainty a little better, who is less scared of looking out of place, who has seen enough unlikely good outcomes that it becomes rational to keep trying.

And no, I am not saying you should start saying yes to everything. That is how people burn out or end up in situations they never wanted.

What I do think is this: more people should say yes when it already makes sense to say yes.

You know the situations I mean. The invite you secretly want to accept but turn down because it is “too much effort”. The trip you would enjoy but decide against because the timing is not perfect. The person you want to talk to but convince yourself is “too busy” or “out of your league”.

Those are the moments where a small decision compounds. If your instinct is quietly leaning toward yes, and the only thing stopping you is a bit of fear or laziness, that is exactly where saying yes more often can change your life.

Spontaneity is not about being reckless. It is about giving yourself more chances for your future to surprise you.

Even this blog is part of that for me. The idea popped into my head, and instead of overplanning it, I followed it and wrote.

Maybe the next time an opportunity or idea shows up that feels a little too sudden, you try the same thing.

Say yes, when it genuinely makes sense to say yes. Then see where the story goes.

That’s all.