The Excitement Of Living In A Big City Is Worth The Cost

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 hard 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 don’t like the hustle and bustle 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. 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 boroughs 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 and 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 Niners lost in the Super Bowl. But it was a fun ride.

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.

For those of you interested in investing in private artificial intelligence companies, check out the Innovation Fund by Fundrise. It is an open-ended fund that has ~35% of its investments in AI companies or AI-related companies. The investment minimum is only $10 and you can see what the fund is invested in before committing any capital.

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

  1. New York City
  2. San Francisco
  3. Singapore
  4. Hong Kong
  5. Beijing
  6. Shanghai
  7. Kuala Lumpur
  8. Taipei
  9. Kobe
  10. Tokyo
  11. Barcelona
  12. Amsterdam
  13. Paris
  14. London
  15. Rio de Janeiro

Related: The Unhappiest Cities In The World Based On A New Wealth Ratio

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?

Invest In Smaller Cities With Higher Yields

Living in a big city is exciting, however, home prices tend to be very high. As a result, you may want to implement my real estate buying strategy called BURL, where you Buy Utility Rent Luxury. This means buying smaller city real estate with lower valuations and higher yields, and renting in big cities with high valuations and lower yields.

Thanks to the internet, investors can now invest in private real estate deals in lower-cost areas of the country. In 2016, I began investing in the heartland of America because I felt there would be a demographic trend to lower-coast areas of the country thanks to technology and work from home.

If you want to do the same, take a look at Fundrise, a private real estate investor that has been investing in the Sunbelt since 2012. The firm manages over $3.5 billion with over 500,000 investors. Fundrise primarily invests in residential and industrial properties for income generation.


Subscribe To Financial Samurai

Listen and subscribe to The Financial Samurai podcast on Apple or Spotify. I interview experts in their respective fields and discuss some of the most interesting topics on this site.

For more nuanced personal finance content, join 60,000+ others and sign up for the free Financial Samurai newsletter. Financial Samurai is one of the largest independently-owned personal finance sites that started in 2009. 

46 thoughts on “The Excitement Of Living In A Big City Is Worth The Cost”

  1. I’ve lived in and around DC for most of my life. McClean is like a job center and a suburb combined. It’s close enough to DC to be accessible to the city but it is not DC proper. DC metro has about 5 million people but DC itself is only about 700,000 and it may be shrinking. The pandemic took a toll. And like SF there’s a lot of crime right now. To the point where the justice dept has gotten involved. Hopefully it comes back but it isn’t helping that the VA governor is peeling off two of their major sports teams. DC has some good to quite good urban enclaves like Alexandria, parts of Arlington, Bethesda and Silver Spring.

    I’ve traveled to most major American cities and a large number of minor 18-12 hour cities for work or leisure.

    I basically agree with Sam here. New York and San Francisco are unrivaled for diversity, culture, arts, and industry. These are the two world class American cities even though they are very different.

    Also rans are probably Miami (I don’t know how they deal with rising seas though), LA, and Chicago.

    There are more affordable and still interesting cities (due to their size and more recent growth) like Atlanta, Charlotte, and Houston.

    Brainy cities like DC, Boston, Seattle, Minneapolis/St Paul, and Austin.

    Outdoorsy cities like Salt Lake City, Denver, Portland, and the crown for weather and outdoor fun, San Diego. I guess you could put Las Vegas in this category too although the best of the outdoor fun is several hours drive. Did I mention how nice San Diego is?!

    There are a number of smaller cities like Santa Fe, New Orleans, San Antonio, and Charleston that have real appeal.

    And then there are a lot of cities that I don’t think make the lists but that doesn’t mean that you can’t have a wonderful life there. Phoenix, Albuquerque, Jacksonville, Buffalo, Cleveland, Pittsburgh, Oklahoma City, Dallas, Sacramento, Richmond, Raleigh, Columbia, Tampa Bay, Columbus, Detroit, Philadelphia, even Baltimore. But a number of these formerly industrial giants are still in the throes of depopulation and that’s really hard.

