How do I become fervently dedicated to something?
March 16, 2014 1:10 AM   Subscribe

Suppose you’re a 28 year old who, after spending 18 years as a shut-in, is finally able to experience things most people experience in their early teens. How do you dedicate yourself to an idea, a cause, a company, or a domain of knowledge while being incessantly hounded by the realization that there is much more to life than the object of your obsession?

From the age of 9 onward, my life was entirely confined to a 15” monitor and a pair of dandruff-coated headphones. But this isn’t about that.

One year ago, I made my first friend since prepubescence. In the past year, there have been many firsts. The first time I entered a bar. The first time I ate at a restaurant. The first time I had sex. To use a clichéd phrase, I finally feel alive.

And now, less than a year into this new life, I have to might have to kiss all of that goodbye.

As a case of cosmic humor, my career - the one thing other than my computer that got any attention after I entered the workforce - has transformed a source of mild enthusiasm into an intolerable, desolate hell. I’ve worked in entry-level positions at a radio station, an ad agency, a large bank, and a tech startup. In all cases, I’ve left either due to insane hours or due to existential depression (usually a combination of both). I figured out three months after quitting my last job that I will probably never be happy trying to scale the ladder one rung at a time. There has always been an unshakable sense of urgency, a feeling that the seconds are ticking by and that I’m wasting the best years of my life doing the bidding of jackasses who organize two-hour meetings to tell everyone that in their unsubstantiated opinion, a lighter shade of green will boost click-through rates by 79%. Meanwhile, Elon Musk is launching rockets into space and researchers at universities around the world are pushing the boundaries of what we know.

So I have no option but to take up an extremely demanding job as a senior level employee (with stock options) at a Silicon Valley tech startup, or start my own company. Both cases will leave me with virtually no free time. I will have to dedicate almost all my waking hours to the company. I thought I was ready for this, but in light of my newfound social life, I’m not so sure.

While I genuinely love learning anything about mathematics and computer science, I’m as curious about them as I am curious about anything else - very. I’m just as interested in physics, microbiology, robotics, and a whole bunch of different things. And this isn’t the “I heard last week’s episode of Radiolab and it was pretty cool” sort of curiosity. I’m talking thinking-about-electron-diffraction-after-four-drams-of-scotch curious. Add to this the sheer variety of experiences I’ve had in the past year and it becomes very difficult to justify being obsessed with any one thing to the exclusion of everything else. If I’m truly honest with myself, I have to admit that I remember the time four buddies and I social-engineered our way into an exclusive party after scaling a chain-link fence, evading CCTV, and sneaking past private security. I remember the time I went out on a date with the most vivacious woman I’ve ever met. I don’t remember the time the Church-Turing thesis finally clicked for me.

I know what I have to do. I’ve tried all sorts of things to convince myself that my calling is a tech company somewhere in San Francisco. I’ve told myself that it’s no big deal if I pick the wrong option because my current life is nothing more than a bonus. I’ve tried to tell myself that a vibrant social life is a distraction (my own sour grapes). But while I understand that at an intellectual level, my belief doesn’t withstand sights and sounds that remind me of the other option. For example, I saw a couple having brunch at a café earlier today and wondered to myself if I’m about to squander the next 10 years of my life the way I squandered those miserable 18. What if I end up penniless at 38, having wasted 10 years at a failed startup (or two) and the best years of my social life? The opportunity costs are enormous. Even if we ignore the social life for the sake of argument, how do I focus on something as narrow as a company when there is so much to learn? How the hell do guys like Mark Zuckerberg and your typical Fields-Medal-winning professor stay so single-mindedly passionate about the things they do?
posted by monad to Human Relations (41 answers total) 15 users marked this as a favorite
 
Hey. You are only 28. The world can wait. Take some time for YOU.

Silicon Valley will still be there in a year, in five years. The tech industry, as well. Your youth, your twenties, not so much.

You have decades ahead of you, is how I see it. Can you resign yourself to having lived 5% of the past twenty years. I feel like you finally found something that satisfies you, but previous habits are difficult to slough off....

Yes, use your skills. Yes, support yourself financially. But perhaps you can postpone that part of adulthood for another year or so. After all, you've postponed adolescence, for eighteen years (in your own words).

Whatever choice you make, sounds like you have a lot of cool things ahead of you. Don't sweat it too much. Good luck.
posted by tenlives at 1:37 AM on March 16, 2014 [1 favorite]


I found that my late twenties was one of the most frustrating times in my career. I knew enough to be over the early excitement of work and getting paid, but didn't quite have enough credibility and experience to be in a higher level position - although at the time, I didn't really see that, so was frustrated at what seemed to be a lack of progress. The problem with continually changing sectors or types of jobs is that it will make it hard for you to climb the ladder, because you keep resetting your career. So it might take a few shots, but when you find something you think you do quite like, you may be better to sit through a little bit of tedium for a longer term return.

One solution to the career vs life is to work somewhere with a culture that is a great fit for you, because most of my friends these days are people I have worked with at some stage. I worked for a few years at a not-for-profit which was filled with people I had a lot in common with, so even when we did have to work hard, it was with a bunch of people I really liked. It was more than just a job, it was a lifestyle.

Slightly tangentially, make smart financial decisions because this will give you the greatest freedom in terms of what you have to do for work. Don't get into debt (especially credit cards and car loans) and make a habit of saving a good portion of your salary.
posted by AnnaRat at 2:13 AM on March 16, 2014 [2 favorites]


You sound like you are still trying to fit your life into a little two dimensional panel.

We can't all be Mark Zuckerberg, or your "typical Fields-Medal-Winning professor." For one thing, that you've even heard of Mark Zuckerberg has as much to do with luck as it does any particular "virtues" he embodies.

Your misgivings about throwing your life and soul into a startup are well founded. You really can't make plans to be a superstar in your 20s, period, but particularly when you are already 28. Moreover, you sound like you are half-under the spell of a mythology that exists primarily to get young smart, naive, people to take most of the risk so wealthy investment managers can get rich while investing other people's money. That bullshit isn't worth sacrificing any of the things you are worried about sacrificing.

