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Why I’m Quitting My Job and Leaving San Francisco (future-bits.com)
84 points by endtwist on Dec 12, 2012 | hide | past | favorite | 84 comments



I think Daniel buried the lede on this one: there’s an apartment available in San Francisco!


It sounds like you had held up San Francisco and a startup job as being some sort of perfect ideal. This type of thinking usually results in feeling unhappy later.

San Francisco is just one city among many in the world. It may or may not be right for you. Believing the hype that "NYC is the greatest city on earth" or "San Fran is the only place where smart developers go" is a surefire recipe for disappointment.

It's your life and it's up to you to find the balance that makes you happy. Congrats on realizing this and having the courage to do a 180.


Yes, you are right that I thought a startup job in San Francisco would be ideal. However, I have zero issues with San Francisco as a city and lifestyle (other than cost of living, which I dealt with fine). The decision to leave is mostly based on how it will serve the next steps in my life. There is a solid chance I will end up back in San Francisco at some point in life, if only for a short period.

I need to write a follow-up post about why I decided to leave San Francisco to start a company.


But NYC is the greatest city on Earth ;)

Disclaimer: I haven't been to all the cities yet.


"Getting your foot in the door" cost me a large part of my career. I did something I didn't really have my heart set on at a large financial services company and the OP is right: it's hard to work on the craft you love at night while doing your day job. I wish I'd have picked up on this years ago but that's life.


> it's hard to work on the craft you love at night while doing your day job

I was going to comment on this. As someone going through it now (working for money in the morning, and working on craft in the nights,) it seems that many of my peers who do the same thing are burning out because they charge on until 2-3am, and get up for work at 6-7am.

You aren't going anywhere faster because you work yourself to death. A solid 3-4 hours at night, some great sleep, and I'm good to go. I just expect the payoff (of working on the craft) to come much, much slower than if it were my full time gig.

It works for me, and I take plenty of breaks from working at night because girlfriend, friends, and family would all leave if I didn't. I just take it slow and steady.


I'm in the same boat. It's a love-hate relationship. If I've had a particularly rough day or just don't feel like working, it's nice to just say "screw it" and drink a beer, play with the dog and talk to my girlfriend. I don't feel particularly bad because there is always tomorrow. If you take the long timeline perspective, it doesn't really matter much if you slack a little today.

On the other hand, it's easy to become complacent and lose motivation to keep toiling away. Maintaining a steady regimen of working, even just a little, each night seems to be the best way to not lose interest. Otherwise it's easy to continually say to yourself "well, I'll work on it tomorrow" for the hundredth time in a row.


Careers are long, and you don't look that old. ;)


Another reason to get out of SV: people won't think you're over the hill at 35.


This is exactly why I wrote the post. It was 100% a personal decision, but I hope that other people might relate and find a little courage if they are feeling the same way.

Thanks for your comment. I really appreciate it.


Welcome back to Chicago! We're a great city from which to operate tech companies. I still remember moving back to Chicago from San Francisco and how good it felt to be back where the leaves change color and every coffeshop in the city isn't filled with people talking about tech products.


I'm considering moving from Chicago to California for grad school and the lack of real seasons is one of a few things that's making me lean towards going out East (Boston or NYC) instead.


> My problem is that I also took a job that wasn’t exactly what I wanted to be doing so that I could be in San Francisco, instead of staying where I was and honing my craft.

Nothing wrong with that. When it comes to finding a career, learning what you don't like about a job can be just as valuable as learning what you do like.

A lot of my friends in college already knew exactly what job they wanted the day they arrived at school (or so they thought). I don't know of a single one who got the job they'd been striving for and ended up genuinely enjoying it. Many are now in grad school and still trying to figure out what they really want to do.


Good luck, hopefully you find the experience that you're looking for!

San Francisco has only been considered a hub for startups in the past few years. Before that, very few companies made their home in the city, and it was generally down in the South Bay or the Peninsula. Before Twitter, et. al started moving to SOMA, it was mainly banks, and retail companies like the Gap, Red Envelope, etc that were up here.