    I haven’t been to Hawaii so I can’t speak for Honolulu. Maybe it’s on the outdoors list?

      1. I seems like an obvious bucket list spot, but I take your enthusiasm to heart Sam! I need to get the kids a little older coming from the east coast. Just such a massive trip distance wise. Do you think it’s better than other Polynesian or South Pacific locations?

        1. Makes sense. Take them when they are at least seven years old. Kids don’t seem to remember much before five.

          I haven’t been to Guam or Samoa yet. No need to when Hawaii is closer. I hear the Maldives are nice.

  2. Christine Minasian

    We raised our kids in the Midwest/Chicago, and loved it but need a change in semi-retirement life now. We spend 4 months in Florida for tax purposes, renting in NY for a few months to be closer to our daughter in Brooklyn and Boston. I agree with you Sam- city life is AWESOME! We are seriously considering buying a property in Manhattan 2 bedrm, nothing crazy expensive- to spend several months there- thoughts?

    1. I would just rent in Manhattan. The city/state might get you for taxes given your residency.

      What are the tax benefits of living in Florida for 4 months? I thought the time threshold was 6 months +.


      1. Christine Minasian

        We spend 4 months in FL and 2 months in cities- NY & Boston. We were tired of IL misspending our taxes! We own in FL, and rent in NY & Boston. Good advice about buying in NY. Thanks!

  3. While cost of private education is an additional cost, there is another big one at least living in NYC which you haven’t addressed which is NYC taxes. As I’m sure you experienced these are additional to state and federal and are quite substantial as an addition to our already high state tax. That said, raising my family in Manhattan is a non negotiable as I don’t want to lose an hour of morning and evening time as family time, thar would be eaten up with an out of borough commute. Living in Manhattan now for almost 25 years I’m still addicted to the overflow of art diverse cultural experiences, restaurants, activities, and history. 10,000 steps are achievable walking my daughter to school and with a round trip subway commute + walk. What is the tax responsibility like in San Francisco, have you ever written about the impact of taxes and the retire early lifestyle?

    1. Yeah, city taxes stink! We don’t have city taxes in SF, just state and federal.

      I’ve written a lot about taxes and lifestyle. Pls Google it or search my search bar on my site.

      The thing is, as an early retiree with no active income, you generally pay LESS taxes. Some can also get subsidized health insurance as multi-millionaires!

      1. So many great posts on taxes! Just want to mention I have zero qualms with paying my share in taxes, these flow to the teachers, cops, subways, buses, ferries, everything that makes the city unique and possible for all. Taxes are a big factor in how one can plan for early retirement, as they are a lifelong obligation, I would love to read more about your unique scenario as I game out my own.

  4. Happy Lunar New Year to you and your family! Looking forward to your upcoming startups or TV shows! I don’t think I can ever move away from a big metro area. I live in the burbs of SF in the Peninsula but am close enough where I can get to the city. The only cities I’ve ever wanted to move to are LA, NYC and HK. I don’t think I can live in a nowhere town. It’s just too exciting to be in a big city and I need the vast food options. I’m hooked on the excitement of being around a big city. It’s worth the premium to be around good food! :)

  5. Chicago gets my vote for best big city. It’s far more affordable than cities on the coasts, but offers outstanding dining, arts, culture, sports and walkability. It’s a city of neighborhoods, each with its own vibe. And, unlike other iconic cities where you’ll never be an insider, it’s easy to lay down roots in Chicago. Summers here are magnificent with the lakefront and the beaches and the winters make for cozy nights cooking in. To be sure, there is crime in Chicago, like other big cities. But you don’t live in a place like Chicago to be 100 percent safe all the time. You live here to be part of something great!