You are right though, you are wasting your life working for jackasses. The solution is reframing the attitude with which you approach work. That isn't just to say I suspect you have an attitude problem that will lead you to hate any place you work, but also that if you can shift your perspective, you'll be able to more clearly see your way to finding or creating work situations that actually suit you. For my own part, I have't always been unhappy in working life, but I found that switching from being an employee to making my way as an independent consultant has, somehow, helped me fix problems that I previously felt I had to accept.

Really though, just keep trying things, then take a step back and consider is this working for me, or not? If not, can I identify what would make it better? If no, then time to try something new.

When I wrote my college entrance essay, 25+ years ago, my father urged me to drop the bullshit I'd written about the risk of nuclear war, and instead write about how I hadn't really discovered anything I was really passionate about. In college I ended up getting pretty into biology and chemistry, but after graduating, I found the internet and software more interesting, that interest has waxed and waned and shifted, and honestly, some days I still wish I could really really sink my teeth into something for years on end.

But then I realize, I really have, I am really good at digging into things deeply and then synthesizing what I have learned and communicating it to other people. I do it over and over again, and each time, I get a little better.

There is something else too, some volunteer work that I find I have to keep returning to. It is something I started in large part because I could just dabble in it, but it has become just the opposite, it is something I can't stay away from. A big part of the reason why is that I just kept at it, even when it didn't seem like I was getting anywhere with it. The risk was low though, and the potential benefits (to others) was high so I kept trying. There was a time I felt like i couldn't do it any more and I actually had to step back. In doing so though, i realized the ball had started rolling, and was picking up momentum, even without me. That gave me the inspiration I needed to keep going, and I'm still doing ti, and may well stick with it until I die.

Some people are fortunate enough to have things click early in their lives, but life is longer than you think, and the longer you keep at it, the more opportunities there are for things to click for you. That might mean you find the one thing you can commit most of your attention to, of it may be the good-enough job, and friends and family you love, and time to have a succession of hobbies.
posted by Good Brain at 2:17 AM on March 16, 2014 [7 favorites]


"We thought of life by analogy with a journey, a pilgrimage, which had a serious purpose at the end, and the thing was to get to that end, success or whatever it is, maybe heaven after you’re dead. But we missed the point the whole way along.

It was a musical thing and you were supposed to sing or to dance while the music was being played."
posted by empath at 3:41 AM on March 16, 2014 [8 favorites]


If I read this correctly, it seems you’ve begun to live and feel you cannot work and live simultaneously in light of your discovery, socializing. If you feel deeply ardent about your work, you couldn’t have found something else to be so utterly passionate about and wouldn’t consider the work as interference to your new social activities. Everybody (I believe) sacrifices but you seem innately unhappy with your job. You’re young though and can possibly discover a job were you feel good and have some time to kick back and let your hair down. Or, you could take some time off and breathe before diving into the work you seem so apprehensive about but also very suited for. If time off isn't a possibility then do the job a bit and see where it takes you and maybe you'll be surprised that you have more time to socialize and live than you realize.

Maybe while taking time to see your way through this, you can seek out and discover other jobs that deeply interest you, see what it takes to do them and if you can manage both it and a social life. Compromise. There’s no need to have one or the other. Also, no need to toss aside work altogether – if you do that, you may find yourself sorry later. Money can be a great deal of freedom, it affords you the luxury of travel, dates, drink, and time from work and to do what you want to experience and believe it or not, there will always be time to do those things and those who care will understand the demands made on your time now so that you can play later – it’s you that you’ve got to please. If you feel you cannot do the job, perhaps you are experiencing some burn out and should seek someone professional to talk to about it with.

Most people juggle their time and lives. Most people get tired and wish they could do more of one or the other - ultimately those who are largely successful sacrifice a lot of social experiences until later, including missing out on people that may have become lifelong friends - sometimes work brings them those people too - it depends on you and your outlook while working. If you see your job as negative and all time consuming, it will be that - your attitude makes up a large part of your experience in anything, whether social or work related.

Some wise words: The worst life lived is the one with regret; never immerse yourself so deeply into work you toss aside experience that make you who you are – also never choose fun over a secure future. Try to take time for yourself now so you can feel and think your way through this and discover what you really feel passionate about - and if its both, place work and socializing where they belong in the perimeters of those two things. If your work is your passion and so is socializing, maybe it’s a matter of placing one a little lower than the other – it doesn’t mean you must get rid of one altogether.

You’re young, no need to look back and think “what if” make yourself happy, this is your one life. This is your time. So think about it and be honest with yourself.
posted by Fayrose at 3:52 AM on March 16, 2014


So I have no option but to take up an extremely demanding job as a senior level employee (with stock options) at a Silicon Valley tech startup, or start my own company.

The line that I quoted makes it seem like you think this follows logically from the previous part of your question, but it really doesn't. I don't know you, and I don't know what you're capable of or what would make you happy, but I have to believe that there is some middle ground between, "wanting to claw your eyes out in a soul-sucking entry level position" and "devoting yourself 24/7 to a being a big shot in Silicon Valley." I may be misreading things, but it's also not clear to me how you're planning to jump straight from a string of entry level positions to "a senior level employee (with stock options) at a Silicon Valley tech startup."

It sounds like you would be happiest in a job that lets you explore a variety of interests and gives you some amount of control, with as little b.s. as possible. You probably won't be able to find the perfect job, and that's okay. Very few people do. Instead, they focus on filling their non-work hours with all the other things they enjoy doing. Anyway, even if you were 100% devoted to your work, you still probably wouldn't be satisfied if that was all you did in life. Listen to the part of you that knows is this is the wrong path to take.

There is a middle ground here. You just need to find it.
posted by litera scripta manet at 5:46 AM on March 16, 2014 [8 favorites]


Upon re-reading your question, one other thing that sticks out to me is the fact that you've left your previous jobs because of "existential depression."

I can't explain exactly why this is, but when I feel connected to the world around me, I cease to be hounded by this kind of existential angst. When I'm surrounded by friends and people I care about, when I'm doing work that is rewarding and meaningful, I don't find myself lying awake at night thinking about the futility of life, the meaninglessness of existence, and the insignificance of my actions.