Ever since startups have decided to move to SOMA, the rents have skyrocketed, from 2000/month for a 1 br to over $3000, all in the span of maybe 18 months.


while focusing on short-term, ego-stroking opportunities makes things exciting, i'd also recommend setting 10-year goals.

what do you want at 30? at 40?

the chain of your short-term decisions should connect to fulfill your ten year goals. this will help make whatever short-term decision you need to make not feel so aimless, soul-crushing, or rash.

at the end of the 10 years, you can proudly look back and see how each opportunity help fulfill a larger purpose.


"…my actions felt like they were driven mostly by ego and the desire to be known in the startup community."

This is not exactly unique for people working in SF as part of the current boom cycle.


Exactly. That's another reason I felt the urge to leave, particularly if I was going to start a business. I didn't want to be influenced by the bad habits of the Valley and SF. It seemed unnecessary to touch on that in this particular blog post, but maybe in a future one.


It was great getting to work with you at Twilio. Good luck with everything in your future!


In the past, my actions felt like they were driven mostly by ego and the desire to be known in the startup community. If being out here has taught me anything, it is that none of that stuff matters (obviously).

Sounds like this was a great learning opportunity for him. If someone gave him that advice before he joined Twilio, it's possible he would have ignored it.

Sometimes it takes experiencing something first-hand to truly learn it.


What is the craft you love and why does going back to Chicago help you work on it?


It's not clear in either case. He says that he ideally would like to be a product designer, but then says it's tough to stand behind a developer and watch them build code instead of doing it himself.


Product designer is what I should be doing, and will be doing from here on. In my definition of product design, the ideal skill-set is a UI designer who works mostly in front-end code.


Good plan. 2 dirty secrets of the software industry:

1. Programming itself can be more fun than 99% of what people get paid to do, at least if you're building new stuff and in at least enough of a leadership role that you're not constantly keeping up with other peoples' changes.

2. 85% of real-world programming work is crappy maintenance and you need some independent credibility (e.g. "X who programs") in something else-- product, data science, finance-- to dodge it and keep getting the good stuff that builds your career.


Fantastic advice. I think you are definitely correct. Luckily I am design/product who can code (a bit), plus the added business and sales ability.


Good advice.


what do you mean by "product"?


I'd be a little concerned that you're abandoning the network you've built in SF. I guess it depends on the business you're starting, but when I co-founded my consulting company, all of our initial clients came from my existing network.


It's true. Now that he's wandered into a snowy wasteland from which nobody ever emerges, surely his San Francisco network will never get in touch with him again; even if they could (I guess there's always telegraphs and morse code here?), they'll be afraid of catching Yetis from him. Chicago has Yetis like NYC and SF have bedbugs.


I seriously had problems with my slowly but strongly built network when I moved from Boston to Charlotte. I still have plenty of references and people I can ask for help and technical problems, but in terms of finding permanent jobs or consulting gigs, location matters.


Hey, fellow Charlottean here! I've found a similar situation here, where my SF network still exists but isn't quite as useful as it was when I was living there.


I used to live in Chicago and have a very strong network there. I actually grew my network in Chicago while not living there because I continued to work on good things and by being active on the internet. I expect that the same thing will happen with my SF network as I move back to Chicago.

It all depends on how you interact with those people. If they are actually strong connections, which mine are, then you will not lose them by being in another city. They will also want to stay connected to you even though you are gone.


It's cool. You're still young. You'll look back at these years and realize how much you really learned with Jeff and the gang at Twilio. Keep writing and reaching out to people and above all have fun. Chicago is a pretty nice backup city. :)


How on earth does someone quitting their job and moving back home constitute news on hn??? I realize tumblr's down, but this really is a lame story. Good luck to the guy, but seriously, this is not newsworthy.


Read the other comments. You'll see why I wrote the post... other people are dealing with the same problems and questions that I dealt with, and reading about other people who have figured it out is reassuring.


I would imagine that many others also have to go grocery shopping this week, but that doesn't make it newsworthy.

I find trying to use hn as your support group a little distasteful.


I don't think the "cheating" was anything unethical. I wrote about the pervasiveness of that (anti-)pattern this morning.

http://michaelochurch.wordpress.com/2012/12/12/fundamental-s...

