A New Life in Chicago

A self-evaluation of habits and headaches

Post-writing notes: nothing particularly insightful in this reflection. Just an update on how life has been for me since moving to Chicago. Some thoughts about the struggles I’ve been facing, some parts of life I’m proud of, and generally what I’m trying to improve on! Hope you enjoy.

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Hi friends, family, fellow audience, and strangers across the internet. It’s been a while since I’ve written about this personal newsletter, and I’m not too proud of that lack of motivation, discipline, or maybe both (throwback to my other piece here). I’d say it’s almost too easy for me to just blame it on the working hours because those frankly haven’t been too challenging to manage. I’d also say it’s easy for me to blame it on just settling down in a new city, but I think I’ve had enough time to get past that phase. I’m pretty comfortable now, but is that a good thing?

As a few of you may know, I chose to move to Chicago for the prospect of forcing myself to be uncomfortable; the prospect of pushing myself harder was intriguing in a new city where I didn’t know many people. I think similarly to how I felt when I started solo traveling, there was a stage of uncertainty about what the new city would bring. But within a few months, that desire of seeking discomfort was fulfilled, and it no longer felt as challenging. I think I’m approaching that stage in my move to Chicago, and I’m increasingly considering the next move I want to make. Is it to SF? NY? Back to the ATX?

At the same time as writing this, I know that I have plenty of time in Chicago to figure it out. It’s the same issue I faced back in college where my free time would allow my brain to roam freely in thinking about what the future may hold—maybe not the healthiest use of my time, but a reoccurring instance, nonetheless. So that brings me to the point of this update post: what has been new in my life, the few learnings I’ve had, and what I want to improve on moving forward. I’ll start with the bulk of my time: reflections on work itself.

Part A: My life at work

Work has been a really interesting experience thus far. I’ve told a few people this, but Vista is a place where, in a world assuming finance is what I want to do long-term, I can easily see myself ending my career. The biggest caveat, noted above, is simply my uncertainty about my desire to be involved that deeply within the financial services space. To note the non-finance aspects of the job, it’s everything I can ask for right now: incredible culture, incredible people, sustainable pay, and just a constant opportunity to learn.

I think the part I’ve loved the most about work is the people I’ve worked with. The mentorship has been unparalleled compared to my, albeit limited, professional working experience. There’ve been some incredible people who have helped me significantly since I started, and I can very easily say they’ve not only been an instrumental part of my experience being enjoyable here but are also friends I hope to cherish for a long time coming.

Work itself has been interesting. I’ve been placed on some very interesting deals across different industries, but ultimately I always fall back towards asking myself the question of whether am I really getting the learning that would be valuable to what I truly want to do long-term. That question I just noted is incredibly vague since I don’t have true visibility on what it means for myself yet. But, given that there are weeks when I have quite a bit of free time, I have the freedom to ideate and work towards the next big thing for myself, and I really do want to continue scratching the itch of entrepreneurship.

This has given me the idea of writing an upcoming blog on the different startup ideas I’m thinking through. Hopefully, I’ll follow through and write it maybe next weekend. Moving onto Part B.

Part B: My (figurative) headaches

I think I’ve been inefficient with how I’ve spent my free time here in Chicago. I’ve been going out more trying to meet new people, and although that’s important, and I’ve been relatively successful at making a few new friends who have been incredible, the task itself of going out isn’t meaningful or fulfilling. This section will cover a few of these headaches I’ve been struggling with. I could write long pieces on a lot of these items, but I’ll try to keep them relatively short and sweet:

• Keeping in touch with old friends

I think I could do a better job of this. The concept of friendship is hard to maintain virtually, but that isn’t an excuse to not put in the effort of reaching out to old friends and keeping those relationships strong. And although everyone’s lives are busy, at which point do you reconnect? When you go visit another city? If you don’t reach out over a longer period of time, do you keep that relationship? Is it as close as it was before? Or as close as you’d like it to be?

To me, the struggle is more so knowing who wants to actually hear from me vs. making that assumption. I’m at peace without knowing, but again, not an excuse to not put in the effort. I think there is a circle of relationships of individuals that I know will always be dear to my heart, but that second ring is hard to gauge. That’s not to say anything negative about them at all, that isn’t the purpose of this reflection. It’s more so just not being so sure since you’ve always been the one to reach out to people first. It’s a struggle I’ve had discussions about recently, and honestly an interesting reflection to think about. Regardless, I can do a better job of this.

