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Portland, Where the Young Go To Retire

Portland, where the young go to retire. I am not sure how this descriptor of Portland first became popular but it has certainly stuck which means there is some truth to it. Imagining young people moving en masse to Portland to retire is an interesting concept and it’s not really what this Portland is all about.

Portland has a mellow vibe. It’s hard to be a gunner in this city without standing out. If you’re fake then people distance themselves from you. Though if you’re being fake-nice because you’re trying really hard to be a better person – that’s excusable.

Even the healthcare professionals here are more mellow. The majority of the urgent care doctors whom I worked with were part-time clinicians. Popular ways to spend the free time include:

  • taking local weekend trips
  • hiking the local parks
  • beers with friends
  • arts/music/shows
  • tending to gardens
  • brewing beer

We don’t have a mall culture. There are a few big box stores but that’s not really what Portland is about either.

I don’t think Portlanders are big spenders except when it come to REI – that’s a favorite shopping spot for them.



I haven’t noticed much overachieving going on here. Few healthcare professionals are about buying an investment property, adding more cars to their household fleet, trying to buy designer clothes, or getting the latest gadgets.

I felt like I stuck out in California when I wasn’t trying to overachieve. I realize this is a personal flaw but I’m not immune to my surroundings and perhaps why I fit into the Portland culture more than Cali culture.

The Family Medicine residents and Internal Medicine residents whom I have interacted with are the polar opposites of those I met in San Diego, not to mention Los Angeles.


Lifestyle Over Work

Portland is the kind of place where you can live off of whatever income you have and still be friends with those who are making hundreds of thousands of dollars a year.

It’s common for young people to not pick up extra shifts at work and avoid more ‘serious’ jobs because their focus is to actually live their life and not enter the rat-race.

I wrote about the utility of excess wealth in this post.

It seems to me that Portland is the kind of place where you are judged more on the kind of person you are and how you live your life rather than what you have accomplished in life and what assets you possess.


Portland, Where the Young Go To Retire

I don’t know any young people who are actually retired in Portland but I know quite a few individuals in their 20’s who live the retired lifestyle which I live myself.

Retirement For The Young

Retiring of course doesn’t mean that you don’t do anything worthwhile with your time. Instead it refers to a time when you no longer worry about career advancement or paying off debt.

In Portland I meet a lot of individuals who have little in student loans, most are living with roommates, and few own cars. I mean if that’s not the retired life then what is?

Perhaps, fortunately, this lifestyle here isn’t the American dream as defined by the majority of Americans and is why it’s still possible to live that lifestyle here.

The Right Personality Type

Portlanders are progressive in ways that some of the more ambitious individuals or overachievers aren’t. In Portland you can live a good life if you are open and progressive. It’s the kind of place where you want and can get along with anyone – except for assholes.

With a couple of roommates, no automobile expenses, a cheap cell phone, shared utilities, and the occasional dog-walking gig you can live a financially sustainable lifestyle. It doesn’t mean that you have to live this lifestyle indefinitely.

Instead, it allows you the opportunity to live the lifestyle that’s in sync with who you are, offering you the best chance to discover the kind of work that’s suited to you.


Portland is Expensive

Yes, you hear that a lot, that Portland is an expensive place to live. But it’s worth putting this thought into perspective – we primarily spread this rumor to keep more people from settling down here.

For those who live in California or Nevada and are looking for the same secluded lifestyle behind a picket fence, Portland would be an incredibly expensive place.


Housing is what’s expensive in Portland.

Everything else is inexpensive. Add in the solid public transport infrastructure and you have a cheap way of getting around in a cheap city.

You can still buy a studio condo for under $180k in the heart of Portland. That’s cheap for any metropolitan city.

A house east of the river can be bought for $500k with 3 bedrooms. And if you rent out the spare bedrooms then your housing payment can be fairly affordable.

State Income Taxes

State income taxes are 9% but if you’re in the service industry then I doubt that you’re reporting the majority of your income to the IRS.

There are other states with cheaper or even zero income taxes but it’s common to move to such states and develop an expensive lifestyle. I could move to Nevada and buy a nice house in the middle of nowhere for $90k but my lifestyle would greatly suffer – I would need to spend a ton to make up for it.

There is no sales tax in Portland and though I thought that this is a big deal, I’m not sure that consumerism is strong enough here to make a big difference in people’s pockets.

Fancy Living

Just like any big city, we have $300 tasting menu restaurants and $8M homes up on the hill. We have $3M high-rise condos and designer boutiques.

You can see the occasional Ferrari and Lamborghini driving around in the Pearl District. There is even an Apple store here – that’s right, ballin’!


Income In Portland

The income for professionals in Portland matches that of any major city. Our per diem rate for Urgent Care physicians is the same as for those who work in San Francisco.

Even better, if you are in the service industry and are a barista, bartender, or a waitress/waiter, you are likely earning $20-$40/hour, with a good portion of this income being cash.

I know a good number of individuals who are making a respectable income from dog walking, house sitting, babysitting, copywriting, driving for Lyft, and a few who are doing so-so doing food deliveries.