TL;DR: People have to seem more open to subordinate roles than they actually are in order to get jobs.

It's not always greener on the software side of the fence, though. Much of the job is dealing with bad legacy code, which seems to hurt you more if you're a good designer (cf. first and second design paradox) which your well above-average writing skills suggest you are.

I like Chicago a lot and think that it's a great place to live. Honestly, I think the obscene cost of living in New York and San Francisco has a negative overall impact on the quality of businesses that can be founded, but that's a rant for another time.

Good luck!


> I like Chicago a lot and think that it's a great place to live. Honestly, I think the obscene cost of living in New York and San Francisco has a negative overall impact on the quality of businesses that can be founded, but that's a rant for another time.

Well, I'm going to talk about it now, if you don't mind :P

If you look at a list of US MSAs[0], you can see that there are quite a few very large cities with low costs of living. For example, the Dallas and Houston MSAs are ranked 4th and 5th (SF is 11th), and are in a state that has a relatively low cost of living, not least due to the 0% income tax. Houston in particular is known for its lack of zoning laws (though some say not a complete lack), which drives down housing costs - the direct opposite of SF.

Although many people might think that they'll be surrounded by teabagging creationists if they go to Dallas or Houston, you'll actually find that there are a lot of young people in the cities that aren't your average Texan (and often aren't even from Texas).

You obviously lose some of the network effects advantages by moving to the Midwest, but I think such issues are becoming less and less important with each passing day, partially due to the connectivity provided by the internet, and partially due to a geographical diversification of the tech industry.

0: http://en.wikipedia.org/wiki/Table_of_United_States_Metropol...


I live in Dallas and there is a significant level of opportunity here for both employers/entrepreneurs and employees. Anecdotally, neither myself nor other talented devs I know have ever struggled finding intriguing work (I work at SoftLayer) or finding qualified coworkers.

I will say though that Dallas does not have anywhere near the scene when it comes to the social aspect of development/employment. The conferences are sporadic and not very big. Then gain, I am not a big conference person, so it does not bother me.


Can you provide your personal perspective on the cost of living and quality of life in Dallas, as opposed to SF or NYC?


I can, for Austin. I lived in the Bay Area for 10 years and ran a tech company there. I chose to locate my current startup (now 6 people; 4 Austin/2 remote) in Austin.

Here's my perspective: http://www.erica.biz/2012/austin-vs-silicon-valley/


> you can save $20,000+ a year on taxes here

I can't believe this hasn't attracted a lot more people already, you can do quite a lot with $20k extra every year!

One other question - how is the transportation situation in Austin? Can you drive everywhere? As someone who grew up in the Midwest, I don't really like having to use public transportation. Is there parking everywhere you go in (downtown) Austin?

The religiosity in Austin is unfortunate, but from what friends in Dallas and Houston have told me, this is not so much the case in those cities (partly due to more out-of-state people).

The weather in the summer (and winter) can be quite unbearable in the Midwest as well, but I've dealt with that since childhood by just staying inside (as I am happy to do pretty much all year round, actually). If you buy a house, it's quite easy to ensure you have double-paned windows and good insulation, and energy costs are relatively low, so you can keep the temperature at a comfortable 70-80 F year round.

And it's amazing how you can buy houses in the Midwest that would be considered palatial in SF for a fraction of the cost of renting an apartment!


I am from Indiana and I drive everywhere in Austin. However, I also live near a bus stop... just in case! There is plenty of parking except when South by Southwest Interactive is in town (1 week out of the year.)

Weather is similar to what I had growing up in Indiana, so it doesn't bother me at all.

I just paid my last year of taxes in California, and living here will save me over $30,000 a year in state income tax alone. That is probably what you will save as a dual-income household in the Bay Area. The savings more than pays my mortgage and utilities for a house close to downtown in a good neighborhood.


The issue that you run into in smaller cities (e.g. Minneapolis, Dallas, Austin) is that you can't have as long a SELECT query when you're hiring developers (or looking for jobs). If you demand a Scala expert with production Cassandra and Hadoop experience, plus 4+ years of Javascript.

