Squeezing the most juice out of New York City

Posted May 12, 2025

I was recently talking with a friend about "squeezing the most juice" out of New York City. This was a friend who already agrees with me that there is something profound about being here -- a position I have difficulty explaining if one does not already agree with me. At best I can sound kind of out there, talking about "the energy" that the city offers and lately I have settled on telling people "I just like it."

The concept of making the most out of this city which people pay inordinate sums of money every month just to continue living in -- plus the real cost is far more than just financial -- feels a lot more tangible than discussing why life feels profound here in the first place. Ironically, I felt like talking through this topic did a better job of explaining what I think actually makes NYC special and profound without mentioning energy or vibes.

Below are my thoughts on how you can leverage the opportunity that NYC offers. You'll notice that a lot of it focuses around friends and relationships. One of the things I realized writing this article is that this is probably where that "energy" comes from. A city filled with interesting people who truly want to be in this specific place is probably what makes it feel the way it does.

Balance your early coffee mornings : late bar nights ratio

My first experience living in NYC was a 10 week internship with J.P. Morgan Chase in 2016. I had an absolute blast in the city and in many ways made the decision then that I would like to someday commit to living here long-term. I had also just turned 21 and was enjoying the bar scene with friends and fellow interns.

When I moved back here at 28, I found myself in a situation I had become far too accustomed to during my internship. In the subway station, at some ungodly hour, waiting for the next train. I don't know what temperature it is in the station, but I'd conservatively guess 200 degrees Fahrenheit. Some guy is still singing the last song he heard in the bar before he got kicked out. For some unannounced reason (I assume to personally inconvenience specifically me) the dot matrix screen just upped the estimate from 10 to 25 minutes until the next train arrives. At 28, this is a far more painful experience than at 21.

I wrote a note to myself that I don't enjoy these late nights. I'm more of a morning coffee person, after all! So I went out less and enjoyed more of those mornings, grabbing a $6 latte and a book to post up at the park with. Until, of course, these mornings got boring and I found myself wanting to go out at night again. Like many things, the true answer is somewhere in the middle.

I'm focusing on these two experiences because they are quintessential NYC experiences. The coffee stroll in the park, witnessing so many different parts of the human experience right in front of you with the backing of beautiful scenery and genuinely talented musicians, is something everyone should experience and New Yorkers take for granted. And of course, there is the bar scene. Maybe this deserves its own section, but learning to enjoy the bar scene with friends while making new friends here will unlock incredible experiences.

I see many people focus on just one of these experiences and when they grow out of it, they think they have grown out of New York. In reality, you can figure out how to enjoy both of these special experiences in moderation. The categories are large; "going out" is not just going to a bar and you can go to your favorite diner with friends instead of getting coffee in the park solo. You can and should do both, and you will improve your relationship with the city.

Meet your neighbors

You should make an effort to be friendly within your building to an extent that maybe even risks coming across as annoying. Put more plainly, you shouldn't worry about being too friendly or being perceived as odd because the value of knowing the people who live right next to you is so great for both of you.

When I lived in apartment #15 in my first building, an East Village walkup, the couple in apartment #13 knocked on my door asking to borrow a wine opener. A parent was visiting and had brought a bottle of wine. They asked if I'd like to join them and have a glass in exchange for lending my wine opener. I had just come back from the gym but was overjoyed at the opportunity to make friends in the building. This excitement was well placed, as over the next year I grew much closer with these individuals and we helped each other out on numerous occasions.

I have since moved out of that building and we still maintain contact. These people quickly became dear friends. It was funny to me because I had many opportunities to make that introduction earlier and chose not to out of fear of being seen as weird. They later shared that I was their first friend in the building after living there for over two years and they also thought it was silly that we saw each other in the staircase regularly and never really said hello. I watched their cats when they were away and received packages for them, and when I moved into my next building they wrote one of my co-op recommendation letters.