  6. SF is very expensive for its size city. Charlotte is about the same size as SF and cost of living is 50-70% lower, not even counting the higher taxes in California. I personally like 18-hour cities over big cities and rural is definitely too small. In a market like Charlotte or Atlanta, its super easy to get a direct flight anywhere you may want to visit, and the geo-arbitrage would easily pay for many months of traveling vs SF or NYC, and both have MSAs of 2m+. Plus, do not have to pay for private schools.

  7. Good read, Sam! I agree, it’s hard to leave a big city. In addition to all the quality of life and perks of living in a big city, I’ve found that living in a city can even become a part of your identity over time. This is even more so with a city as romantic and culture/history-rich as San Francisco.

    5 years ago I used to say “I could see myself living in San Francisco for the rest of my life.” While now after having a kid 10 months ago I try to be more open to the idea of living elsewhere in the future (“whatever makes the most sense for raising kids” I tell myself), there is still a strong possibility that that somewhere is SF. You make certain trade-offs living in SF for sure (not as much space, kids can’t play in the streets, cost, etc), but there are also many, many upsides for kids (diversity of people, access to so many activities and nature, fantastic weather, etc).

  8. Hello Sam and All,

    I take the chance to share one of my deepest desires with you: I would really much like to move to NYC (Manhattan ideally), but realistically I’m still far away from that and think about that is a big decision and bet that I have to carefully weigh up from all point of view, especially as I have a small family (wife and 3 years old boy).

    Why I want yo live in NYC with my family if I have a decent life in Montreal,QC, Canada (a GREAT city to live in!!! even though the Canadian winter :))? is a question that the deepest of me think that would be “the best life move ever” for better in many ways, though my “shoulder-angel” tells me that in reality the economic cost for that though…would need a dedicated and still a years-planning to eventually make it real.

    My thought about to live in NYC are more than the “cliché” to live “the American dream” as for many immigrants. I have visited NYC since 2010 until now about 10 times and is I always love it, first as young//single professional and later with my by then girlfriend, today wife and our kid. Is always exciting and we adore all what the city can offer in terms of entertainment, services, education, diversity and even peaceful moments/spaces in the hustle and bustle of the city (I always remember the quiet and adorable moment when my wife take a short nap in Central Park, YES THERE, whereas I observed her and all the quite and peaceful greenery and aquatic scenario around that these place can offer), priceless!!!

    Besides, another “essential need” for me is that I want to live closer to the ocean and spend time-off just walking through the beach or boardwalk. Montreal is an island with great outdoor activities but it lacks of ocean/beach access (you got drive up north 6-7 h on “summer” or another 4.5h to get to Maine in the US for some coastal benefits.vs living in NYC, where you can take a ferry or train and get in about 1h to places like Rockaway beach, Queens on Long Beach in LI. Just to have such a benefits of “both worlds” (all the greatness of NYC with amazing public education for our kid, plus decent jobs for both well-educated professionals with PhD and more credentials; along with easy access to coastal moments) would really worth it such a move to NYC. I do not want to wait until I retire/older to get this that I need now in my 40s.

    However, the reality is more complex to fulfill my desires: My wife has a solid job (well paid, love it) and our circle of friends/family are here in MTL. Unless I would have a job offer that may cover much of what we do currently together in Canada, it would make her really think about to move to NYC. Though we love it, and if we would have a chance in the short-middle term (next couple of years), we should definitely take it, even if that means to live primarily in a smaller apt (1-2br) somewhere in Manhattan, NY.

    Well, following your blog since almost 2 years, I have been trying to improve my investments, savings (both getting better) and why not thinking to design a plan this year to materialize our desire to move to NYC somewhere in the next couple of years. It is a long term though in terms of how our life may happen and eventually our decision could change, but DREAMING BIG WITH A REALISTIC (WORKING HARD FOR IT) AND OPTIMISTIC ATTITUDE, you can really attract the things that you want in life.