Outside of the star cities, you have to grow your own talent. On the other hand, people don't leave you every 2 years and you don't have to give people 20% raises every year to account for the disgusting housing prices.


This is true. When my co-founder and I looked on LinkedIn for developers in Austin with Python and Erlang experience, there were only 6 total people--and one of them was my co-founder! Fortunately, we managed to hire one of the other 5.

Anecdotally, I've heard that many startups here in Austin are funding relocation packages for developers who are tired of living in a tiny town in the Midwest or tired of paying $4,000+ in rent in SF. There's a lot of talent moving here, and since the cost of living is sane, it's easier to attract people who want to own their own property and/or raise kids.


Right. I think that most companies are going to need to grow their own talent if they want to be located in a second-tier tech hub. You find generally good people and teach them what they need to know, which means you can't expect them to be responsible for major deadlines in the first 6 months. Many companies aren't willing to do that, and the grow-fast-or-die build-to-flips can't afford the time.


It is, in particular, from several years of experience, much easier to recruit in Chicago. We have offices in NYC, Chicago, and Mountain View, all of comparable excellence.

Cost of living is lower in Chicago, there's less intense competition in Chicago (in particular, there's no equivalent of Google looming over every Chicago team member), and people in Chicago tend to live here because they want (or need) to live here; they're "stickier".


I would like to hear your thoughts on the cost of living and how it affects business quality?

I think 'obscene' is the perfect word when talking about the cost of rent in SF. It's the number one factor in making me consider moving away from the area.


I actually did the opposite. Owned a house in Chicago. Sold the house, moved to SF, bought a house in the suburbs, and now take the BART to twitter everyday. Rents are obscene if you want to live in SF proper...as you start moving out to the south Bay or better yet, East Bay, they drop quite dramatically. If you are willing to live in Concord or Pittsburg, you can easily find a 1K/mo rent. Even in Pleasant Hill I was able to land a 1.5K, and Walnut Creek & thereabouts will still be below 2K. Ofcourse you spend 45 minutes on the BART...but hey, there's a reason machine learning textbooks are 800+ pages....:) I have learnt so much in the past 3 months, & all the credit goes to BART.


Sure I can live an hour away from my workplace and sit on the BART 2 hours every day but it's quite well known that this kind of living is bad for you [1] and I know from experience I would hate doing that again.

Why commute all that way when I can move somewhere much more reasonable and get a 3 bed house with a pool for the same price as a small 1 bed apartment in SF, AND only have a 10 minute drive to work? These places exist all over the world and contrary to popular belief around these parts, smart people and businesses do exist in places other than SV.

[1] http://www.slate.com/articles/business/moneybox/2011/05/your...


To each their own. I rather enjoy riding the train. It forces me to do things I should do anyways.

For the vast majority of jobs it would be time wasted. But as a software developer it's an automatic 1.5 hours per day I have to spend thinking about what I need to do.


I used to feel exactly the same way, but eventually the novelty wore off after I started a family. The prospect of spending 2 hours every day commuting for the next 20-30 years got me looking at real estate and job listings real quick.

Two hours a day is 500 hours a year on the train. That's a tremendous amount of time to be away from your loved ones for the sake of a Good Job or a Nice House.


That's assuming you waste those 2 hours. I do work while on Caltrain, and count those hours as work, not as missed private time.


Does that 1.5 hours per day count as part of your work day, allowing you to leave work earlier? Or are you just doing extra work every day and not being compensated for it?

I can understand using that time to better yourself in some way, but working for free I don't agree with.


There aren't any particular number of hours I have to be there. Usually I just leave when I hit a good stopping point for the day.


Agreed. I was job hunting a couple years ago and decided to stay in Austin after looking at SF and Seattle areas. The cost of living + commute just wasn't worth it to me.

In Austin I can get pay pretty close to Seattle, but live within 30 minutes of my office (fairly easily) and have a nice house to live in.


Totally agree, that's the reason I'm in Austin.


+1 for Austin. My base salary is slightly higher in Austin, mostly due to moving to a later-stage company, though the salaries really aren't that different. My take-home pay is noticeably higher because of that and the lack of state income tax. Couple that with a substantially lower cost of living [1], and my dollars go a lot farther.