I think maybe if you step back from these ruminations and allow yourself to become more involved in the world around you, continue to pursue these new relationships, and explore your other interests, you won't find yourself plagued by these thoughts quite so frequently.
posted by litera scripta manet at 5:58 AM on March 16, 2014


Most sane people find a way to balance their social lives and careers. Not in the sense of perfect balance all the time, but they make compromises to have both in satisfying ways. That's what you need to do, I think -- not find a way to accept that you can only have one or the other.
posted by J. Wilson at 7:13 AM on March 16, 2014


I’ve tried all sorts of things to convince myself that my calling is a tech company somewhere in San Francisco

If it was your calling, why would you have to try so hard to convince yourself of that? I suspect that this isn't what you want - it's what you think you should want.
posted by thelonius at 7:21 AM on March 16, 2014 [2 favorites]


How the hell do guys like Mark Zuckerberg and your typical Fields-Medal-winning professor stay so single-mindedly passionate about the things they do?

There's a lot of stuff in this question but I take you to mean -- how can I realize my ambitions of extraordinary success in a demanding field when this would mean devoting every hour of my life to a single, narrow pursuit?

I think the premise is false. I don't know so much about SF startup culture but I do know a lot about research mathematics, the other interest you mention. I don't have a Fields Medal but I work closely and am friends with Fields Medalists. Are they passionate about pushing the boundaries of mathematics, and am I? Of course? Single-mindedly passionate? Not in the sense you mean. We get married, we have kids, we read books, we go to parties. Mathematicians at every level, including the very top, have the things you've told yourself you're going to have to give up.

I would be shocked if startup life were any different in this respect. Mark Zuckerberg is married to his long-time girlfriend. I very much doubt he forged that relationship on a ten-minute coffee break.
posted by escabeche at 7:25 AM on March 16, 2014 [8 favorites]


From one chronic job-quitter with an awesome social life to another; I think you have some serious all-or-nothing thinking going on here, and a misunderstanding of just how much work it takes to get to the point of being Elon Musk.

Do you have an abusive boss or bosses in your past? Like, not just a jackass who hijacks your time in meetings, but someone who's questioned your competence in especially cruel or demeaning ways? Because I do, and one of the ongoing consequences of that is a voice in my head that says "You should never work under anybody else again, ever!" It's a defense mechanism to try and keep me from getting hurt in a way that profoundly affects my life, like my first boss did to me. And as much as brain knows that abusers are outliers rather than the rule, it's a remarkably persistent voice. The only things that have come anywhere near silencing it are working a totally dead-end, entry-level temp gig in a field I never thought I'd like with a genuinely nice boss who valued my time, and lots of therapy.

So my suggestions here are two-fold. One is the classic metafilter therapy suggestion, because it's worth looking into why you assume a job and an awesome social life must be mutually exclusive. The second is looking for jobs with an eye to a sane and stable work environment, rather than doing the most earth-shakingly groundbreaking work ever. Nobody talks about the boring grunt work Elon Musk must have weathered to get where he is, but no one starts building rockets like that from nowhere.
posted by ActionPopulated at 8:44 AM on March 16, 2014 [3 favorites]


Stop thinking of yourself as special. Everyone spends their 20s learning how to do things they've never done before: hold a job, cope with being at the bottom of the totem pole, be married, have children, live in a different city, not rely on their parents... Whatever. Its also a time when "you can do anything" becomes "I'm going to do this".

The fact is that most people examine the opportunities available, and choose the best. Who comes out of school saying "I want to be an insurance accident adjuster"? To me, your comments suggest you don't know how difficult it can be to make a particular dream come true.
posted by SemiSalt at 9:10 AM on March 16, 2014 [4 favorites]


This is tough, man, I know. It sounds to me like you're in a crisis of "work to live or live to work," and only seeing the extreme ends.

I'm in a low-to-middle-free-time job with a high mental load that haunts me even when I'm not at work, but I do that by choice because I love what I do. I mean, when I take time off, I miss not being there. My work is fun for me. I like being the person who can do this, and want that feeling as much as I can get it. I get paid fairly well for that (though not exactly getting rich,) but that's not why I do it.

What's that got to do with it? Well, it sounds to me like taking a crazy startup job is an attempt to force that. But you can't. If you want to be out on dates and seeing what life's about, then you probably should do that, because you'll end up resenting the job no matter what it is. Maybe your answer is to take a simple job that just pays the bills, that you don't have to care about the other 128 hours of the week. But no, because that's also an extreme position.

There has always been an unshakable sense of urgency, a feeling that the seconds are ticking by and that I’m wasting the best years of my life doing the bidding of jackasses who organize two-hour meetings to tell everyone that in their unsubstantiated opinion, a lighter shade of green will boost click-through rates by 79%.

The thing about the part I quoted above is, that's within your control. What are you doing for you? If you start working there with no savings or assets to speak of, but you're saving money little by little and you end up better off a year, five years from now, it doesn't really matter what you did for them, you also did something for you. If you want to go out and spend some of that money on experiences, then that's only trading off your future freedom for your 'now' fun. It sounds like you're dissatisfied that you have to do this.

But the answer isn't doubling down on working even harder, that's just amplifying the original problem, unless you find something that you do truly enjoy doing for it's own sake. Something that would count as enjoying life. If you find that cause or startup, do it. But you can't force that by randomly picking a thing and charging at it, I don't think.

It's a thing we all struggle with. You can't have all the free time you want, all the money you want, and advancement through/past 'the ranks' all at the same time. You'll always wish for more of one or more of those and wish you had done things differently. We all do. But your best bet is going to be to aim somewhere in the middle, not at the extremes. That way you don't get ten years down the road feeling like you've completely lost a decade.
posted by ctmf at 10:25 AM on March 16, 2014


And your "existential depression" is just burnout. You've put too much into those jobs without having anything else. Like playing your favorite song too much.
posted by ctmf at 10:35 AM on March 16, 2014


Response by poster: Hey. You are only 28. The world can wait. Take some time for YOU.

Silicon Valley will still be there in a year, in five years. The tech industry, as well. Your youth, your twenties, not so much.


