A common suggestion people have made to help me regain my financial independence is to move to a cheaper area of the country or the world to save money. I’ve resisted relocating so far because I believe the excitement of living in a big city is worth the cost.
I’ve lived in big cities all my life. I was born in Manila (population 1.8 million), lived in Lusaka (3 million), Kobe (1.6 million), Kuala Lumpur (1.8 million), Taipei (2.7 million), New York City (8.5 million), and now San Francisco (810,000). Big city living is almost all I know. As a result, it’s harder to change, especially with two kids in school.
The thing is, there was a four-year period during high school where I didn’t live in a big city. I lived in McLean, Virginia (50,000), a suburb of Washington D.C. (5.6 million) 10 miles away. And guess what? I didn’t particularly enjoy the experience. There wasn’t much to do except go to the mall, hang out at McDonald’s, and get into trouble with my friends.
If you thrive on the energy of others, big city living might be the right fit for you. If you’re actively working to build your net worth for financial freedom, larger cities are likely to provide more financial opportunities. On the contrary, if you identify as an introvert and/or have already achieved financial independence, you might prefer a quieter pace of small-town life. There is no right or wrong answer, only preferences.
Living In New York City Was The Best, Despite The Cost
Moving from Williamsburg, Virginia (16,000), where I went to The College at William & Mary, to New York City was the most thrilling time of my life.
Can you imagine going from a small college town to to the busiest city in America? I lived in a studio apartment at 45 Wall Street and walked 0.4 miles away to One New York Plaza, where Goldman had its Equities department.
Once you jammed into the elevator to take you to the 49th floor where the international traders were, you stepped off to a buzz that kept growing until shouting commenced when the stock exchanges opened at 9:30 am.
If you then took the stairs up to the 50th floor, the buzz got even louder because the U.S. equities department was five times bigger. Along the sides of the floor, Goldman partners had their offices with glass windows.
I still remember when Patrick Swayze, the actor from Dirty Dancing, dropped by to pay a visit. Every month, there seemed to be some random celebrity making the rounds.
The Yankees Win Again!
When I started interviewing for GS in 1998, the New York Yankees had just won the World Series. When I joined in June 1999, the New York Yankees repeated again. Then they won again in 2000! I still vividly remember seeing the parade come downtown from our windows, and then rushing down to partake in the madness for 15 minutes during my bathroom break. It was shear joy!
New York City knows how to eat your money if you let it. But the nightlife was amazing, the shows were world class, the food was to die for, and the people were as diverse as could be.
It didn’t matter what time of the hour it was, you could always find something exciting to do. As an extrovert, I loved living in New York City as a first and second-year analyst living in a shoe box on a $40,000 and $55,000 base salary.
When I “accidentally” picked up a phone call and overhead my big boss say I wasn’t going to get renewed for a third year, my heart sunk. So I interviewed on the Bear Sterns to no luck, thank goodness! The Dotcom bubble had burst and Wall Street had begun laying people off in mass.
My two-year stint in NYC was over. Luckily, I was able to finagle my way to a new job at Credit Suisse in San Francisco. A new adventure awaited.
A Big Step Down In Excitement Living In San Francisco
Before arriving in San Francisco in 2001, I had visited the city once in college. One of my good friends was attending UC Berkeley, so I thought I had a decent idea about the city. But I wasn’t prepared for how different the pace of living was compared to NYC.
In comparison to New York, San Francisco was a sleepy town with only 1/10th the population. The bars closed at 1 am and it was strange to have so much room to walk on the sidewalks. San Francisco was a letdown in terms of excitement, but there was a better balance between work and life.
The moment that made me love San Francisco was one Friday afternoon my first winter there. It was raining so I decided to drive up to Sugar Bowl in Lake Tahoe, 2.5 hours away. It had just snowed 12 inches of fresh power and we had a blast on Saturday. On Sunday, the sun was shining and I ended up playing tennis in 68 degree weather with my pecs out kissing the sun.
As a 25-year old young buck, I was thrilled to be able to have such a fun and affordable weekend. In New York City, I didn’t play tennis for two years because I was working all the time. In addition, there was nowhere public in the city to play. Private courts cost $50-$80/hour at the time, and you needed to know someone.
San Francisco Is Cheap Compared To Manhattan
I don’t care what anybody says, but San Francisco is cheap compared to Manhattan. It was 30% cheaper back in 2001, and it’s likely 40-70% cheaper today, depending what type of property you’re buying.
Yes, I know there are cheaper Burroughs to live in, such as Queens. But I think comparing San Francisco to Manhattan is most appropriate. Brownstones in Manhattan cost $15 – $25 million and are on <3,500 square foot lots. In San Francisco, you can get a similar property for only $5 – $10 million, but with a lot more land. What a bargain!
