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Bye Bye, Bubble! Enter, Adventure.

Updated: Mar 8, 2021

Remember when Rachel Green abandoned a career as a rich housewife to move to the city and become a waitress? While it’s true that I will find any excuse to compare myself to Jennifer Aniston, Rachel once again proves that the best stories begin with leaving home and “making it on your own.”

As over-privileged 20-somethings, we tend to succumb to our lazy instincts, complacent with ourselves and our surroundings. When we settle with what we are comfortable with, are we really becoming the best versions of ourselves? Are we really developing our likes, belief system and goals? The narcissist in me believes that a job offer in Chicago was my calling to begin my expedition to learn about myself – as if I am some hero.

While I glorify my San Francisco days, which I refer to as Berkeley 2.0, I lacked the character development inherent in all our favorite protagonists’ journeys. I could bump into at least 20 familiar faces on Taco Tuesdays and frequently visit my family, a short 45-minute drive away. But after a short year, I realized I needed a change and embarked on a new adventure, taking a more challenging career path in Chicago.

I arrived in Chicago with two weeks to winter. The brutal winds welcomed me with open arms into a city filled with frostbite, blue skin and utter loneliness. As any hero does, I initially did not reciprocate the love and feared this mistake I had gotten myself into. I deplored the frigid cold, which would frequently shut my phone off at the middle of my walks – yes, iPhones now have the capability to withstand the Polar Vortex. I longed for a local support system to hear my cries. I couldn’t relate to anyone in the office – none of them even watched Gossip Girl! Frequently, I would spend my evenings after a 16-hour work day for an hour in my walk-in closet, smoking hookah by myself. I would blame this “crappy city” for my unhappiness, and soon come to know my new label as the complainer of the office. Interestingly, people don’t like their homes being criticized. Let me validate those who have or are currently experiencing a new move and say that it is completely normal to resist change and undergo frustration of a new environment.

That said, assimilating to a new place starts with the right attitude. As I condemned every portion of Chicago to my family over Christmas break, I received some much needed feedback. While I will probably deeply regret comparing parents to some sort of prophet, their words struck a turning point for me. For those of you that have read my prior posts, you know I love my number rules. My parents introduced me to the rule of six months: before deciding if you should run away from something – unless your Tinder date is stealing your wallet – try approaching the situation more positively and narrativize your new life change as a learning experience for six months. Then reevaluate. As any entitled millennial, I lamented my parents for not comprehending my experience. Nevertheless, I secretly took their advice to heart and started exerting genuine effort towards appreciating Chicago, thereby beginning my metamorphoses.

I endeavored to make my experience more enjoyable, drowning myself in various activities, most of which did not pan out. I signed up for competitive beach volleyball. Turns out, it’s not going to work out when you are an embarrassment to sports and people are pitying you left and right. I ventured into the Midwest dating scene. Let the records show that I am also geographically-challenged. The Midwest is actually quite large, so I should have narrowed my dating search to a 1-mile radius from 500 miles. I tried retail therapy – the absolute temptress. Note to self – The Sex and the City lifestyle is fictional: an average 23-year-old’s wealth will quickly plunge post six pairs of Louboutins. I advise fellow adventurers to persist and explore hobbies and social groups that you never would have – something will eventually stick.

Finally, I was at a crossroad – should I immerse into the quintessential post-grad Chicago lifestyle and let go of my past? After the various tests that Chicago put me through, which I seemed to keep failing, it appeared easier to go back home. I pushed myself with one more good old college try. I started hanging out with one of my coworkers, who so kindly welcomed me into his inner circle. I started embracing the “beach” that everyone in Chicago raved about, as opposed to mocking it for being on a lake. I accumulated appreciation for the food, drinks, parties, sports (watching, to be clear), and more. I. LOVED. Chicago.

Further, upon reevaluating Chicago, I decided to attend real therapy to address my internalized negativity and desperate desire for validation. A third party perspective on my daily life and the difficult decisions I often have to make is invaluable to me. I applaud New Yorkers, who are largely progressive in this aspect and view therapy as a requisite to maintaining a healthy lifestyle; fellow Silicon Valley-ans and Chicagoans, we need to catch up. Through my self-learning, I introspected on my career and realized I indeed am a masochistic deal junkie who loves finance.

The above marks an example on the obstacles one goes through when stepping out of their world. But honestly, that’s only 25% of the journey – the bulk of it comes from true self-development. Before moving to Chicago, I had ignorant beliefs about discrimination because I spent my late-teens in a bubble. I didn’t interact with the diversity of people needed to realize that those ideas were patently false. Despite the fact that the Silicon Valley technically has a wider variety of ethnic backgrounds than Chicago, I found that the average millennial San Francisco professional does not necessarily acknowledge the privilege they have. Many of us grew up in tech and were raised by parents who worked extremely hard to provide us a comfortable lifestyle. However, with that, we tended to be hyper-competitive and may have not always thought to empathize with those who experienced much deeper struggles.

