33m married — Seeking city that is not San Francisco to live in.

San Francisco, I’ve got a problem. I missed out on the land grab. I didn’t have enough money when it was cheap, and I wasn’t smart enough to ask for more options so I can’t afford it now. I’m talking about decent real estate in the San Francisco Bay.

The problem gets worse.

Now I’m a dad. My wife and I can’t share a two bedroom apartment with laid back stoners anymore. We have to live in a suburb that is at least 45 minutes away from San Francisco so that we can stay afloat as a family on a single income.

That’s 45 minutes on a good day: No traffic, no protests, no someone committing suicide by throwing themselves in front of BART. On a bad day, I’ve just said “fuck it” and quit my job.

The last 9 years of living in big cities like San Francisco and London have been superb. It was college except I had all the money I needed to actually enjoy it. (However, the days of careless spending are over as my interests shifted similar to Mr Money Mustache and other financially independent methodologies.)

Now, I look at my 2 year-old kid. He’s too young to be my stoner roommate, I think to myself, despite him acting like he’s on drugs. This kid needs a yard, some friends to grow up with (e.g. their parents aren’t transiently located there), and maybe a dog! Not a dog that I leash up and clean his dumps from a square meter of grass on a SOMA sidewalk next to the homeless guy with last gen’s iPhone. My kid needs a dog that shits in its own backyard and runs around in a circle with his tongue flinging saliva in the breeze. That dog represents my childhood, and my childhood was pretty good. I want that for my kid.

I look at my wife. She’s happier than I’ve ever seen her now that she is a mom. No chance in hell I’m going to be able to convince the woman to go back to the work force any time soon to help out with the rent, not with her asking for a second child every other week. Plus she has got a glow about her now, and it’s sexy. Like bow chicka wow wow sexy.

I look at myself. Just a guy enjoying building software companies and telling jokes. I could do that anywhere, like on a beach, or on Reddit.

I did the math. In order for me to buy a house in the Bay that would satisfy my conditions, I would just need to work with this incredibly high software engineering salary until I’m 56. I can stay relevant in this ever-changing landscape of frameworks and languages and whatever the hell javascript is for 23 more years, right? I’m smarter than those kids in university looking to usurp my salary, right? I got a job offer at Google, and I’ve been CTO of multi-million dollar companies, and I helped build a unicorn (please, just sell to Facebook already, Eventbrite) — I should be set for life, right? Not in the Bay?…Okay. You’re right. I guess it’s time.


San Francisco, I’m getting my coat.

I gave my 30 day notice to my apartment. I sold all my IKEA furniture I’ve collected and sold and collected and sold over the years. And I’ve shipped my wife/son to Bulgaria (the wife is from there) where it’s cheap. The next half-year(ish) is going to look like this:

Tell me where you live and why you like it so much, but most importantly, what you find wrong with it.

I will do the following procedure to determine if it’s a good fit for me.

  1. I’ll Redfin and Zillow the shit out of your area to get price ranges, walkability scores, schools. I’ll open source any automation I do here. :partyparrot:
  2. If #1 passes, I’ll grep AngelList for startups and Glassdoor some salaries to see if there is any interest and if the salaries line up with Cost of Living. If nothing really lines up, I could always resort to remote work.
  3. If #2 looks good, I’ll join your Slack channels and your Subreddits to chat about schools, and coffee shops, and local sports teams. We might even go as deep as me expressing my love for card games with neighbors or aggressive amateur ping pong. I might also do some light Google Street View stalking so that I can walk your streets.
  4. If #3 feels right, I will fly to your city and spend a few weeks mingling with your people. At this point, you’ve earned yourself a free beer or dinner or incredibly flat dad joke, your choice.
  5. If #4 doesn’t make me nervous, I’ll get approval from the wife and then I’ll move into your basement. Just kidding. Your neighbor’s basement. The wife will then proceed to make you баница (a damn good pastry).

Other Nice-To-Have’s:

  • Close proximity to water and/or mountains (we’re outdoorsie sometimes).
  • Weather
  • International presence (sometimes I just need a conversation about the gnocchi in Italy with a couple from South Africa while we all wear kimonos)
  • Close to something that provides lasting real estate value (like Disneyland, a college university, or a major city). Always on the look out for streams of side income other than the stock market and random apps that I build.

To be clear, I’m not looking for a cheaper replica of San Francisco. I’m looking for a slower pace of life that’s not too slow, with some qualities of San Francisco. I want this to be a transformative but not shocking move.

America, the search is on.

I’ve already compiled a shortlist of places that are in the first leg of my journey.

Denver, Boston, and Seattle are on the high end of the expense scale, but I’m more certain about happiness there as they have most of what I’m looking for. None of them are perfect from what I can tell (Seattle/Boston have small weather issues, and Denver is high as fuck. (get it?!)). For real though, Denver is pretty good.

Portland, Austin are the middle ground. While all the really great spots are still expensive and there are gaps on what is on the nice-to-have checklist, with enough digging I think I could find a decent spot.

Raleigh, Nashville, Provo. Amazing prices, but I’m afraid of the homogenous lifestyle. Your slack channels and subreddits don’t reveal too much except where to get old mulch and why tailgaters make you so angry you could piss. RealTalk : big cities have ruined me and I’m so scared I wouldn’t fit into these lovely places.


Here’s my promise to you. With every city that I visit, you can expect a detailed explanation as to why I passed on or chose that city. It should be mildly entertaining as I journal an incredibly expensive and nerve-racking decision.

How to contact me:

  • Right here on Medium
  • /u/mediumbuf on Reddit (throwaway account)
  • mediumbuf [at] gmail [dot] com
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