I’ve worked in San Francisco, Chicago, and Silicon Valley. Only one has the best mix for career, family, and socializing.

Manalan with his wife and son on the rooftop of Google’s Chicago office in June 2024.

This as-told-to essay is based on a conversation with Mike Manalac, a 39-year-old accounting manager at Google. It’s been edited for length and clarity.

Over the past eight years, I’ve worked in the tech scenes of San Francisco, Silicon Valley, and Chicago. The three places couldn’t be more different in terms of lifestyle, and they’ve each appealed to me for different reasons.

Here’s how the three places compare:

San Francisco is fun but not for the faint of heart

Manalac in San Francisco.

I moved to San Francisco in 2016 to pursue world-class career opportunities and adventure. I’d spent the past eight years as an audit manager in Baltimore and the cross-country move was a big change for me.

As someone with ambitious career goals, San Francisco was the mecca of opportunity, so I joined PwC to get closer to Bay Area tech jobs. Some of the world’s most innovative companies were basically next door, and their corporate headquarters lined the city’s blocks like Lego bricks.

I once interviewed at Salesforce’s headquarters while on my lunch break since it was only a few blocks away from PwC. When doing phone screens for Uber, Twitter, and Dolby, I knew I’d be able to walk over to their offices for an on-site interview at a moment’s notice.

As a young professional with limited life responsibilities, San Francisco turned out to be the perfect place to live fast and loose. The social scene was amazing — a night out for drinks could mean stopping by a speakeasy with no sign, sipping a mai tai on a floating tiki bar, or drinks served from a bathtub at a bar the size of a walk-in closet.

San Francisco also has the best park scene in the country; I’ve yet to find a better party than a regular Saturday afternoon at Dolores Park.

An afternoon in Dolores Park

It’s also a walkable city. For the first time in my adult life, I was car-free. The city was full of trendy coffee shops, unique bars and restaurants, and charming neighborhoods to explore.

But living in San Francisco also isn’t for the faint of heart. Outside of coworkers, my then-fiancée (and now wife) and I found it incredibly challenging to make friends; everyone seemed to assign others a level of importance based on where they lived and worked. I also would’ve needed an absurd amount of wealth to purchase a home and raise a family there.

I felt that the city’s biggest blemish, though, was the seedy Tenderloin district, which sits smack dab in the middle of downtown. I had to walk through the neighborhood to catch a corporate shuttle bus to work, and I saw my fair share of sketchy characters and shady dealings at the time.

Silicon Valley’s career opportunities were unmatched

Later that year, I started working in Silicon Valley after I joined Walmart’s eCommerce division in San Bruno. And the following year, I landed a job as an accounting manager at Google’s Sunnyvale campus.

Silicon Valley offers the coolest places to work and its career opportunities are unmatched. I was amazed by the sprawling corporate campuses. Walking through Facebook’s invite-only campus, which is like a walled garden city, and down its main street, Hacker Way, I was in awe. In nearby Mountain View, I couldn’t believe how nearly every building in the city was branded with Google’s logo.

Manalac at Google’s Android Statue Garden in July 2018. 

I saw corporate buses and colorful bikes whizzing around and young professionals with corporate badges on their hips and branded backpacks on their backs.

While Silicon Valley may be the tech capital of the world, I’d never live there. For one thing, I couldn’t afford it; the cookie-cutter neighborhoods of Silicon Valley are reserved for millionaires and the hillside mansions for billionaires. I, on the other hand, commuted from San Francisco via corporate shuttle bus.

But I wouldn’t have wanted to live there anyway. The social scene was dead, the city wasn’t walkable, and the nightlife was nonexistent. Nobody I knew went to happy hour after work, restaurants closed early, and most people only lived there because of the proximity to work.

Chicago has a down-to-earth social scene and affordable, family-friendly neighborhoods

I moved to Chicago with my wife in 2019, transferring to Google’s Chicago office. The cost of living in Chicago was much cheaper, my commute would be shorter, and we’d be closer to her family in Michigan and mine in Maryland.

Chicago doesn’t have the buzzy tech scene or beautiful weather of San Francisco and Silicon Valley, but it’s no slouch when it comes to career opportunities. More Fortune 500 companies are headquartered in Chicago than in almost every other city in the US, and the job opportunities are much more diverse than what you’ll find in the tech-centric San Francisco and Silicon Valley.

From Google’s office in Chicago’s West Loop, I can see McDonald’s global headquarters down the street and a number of other premier employers dotting the city skyline.

Chicago is a city that likes to party, making San Francisco look sleepy by comparison. Bars don’t close until 2 a.m., with some staying open until 4 a.m. Chicago’s Lake Michigan beach scene is much livelier than that of San Francisco. But the social scene also has a down-to-earth vibe; people are Midwest nice and seem to live at a more casual pace.

The best part about Chicago is the moderate cost of living. I was able to afford a three-unit home with rental potential in Chicago for $830,000 — a price I’d never find in San Francisco — that’s in a walkable neighborhood. It’s the perfect blend of family-friendly city life. Our three-year-old son loves taking the train home from daycare and running wild at one of the city’s many playgrounds.

I think Chicago is the best of the three places to start a family

After working in these three awesome places, I’ve realized that even the best cities have their flaws.

San Francisco has the coolest social scene and overall vibe, but it’s one of the worst cities for settling down because of its high costs.

Silicon Valley offers the best career opportunities, but its social scene is lacking since everything there is about work, work, work.

Chicago is the best of the three locations to start a family due to its affordability and comfortable pace of life, but it’s not quite as cool as San Francisco and can’t match the career opportunities offered in Silicon Valley.

Overall, though, it’s hard to beat Chicago’s mix of career opportunities, vibrant social scene, and opportunities to start a family.