Great cities — a forgotten key to your pretirement

Lovely Vancouver, BC -- photo from a recent trip. If you're looking for great cities, you can't do much better than Vancouver.

Lovely Vancouver, BC — photo from a recent trip. If you’re looking for great cities, you can’t do much better than Vancouver.

As infants we begin with barely a dim awareness of our surroundings. Eventually that blurry upward view of crib rails and ceiling lights turns into faces and walls. Shapes, colors, figures. Next an awareness that this is MY room. Then MY house.

We get older and learn to recognize our own street. We become familiar with our own schools and eventually our own neighborhoods and cities.

Some of us move away from these first towns and make our own homes elsewhere. A very small subset of the population identify specific criteria for the place they want to live and seek out that perfect place. Most of us, however, stay near where we grew up or move for employment.

Here’s the thing, though: For those in already pretired or driving toward pretirement, the city where you choose to settle matters. A lot. And, yet, it’s one of the most ignored keys to finding your freedom.

I think we tend to ignore this because it feels intractable. Maybe we don’t want to move away from family. We already own a home here. All our friends are here. I could ridicule each of those as excuses, but they’re actually all really great reasons to stay put.

But as I’ve said many times, pretirement calls for sacrifices. Even if you made a high salary, saved a massive percentage of it, and theoretically could pretire comfortably, it’s all for naught if you are set on living somewhere extremely expensive, such as Manhattan. It’s not just the expense of your home. Cities themselves have widely varying costs.

And it goes beyond cost as well. What’s the point of living inexpensively if you have to dodge bullets every day? Or have to breathe polluted air and drink polluted water?

What makes great cities great?

It’s impossible to make a comprehensive list of what makes a city great. But I’ll share a few things that top my list of things I find in most great cities. Feel free to add your own in the comments. It’s a topic I’m very passionate about, so the more ideas we can collect, the better.


I guess this one is obvious since it’s so fundamental to a place not sucking. But it’s not a binary element. You’re not “safe” or “not safe”. You’re more or less safe. And that can vary quite a bit even by neighborhood. Unfortunately there is some correlation (somewhat overblown, however) between the cost of an area and how safe it is. Because you’ll want to be living a low-overhead lifestyle AND be as safe as possible, it’s something of a balance. The way I look at it is there should be a reasonable level of safety and once that’s met, I’ll just move on to other factors. Besides you probably have about the same odds of being flattened by a latte-slurping soccer mom in her SUV as you are to get mugged in most cities.


I won’t dwell on this because it’s somewhat obvious, but the cost of living and especially the cost of real estate is a key determining factor. This can be tough, though, because there’s a conundrum at work here: When a place is nice, rich people want to live there and thus drive up prices. If an area is a craphole, the people who can move away do so and you get self-selecting conditions for blight. Cities struggle with this all the time when they try to keep housing affordable. They allow cheaper construction and the area turns into a ghetto and they end up paying a fortune for police service and basic public safety. They make an area nicer and wealthier people move in and drive out the original residents. But if you’re pretired, you may be able to live farther from job centers and thus be able to keep your housing costs low while still enjoying a great area.


This one is so often overlooked but it’s so important in allowing you to drop your car expenses. If you and your spouse no longer need to commute, you might be able to drop down to one or even zero cars. Plus you’ll enjoy your lifestyle more than ever as you don’t have to get in the car to go anywhere. Another thing to think about is your transition into traditional retirement, or to be blunt, think about when you’re old. Driving is difficult and scary for seniors. Build yourself a lifestyle now that takes that strain off your future self.


I’m a huge public transportation fan. Unfortunately I live in one of the worst cities for getting around without a car. Here in Seattle, they’ve had many opportunities to build robust transit systems and they’ve been voted down repeatedly by short-sighted voters. It’s surprising given how liberal we are here. It’s only been in recent years — decades after nearly every other major city has deployed at least a light rail system — that we’ve taken the plunge. Our bus system is OK, but depending on where you live and where you need to go, it could double your travel time. It was disheartening returning to Seattle from a trip to Tokyo a few years ago. Their system is mind-meltingly awesome and to step off the plane in Seattle to our rinky-dink system was just pathetic.

Bicycle friendliness

A Barcelona bike path. Note the grade separation from walking path to bike path to roadway. Picture taken from upper deck of tour bus. Also note the entrance to the underground subway.

A Barcelona bike path. Note the grade separation from walking path to bike path to roadway. Picture taken from upper deck of tour bus. Also note the entrance to the underground subway.

