This email is a sample of the type of stuff I email in my exclusive travel newsletter, dedicated to my journey traveling the country. I don't promote or open up signups to this newsletter often. This is one of those times - if you'd like to join that newsletter, reply to this email and let me know. I'm sharing this to my main personal development newsletter since it's valuable self help advice too.

For the several years after college, every day, I went to work and went home in the suburb hometown area I grew up. It was getting slowly more boring to me, but I made the most of it. Until one day, I realized how much I fell into my comfort zone and a level of mediocrity living there when a new opportunity came up that let me work remote.

From that moment, I seized that opportunity, pitched the idea of traveling the USA while working remote, surprisingly got it accepted, and packed my possessions into my Camry and hit the road.

It's been about 15 months since I started traveling, and the last four months I've spent longer than I expected in Florida. One of the greatest contributors to spending so long here was spending time living in my sister's home with her roommates, coworkers, and friends. I realized I hadn't got to spend time with her for more than a couple days a year around Christmas since 2010 or even before that ever since I became a teen that was "independent." We had grown distant, and I figured it would just stay that way forever as I continued adulting - but then this opportunity came up to visit her. It was one of my most memorable adventures because unlike living alone in an airbnb, you get so much interaction for good and bad with your roommates as you're lounging or walking through the living room with the TV playing.

I went through a hurricane with them that blew out our power and internet for a week. We barbecued, went to office work parties, danced with the neighbor, saw a SWAT team raid a neighbor's house, played with the dogs, ate at new restaurants, worked a lot, played card games together, watched movies together, got to know each other, drank boba tea, went thrift shopping, and more.

My sister works a lot. About ~60 hours a week consistently. So, I didn't get to spend that much time with her in the middle of the week, but we still made the most of it, and did all those things and more on occasion when she wasn't feeling tired and outside her work hours.

There were small challenges too. She has a much more "live and make decisions off the cuff" personality and partially because of how busy she is, so that clashed against my planning type of personality at times when she would do stuff like invite me to a work/social event right before it started. There were moments where that clashing personality was enough for me to want to move on and live independently again. The good far outweighed the bad though. We both expressed to eachother how thankful we were to spend time with eachother, get to know eachother, how awesome we were, and all the good times we had.

I said goodbye to her twice, once when driving south to Miami, then once, after staying with her again while driving up north from Miami. It was a bittersweet thing. I had learn so much, came out a different person.

The biggest challenge and call for me to move on was the feeling that I was stagnating staying there. She lived in a smaller city in Florida, and I knew I wasn't growing much staying there. I devolved to a point where I worked at my job, worked out at the gym, cooked/ate, entertained myself with TV, and tried to spend time with my sister and her social activities. There wasn't much to do there, or at least, I had trouble finding things to do. Occasionally, I would go to a dance class or restaurant or town area, but there's only so much to that. It was starting to feel a bit too much like my old routine without much growth or experience, plus palm trees and better climate. I had social goals and life goals around exploring, interacting, meeting new people that I felt that were better suited to a larger place.

It was really tough saying goodbye and making that decision to move on. Part of me wanted to stay and so did my sister. I grew close to her friends/roommates as well, which made it tough for me. There was a level of comfort and familiarity that made it hard to detach. I wanted to cling to it rather than venture into yet another unknown city/area full of potential dangers or disappointments.

Ultimately, when I left, I felt that fear of discomfort. I questioned if I left too early. Within a couple days of Miami, I had found my footing again, felt excited about the city, and independent again - that doesn't always happen that quickly, but the fresh, clean, big, unique nature of this city had its charm.

Now, I said goodbye a second time after a brief stay with them as I head north out of Florida. I question if I left too soon again, but likely not. Most people's road trips are like a city per day or per week. To have the luxury of spending a handful of months in one location is a unique blessing.

I learned a lot, and if I had to pick one thing, I came out of the experience realizing how happiness, joy, and good relationships can be formed anywhere, even small cities. I saw that with my sister and her boyfriend. They're almost always upbeat, laughing, positive, and enjoying eachother's company even though they work so much every week. Their work takes up their lives and makes up their social lives and activities too. They're upbeat about it. I was reminded to stop optimizing or deliberating too much about what the perfect city is for me to live. I was being too picky, always analyzing, always finding cons to match some pros, when right in front of me, I could see happy people. While I do still think some optimization helps (a larger city is still for me), I was reminded to stop beating myself up - live life, enjoy, and realize that what I seek - happiness, good friends, a good partner, all of that is possible, even in a small town/city.

So thankful for these memories. Until next time,

Will Chou