I don't know if this is true. Part of the reason why I feel like it's now or never is that most entrepreneurs in The Valley start very early. The average age of a cofounder in Paul Graham's Y Combinator fund is 26. I'll probably be 33 by the time I'll have enough contacts and experience to start my own company. Ageism is pervasive in that subculture and nobody really gives a shit about it.


Really though, just keep trying things, then take a step back and consider is this working for me, or not? If not, can I identify what would make it better? If no, then time to try something new.

That’s exactly what I’ve been doing for the past five years. I was fortunate to discover very early in life that it’s impossible for me to know what a meaningful (more generally, optimal) life is a priori, so the best thing I could do was approach the ideal with a series of approximations. That’s what drove me to fix my personal life as soon as I was psychologically able to. But my attempts to apply that to my professional life have gone nowhere. It’s not that I fundamentally dislike one thing and like another; I can become deeply interested in anything. I just have a part of me that keeps urging me to do more with my life, to go out there and put a dent in the universe. I have the ability. I have the drive. But I’m not as single-minded as I need to be, and the recently resuscitated social part of my brain tugs in the opposite direction, telling me that “doing more” is having adventures with friends and nights of wild sex with women I love.


I have to believe that there is some middle ground between, "wanting to claw your eyes out in a soul-sucking entry level position" and "devoting yourself 24/7 to a being a big shot in Silicon Valley."

I have been searching for a middle ground. After trying many different kinds of jobs over the years, I’m not sure one exists. If I were forced to spend all my working hours making bullshit Powerpoint presentations stuffed to the gills with buzzwords, I’d probably treat it as an art and give it my very best. If I’m going to be a Powerpoint bullshitter, I’m going to be the best bullshitter in the world. I’ll make a dung heap so large it will make the entire middle management team quit their jobs and fly off to Cambodia to forge a new life of selling street food because they know that they’ll never be able to top my work. But I know resigning myself to that kind of work would be defeatism. I’d rather direct that craftsmanship toward building rockets or founding world-changing companies.


We get married, we have kids, we read books, we go to parties. Mathematicians at every level, including the very top, have the things you've told yourself you're going to have to give up.

I would be shocked if startup life were any different in this respect.


It is and it isn’t. You’re right - not everyone works themselves to the bone in startups and academia. In my time working at a tech startup, I met a lot of CEOs and CTOs whose only life outside of work was trying to hook up with someone at a bar on Friday night. Many other founders had a more balanced life. I don’t think I’ll be able to maintain a balance because I feel like I need to spend my free time catching up. I’m a 28 year old with the professional skills and experience of a 20 year old. I can’t be a technical cofounder without knowing the ins and outs of securing distributed systems, knowing the comparative advantages of Docker-separated processes vs. conventionally hosted processes, etc. I need to play catch-up for at least the next five years in both the personal and professional domains.


Do you have an abusive boss or bosses in your past? Like, not just a jackass who hijacks your time in meetings, but someone who's questioned your competence in especially cruel or demeaning ways?

Never. The worst have been two bosses who just didn’t give a shit about their jobs, but they were otherwise professional.


Nobody talks about the boring grunt work Elon Musk must have weathered to get where he is…

His period of grunt work was extremely short in comparison to the average. He founded his first company at the age of 23, while studying physics and economics at the University of Pennsylvania. He sold that company at 28 and made a cool $22 million in the process. Dude had hustle from a very early age.
posted by monad at 11:20 AM on March 16, 2014


If I’m going to be a Powerpoint bullshitter, I’m going to be the best bullshitter in the world. I’ll make a dung heap so large it will make the entire middle management team quit their jobs and fly off to Cambodia to forge a new life of selling street food because they know that they’ll never be able to top my work.

You can't just be a pretty fucking good Powerpoint bullshitter who also has a satisfying personal life? I guess I'm seeing that as the problem here, the need for extremism.
posted by ctmf at 11:34 AM on March 16, 2014 [5 favorites]


I can’t be a technical cofounder without knowing the ins and outs of securing distributed systems, knowing the comparative advantages of Docker-separated processes vs. conventionally hosted processes, etc.

This is totally false, even if you limit yourself to the y-combinator world. You know less than you think you do even about what you don't know. The secret to a good life that you are missing is humility.
posted by kelseyq at 11:38 AM on March 16, 2014 [10 favorites]


Honestly to me it sounds like you are having a manic episode and you probably shouldn't be making any rash decisions right now.
posted by empath at 11:56 AM on March 16, 2014 [14 favorites]


I think you've got your ego and a heavy dose of perfectionism all wrapped up together.

Do you believe that if you don't become wealthy and famous, you'll be a failure? Because a huge part of that is luck, and basing your life happiness on luck is a bad gamble. If you don't enjoy the process leading towards your long-term lifelong goal, try to find a different goal. The process is the bulk of your life and time, and that should be spent doing something you enjoy if at all possible.

I've known a lot of men who have the "I'm going to be a successful bedazzled millionaire by 30!!!1" goals at 18-20. If you're hitting your delayed adolescence like you say you are, you may just be having that stage, but at a period of your life where you realize you have less time than an 18 year does.

And yah, this is coming off as more than a touch manic.
posted by Dynex at 12:32 PM on March 16, 2014 [3 favorites]


I think you're poorly grounded (as I was at various points in my life) and don't know you're spewing highly verbose nonsense.

This, in your reply:

I’d rather direct that craftsmanship toward building rockets or founding world-changing companies.

is really unnerving. If you don't build rockets or change the world, your life is unlivable?

Why is this? There are 7 billion people in this world and 6.9999 billion of them have to figure out a way to live good lives without become world-historical figures who transform the nature of existence. What do you recommend, mass extinction for them?

I've worked a variety of interesting jobs (reporter, designer, teacher), learned a few amateur trades (music especially) and formed a few meaningful social ties (now as many as I wished for). Sometimes I wish I'd been Leader of Men and Subject of Biographies but I shake it off because that's just unsustainably stupid.

Please, find someone you trust who can bust your chops until you can think straight. A therapist is always an option.
posted by argybarg at 4:04 PM on March 16, 2014 [3 favorites]


This is anxiety. Hello, fellow busy brain. We aren't single-taskers. It's okay. We're flexible, it's good.