Bicycling is by far the most efficient way to travel short distances but so many cities and towns make this so difficult. Seattle has been improving its bicycle infrastructure in recent years, but I’ll be honest: it’s still ridiculously bad to the point where I do not feel it’s safe. A bicyclist dies here every couple months and our city leaders are still thrashing around and throwing tons of money at the car culture still. On top of the safety issue, we are renowned for our many steep hills. I’ve actually never seen a bike going up the hill I live on, although we see bikes going down quite often. The best way to end up in a bicycle friendly town currently is to move out of the U.S. or to a smaller town. Hopefully in a few years that changes drastically.

Take a look at my picture of the bicycle lanes from my recent trip to Barcelona. Cars, separated from buses, separated from grade-separated bike lanes, separated from a lovely walking path. Brilliant and simple. (And they have a wonderful underground subway system.) Contrast that to here where you’re lucky if you find a crosswalk that still has some paint on the road.


We all like a clean city, but this goes beyond where there is litter blowing down the sidewalk (important as that is). Cleanliness extends to things like the air you breathe or the water you drink. It’s important to think about the long-term risks to your air and water. Are they fracking near your home? Are there coal-burning plants nearby? How clean is the water in your area? This is important not only for enjoying the many, many years of awesome life you have in front of you, but also for ensuring your health. What’s the point of living an amazing life of pretirement if you end up hobbled with chronic illness?

There’s another important point to finding an unpolluted city: Your home value. Those homes that had their wells poisoned by fracking are now valueless. Those people who thought they were being so clever by leasing some land to natural gas companies have wound up trapped in a house they can’t sell, suffering from devastating illness. It may not be as dramatic, though. Just in general, a rundown, dirty or polluted neighborhood can mean lower equity growth and a harder-to-sell property.


I used to always say that if I ever moved again, I wanted an upgrade from Seattle’s dreary weather. That’s actually becoming less important to me in recent years, although I still often long to live somewhere with more sun. As a native Washingtonian with webbed feet, however, I’m finding it harder to deal with the heat than the cold. Although I still hate being cold. Probably I’d adjust after a few months somewhere warmer and that’d probably be good for my overall health. The important point, though, is that I’m not moving somewhere where the weather sucks just because it’s cheaper. Nasty muggy summers and frigid snowy winters? No thanks! I do like the weather in many parts of California, for example. In Northern California, the weather is quite temperate and when I lived there I rarely remember being either too hot or too cold. That could be why it’s so overpopulated, though.


What do I mean by infrastructure? I’m not necessarily referring to the classic governmental meaning or roads and bridges. Rather, I’m talking about the various functions that support your lifestyle. For example, transportation, medical facilities (you may not want to be too far from a hospital for instance), grocery stores or anything else you might need. This is probably the main reason I’ll likely stay within or near a reasonably large city instead of moving to a rural location. I once considered moving out to the country but I imagined rushing to a hospital an hour away in case of an accident, and the move just didn’t seem too wise. Add to that the need to drive nearly everywhere and country living just wasn’t as inexpensive as it first appeared. So I’m focused now mostly on medium- to small-sized cities.

Open space

Humans have a very real need to be outside. Beyond fresh air and exercise, there is something in us that needs the natural world to keep us functional. I think it’s safe to say that someone who is outside in nature every single day is highly unlikely to suffer from depression. Open spaces act as the lungs for cities clearing the air and softening the landscape. We have some great in-city areas here in Seattle, where you almost forget you’re in a city. And we can be deep in the mountains within a 30 minute drive. From an open space perspective, Seattle is hard to beat.


If your local town looks like a Long John Silver’s raped a Wendy’s it may be time to re-evaluate your life choices. Car-oriented, strip mall development is extremely hard on the psyche and is a very expensive way to live, especially if you’re still commuting to work. This cheap development also leads to a cultural desert, where there’s nothing to do and nowhere to go. Contrast that with a similarly-sized city with a cute downtown area, parks and open space. You’ll find charming restaurants opening in such an area, art galleries, plus many free entertainment options will sprout up in the shadow of the trees. You might say work and money are HOW we live, but culture and family are WHY we live. Don’t overlook it.

Aesthetic beauty

Not everyone will agree this is important, but to me it’s critical. Something about my temperament demands I live without being visually assaulted by atrocious surroundings. I paid way too much for my current house because I (thought I) needed to see the shimmering Puget Sound every day. Not unlike the importance of culture, living in a beautiful place brings a lot of light into your life and will make all those pretirement years that much more enjoyable.

I could probably come up with another 50 important things, but I’d rather hear from you about what you look for in a place to live. What am I missing? I’d really like to have a robust list of criteria because if and when I decided to move to a different locale, I want to make sure I approach my choice intelligently.