• A dying attention span

This one is super random, but I think my attention span has been drastically shortened. Sometimes work is really tiring, and I fall into the rabbit hole of TikTok. It’s easy to stimulate your brain with those pumps of dopamine, satisfying my attention with honestly a lot of noise. I think a re-emergence of more habit and routine in my life of reading and writing can help combat this a lot. I want to slow down my thinking and be more intentional with how I approach my usage of time. I want to go back to my ability to focus as I had in college, where I knew my priority clearly and truly worked towards it: a) maintaining healthy relationships with family and friends, b) keeping myself mentally healthy and fit, c) maintaining physical health, and d) building something impactful while working towards financial independence.

I don’t want to add another section for this offshoot of thought, but I think this lack of routine has made my brain a bit less organized than I’d like. I want to get back into the habit of categorizing ideas and creating better silos between the different projects and tasks I have or am working on. I want to rebuild my focus. What I plan to do: input more reading and writing back into my routine (maybe try audiobooks), reduce short-term dopamine hits, and implement more meditation back into my life. Although I am at peace, I don’t think I have the healthiest relationship right now with the speed at which I’m trying to think through everything.

• A weird relationship with dating

This is a peculiar reflection point that I don’t have too much to touch on. I think Chicago has been a hard city to date in, and I think that’s been a mix of aspects of the city that are out of my control, but also the excuses I’ve been making for myself. As much as I can say there is a lack of diversity, and I’ve tried but just faced bad experiences, I also just need to remind myself that there really isn’t a rush to find someone. I think I’m very much at peace knowing that, so why do I bother putting an emphasis on my struggle with dating?

No clue, I don’t think I’m emotionally bothered by this at all. Just an objective statement of a challenge that exists within this city. I don’t really need to make excuses either, and frankly, that’s not how I want to approach any problem that I face. I need to trust my own judgment better and prioritize building the relationships that are more meaningful in my life. The right person will come in time, and there’s no need to rush in finding that answer.

Part C: Things I’ve been doing well

So, this part of the reflection I’ll keep short, as I have a dinner plan coming up with an old coworker here in the city (giving myself brownie points here for reconnecting with an old friend!). I’ve also been sitting at this really uncomfortable seat for a long time now at this coffee shop, my ass is starting to hurt lol. I’ll finish up soon.

• Physical Health

I’ve started going to boxing classes! This has been incredibly fun, and I might even consider sparring soon. I think this has been one of my favorite workouts I’ve ever tried, and the amount of energy I’m able to exude within a session feels great. I don’t even have much stress to punch out hah, I just like the balance of strengthening myself, increasing my flexibility and balance, and just bettering my reflexes. Overall, 10/10, and a big shoutout to my coworker for the introduction to the sport.

Additionally, I’ve been going to the gym a lot more with just doing cardio and weights to supplement the days I don’t go to the boxing gym (trying to just go at least once a week right now, want to try and make this twice a week soon if possible). The sauna has been the true motivation behind my trips to the apartment gym. Big thanks to my apartment amenities.

• Work-Life Balance

Although this is not a product of my own proactive push for balance and rather just a slow period in work itself, I’ve done a good job of exploring some more of my interests and hobbies. Been doing pretty good in the firm-wide fantasy football team (big shoutout to Billy for the draft help), been watching the Rockets a little bit more (meh, given the slow start), watching some more Formula 1 (sigh, Ferrari), trying to do a little bit more cooking, but honestly, my lack thereof should probably be in the headaches section, and ultimately just spending a lot of nice time to myself. Overall solid, and can be a little bit better, but no need to be that hard on myself.

Concluding thoughts

It’s almost time for sushi! I’m pretty hungry, but today was a pretty cozy day to leave the apartment and go to a nearby coffee shop for some work. The table is this beautiful wood (super random comment), but mostly trying to just think about any final points I want to touch on.

I really want to build more personal projects. I really want to start being smarter with my money and how I’m investing it. Maybe real estate? Maybe micro-acquire a business? I’m not sure yet, but I know I want more proactivity in my life.

If you’ve read it all the way, let me know! I appreciate the time you’d put into reading my reflections, and if we haven’t spoken in a while, don’t hesitate to reach out. I may be doing some traveling coming up here in the winter season (thankfully avoiding some of the Chicago cold), so would love to know where some of you may be in this vast rock we live on.

That’s all for now, no additional thoughts. Will probably keep an active note on my phone for ideas for my next reflection. Feel free to share any things you’d like to hear.