    Thanks for chance to sharing my thoughts. Happy to get any feedback


  9. The first 10 years of my life was in a very small town in Central Texas, then my family moved to Austin. It took 30 years, but now I’m back in small-town Texas (Piney Woods) and never plan to live in a big city again. Even with all that the big city offers (I also spend several weeks a year in the Bay Area visiting relatives), I find the quality of life immeasurably better in a small town. And because of the low cost of living here, my finances have never been better—even on a modest salary.

  10. I am a lifelong NYC resident, Queens in my youth and Manhattan for the past 30+ years. There are many reasons to love NYC but only if you value those aspects. For me, it’s the arts & culture, diversity of people, quality and diversity of food, healthcare quality and walkability. As I get older, I value the ease with which I can meet up with people. I read somewhere that longevity and happiness had much to do with the quality, quantity and frequency of connections. It’s so easy to quickly meet up with someone for a drink or meal. In fact, I try to talk my friends who live in outer boroughs or LI/NJ/Westchester etc. to move into Manhattan as they usually decline weekday and last minute opportunities to meet. btw, spelling borough as “Burroughs” will get your NYC card revoked!

    1. Good thing I never had a NYC card in the first place! But not a bad article for English as a second language right?

      NYC is great for 8-9 months a year. As I get older, I can’t take the cold. I have been accustomed to going outside for a walk, hike, or sports activity often. I get the seasonal sadness disorder. Much happier when there is more sunshine and warmth.

      1. ESL is my favorite excuse as well. Being a skier, I don’t mind NYC winters too much. I actually think NYC summers are worse than its winters. Especially given the garbage… I did wish I was in SF for the Botticelli drawings exhibit which is not traveling at all, let alone NYC!

        1. Well, if summer is worse than winter, then we’re talking 6-7 months of unpleasantry in NYC.

          Have you written any articles in English or your first language? If so, I’d love to read it. Thx

  11. Finance Ronin

    I think most young people should give it a shot to make it in a big city–more career opportunities, diversity of friendships, things to do, etc. It’s certainly tougher to buy a house, start a family, etc. in a big city, but if you can make it here, you can make it anywhere. I should write a song about that. ;-)

    It’s easy financially to move from a big (expensive) city to a smaller one. The other way is nearly impossible, especially as one ages. I’ve had many friends move to lower cost of living areas as they hit middle-age, and I think that was the right move for them.

    I’ve lived in many big cities. I’ve visited every city on your list. I’d add Sydney, LA, Miami. I hope to live in a few more big cities before I’m done on this world. That being said, the big city isn’t for everyone–crime, loneliness, homelessness, etc. It’s not all about affordability.

    1. Financial Samurai

      I agree. Everyone should try once! You never know. You might have a good time and make a small or large fortune. And if you do make a fortune, you will find it easier to afford living in a big city.

      I haven’t been to Sydney, even though I lived in KL. On my bucket list as I visit the Australian Open in Melbourne, also on my bucket list!

  12. IMHO,,,,, I would rather be financially independent with my kids in a good school in the Sacramento area than a wage slave in Sn Francisco. We can be in SF or the mountains easily and retain a high degree of financial flexibility at the same time. Just sayin.

    1. Financial Samurai

      Sounds good. Does that mean you wouldn’t have to work if you lived in Sacramento or don’t work currently with kids? If so, having the freedom is nice. Let us know how long you’ve been retired with kids.

      For me, Sacramento doesn’t have the excitement of SF. It’s not easy to get to frequently as it’s about an hour drive away.

  13. I only lasted 10 months living in NYC. I spent all my time in the parks. I do enjoy the real estate price appreciation of living in the rural communities 90 min outside of NYC however.