You don't need to sign up for the toxic fake-it-'til-you-break-it tech work culture grind. If you don't want that life, do something else. I opted out too, because I want my time for ME.

Luckily we truly are interested in everything. You could go be the director of IT for a nonprofit and you would be incredibly valuable and interested and you could have a social life and interact with a different crowd. Win-win.

You need to find happiness in yourself, you need to find NOW. Now is when you need to develop satisfaction with yourself and your work and your life. Now is the only time you have.

You were not a Silicon Valley Tech Guru at 23 and you won't be. You have a different path. Don't fall into anticipatory regret.

I don't know what your lost 18 years is about but I know you're still recovering from the change. Give yourself time. Live YOUR life. Be you. Be here now.

Meditate. Exercise. Read Things Might Go Terribly Horribly Wrong. Find your values and chase them. Embrace your 30s when they come. It gets better.
posted by heatherann at 5:24 PM on March 16, 2014


Hm. I am going to start by saying that the prospect of someone being a shut-in for 20 years and went from getting a few entry level positions at a radio station and an add agency to an offer as a senior level employee at a Silicon Valley tech startup within the course of a year seems.... implausible.

At the same time, this all sounds somehow familiar. You should meet my therapist who had upped my anxiety/depression meds. His take on me (and I think you): "You are a workaholic who is that way because you like the structure that the workplace gives you."

The thing is that you lack structure in your life, and you are looking for the workplace to give it to you, rather than structuring your own life so that you can accomplish what you want to accomplish and do what you want to do.

The best thing I ever heard was, "You can do anything you want, but you can't do everything." You can make rockets, or you can be a microbiologist, but you can't be both. At best you could be a rocket scientist who works on a project alongside a microbiologist trying to combine your expertise. You pick one based on your passions, talents, and the prospect of the field having realistic prospects to accomplish something within it (eg, it is not a good time to be a particle physicist).

Also, fuck Y-Combinator and all its bullshit. Their startup model is the following: do a startup that is similar to other startups but hope that their startup is the one that has the good luck to become the market-leader (ie, what facebook did: create a social network application like MySpace and Friendster and College Connection and all the others, but be lucky enough to have everyone abandon all the others for it). The most important qualification to get funding from them seems to be having dropped out of Harvard or Stanford and a passing resemblance to Mark Zuckerberg. That is the lottery economy, not business and technology innovation. If you actually want to innovate, you need to learn stuff. If you still feel like the only way you will get funding is if you're 22 years old, find a young kid to be the "public face" of the startup so funders can fool themselves into thinking that it is one of those sort of things.

And even that crowd socializes: they hang out with each other, travel together, go out drinking together, and socialize with people they meet at conferences and people in their field. They're not monastics living in a cave for 5 years while they code.
posted by bright colored sock puppet at 6:01 PM on March 16, 2014 [2 favorites]


Response by poster: Dynex: Do you believe that if you don't become wealthy and famous, you'll be a failure?

argybarg: Sometimes I wish I'd been Leader of Men and Subject of Biographies but I shake it off because that's just unsustainably stupid.


This question keeps coming up so I’d better answer it. No, I’m not doing this to be on the cover of Fast Company or drink the world’s most expensive scotch on my private jet. I have never cared about what will go on my epitaph; I’d rather live my life as I want to than worry about what others will think of me long after I’m rotting underground.


I've worked a variety of interesting jobs (reporter, designer, teacher), learned a few amateur trades (music especially) and formed a few meaningful social ties (now as many as I wished for).

And as patronizing as this sounds, I’d love to do all those things. As I said earlier, I can’t understand how Zuck and other members of his species can do the same thing for more than a decade when they have the means to do so many other equally interesting things. I think almost anything can be interesting, so all these things are on equal footing in terms of ‘meaning’.

But they’re not equal in earning power. Reporting is just as meaningful and interesting as software development, but even the least competent software developer makes a significant amount of money where I live. And unlike reporting, software development gives me a chance to make $MEGABUCKS (or $GIGABUCKS in rare cases).

Why do $MEGABUCKS matter? I don’t want to spend the next 30 years doing the same thing, be it teaching, or music, or coding. I don’t want to be “locked into” my career if I can avoid it. Yes, I know that the odds of making that much dough through a large exit are much lower than what Hacker News would have me believe, but I’m willing to give it a shot. It’s not nearly as bleak as gambling in Vegas. Besides, I fucking love programming.

I realize that I’m extraordinarily fortunate to even have the chance to lose sleep over it. This is a first world problem. It’s also a rare opportunity that I don’t want to regret having dismissed 20 years from now.


You were not a Silicon Valley Tech Guru at 23 and you won't be. You have a different path. Don't fall into anticipatory regret.

Oh, I know. I’m not trying to one-up Elon. He’s singlehandedly doing the work of four highly driven entrepreneurs (or sixteen founders of bullshit startups of the “Groupon for cats” variety). The guy is literally superhuman. I’m just using him as an example of someone who approaches his life with single-minded dedication and unrelenting grit. What I’m wondering is how he maintains his focus on SpaceX and Tesla when there are so many other crazy ideas he could be attempting right now (teleportation, nanobots, AI, etc.).


Hm. I am going to start by saying that the prospect of someone being a shut-in for 20 years and went from getting a few entry level positions at a radio station and an add agency to an offer as a senior level employee at a Silicon Valley tech startup within the course of a year seems.... implausible.

Shut-ins have lots of time to contribute to open source projects. All my work is publicly visible on Github.


If you still feel like the only way you will get funding is if you're 22 years old, find a young kid to be the "public face" of the startup so funders can fool themselves into thinking that it is one of those sort of things.

That’s the plan.


And even that crowd socializes: they hang out with each other, travel together, go out drinking together, and socialize with people they meet at conferences and people in their field. They're not monastics living in a cave for 5 years while they code.

