My Story

Growing Up

I grew up always playing by the rules. I got good at playing “the game,” whatever that game happened to be. I did well in school, got good grades, and balanced sports/extracurriculars with classwork. At the same time, I feared getting in trouble, being wrong, and always avoided conflict.

Thinking back to this period of my life, I’ve viewed it in both lights (positive and negative). However, from this experience I developed a lot of important skills. I developed work ethic, how to juggle a lot of things, and the benefit of having structure, all skills that served me well throughout high school, college, and beyond.

I never questioned the trajectory I was on, maybe because I never had the time to think about it, or maybe because I didn’t know what else was out there. I knew what I knew, but I didn’t know what I didn’t know. A seemingly simple statement, but there was quite a lot I didn’t know.

College is where things started to shift.

College

I decided to major in computer science after I was introduced to programming my senior year in high school. I enjoyed programming, building stuff, and was generally good at it. However, as time went on it never quite felt like “it” (i.e. my “passion,” to use terms I focused on at this point in my life). I worked on a multi-year project that I’m very proud of, but besides that I wasn’t spending a lot of my free time programming. I spent many of my college years just wanting to graduate and “get started” as a software engineer, actually building stuff rather than doing wildy-unrelated homework assignments.

It was sophomore year that I came across Gary Vaynerchuk on YouTube, known online as “GaryVee.”

Since around high school I had the seed in the back of my mind about entrepreneurship, joining a startup, doing my own thing, creating my own business. But, it was around this “GaryVee time” that the entrepreneurship seed grew. I decided to minor in Entrepreneurship & Innovation, getting more exposure to the entrepreneurial side of business and life. Despite this, it wasn’t enough for me to jump off the tracks I was on. Becoming a software engineer, achieving that goal, was still top of mind.

After an internship with Microsoft the summer before my senior year, I had the opportunity to go back full time as a software engineer, to achieve that goal and finally “get my life started,” as I saw it.

I desperately wanted the real experience to know what I liked about software engineering and what I didn’t like about it. I wanted to know if that was for me.

And this was where things started to get really interesting…

Post-College

I was on my own now, finally out of the structure of school, figuring my life out.

After graduating in 2020 I joined Microsoft, then immediately got re-org’d into GitHub, a company Microsoft had acquired. I was then effectively a GitHub employee.

I worked at GitHub for 2 years before making quite a major change in my life.

This is how that change came to be…

Starting work (Summer 2020)

Finally, it was here. I had been looking forward to this moment all throughout college. I hit the ground running with a lot of motivation and discipline. My team was small, working on a new project from the ground up. Every day was new and different, there were a lot of unknowns and chaos. It was gripping and fun. I had a ton of support from my manager, intentionally putting me in difficult situations to learn and grow. After only 6 months, my efforts were rewarded and I was promoted to Software Engineer 2.

I characterize this period as “high growth.”

As soon as work started I moved out to San Francisco. SF was what I considered to be “the dream” in college – it’s the tech and startup hub of the country, what more could you possibly ask for as a software engineer-seeking kid? I wanted to be in that culture and closer to GitHub’s headquarters. I was never really a “city person” but I had never actually lived in a city, so this was my chance to try.

I shipped all my stuff via UPS from the east coast so the first couple days I slept on the floor of my new apartment – I absolutely cherish this memory.

Outside of work I was really intentional about learning and trying new things. For months I set up 30-day habits (like read for 10min a day, gratitude journal, create a 5 min video every day etc.). It was in this period when I also discovered Obsidian (a note-taking app on the surface, but it’s so much more) and the concept of building a second brain.

Outside of my motivated “30-day habits,” this was when I was first introduced to van life, through Kara and Nate on YouTube. I didn’t really think much of it during this time, other than it being a cool life and very entertaining to watch.