  14. Fascinating; I didn’t know you were born in Manila. I think you left off a decimal place on Manila’s population. :)

    I believe it’s closer to 13-20 million depending on where you draw the circle. (I also lived there from 2009-2022)

  15. Ha! love your comment about who or what you might see on the trading floor. Last week, on mine Michel Bloomberg just walked in shook some hands and went on his way. Love the energy of NYC!. BTW, you and I might have crossed path. Used to work on same building as you during the same time!

  16. It’s interesting that you use McLean, Virginia as an counter-example to big-city living. To me, that would be big-city living, because McLean is part of the Washington, DC metro area, which is home to millions of people, and I’m pretty sure you can take the Metro from there into the heart of DC. But I grew up in a sparsely-populated rural area, so my perspective is different.

    I think if you’re happy with San Francisco and can afford to live there, then you should stay. However, if you want a change of scenery, I would guess that you could probably find several large US cities that would still have lots of activities, but that are cheaper than SF. But maybe they wouldn’t have the same level of excitement as SF; I don’t know. If I were rich and could afford to live anywhere, I would probably live part of the year in New Orleans — a beautiful city with great local music and great food. But I would probably go somewhere else during the hot, humid summers.

    1. Financial Samurai

      New Orleans is great. Love the food, culture, and historical buildings. Alas, not for me as I want to have a greater cultural affinity to Chinese language.

      McLean is definitely a sleepy town. No way would I consider McLean similar to living in Washington D.C.

  17. I’m an introvert who loves cities, particularly NYC. Fun fact, one can disappear within crowds. I find small towns where everyone wants to talk to you and get into your business to be exhausting.

      1. San Diego is the best city in America, all things considered (weather and lifestyle).

        Irvine is incredibly clean and has incredibly low crime for its size. It’s almost like a utopia. Close proximity to Newport and Laguna Beach, some of the most expensive real estate in the country. OC, what’s not to love?

        Bellevue is another Utopia type of vibe. The only thing it doesn’t have going for it is sunshine. Political environment is also wonky. Might even have more extreme liberal views than the Bay Area of Cali.

        Miami is the San Diego of the East Coast. Humidity makes it unbearable in the summer though and storms are too intense. There is also the crime and drug trade that has been historically bad (think Scarface/Miami Vice) but I believe they’ve cleaned a lot of that up. Could be too diverse for some in terms of trying to fit in. A lot of energy though.

        Austin, particularly the hill country around Lake Travis. Humidity is brutal in the summer though and the rain/electrical storms/tornados, scorpions and fire ants are also a turnoff. The hill country has also gotten pretty crowed over the last 20 years. Far from a hidden gem like it once was.

        Chi-town destroys NY IMHO. The loop is just awesome next to the lake. Incredible food and sports town. Best in the country in that regard. Extremely liberal politics are destroying it, not unlike San Francisco. Crime is beyond out of control. The Loop is a great place to visit though (safe areas).

        1. Would rather live in Honolulu than San Diego. But San Diego is a lovely place. Las Ventanas Hotel in La Jolla is one of my favorites.

          The thing is, I don’t find San Diego to be very exciting. Maybe I just wasn’t looking in the right place? The networking and financial opportunities are not as great. I would probably move to Los Angeles instead.

          But I think San Diego is good for someone in their mid 50s and above, just like Honolulu.

          Will take NYC over Chicago. Can’t do the extreme cold for 3-4 months a year even though NYC is cold too. I’d get too depressed.

          What do you do in San Diego if you live there?

          1. First, flip flops year around. Can’t say that about many places. Little Italy, Gaslamp, Padres, Balboa Park, watch hand gliders run off the cliffs at Torrey Pines, evening views from Mt. Soledad or Mt, Helix, pickup bball at Solana Beach’s version of the La Jolla Cove, SDSU bball games, breakfast at Sugar & Scribe in La Jolla after a workout at Lifetime Fitness, dinner at Phil’s BBQ (best outside of TX & KC), dinner in downtown Encinitas, followed by ice cream at Cali Cream and a short walk to the beach, shopping and food at UTC, wave running on Mission Bay. I mean, I could go on all day…

            1. Yes, have done most of those things. I’ve literally been there over 100 times given I had clients there. It’s a nice and beautiful city. Went to Tijuana too. Oh, and did jet skiing around downtown and Coronado island. Now that was fun!