I’d love to hang out with them but as I said earlier, I’m pretty far behind and need to catch up. This entire thread is me wondering out loud if sacrificing my free time trying to catch up is even worth it or if that time would be better spent nurturing social relations.
posted by monad at 7:10 PM on March 16, 2014


Try thinking in more particular terms. You may not have to choose between one extreme or another for the rest of your life.
posted by amtho at 7:29 PM on March 16, 2014


Catch up to where? How? That's this missing part in all your questions - what do you think the end result is going to look like? You can see that result without having to exclusively devote yourself to one thing and one thing only - but trying to do that, and play catch up, without a clear goal? That's just running in place.

And the way to focus is to stop thinking about the other shit. That's it. If you spend half your time thinking about where you could be and what you could have done, you're actually wasting time. Doing is not wasting. All the coding you've done is worth something. Have clarity of purpose and stop flailing about trying to find some external thing to magically bestow upon you some internal worth.

(And maybe meditate on why some random couple having a nice brunch sent you into an existential spiral of doom and destruction - I mean, they could have been anyone, doing anything, but your mind immediately went 'squandered time' and that's probably something you need to rein in, if you want to be able to focus)
posted by geek anachronism at 7:57 PM on March 16, 2014 [2 favorites]


software development gives me a chance to make $MEGABUCKS (or $GIGABUCKS in rare cases).

Even $MEGABUCKS is uncommon. Yes, there are startup millionaires and billionaires all over Silicon Valley. But there are also plenty of Stanford alums who got venture funding for a startup, it didn't go anywhere, they got venture funding for another startup, THAT didn't go anywhere, and they end up working at a tech company supporting a very nice upper middle class lifestyle that could just as easily been accomplished being a pediatrician or nurse anesthetist. Not that anything is wrong with that, but that's precisely the point: you have to accept that you might be doing what you're doing by doing "decently" but not being the superstar.

There are a lot of people who are now in their late 30s in investment banking went into it at 22 with the assumption, "I'll work for 20-25 years with a lot of 80-100 hour weeks, become the guy getting multi-million bonuses in my late 30s/early 40s, and then retire and do whatever I want." Then 2008 happened, and they realize what is going to be their peak earning years, they aren't going to be doing much better than a suburban orthodontist-- which is doing really well, all things considered. But what they thought was going to be a private jet and european vacation villa lifestyle has been downgraded to first-class flights and a nice hotel suite near the beach where they still have to work for a salary.

I'm not really sure what you think you need to "catch up on" that other people have done in the tech world that means you can't live the same kind of startup lifestyle that other startup people lead. I'd do a startup and figure it out from there. Maybe it will work, maybe it won't. But you might as well do it if that's what you want to do. Don't fall into the myth that you have to be a 22-year-old wunderkind who actually doesn't know very much and just ends up having fallen into the right place at the right time.
posted by bright colored sock puppet at 7:57 PM on March 16, 2014 [1 favorite]


Response by poster: Catch up to where? How?

Catch up on technical knowledge and experience. Having worked with some utterly brilliant people at my last job (a tech startup), I realized that there are gigantic gaps in my knowledge that I need to address before I can hang with the rest. I can't be competent as a senior developer or CTO in my current state. My rudimentary plan was to take a year off and hole myself in my room, immersing myself in whatever content I need to absorb to get to the level of your typical 29-year-old mid-tier developer in SF. Explain the employment gap with some bullshit story about travelling the world, get my foot in the door as employee #40 at a me-too startup, build connections, then bail after another year for a better position with stock options. Do the same for another year or two, then seek a cofounder and try my own luck at the game.

This plan requires me to spend every waking second on programming, CS, math, and (later on) business case studies. Basically, it's a gruelling training regimen for becoming a founder who knows what the fuck is going on.
posted by monad at 8:25 PM on March 16, 2014


The thing is, the best way to fill those giant gaps in your knowledge isn't by holing away in a room and reading stack overflow. I sympathise, because I used to think that, but it just isn't true. From the sound of it, you've done that (or something like that) for the last 18 years. If that worked, you would be one of the best-qualified people in the world right now.

The best way to fill those gaps is to get out there and have a life. By thinking you have to choose one or the other, you're creating a false dichotomy, a choice between two extremes that don't exist.

Here's what you should do:

Go out, get jobs at whatever tier you're qualified for, socialise with people at the jobs, learn the ropes by talking to them and figuring out what you need to know and fitting in the textbook-and-coding-learning around that. Seriously, someone who was a CTO at age 23 didn't get that way by hiding away in their room and working really hard -- they got it by having a life and meeting people who were in the game and then spending their spare time coding and reading and so forth. You learn SO much by just knowing people and talking to them and figuring out from them all of the hidden tricks and skills, as well as building a network of your own.

tl;dr: Knowing people and building a life with them will let you learn more in less time, because you'll be working smarter rather than harder. Plus, you will also get to meet people, have fun, and enjoy life in the process.
posted by fluffysocksarenice at 8:49 PM on March 16, 2014 [1 favorite]


The guy is literally superhuman.

Zuck and other members of his species


To quote the closest thing we have to an actual cyborg (Cher): SNAP OUT OF IT.

These people are NOT literally superhuman. They are maybe, MAYBE, "literally," as in figuratively, superhuman. They are not another species. They aren't frankly even very impressive members of OUR species. Zuckerberg is nothing more than a very smart, thieving, arrogant shitheel. He is not a god-man or an alien.

OK. Now, that critical bit aside:

This is life, man. You don't get to know the ending before you start, you just have to roll the dice. It will mostly be out of your hands anyway. You have all the information you're gonna have, and all that we can give you. It's not enough. But it's all there is.

You are having the panic attack of lost time; it's really rough stuff, but we most all of us go through it. I for one lost at least 4 or 5 years to crippling depression, and yes, when it lifted it was a whole 'nother kind of hard, realizing what I had left behind. I'm sorry that you feel you've lost so much time; and suggest verrrrrry strongly that you find a therapist or a mentor to help you come to terms with it.
posted by like_a_friend at 8:54 PM on March 16, 2014 [2 favorites]


It's a mug's game to try to plan forward for as many years as you're doing. It's an inherently stochastic process with a huge amount of noise, and you need to be able to roll with it and adapt on the fly. Tying yourself into knots trying to come up with the perfect plan now, and tying your happiness to that, is a recipe for unhappiness in the long run.