Let me know what you think in the comments! 

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45 Thoughts on “Great cities — a forgotten key to your pretirement

  1. Good read Nicholas, your points are well-taken, as usual. As you know I live on an island just a ferry ride away from downtown Seattle, and that is something to consider too. Though the longer I live here, the less I need or want the big city. Should I want to hit an exhibit or concert or event, the ferry and bus can get me there, and then upon my return, it only takes about 45 very scenic minutes to find myself back in slowpoke paradise. Small towns with easy and affordable access to big cities are a great way to go, too.
    Tom | Tall Clover Farm recently posted…Orcas Pear: My One and OnlyMy Profile

    • Pretired Nick on October 2, 2013 at 12:55 pm said:

      Thanks, Tom! You’re close enough to the city to have all your needs met, especially since you don’t have the expensive commute in anymore. It’s hard to beat your little slice of heaven! I wonder if you’ll be sick of driving on dark, rural roads in 20 more years, though.

  2. “If your local town looks like a Long John Silver’s raped a Wendy’s ”


    Regarding affordability, I’d throw taxes into the mix. income taxes may not matter much in retirement, but property taxes do.

    Regarding culture, I’d throw in politics as well. I’ve lived in both hyper-conservative (we’re not spending even a dime on schools!!) and hyper-liberal places (let’s spend $25,000 (debt financed) to put solar panels on the bathroom at the city park) and I don’t like either. I think that having a good mix of people makes for a better place.

    My ideal place to retire is a smaller city (100,000 to 200,000 people). At this size, there is stuff going on, but it’s not big and expensive like Chicago or New York. Smaller cities seem to be more efficient too (looking at you again Chicago).
    Mr. 1500 recently posted…A Blueprint for a Better LifeMy Profile

    • Pretired Nick on October 2, 2013 at 12:57 pm said:

      Thanks, Mr. 1500! Totally agree on your thinking regarding city size. That’s about what I’m thinking as well. Although there are outskirts of big cities that have the same smallish vibe without the distance issues. Do you have some favorite cities in that size range?

      • My hands down favorite is Fort Collins Colorado. It is frequently written up in outdoor magazines for having a fantastic lifestyle. It does.

        It also has a thriving downtown. There are little bookstores and microbreweries everywhere (New Belgium started here). What could be better than great beer and books? Not much in my opinion.

        FC is also very bike nuts; bike trails and lanes everywhere. I’ve never been to city that is more bike friendly actually. They even have a bike library where anyone can check out a bike.

        Finally, it’s an all around beautiful city. The streets are clean. The mountains are right there. The people are good. I would have moved there if there were more tech jobs.
        Mr. 1500 recently posted…A Blueprint for a Better LifeMy Profile

        • Pretired Nick on October 2, 2013 at 2:31 pm said:

          I’ve been in Colorado several times, but I don’t think I’ve been through Fort Collins. Next time I’m through, I’ll check it out for sure.
          Thanks for sharing the bike library link. That is super cool! I’ll have to share that with some peeps here locally.

    • Hahaha, I love that too.
      retirebyforty recently posted…September 2013 Goals and Financial UpdateMy Profile

  3. Great points! We’re currently in a very high cost of living city. We’re planning on moving to a different city closer to family and friends in a few years after hitting FI and it’ll have a much lower cost of living. This will make a big different in our finances. Great article!
    Gaming Your Finances recently posted…What is financial independence?My Profile

    • Pretired Nick on October 2, 2013 at 12:58 pm said:

      We might need to move farther away from family to reach the same goals. That’s great you can have family close by and still lower your living costs. Thanks for commenting!

  4. Great post! I definitely agree with the factors you’ve listed do make cities great. I think where I live in NYC has most of those factors minus the affordability and probably the cleanliness. Weather: I guess it really depends…there are hot summers and cold snowy winters but I sometimes like seeing the different seasons rather than having the same weather year round. I might change my mind as the weather has been lovely lately. And I do think Vancouver is a lovely city…drove up from Seattle to Vancouver a few years back (and then to Whistler Mountain). I’ve never noticed the dreary weather in Seattle as the times I’ve been there it was usually in the summer time.
    Andrew@LivingRichCheaply recently posted…Broke? It Might Not Be Your FaultMy Profile

    • Pretired Nick on October 2, 2013 at 1:02 pm said:

      Thanks, Andrew! NYC is a good example of when all the right elements are there, then rich people will want to move there and the price jumps up. Plus you have what we have in Seattle, which is a lot of water, which means to be anywhere near the city core you have to pay more.
      Our dreary weather definitely has a season and it’s the time of year no one comes to visit. We have easily the best summers in the continental U.S. and it rarely snows in the winter here. However we can be a little light deprived. In the winter, we may not see sun at all for weeks! It’s a little maddening.