Promotion (Spring 2021)

Following my promotion to Software Engineer 2, there was an immediate slowing in my growth and motivation to keep climbing the career ladder. I quickly realized that Software Engineer 3 was a whole lot further away than Software Engineer 2 was. It would take at least another year, not 6 months. Besides a little 8% pay bump, not much changed about my day-to-day work life in my new role. My “high growth” discipline and motivation started to fade.

That said, a couple meaningful things culminated during this phase.

I started to get a lot more aware of my energy – where I was contributing energy as well as where and when I was actually getting things in return. Something clicked in my mind one day and I thought:

So… If I put in a TON of energy and effort this week at work, really grind out my tasks and make a huge difference… MAYBE in 6-12 months I’ll get something in return via a little extra bonus of promotion?

Why is that time delay so long???

Putting energy in did not result in getting tangible energy out.

In this time I focused a lot on happiness and fulfillment, so this realization really hit home that how I was spending my time wasn’t bringing me a lot of fulfillment. I made a video summing up my feelings (which I cringe at nowadays 😅).

My work just wasn’t giving me the energy out in return for what I was putting in. I started to question if joining a startup was really even still a goal, if even being a software engineer was a goal.

As this was brewing, life outside the apartment was getting quite rocky (probably an understatement). I was starting to question living in San Francisco, what I considered less than a year ago to be “the dream.” It’s amazing how much can change in a year.

I loved biking around the city, grabbing ice cream in little neighborhoods and walking around endlessly. It was so much fun to explore.

The landscape out there is absolutely beautiful, but parts of the city were rough. Every day I would open the door questioning what in the world would be waiting on the sidewalk… Some days I’d step over the legs of a sleeping homeless person, some days I stepped over needles, most days navigating around trash – but that just became normal, there was a lot of trash. It all culminated one Saturday morning as I watched from my window an ambulance take away a “sleeping” homeless person in a body bag, absolutely awful… This life was NOT what I was expecting.

Something needed to change.

Fortunately there was hope as I started taking more and more trips in a rental car outside the city to explore the surrounding areas. I went up the the redwoods, skiing in Tahoe, and down south to Big Sur. I started to get more intrigued by van life and car camping.

I always took day trips, as I never wanted to spend hundreds of dollars on hotels just for a place to sleep, it didn’t seem even remotely worth it. I started to wonder, what if I could just throw a foam pad in the back? I wouldn’t be constrained by hotels on road trips. I could stop whenever I wanted.

This idea pushed me out of San Francisco to somewhere with a lot more space and nature…

Moved To Denver (Summer 2021)

At work our product and team grew. It was a rewarding experience to build, but things started to slow down. Less daily chaos, more predictable maintenance. We hired a whole bunch of new people, split our team up, and I got a new manager. The team culture just wasn’t where I wanted it to be and work just wasn’t that exciting anymore. I began putting in drastically less effort, mostly just being present when necessary. “Clock in” around 9:30am and “clock out” at 5pm.

As a contrast, life outside work started to get a lot more exciting.

Within days of moving to Denver, I bought a Toyota 4Runner, threw a foam pad and a bunch of stuff in the back and headed northwest to the Grand Tetons and Yellowstone. This was my first real car camping experience. I can count on one hand the number of times I went camping as a kid so this felt like quite an unexplored territory for me.

For just over a week I was sleeping in the back, hiking during the day, exploring, taking photos, and just being present. I remember thinking on the way back, “if I could only figure out how to add some fulfilling work, some impact, to be able to make money while out here, I’m sold.”

As the leaves started to fall, I discovered a new passion: working in coffee shops.

I started going to coffee shops early in the mornings on the weekends to journal (in Obsidian), edit photos, organize my digital life, and just work through ideas. I began realizing how quickly the time flew by and how focused I was. I was coming up for “air” after 3, 4, 5 hours of deep flow. There was something exciting, something aligning about the bustling of people, espresso machines in the background, and other people chatting or working away on their laptops.

Weekends quickly turned into weekdays as I wanted to squeeze some coffee shop “flow” in before having to work at 9am/10am. Pretty soon, I was at coffee shops a couple days a week, journaling in the mornings, then working until lunchtime before heading back to my apartment for lunch.