The neighbor relationship is special because it is both practical and can be a closer experience than with many friends you are already close with. Inviting them over when you made too much dinner or spontaneously getting asked to try out the new restaurant on your street -- these are really cool New York experiences. Meet your neighbors!

Try to find a consistent living situation

On a flight back from a friend's wedding, I sat down next to another passenger traveling back home to New York and struck up a conversation. We ended up on the concept of living in the city and the real estate market, as I had been considering purchasing in the city and had an open house I was considering attending almost as soon as I landed.

This passenger told me that many years ago, he had the opportunity to buy an apartment. It seemed like more money than one could ever justify spending on their home at the time, but he made it work. Eventually, his neighbor was selling their unit. Doing better in his career, he bought their neighbor's unit and combined it with his. This repeated two more times and he ended up owning nearly 4000 square feet in the Upper West Side. Obviously this is an extreme case but he certainly had my attention. He showed me pictures of the renovations over the years and you could tell he had really made this beautiful apartment his own.

Eventually we got back to my situation and he told me something to the effect of: "I was fortunate about the extra units, but I still remember how I felt buying the first apartment. I thought I'd never recover from that decision, but very quickly I continued growing in my career and even found myself in the position to buy all these other units. The most important thing I want to tell you, because you say you love living in New York City, is that I lost count of friends I had who made the opposite decision. They continued renting. As my decision to buy looked better with every passing year, the rent kept rising and eventually it became too much for friends who were renting for years. These were people who also excelled in their careers, but not faster than rent rose."

After I made the decision to buy, I found myself around others who made this decision as I introduced myself to other residents of my building. This sentiment by the passenger I met on the flight was echoed constantly. I cannot possibly offer financial advice and I need to stress that the reasons to NOT buy in NYC are many and they are compelling. Many financial experts advise against it. For me, it works and it has multiplied my enjoyment of the city. I feel more secure here. The landlord cannot suddenly increase my rent 15%. I can make the right adjustments I need to tailor the apartment for me and how I want to live life.

One way to do this without buying is to find a rent controlled unit. Especially when you consider the potential drawbacks of co-op/condo boards and management, rent controlled units start to seem like a very similar setup to owning with the same cost benefit analysis. I do not know much about this subject but I do think this is an achievable goal if you pursue it the same way you would pursue finding a place to buy.

I also totally recognize that I was very fortunate to be in the position to buy at all. I have always worked hard, but luck is a factor as well. The only point I want to make is that you can spend that combination of luck and work in many different ways. I chose to spend a lot of it on solidifying my living situation so I can more likely stay in New York long term and compound the benefits of living here. Buying is an emotional decision, but I do think what the passenger told me about rent forcing people who loved the city to leave is something you should consider.

Supplement Vitamin D during the winter

Get enough sun when it's out. Unsurprisingly, very few New Yorkers need to be told this. However, you should absolutely be supplementing Vitamin D during the winter here. The difference in people's attitudes during the winter vs. when the weather finally starts to change in spring is startling. Everyone just feels better. You should be doing a lot to combat winter melancholy that is common here, like maintaining regular exercise, getting good sleep, and going to therapy if needed, but Vitamin D supplementation is really high bang for your buck.

Maintain friendships and always grow your circle

Something that I've found to be true in large metros in general but is particularly pronounced in NYC is the fact that friends will move out. Life is unpredictable and even those who claim they will be located somewhere long into the future are surprised by a change and a need to move.

I've heard a lot of people describe their post-college friendships as "enough" or "I don't have any friends." It seems like people can be devastated by friends moving away and suddenly they feel like they are totally alone. Conversely, this same person previously felt that their small group of close friends was enough, and it was probably emotionally fulfilling enough. However, I feel that this is a trap. It is a blessing when you can maintain these strong friendships for most of your life, but it is like building a house out of extremely weak material. A hurricane is one thing, but if your house can fall over from a once in a 10 or 20 year storm (if either of those are even a term) then you will eventually be devastated.