The financials of it isn't the end of it, though. The nightlife is better, the people are nicer, I can have a backyard, I'm not severely limiting my options by having dogs, and the weather is better (for me, but I'm used to hot). I'm significantly happier in Austin.

[1]: My 2-bedroom house that I live in by myself costs about what I was paying for my share of a 2-bedroom apartment in SF. Both required about a 10 minute commute, though I drive in Austin where I could walk in SF. It extends beyond rent, though. Everything in SF is more expensive, though nothing is quite as dramatic as the rent.


On top of what you said, I think the culture and nightlife is amazing in Austin. There's more to do than in the bay area IMHO (this includes SF which most shit closes down early and has a sorry ass nightlife). The culture is a lot less vapid, people don't care where you work and I find people just more balanced.

Furthermore, if you're fitness, there are so many running clubs, core classes and cycling races that go on.

Note: I moved to the bay area for a couple years before heading back to Austin (I lived in Austin for a decade before wanting to try out the bay area, no idea why people like it so much).


Have they differentiated between commuters who drive and commuters who have public transit? I wonder how much of this is due to the length of the commute as opposed to specific common experience (driving? traffic?) during the commute.


There's not a ton of data, but one study suggested: stress from long automobile commute > long public transit commute > short public transit commute > short automobile commute.


You either love SF or you don't, for me cities are not interchangeable based on factors of convenience.

I live in SF, and love it.


I commuted 45 minutes to work on the MBTA for about two years. I hate commuting...but if I'm going to do it, the train is a pretty swell way to get to work. I would either read or listen to podcasts. As an adult, I never get much time to just sit down and read (either fun fluff, or educational). The train was pretty great for that.

That said, since moving from Boston, I'm so much happier. No commute, three times the space and a nicer apartment for half as much rent, better weather, close to the beach. South Carolina isn't exactly the mecca of technology, but telecommuting makes up for it.


Coming from NYC and commuting on the subway everyday for around 40 minutes was a pleasure (as you could read a book, listen to music or do something else to amuse your time).

Driving is any longer than 30 minutes to work (each way) is going to be more of a pain as you can only do so much in the car without endangering others.

Public transportation when it works well in cities leads to people tolerating longer commutes to work. If I had to commute 45 minutes in CA traffic I would be very upset.


I lived in Pleasant Hill and commuted on BART for 2 years. I ended up really hating it after a while.

Later, I moved to Austin, where house prices are reasonable even if you want to live close to downtown, and you don't have to worry about long commutes just to save money. I have no regrets over gaining so much of my time back, and Austin has a thriving tech community.


Expensive real estate ruins the culture, makes personal burn rates high, and creates a sense of transience. You don't feel like you really belong until you have enough money that you don't need to work and (for most) have ceased to be a productive part of society.

When people have to beat others down just to afford to live in the city, it's bad, and most people lack the talent or opportunity to make that amount of money (300k+, for a family) through decent means.

The transience, I think, is behind a lot of the build-to-flips that are degenerate gambles on social trends.

Silicon Valley happened because California land was cheap-- at one time.


I recently left SF, and the culture, along with the rent, are two big reasons why I decided to leave. I hadn't put the two together, though, but I think it's a pretty accurate conclusion.

The sheer number of startups and engineers in the same place can be pretty fantastic, and there isn't anywhere else that can compete (NYC to some extent, I suppose). In the end, though, it's just an unusually large collection of tech-minded individuals in what amounts to a fairly terrible place to live. YMMV, of course.


This was exactly my experience living both in SOMA and in Noe Valley at two different times in San Francisco. There was never any sense that the place we lived would be the place we'd be living 5 years from then. There was no realistic chance we'd ever raise kids there.


You echoed my thoughts exactly about Noe Valley. We absolutely loved living there, but when it came time to raise a family it wasn't even an option. That's coming from a couple who both worked at Google! Obscene indeed.

I absolutely love SF, but I never felt like home there. I think what we were missing was that sense of permanence, resulting from the high cost of housing (and therefore lack of future options).