              It just doesn’t have the same amount of excitement as LA, SF, NYC. Heck, the Chargers left!

              What is that you do there?

              1. Doesn’t feel as congested as LA, SF and NYC for sure. I think that sometimes gets confused with excitement. That’s what makes SD so great. You can quickly get from downtown to North County without ever feeling like you are in a congested sea of people and vehicles. It’s like a big city that is laid back like the suburbs. Nothing quite like it in that regard. I mostly go down for pleasure. Daughter was enrolled at UCSD pre-COVID at played softball for them.

    1. OMG. AGREED AGREED AGREED. I work from home and have lived alone for years. Growing up in a small town meant getting “appropriately dressed” and ready to run in to 10 people you knew, at least, and in my case, at least five I didn’t like and three who were nosy. Exhausting. Even more exhausting was the assumption i wanted to know everything they were doing. I didnt.

      In Chicago, I can go to the grocery in my pajamas and if I don’t want to run in to anyone, I go the store two blocks west instead of across the street and it’s completely full of strangers. bliss!

  18. I have never lived in New York City but I have stayed in Manhattan for a week and absolutely loved it. The walkability, nightlife and constant activities and the northeastern climate agreed with me. But actually owning a condo in NYC did not pencil out–at all. It takes super hustle skills to own in that city.

    We also love having a place at Lake Tahoe to get away from the SF Bay Area. I was surprised how nice it is to spend a summer in the mountains when one typically thinks of Lake Tahoe as a ski destination. That vacation home does not “pencil out” either, but we want to have some fun while we are young enough to enjoy skiing.

    I have conversations with family about the cost of living in San Jose and how I should move to a more affordable area. The focus is on coastal housing cost relative to similar real estate in the Midwest, for example. There are two contributions to real estate value, the land and the improvements. In the Midwest, the land adds little value to the real estate and most value lies in the house, a depreciating asset. In a big city, the value is mostly in the land, an asset that grows in value with inflation and the local economy. When we bought a house last year, the county tax authority assesed our real estate value at 80% land and 20% improvements, an admission that the land is actually what holds value here. So, expensive big city property makes better investment, IMO.

    Also, I grew up near Kansas City…go Chiefs!

    1. That’s tough to own Midwestern property if the appreciation is in the house, which gets old and needs maintenance.

      Vacation properties generally do not pan out at all. I have been warning people about buying vacation properties with her disposable income for over 10 years after ill-fated purchase in 2007.

      The Chiefs already won the Super Bowl. Time to share! We need to win in order to attract more folks and capital to the Bay Area!

  19. I’m more partial to country living so to speak as I was born in a small town in Iowa and grew up in an outer suburb of Milwaukee. Today I live in a rural community of a major metro area.

    Cities are nice to visit, but I prefer to live and rise my family in an area far from the city metro. Cost of living is less, plus you have lower pollution and less crime.

  20. We moved to the LA area from the Midwest and it has been fantastic! The only thing I wish is that we’d moved even closer to the city rather than buying in the suburbs. Living in close proximity to the big city and what it has to offer has been a wonderful upgrade to our lives, and we’re just getting started!

    1. If you have kids, perhaps living in the suburbs within 30 minutes drive away from a big city could be the perfect combo.

      We decided to stay in San Francisco, but move to the more spacious west side. It’s been a better balance with kids.

  21. I grew up in small towns and longed for city life. I found my way to big metros after college and never looked back! So I understand what you’re saying about the value city life can add to one’s life. Maybe once my kids are in college I will move to a quieter area. But I have no desire to move any time soon.

Leave a Comment

Your email address will not be published. Required fields are marked *