When I moved to Chicago, I learned how important it was to be aware of the world around you and the discrimination that others face. I further cringe thinking about how apathetic I was towards the infamous Prop 8 in California, which took away gay people’s rights to get married. I don’t recall the exact day that the switch happened, but between the various friends I made, my liberal uncle and aunt who I would frequently visit and simply observing people’s entanglements in this new city, I concluded that the world is not fair to a lot of people, and I am privileged in a lot of ways. That would help me make changes in the future.

I would work towards making sure people feel comfortable with me. I would actively try to eliminate any unconscious biases I previously had and I would vehemently push for diversity in the workplace.

This is not to praise myself. This is to illustrate to you that you will change for the better as you gain more awareness when you are put in a completely different environment and forced to look at the world with a fresh set of eyes. I found enlightenment in my new world and believe I truly grew from my experience.

All of this to say, take that risk and move out of your bubble! You don’t have to limit yourself to one – I have made eight “significant” moves! I have spent my 20’s in San Francisco, Chicago and New York. I initially despised both the latter two, but came to eventually love them. Without beating around the bush, at least the first six months will be challenging. But when you encounter a new world, you face many hurdles and end up evolving into a different, and likely better, person. I recommend mitigating the initial obstacles with persistence, therapy, introspection, observation and a positive attitude. I’ll let you know when we gun for our next move – j’aime Paris!

As an aside, here are my picks of spots I love in San Francisco and Chicago! I am still working on my New York list and hence, will wait to share that one! Please note that obviously the trendy spots likely have definitely changed since my time at these places, but for what it's worth, I have great memories in these places.

San Francisco


* Smugglers Cove – My favorite SF bar. 49 person capacity and known for its tiki vibe, but overall feels cozy and has really unique drinks

* Bourbon and Branch – Classic speakeasy with a great vibe

* Marrakech – Moroccan restaurant, which I would go to for hookah

* 620 Jones – Classic rooftop bar

* Novela – Literary themed bar with drinks named “Leopold Bloom” and “Jay Gatsby”

* Local Edition – Newspaper themed lounge-like bar

* Nick’s Crispy Tacos – Taco Tuesday

* Charmaine’s – Rooftop bar with a fire pit

* Tipsy Pig – Marina and probably for under-25-year-olds. But gotta love the Strawberry Fields!

* The Brixton – Another good marina spot


* Z & Y Restaurant – Bao bing and famous chicken pepper dish

* La Mar – Great Peruvian place - Nigiri criollo

* Hamano Sushi – amazing hand rolls and sashimi

* The Spinnaker in Sausalito – Seabass

* Hillstone – Ahi Tuna Salad with Mango

* Prospect - Seared Hudson Valley Foie Gras and Ahi Tuna Tartare

* Flour and Water

* Zero Zero

* San Tung – Best fried chicken

* Yummy Yummy - Salt and pepper crab

* Yank Sing – Expensive Dim Sum

* City View – Brunch Dim Sum

* Akiko’s – Omakase

* Kokkari

* Harper and Rye – great drinks and pool table

* Tony’s Pizza – Porto Pizza

* Dim Sum Bistro – Takeout dim sum

Quick drive from Berkeley which has way better food

* Brazilian Café - Tri tip sandwich

* Turkish Kitchen - Lamb beyti

* Cheeseboard

* Gypsy’s – Godfather’s favorite

* Steve’s Korean BBQ – Spicy Pork

* Kimchi Garden - Kimchi Fried Rice



* Berkshire Room – lounge; Dealers Choice drink where you choose your flavor / liquor

* Three Dots and a Dash – Similar vibe to Smugglers Cove (tiki bar) with super rum drinks

* Green Mill - wonderful live jazz performances and Al Capone's favorite booth

* Kingston Mines - One of the oldest blues bars which is spacious and fun for dancing

* The Hangge Uppe – Only if you are < 25 and super drunk and it is past 1AM. I love my trashy bar dancing to throwback music

* Untitled – Spacious speakeasy

* Violet Hour –speakeasy

* Watershed – Awesome cucumber mule

* Cindy’s – rooftop bar overlooking millennium park

* LondonHouse – rooftop bar

* Cerise – Rooftop bar at the Virgin Hotel

* Palmer House lobby –generally fun to drink there when studying

* Lost Lake – Speakeasy version of Three Dots

* Aviary – Expensive but worth trying once

* Old Town Pour House – about a billion different beers


* Alinea – you have to try it at least once. One of my favorites of all time

* Next – I sound like a snob, but also have to try it

* Roister – Alinea Group's "casual spot"

* Carnitas Uruapan – authentic, delicious carnitas tacos

* Sun Wah BBQ – I have finished an entire peking duck with one friend in one sitting

* Furama – Great dim sum

* Superdawg – Best Chicago style hot dogs

* Pequod’s – my favorite deep dish because of the crust

* Honey Butter Fried Chicken


* Ras Deshan – Ethiopian

* Roost

* Café Iberico – tapas and liveliness

* Wakamono –softcore homoeroticism permeating a delicious sushi spot

* Shaws

* Prime and Provisions – steak

* Chicago Cut – steak

* Girl and the Goat – Wood oven roasted pig face

* Little Goat Diner

XoXo Nish

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