It's hard to have a reasoned discussion about cities because there's so much ego tied up in your decision of where to live. People don't want to feel like they'

It's hard to have a reasoned discussion about cities because there's so much ego tied up in your decision of where to live. People don't want to feel like they've made the wrong decision, so they'll say bad things about other cities to rationalize their choice. I moved to SF from Chicago about five years ago, and on the whole it's been an improvement for me. The comp increase more than made up for the cost of living difference, I have a stronger network of classmates from college, and there are more job opportunities. Certainly if you want to quickly grow a tech company to 100+ people, it will be much easier here than in Chicago. Outside of work, there are many outdoors activities (cycling, hiking, surfing) that aren't easy to access in Chicago. There's no snow and no suffocating summer. There's plenty to be cynical about, but that's true in any big city. What I miss about Chicago is knowing people with a more diverse set of professions, being closer to family on the east coast, and having a more moderately-priced restaurant and bar scene. Things generally feel more relaxed in Chicago because the cost of living is lower. A downside is that Chicago tends to draw mostly Midwesterners, so as an east-coaster I actually know far more people in Seattle and SF than I did in Chicago (if you're from Iowa, Wisconsin, etc, then you'll probably find the opposite to be true). I have a tendency to get enamored with cities I visit, or miss cities that I used to live in, so my trick is to try and spend time doing things that are specific to where I live. After moving to SF I started hiking and visiting wineries and eating Mexican food. If I moved back to Chicago I might start jogging on the lakefront again, or going to more improv shows and brewpubs. At any rate, it's a bit more enjoyable of a way to feel like you've made the right choice on where to live than bad-mouthing other cities.