Living A Better Lifestyle in Portland

I moved to Portland because I realized that in San Diego I was living a riches to rags lifestyle.

I was headed for a 40-year career in medicine – and not the floral kind.

If you come to Portland to seclude yourself within your 4 walls then Portland will suck. All you’ll see is the gloomy weather, albino faces, homeless people, traffic, high state income taxes, polyamory, and weed.

But if you make Portland your backyard and your living room then it can be a wonderful place to make new friends and experience new things.


My Portland Retirement Guide

You’ll fit in Portland nicely if you:

  • are open-minded
  • prefer dogs over children
  • accept homeless people as humans
  • aren’t judgemental
  • don’t keep your extra shit in storage
  • don’t care about a fancy, luxury lifestyle
  • don’t mind the rain with plenty of sunshine
  • are a social introvert
  • don’t find second-hand stuff gross
  • understand that this isn’t America, it’s Portland


1. Moving Here

Rent isn’t cheap but start renting here first because each neighborhood is incredibly unique. It’s worth taking 6-12 months to experience each neighborhood before figuring out where you fit in most.

If you are open to roommates then pay a little more for an extra room and put an ad out for a roomy. It’s a great way to get to know the city more and it’s more cost-effective.

Forget the storage thing. Sell your unwanted junk. There are a ton of second-hand stores here and people are great about selling/buying used online.

2. Working Here

There are a lot of ways to make money here.

It’s a competitive market but also a high turnover market. As you’ll read online: “OMG, I went to Portland for a year and hated it. All you see is homeless people and heroin needles and it rains all the time!”… which means that this person fled back to Texas or CA and a job opened up.

Part-time work is both encouraged and easy to come by here in Portland, especially for healthcare professionals. Your employer will have a very easy time understanding that you’re here to live a good lifestyle and not be a slave to your job.

There are a ton of service industry jobs. Many are listed on CL but the rest you can find out about by making friends and having them refer you to their employer.

If you’re a healthcare professional then you can sustain your single lifestyle on less than $2k/month which is somewhere around 8 hours a week of work – people spend more time tending to their gardens in Portland.

Work a few weeks in a row as a per diem and take the rest of the year off. If someone asks you what kind of work you do and you reply that you are currently unemployed they’ll possibly nod in agreement since they are in the same position.

3. Housing

As a young healthcare professional buy the cheapest condo in the best neighborhood you can afford in cash.

If you’re a true Portlander then you’ll spend the majority of your time outdoors. You’ll head out to the mountains or the coast on the weekend and you’ll spend your evenings at cafes and bars with friends.

I paid $100 less a month for my tiny studio in San Diego but I also had to sleep with the landlady to get that apartment. I needed a car in order to commute to work and socializing with friends meant expensive dinners and $18 cocktails.

4. Leisure

People in Portland hang out with friends, read, go to shows, drinks awesome local beer, go to the coast, go to the mountains, ski, rock-climb, surf, bike, paint, write, and smoke weed.

If you can see yourself fitting into that scene then you can do all that for quite cheap. A beer during happy hour is $4-5. There are a ton of food carts. You can lounge at a low-key cafe for hours and write or read. The price of admission is a $2 coffee.

The main question is, can you lounge and just relax?

If you’re a go-go-go type of person then you might stand out here. I’m sure you could find some like-minded souls but it’ll be tougher.

5. Making Friends

Just talk to the person next to you. It’s normal here for men and women to talk to each other. If you are a dude and talk to a woman it’s generally accepted and normal – I know, crazy right?

Online dating here is mostly for fucking. Otherwise you’ll meet more people than you can keep track of. I actually keep a log of the names of everyone new I meet because I’ve never met so many new people in my life.

Of course, it helps if you frequent the same cafes, the same gym, the same happy hour and the same hiking spots. You’ll run into the same people and after a while, if you’re not a total creep, you’ll strike up some great conversations.

Also realize that the hipster looking dude next to you who looks like he could be an out-of-work artist, might also be a $200k/year engineer, or a famous author, a local comedian, or a surgeon.

6. Upgrading Your Lifestyle

Moving to the suburbs in Portland seems counterintuitive to me but in case you are done with the hectic Portland scene and want peace and quiet then there are fancy suburban neighborhoods available. Your housing budget will go very far here and you’ll find a lot of peace and quiet.

Alternatively, you can get a $3M high-rise condo in the middle of downtown. Or a gorgeous mansion on top of the hill inside Washington park for $2M.

You can buy a small house on the Oregon coast for $250k or a big house with lots of land for $400k in the mountains.

2 replies on “Portland, Where the Young Go To Retire”

Sounds like my kind of place.

Have you ever been to New Orleans? What are your thoughts on Portland vs. New Orleans for residency and car-free (not carefree, lol) living?

I really like that people in Portland are more about living life, lounging, and just chilling out.

1st Year Medical Student with a Vision

I haven’t but people tell me NO is a great place to live. It’s just not my kind of weather.
I think Portland is a very progressive city, hard for me to imagine others like it but it’s possible. I’m sure some Reddit forum out there talks about the walkability of the city.

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