  5. We like Portland for all the factors mentioned. I would like a little more sunshine, but I’m used to the rain now. We’d probably keep our place and try living in other places first to see if we’ll like it.
    I’m thinking Santa Barbara or the Big Island. Not sure if it will work out because it’s so different than where we are now.
    We’re definitely going to live in Chiangmai for a few years too.
    retirebyforty recently posted…September 2013 Goals and Financial UpdateMy Profile

  6. Nick,

    Great post. I love reading up on great cities. Vancouver is somewhere I’ve always wanted to visit, but have yet to see. It looks absolutely beautiful. And Canada in general seems to have significantly less crime and other issues assorted with our big cities here in the U.S.

    I’ve heard Colorado has some beautiful cities. Never been to Ft. Collins, as mentioned above, but seems nice. The Pacific NW also seems great. Portland seems really great. I hear that the Carolinas also have some beautiful smaller cities here on the east coast.

    I agree cities around 100k-200k people is where you want to be. It allows a great mix of culture, entertainment and a city “vibe” while also generally having smaller costs.

    Best wishes!
    Dividend Mantra recently posted…Freedom Fund Update – October 2013My Profile

    • Pretired Nick on October 3, 2013 at 5:34 am said:

      Thanks, DM! Vancouver is definitely worth your time. We love it there. I couldn’t do the deep south so the Carolinas are out for me, although you’re right that there are some great smaller towns along the southeast coast.
      I like the 100-200K city size as well. I’d go a little smaller or a little bigger if everything was great.

  7. PTNick!!! Houston meets few of your criteria. Such a pity. It is affordable and aside from the roasting summers, the weather is quite agreeable. Lack of safety and walkabilty are the two most annoying Houston shortcomings. Thanks for a super fun read, PTNick!!!

    ps: I love confirming that I am not a douchebag!

    • Pretired Nick on October 2, 2013 at 6:27 pm said:

      Yeah, there are some nice areas of Houston, but overall, it’s pretty much my personal hell. How did you ever end up there, anyway?
      You can come by and confirm you’re not a douchebag anytime!

  8. There are actually more affordable areas in Hawaii, they are located on the outer islands. It’s kind of depressing though, and there really isn’t anything out there. My family is here so I wouldn’t consider anywhere else.
    Charles@gettingarichlife recently posted…Do You Know The Difference Between Twerking And An ETF?My Profile

    • Pretired Nick on October 2, 2013 at 7:48 pm said:

      Yeah, it can be nice, but then you’re basically just living the rural life, which gets you back to the infrastructure issues.

  9. What a great article. Selection of place makes other personal finance issues much easier to handle, or eliminates them entirely. The only one I’d add is tax set up: I want a municipality that taxes in a way that aligns with my frugal lifestyle. That may mean high sales taxes (or even high income taxes, if my income is lower in early retirement), but low property taxes (presuming that we own).

    The cities that match our lists (& much of yours) tend to be shrinking cities in the Rust Belt & Midwest. We like a small to mid-sized downtown with cultural amenities that outperform expectations, coupled with affordable real estate.
    Done by Forty recently posted…The Appalachian Trail & an Interview with Haley MillerMy Profile

    • Pretired Nick on October 3, 2013 at 5:38 am said:

      I guess Washington would be out for you. We have monstrous property tax and no income tax, which is completely backwards.
      I personally eliminate the Midwest completely based on weather alone. (:

  10. I grew up in Alaska. Oddly, I detest the cold so I’m (p)retiring as far away from the Pacific Northwest as I can get. Although it is one of the most beautiful places in the country and even the world.

    We are currently living in North Carolina. I think this state is a fabulous retirement location. Largely due to its close proximity to anything – mountains, beach, city. Pick your poison. The access to fantastic healthcare is phenomenal.

    I’m not sure yet where we’ll end up but I could comfortably stay here. Which is hard to say for a wanderlust like me.
    Taynia | The Fiscal Flamingo recently posted…An Accountability Partner – Why You Need One If You’re In DebtMy Profile

    • Pretired Nick on October 3, 2013 at 5:39 am said:

      That is pretty much as far away as you can get all right! Interesting so many people mentioned North Carolina. I may have to revisit my earlier ban on all confederate states! (:
      I’m a wanderlust as well. It’s hard for me to pick the perfect place and stay there forever!

  11. I like smaller cities and less dense areas as I tend to feel claustrophobic if living around millions of people or being in and around high-rises stuffed to the brims all the time.

