Living in Boston is like wearing a badge of honor.

I grew up in Boston, and lived there for 23 years. It’s a wonderful, walkable, well-loved city for good reason.

But it was ultimately not a tough place to leave. Even as a kid I knew it didn’t fit my personality, and I left as soon as I finished college.

I have an affinity for the city that will last a lifetime. And I truly feel that living in Boston is like wearing a badge of honor.

Why? Because when you live there, you deal with bullshit on at least 12 different levels.

  • The weather is consistently depressing. More rain & snow than nearly every other large US city; including Seattle. On a nice day the city is gorgeous. Too bad there are exactly 17 of these each year.
  • Traffic is a nightmare. Roads are in shambles, while bridges are old, crumbling, and always painted a disgusting green for some reason. One wrong turn anywhere and you’re 25 minutes late.
  • This is why drivers are terrible. The cost of making a mistake is so high that people will swerve across 3 lanes to catch an exit. You need to make your turn at all costs.
  • The T is like a kid’s toy train set. Orange and Red lines are okay, but the Green line is horrendously slow. (The lines have colors for christ’s sake!)
  • The housing stock is old as dirt. The “beautiful” victorian I grew up in was built in 1896, and it might as well have been pre-civil war. The place was impossible to keep cool in the summer and warm in the winter. Everything creaked. Both the attic and basement were haunted. Doors and windows would suddenly open or shut by themselves. Because of the weather, “New England old” is older than “normal old.”
  • Cost of living is preposterous for what you get. It’s one of the country’s most expensive cities, without being one of the most exciting. The worst of both worlds.
  • Much of the city has an unmistakeable run-down feel to it. The nice parts are fantastic, but the bad parts are like an expensive Scranton with slightly better food.
  • Racism and especially homophobia is a big deal. In fact, those who are different are rarely treated well. Expressing individuality is a feat for the bold. They’ll laugh at you if you play by your own rules. Now don’t get me wrong – if they like you, they’ll laugh with you. But rest assured they’re laughing either way.
  • People are generally skeptical of new ideas. There’s a reason Silicon Valley happened on the west coast and not the 128 corridor.
  • If you bring up these points to people in Boston, someone who has never lived outside of New England will tell you Boston is the best city in the world, and want to fight you about it. Even when I moved to CA, the reaction I got was, “What, you think you’re bettah than us? What because you’re going to California or something??” Classy stuff.
  • The one exception to this rule is Florida. For whatever reason Bostonians are absolutely in love with Florida. If you move to Florida, live in Florida or even just visit, the envy level goes up 500%. Don’t bother trying to explain there are lots of other pleasant, warm places in the world. On a long enough timeline, every Masshole becomes Florida Man.
  • The “Masshole” stereotype is completely earned. People are often assholes to each other. A lot of it is kidding around, a lot of it is small talk, a lot of it is general frustration. People are at least a little miserable, and sort of take it out on each other.

…And then you go to a bar to drink, watch the game, and complain about it all to whoever will listen. And everyone’s your friend. Life is tough, but we all suffer together. That’s Boston. Once you live there, everywhere else is easier & better by comparison.

Published by Stefan von Imhof

Leading Product at Flippa. Buying & selling micro-businesses on the side. My personal brand is all over the map.

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