My solution to this is to prioritize maintaining your existing friendships first, and also to constantly exercise your muscle responsible for making new friends. Do not take your good friends for granted. To be honest, consistently being there for your already-close friends can be the difference maker between them considering a move away or not.

Another thing to consider is that old acquaintances from the past may have since relocated to NYC. Whenever you hear about these, I think it is really fun to meet up. I've sat down to dinner with people I haven't seen in 15 years and that is just such a neat experience. Because you already share something in common, it can be very easy to revive old friendships.

Finally, you should get good at meeting new people. It takes practice, but talk to new people always. In situations where you can, ask for their phone number and suggest meeting up for a beer. When a friend introduces you to a new friend, especially someone new to the city, treat that as sacred. Make the connection and make plans to meet up again. It's actually a really special thing when someone thinks "wow, I just met this person and they're already treating me like a good friend." Obviously, make your discernments about what dealbreakers are for you, but if you can give them that affirmation early, they will feel safe and will act like themselves which is helpful for developing real connections. Wonderful things can happen as a result, chiefly among them: your circle starts growing fast.

Be a social connector

This is another concept that is true everywhere but is particularly pronounced in NYC. When I had that internship with Chase in 2016, I wasn't really focused on this. I was, however, open to meeting anyone else in the program of several hundred interns but past that I had no real agenda. NYU had dorm rooms available to rent and many interns took advantage of this. One of my roommates, Sean, was an extremely social guy. A lot of the time I felt like I was just piggybacking off of his connections and things went well. People would say things like "Mark, you have to meet this person" and they'd introduce me. This felt so convenient and I was able to meet so many people in a relaxed manner. Towards the end of the program I was joking with Sean about how he was so well connected and he just started laughing. He told me "Mark, everyone I meet somehow already knows you. I don't think I have introduced you to anyone really." I realized that by being relaxed and thinking I was just making connections through Sean, I was actually making most of these connections myself.

I think the key is that relaxation. Almost everyone has some anxiety when meeting new people, but when you recognize that people are waiting to be connected and expand their circle, that anxiety should subside. They want to meet a new friend, someone who might also be single and interested, the fellow artist they could collaborate with, the startup founder working on something they are very experienced in. Take that step to meet new people and introduce them to others you already know, and you will realize it isn't scary at all.

An even better way to do this is to systematically set up a regular get-together that you can host consistently. This is something I am working on at the moment. The kitchen in my apartment was not really cared for so I am repairing things and updating the overall look and utility of the kitchen. My goal is to eventually host dinners on a regular cadence, maybe something like once a month. I'd love to have close friends know that they are always welcome to join, as well as any new friends they met.

I'll have to report back on what my experience was like here, but I think it will be an excellent way to maintain friendships and build new friendships. I love cooking and I love hosting, so I get to be a great version of myself while being social. I think if you can host something like this -- book clubs,

Intentionally design your career

Many people move to New York for work. Often, it is the only way to justify the giant increase in monthly housing costs. Companies know they have to pay more here and that many of their employees want to be here. Nearly every large corporation has some kind of a presence here and many interesting startups either start here or build an office here after their San Francisco office.

Obviously, there are many opportunities here in the corporate world. However, there are incredible opportunities outside of that. Some of the world's best art galleries and major players within that world are here. Jazz clubs, comedy clubs, upstart restaurants -- there are opportunities here to not only patronize these places where you will find people who love what you love, but you can also join in. New York famously is where many now-famous comedians got their start at open mic. They talk about how they got up to open mic and seeing their idols in the crowd sometimes.

There is no magical place where you instantly get acclaim and success, not even New York! However, incredible opportunities to get serious about what it is you truly want to do are all around this city.

Conclusion

As I mentioned in the intro, a lot of this ended up being about the relationships you build in the city with the interesting people who you can find here so commonly. Maybe in the future I can modify this post with more practical information outside of this specific lens, but hopefully you have enjoyed reading my thoughts here.