Since you're a computer programmer, I'll use an analogy that might speak to you. Think of your search for a "the perfect life" as a search problem with a massively high-dimensional and complex search space. What you've been trying to do is step back, look at the search space, and come up with the straight line that will get you from where you are to where you want to be. The problem is, the search space is fuzzy, because you're not sure what the relevant features are that are most important for success: as a result you can't precisely specify either where you are or where you want to me, much less the terrain in between. Plus it is way more huge and complex than you can possibly conceptualise, so any line you think you see is just as likely to be imaginary or local as it is to actually exist.

When you're in that sort of super-complicated space, where you must learn about the space as you're searching, it's never best to try to come up with a top-down algorithm for getting somewhere. Instead you will want to do something like MCMC: wherever you are, just take steps that are small changes from your current state, and occasionally throw a transition from a high-temperature chain in there (i.e., sometimes don't be afraid to take a risk).

Bottom line, though, you can't plan this sort of thing to the level you're thinking you need to. You need to do some sort of more local search instead. It risks getting stuck in a local maximum instead of a global maximum, but that's life, and is the nature of the problem with this kind of search space; and local maxima are still usually pretty nice places to be.
posted by fluffysocksarenice at 9:00 PM on March 16, 2014


Yeah, don't quit your job and try to cram for a tech job. That's about the worst advice I can imagine. You get better at tech by doing tech at a tech job. Not by holing up and cramming for it.

I dunno, I'm enough in this life to have a pretty good chunk of my first degree LinkedIn network be tech startup CEOs and CTOs and SVPs who are friends and former coworkers, and I'm pretty sure none of them went about it the way you're describing. Some of them felt like they didn't have the chops, and they went back for masters in some variant of CS, but most just worked like hell, became senior developers, maybe architects or tech leads (for the CTOs), development managers (for the CEOs or SVPs), then they worked their networks for angel funding, had a brilliant idea, and started their own company. I'd be willing to bet most of them probably don't have the tech chops you're fantasizing about; what they do have is networking skills, charisma, and a talent for picking up enough tech skills to wing it, and hiring smart people.

Find a mid-level dev job (if you don't have one already; it's hard to tell from your post). Do a good job at it, and don't quit in frustration. Get promoted to tech lead. Ask for funding for education, if you think you need more. Get promoted to dev manager (or senior architect). Get hired away to a smaller company as a senior director. Get promoted to VP. Have a beer with your old SVP who's starting his own company, and needs a CTO. (Or at any point after dev manager, what the hell, see if you can network your way into angel funding or bootstrap yourself. Why not? You're youngish and unattached.)

The only person I've known who had a similar "can't work for idiots at a meaningless job" attitude ended up unemployed and trying vainly to launch a startup, declaring bankruptcy, then getting and quitting new jobs at regular one year intervals until at least his late thirties. And he may be doing it still; I lost touch when he moved back home to live with his parents about ten years ago.
posted by instamatic at 9:01 PM on March 16, 2014 [4 favorites]


Sounds like you want to head into the woods and spend a year leveling up by killing boars so you can come out and skip half the game and get right to the good stuff.

Do you know how else you can level up? By playing the game.

I learned more in the first four months in my job than I did in 2 years of schooling. You can learn on the job, it will give you much better experience, there is a large social aspect to actually leaving the house and going to work, and you will have a resume that gets you a new job. Those amazing programmers you met are a valuable resource to you at work, and can't be of any assistance to you if you quit. They aren't going to toss you some knowledge if it isn't work related.

You haven't given any reason why quitting your job and becoming a crazed programmer hermit is better than staying in work and studying on your own time. Thinking you will skip to a higher level is unrealistic, especially if you are prone to depression as you have stated you are. It's far more likely in a few months you will burn out, that fact will be like watching your dreams built on sacrifices sinking into sand and you'll be sent for a mental tailspin.
posted by Dynex at 9:29 PM on March 16, 2014


But ... I have been a reporter, designer, teacher, etc. and didn't have $GIGABUCKS. I also didn't cram for them, and certainly not by being locked in my room prepping for them. I also didn't earn crazy money doing something else, then doing interesting jobs. I just did them, they were interesting. I was never terrifically wealthy and may never be, but my work life, at least, has been very sustaining. I've worn whatever shoes I want, I haven't had to punch a time clock, I've been able to do work to my level of quality.

What is the thing you want that I don't? I don't get it.

I'm not saying be a reporter, teacher, etc. I'm saying: find the tech world equivalents. Find work that fascinates you. Try being a DBA, or design an educational app (consult teachers first, please), or really master software for a ridiculously specific industry.

Above all, find good people to work with and learn from them at every opportunity, instead of trying to humiliate them off the continent with your brilliance or whatever. Get deep into good, juicy, meaningful work with other people who also love this stuff. One week spent this way will be more valuable than a year studying alone.

It's not that hard to suss out, for crying out loud. Do the work (and live the life) that fascinates you with talented (and worthwhile) people. Repeat until you're dead. Forget the rest.
posted by argybarg at 9:34 PM on March 16, 2014 [3 favorites]


Response by poster: You haven't given any reason why quitting your job and becoming a crazed programmer hermit is better than staying in work and studying on your own time.

I'm doing the same shit I was doing three years ago. I'm stagnating. I feel like I'm wasting my time writing one CRUD app (pun intended) after another, one ReST service after another, more web dashboards, more plaintext parsers, etc. I want to use this time to do something novel instead. Something I can put on my resume to tell future employers "I have done this. I have experience. You don't have to make me do what I've done at previous gigs. I'm not a grunt."

Work is taking up 9.5 hours every day (including the time for commuting, which I can't use for coding because I need both hands on the steering wheel), which leaves only 4 hours of free time for personal coding. I can get 9.5 extra hours a day by quitting my job and sinking my teeth into cool new stuff that's used by senior developers at startups everywhere.
posted by monad at 10:38 PM on March 16, 2014


If you're stagnating, it's time to find a new job. Or you could talk to your bosses/coworkers about it and see if there's a way you could stay while also getting to learn new tech.