"and most people lack the talent or opportunity to make that amount of money (300k+, for a family) through decent means"

Effing Norah, that would get you a small stately home in the North of the UK. I'm talking 15 bedrooms and a small park. You could buy a normal family house for a year's rent at that level almost anywhere outside London or Edinburgh

Second decade, 21st century and location still matters so much? What did we do wrong?


You most certainly could live in a mansion up north in the UK for that sort of money. Good luck finding anyone willing to pay anything close to that though!

I think it's common goal for people to try and make their millions in such a place as SF so they can leave the area and live like kings elsewhere. This is fairly obvious just looking at the rents here, and in places that have the perception of creating more millionaires (usually through business) than others. You know the mindset: live rough and work hard for 5 years to earn what most people take a lifetime to earn.

Personally, I think that is possible in many places around the world, certainly places that will have a nicer standard of living, however you wish to measure that.


You know the mindset: live rough and work hard for 5 years to earn what most people take a lifetime to earn.

The percentage of people who get that is small, and it's mostly noise, not talent. I'd be happy to have boring old 7-8% per year growth in exchange for autonomy and interesting work.

Once you reach a certain point of development, your DFA light (DFA = Done Fucking Around) comes on and you're no longer happy if you don't call the shots regarding how you spend your time. The appeal of the idiocy it takes to reach $5m per year disappears after that.


You've described what's happened with me recently. My DFA light is flashing and it's time to get out of the rat race and control my own time. That's worth far more than the tiny chance at the jackpot.

I do, however, still hold onto the romantic notion that if you find a way to earn a living while doing what you love, the chances of hitting that jackpot are significantly higher.


My girlfriend and I both work at startups and make about 170 combined. No chance we could afford a house though. That realization can make this a pretty depressing place though...


My wife and I make less than that combined. We bought a 2br in a very unfashionable corner of the city, during the boom. You could do better now. So 170k is workable... as long as you're willing to lower your expectations.


> ... creates a sense of transience. You don't feel like you really belong until you have enough money that you don't need to work and (for most) have ceased to be a productive part of society

Very well said, I think you just put a feeling/idea into words that I was having difficulty putting into words.


Which is why Berlin is very much a good place for startups right now. The rent is still very cheap, but there's a huge concentration of creative people wanting to create companies. This will fade over time just like in SV, but for now, it's one of the best places to be for small companies.


> that amount of money (300k+, for a family)

What's that number intended to represent? It seems (1) too small to be the cost of a house in SF suitable for a family, (2) too large to be the annual (still less the monthly) cost of renting somewhere in SF suitable for a family, and (3) too large to be the salary you need to be making in SF to afford the rent or mortgage on a house suitable for a family. Is it intended to be the amount you need for a realistic downpayment when buying a house, perhaps?

(It looks to me as if you can rent a pretty decent house in SF for, say, $6k/month, which is certainly a whole lot of money but far less than $300k/year. If you want to buy, it seems like the figure is somewhere around $1M.)


300k per year to raise a family in the star cities-- a conservative estimate. That includes a mortgage (you don't want to be renting once you have kids), enough cleaning that you can both focus on your careers, nannies, vacations, and various educational assistance (possibly prep schools, possibly buying internships) needs to overcome the fact that your kids face a huge disadvantage in college admissions on account of where they live. (It might be a good idea, if you can't afford prep schools whose guidance counselors were hired because they know top-college admissions officers personally, to have your kids go out to Montana for two years to overcome this geographic adversity.)

For a $1 million house, you're looking at a $4300 per month mortgage. You shouldn't be spending more than 30% of after-tax money on housing, so that means you should be making $14,000 per month post-tax, which puts you right around $300k.


Why don't you want to rent once you have kids? Full disclosure: we have a 2-year old.


> Silicon Valley happened because California land was cheap-- at one time.

You're being facetious here, hopefully.

In any case, San Francisco was never cheap, where OP's startup is.


Silicon Valley started in the 1950s: http://en.wikipedia.org/wiki/Shockley_Semiconductor_Laborato... . It was affordable until the mid-90s.


Why in hell is this on HN?


This is actually a fairly typical representation of what has always been on Hacker News. Why the hell are you surprised?


it fits the pattern "Why I'm <verb>ing the <noun>", ever hear of SEO? :)




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