The ability to earn the same amount of money in San Francisco, but live 30%+ cheaper was a benefit to my financial independence journey. Because the hours were also brutal (got in by 6 am, left after 5 pm regularly), I continued to save and invest as much as I could to one day escape early.
Since 2001, the excitement of living in San Francisco improved thanks to:
- The internet boom and bust and boom again
- Getting my MBA at Berkeley part-time for three years and meeting new folks
- The San Francisco Giants winning the World Series three times (2010, 2012, 2014)
- Attending countless startup meetups
- The GS Warriors wining the NBA championship four times
- Consulting with several fintech startups
- Exploring Napa and Sonoma Valley
- Regularly enjoying Lake Tahoe during the winter and summer
- America’s Cup sailing race
- The Ryder Cup and U.S. Open golf events
- Multiple professional tennis tournaments in Tiburon, Palo Alto, and San Jose
- The 49ers reaching the Super Bowl in 2020
- Tthe 49ers getting back to the Super Bowl in 2024
What I realize from writing out this list is that I love tech, entrepreneurship, making money, and sports! New York City got me hooked and San Francisco dutifully carried on the tradition. If you love the above things too, you will enjoy living in a big city over a smaller city.
The entire San Francisco Bay Area is buzzing about the 49ers squeaking by two teams in the playoffs. Everybody feels happy and excited again!
Too bad the Kansas City Chiefs will likely win again. But if the 49ers do win, oh boy, what a victory for the city.
The Thrill Of Getting To Know Some Of The Warriors
Over the years, I got to know my friend Shaun Livingston, who won three NBA championships with the Warriors as a player. I got to hang out with him in the family & friends lounge post game with the players many times. In addition, I went to one of the team’s events to talk investing and crypto. It was fascinating to go behind the scenes and experience what my sports heroes were doing.
As a Warriors fan, I’d gladly take a $40,000 / year job to be a video coordinator since I’d get to travel to the team and hang out. The camaraderie of a sports team is the best type of camaraderie there is. Alas, I have to wait until my kids are in college to leave my family behind so often.
The Energy Of The Startup And VC Community
During the winter, as a limited partner, I attend the Kleiner Perkins’ winter holiday parties with my wife. There I get to mingle with other entrepreneurs and venture capitalists who are all excited about the future. Oh, and the food and drinks were fantastic.
I can feel their energy as many are focused on building artificial intelligence companies to help humanity. Their drive gives me motivation to continue creating on Financial Samurai as well. Getting to know some of these folks also opens up new investment and partnership opportunities.
As an extrovert, I’m not single but I’m ready to mingle! The thing I miss most about working in finance were all the holiday parties I got to attend. Each party was a great time of celebration, appreciate, and reflection.
With my platform, I could run my own angel fund or be a scout for one of the larger VC companies. If so, that role would automatically inject me deep in the VC community. To be a successful venture capitalist, I think it’s important to be in a location where you can regularly meet with your companies.
Relocating To Save On Cost Is Not Worth The Downgrade In Excitement, Yet
Yes, paying ridiculous amounts of money for housing and education hurts, even though I believe the value of learning a second language is high. However, at the moment, I believe the excitement I get from living in a big city outweighs the cost.
Given everything is rational long-term, I am currently willing to pay a ~$100,000 annual premium to remain in a big city. When the excitement is no longer worth the price or when I no longer have the ability to earn, I will relocate.
At 46, I’m not ready to leave San Francisco yet. What I realize is that I’ve got one last hurrah in me before I’m too old and tired to try. Maybe the last hurrah will be working at a startup or filming a TV show. Who knows. By staying in a big city like San Francisco, it offers more unexpected opportunities.
When I’m ready to take things easier as an older man, then I plan to relocate to Honolulu, Hawaii, a medium-sized city with about 350,000 people. I love Hawaii and the peace and tranquility it brings every time I return home to visit my parents.
Until then, I will be enjoying all the San Francisco has to offer. Go Niners!
15 Of My Favorite Big Cities I’ve Been To Or Lived In
- New York City
- San Francisco
- Singapore
- Hong Kong
- Beijing
- Shanghai
- Kuala Lumpur
- Taipei
- Kobe
- Tokyo
- Barcelona
- Amsterdam
- Paris
- London
- Rio de Janeiro
Reader Questions
Do you enjoy big city living? Are you hooked on the excitement of something always going on in the big city? Do you think the cost of living in a big city is worth it? Do we change where we want to live as we get older and as our family circumstances change? What are some of your favorite big cities?
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