    I’ll also echo others’ comments on taxes and the cost of housing. We’ve actually got a post for next week all ready on why moving to florida is a great financial move. I love our “choose your own adventure” approach to taxation here.
    Mrs. Pop @ Planting Our Pennies recently posted…PoP Income Statement – September 2013My Profile

  12. This is actually a huge issue for us, as we’re basically deciding between two cities for where we’d like to settle down: Boston and Pensacola. They’re VASTLY different in so many of these important ways. One of the most interesting to me is cost of living vs. opportunity for income. In this case, they’re pretty much polar opposites of each other, though the possibility of making money online could really change that dynamic.
    Matt Becker recently posted…How to Do an Oil Change for Your Car (Part 2)My Profile

    • Pretired Nick on October 3, 2013 at 5:42 am said:

      It’s a really good point that once you have passive or online income, you no longer need to be near a big (expensive) employment center. Boston is one of the most expensive places to live so that’ll be challenging, although there are some less expensive outskirts. How did you go about narrowing down your choices?

  13. I know I wouldn’t want to retire in Dallas, TX. One of my teachers retired in Chicago. He loves the transportation system there. I would love to live in a city where I wouldn’t have to drive and still get to places. It’s the dream!
    Savvy Financial Latina recently posted…The House Shopping Saga ContinuesMy Profile

    • Pretired Nick on October 3, 2013 at 8:39 am said:

      People are just now beginning to understand what a curse it is to be a slave to your car. I’ve lived in Chicago and to some extent you can live without a car, but only if you have a certain level of wealth. It’s a great town for the well-off, but very hard for everyone else.

  14. Great article! And I completely agree with all your points of what makes a city great. I am ashamed to admit, but I don’t know how to ride a bike so I wouldn’t really mind if the city wasn’t bicycle friendly, but everything else is just spot on.

    I am planning a small “adventure” to see if this really is what I’d like to do: go and live for three months in a different, better-than-Romania country. After a lot of research, I decided that Portugal is the place to go: somewhere with the beach nearby and few tourists (which was difficult to find in the first place). But then, the more I researched the location, the more I understood that as a whole, Portugal is not the best choice: the areas that meed my criteria don’t look good, have few shops around (I used Google Maps street view to “visit” a ton of cities before deciding that) because are way too small towns.

    So yeah, picking your perfect destination and finding a great city is difficult. But once you find it, everything should be perfect!
    C. the Romanian recently posted…September Income Report, Spendings and Great ReadsMy Profile

    • Pretired Nick on October 3, 2013 at 8:41 am said:

      Thanks, C! I’m sure you’d have no difficulty learning to bike when the need arises.
      It is difficult to zero in on just one place! I also find that experiencing places online doesn’t quite measure up to going there in person. Which means it can take a lot of time and expense to figure it out. Guess I have my work cut out for me!

  15. We love Raleigh, NC because it fits many of the criteria you listed (although it fails pretty bad on some, like bicycle friendliness). Very affordable house (most in the neighborhood are $100-150k for 1200-2500 sq ft) in a fairly safe location just a few miles from downtown and surrounded by shopping of all types (not boutique shopping, but places we actually go to frequently). Our neighborhood is 50 years old and has tons of old shade trees lining the streets. The kids go to school in the neighborhood and we walk to school daily. We also get to walk to ample shopping.

    Public transit isn’t bad where we live, and I rode the bus for a while when I worked downtown. It was as fast as driving, and I didn’t have to mess with parking. We could definitely age in place without too many worries.

    The hot, humid summers aren’t ideal, but that’s 2 months out of twelve that are uncomfortable. The other 10 are pretty good with winter, fall, and spring bringing different sights, sounds, smells and sniffles.

  16. We’ve been discussing where we might want to retire to. We know it’ll probably have to wait until we’re almost FI, since a lot of the places we’re looking at don’t have much of an economy where we could find work – but as long as I’m close to an airport and have good Internet access, I could probably talk my boss into letting me work remotely.

    Right now, we (as a couple) haven’t narrowed down our choices, but we’re looking at Canada (we just need to figure out the whole immigration issue), including Vancouver, Colorado, and pretty much north along the Rocky Mountain range. We know we want to be in or near mountains, and I want somewhere where it’s cool, and preferably dry-ish.
    Mom @ Three is Plenty recently posted…I Have Post-Partum DepressionMy Profile

    • Pretired Nick on October 7, 2013 at 1:28 pm said:

      We’re in a similar situation where we’re beginning to eye places away from employment centers for our long-term home.
      We are also interested in Canada (obviously) and are thinking about a few other places. It’s tough to decide on just one place!

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