The gears started turning…

A New Life Emerges (Winter 2021/2022)

Pretty soon my discipline and motivation slowed to a snails pace. It feels embarrassing to admit, but I began spending countless days sitting at my work laptop scrolling on my phone or watching YouTube. I think it feels embarrassing because of my “play-by-the-rules” mentality in addition to my drive to achieve a higher potential. After work I’d move to the couch to continue the same mind numbing activities, waiting for Saturday morning to roll around to get back into a coffee shop.

As snow started to coat the ground, I found another new hobby.

I had gone skiing twice last winter (2020/2021) in Tahoe and absolutely loved it, it was such a blast. Almost like clockwork, I started skiing every weekend in the mountains of Colorado.

• Friday night I’d pack the 4Runner and head into the mountains, camping in my -20°F sleeping bag and waking up early to get those fresh turns on Saturday without any traffic.
  • At night it was typically around 20°F but the coldest it ever got inside my 4Runner was about 0°F (-6°F outside). Bundled up inside my sleeping bag I was typically quite warm, but I would not have called it comfortable. Enduring that discomfort continued to be absolutely worth those fresh morning turns.
• Come Saturday night I’d eat some leftovers and camp again, waking up early again on Sunday.
• After a half day Sunday, I’d try to beat traffic back down to Denver and recuperate the rest of the evening.
• For those that ski/snowboard, I ended up putting in 35 days that season.

Outside of skiing, this became a very dark time for me. Once incredibly disciplined and motivated, it was depressing to see the inaction that had I succumb to. The hours and hours wasted scrolling TikTok, Instagram Reels, and YouTube shorts, laying flat on my couch until I was so uncomfortable and disgusted. I wrote about some of my feelings in this post long before I had created this website.

Man, What A Struggle…

This disgust ended up pushing me to make a change, though. I began to envision my new life – traveling in my 4Runner, working (MY kind of “working” – working on myself) from coffee shops, and exploring the U.S. I would have no rent to pay, no 8-10 hours a day of my time taken away from me. I needed a change and I wanted to gain new perspectives and experiences from life on the road.

I decided that I would quit my job that coming summer and hit the road. It was time to recalibrate my life.

But, it wasn’t until an unexpected trip that I decided to double down and buy a van.

Buying The Van (Spring 2022)

I took a trip out to Telluride, CO to ski. I took 3 days off (M-W), but as I was packing, I realized that if I were gone for 3 days, 2 weeks, or indefinitely, there was no difference in the things that I was packing. That moment was like a lightbulb. The ideas were flowing.

I spent the next 3 days (M-W) skiing at Telluride, an absolute incredible experience.

But, come Thursday morning, I was still there, and guess where I ended up? The local coffee shop to work. Could I spend the entire day working my job not from my apartment? This was my test to myself (and my manager) and I passed with flying colors. Thursday and Friday I worked as if there was no difference where I was working. I thought, “if I can work from anywhere, I can be anywhere…”

Friday night after work, I said f*ck it and hit the road towards Park City, Utah. I spent the next entire week there working from coffee shops and libraries, skiing on the 2 bookend weekends before hitting the road back to Denver.

That was the trip that pushed me over the edge. This life was feasible. I decided to double down and buy a van.

At this point it was just a matter of waiting until that day came, May 27th, my last day at work. What was once a foggy vision turned into a distinct and concrete reality.

Quitting

After May 27th came, I spent the next couple weeks visiting my family and moving all my stuff into a storage unit.

On June 22nd, 2022, I hit the road. Since then, I’ve been recalibrating my life. I’m focused on creating a life I’m excited about and that feels sustainable to me.

I feel like all the roadblocks have been pushed aside. I’m able to spend my time how I want to. The only thing holding me back now is myself…

And that basically drops us off at where I am today, where I’m actively writing the rest of this very story.