Does your current company work on anything you'd like to learn? If not, are there positions being advertised that are a mix of your current skills and desired skills?

Jump to a new job if you must but keep working. Half the battle is learning business social skills anyway, and you can't cram for that.

Something I can put on my resume to tell future employers "I have done this. I have experience. You don't have to make me do what I've done at previous gigs. I'm not a grunt."

Dude. People hire you to do what you've proven you can do (at previous gigs!). Make work work for you.

Look we are in totally different fields. I used to be the person who took nonprofit content and got it onto the website. Now I'm the person who writes and develops content strategy. I made that move by finding my way into situations where I could get content development experience, and then put that on my resume. I had to change jobs to do that. I had to go somewhere they needed someone who could do web and content. If you need to jump, jump. If you can move laterally in this company or pick up a project that helps you out, open that negotiation with your current gig.
posted by heatherann at 4:48 AM on March 17, 2014 [1 favorite]


Well, I suspect that this AskMe has been helpful, if only by helping you crystallize your desires. You sound really committed to this path.

But still-- maybe what you need is to be a mid or entry level developer at a company who's doing work with the technologies you find interesting. Or writing apps which are interesting. I've done freelancing, working for a startup, working for a major company, and hiring for both, and I can tell you I would not be more impressed by someone who quit their job to CodeLikeHell than I would be with someone who had a solid grasp of the basics and a demonstrated ability and enthusiasm for solid work. A phrase I heard over and over again was "s/he seems smart; I'm sure s/he can learn X technology on the job." Thing I heard only rarely: "wow, look at his open source contributions! He rocks!" Also, there is just only so much you can do working on a project on your own equipment and on your own time. Yes, you might learn [sexy new technology], but are you going to be able to really dig deep into scalability, performance, complex architecture, working with crazy requirements, working with crazy people and triumphing, running an agile team, you name it?

At the startup-turned-major-company where I worked with a lot of really smart developers, there were three tracks: master coder, architect, and dev manager. You notice that I didn't mention the "master coder" career track in my message above about how to be a CTO or CEO of a startup. That's because the master coders ("shut me in a room and let me code all day") did not *ever* "advance their career" beyond finding the cool technology and coding for the beauty of it. Which is, of course, a misleading statement, because they were master coders because they were brilliantly happy where they were. But being up to date on The Latest Cool Technologies is about 10% of being a successful developer, and it gets progressively smaller as you go up the ladder. The brand-new-CTO I had drinks with a couple of weeks ago, I first worked with more than fifteen years ago when he was a mid-twenties code-like-hell developer. He was busy ranting about his idea for DIYing cheap-as-hell server racks to bring his new company up to snuff on the absolute basics of infrastructure. Then there's the SVP co-founder who got hired because he's a smart guy and had worked with the CEO for years doing not-at-all-sexy raging client management, release management, and rapid development for web apps. Three months of learning on the job, and he was writing cutting edge iphone apps; 9 more months, and he was building glass apps. Without quitting his job to learn new tech.

tldr; you may be working for the wrong company to advance your career, but you also have a really immature view of how software development works in the real world. But you'll probably still be ok: entry level developers with a strong grasp of new technologies are still relatively employable. Not as employable as mid level developers with a strong work history, but you're unlikely to starve.
posted by instamatic at 4:51 AM on March 17, 2014


The CEO mentioned above has less technical chops than the learn-on-the-job SVP. The SVP hired smart-as-hell developers who had real, though not necessarily cutting-edge, apps in the real world as developers. Then he found brilliant young open source, cutting edge developers, and hired them. As interns.
posted by instamatic at 4:58 AM on March 17, 2014


work is taking up 9.5 hours every day (including the time for commuting, which I can't use for coding because I need both hands on the steering wheel), which leaves only 4 hours of free time for personal coding.

Thank you for clarifying. This is actually a common problem among coders and a major career issue. There are a few ways around it: minimize your commute so you can spend more time coding at home and less in the car. Enroll in any night classes that teach the skills you want to learn. Convince your workplace to let you work on projects that teach the skills you want to learn. Talk your way into jobs where you will be using those skills and technologies even if you're not 100% up to speed on them. Yes, there will be less time for late night outings in a Wednesday night and fewer all-day Sunday brunches, but it doesn't mean you will be holed up with no social life to speak of.

Another sad truth is that if you are primarily concerned about making lots of money, there is more money to be made in investing in startups rather than founding a startup. Lots of people are in the startup game not because they want to start a company and retire with their riches, but because they want to be moderately successful founding a startup and then join a venture capital firm. And their success was not because they were the best coder on the planet. The wealthiest person I have met was a surgeon who made some very shrewd investments in medical technology companies. To my knowledge, he was not America's best surgeon or medical technologist. He was just a guy with a lot of money and very good strategic investment sense about his field.
posted by bright colored sock puppet at 6:33 AM on March 17, 2014


Response by poster: I've done freelancing, working for a startup, working for a major company, and hiring for both, and I can tell you I would not be more impressed by someone who quit their job to CodeLikeHell than I would be with someone who had a solid grasp of the basics and a demonstrated ability and enthusiasm for solid work. A phrase I heard over and over again was "s/he seems smart; I'm sure s/he can learn X technology on the job." Thing I heard only rarely: "wow, look at his open source contributions! He rocks!"

Enthusiasm and the ability to learn quickly are definitely very important to employers, but I think you're underplaying the importance of a GitHub portfolio in the startup scene. Most of the startups I've interviewed with made it very clear at the outset that I shouldn't bother applying if I don't have code I can show them. Perhaps this is because the sort of people who spend their free time writing open source code also go to hackathons and meetups, and since they're utterly obsessed with coding all the time, they tend to know their stuff inside out. This crowd also tends to skew very young and professionally inexperienced, which startups like a lot because they get serious technical chops for low wages.

I've also interviewed with mid/large sized companies and they've never asked to see my GitHub portfolio. Experience matters a lot more here.

Of course, it's possible that I've unwittingly sampled a freakishly narrow part of the entire domain and this GitHub-profile-fetish might just be a local anomaly.
posted by monad at 9:46 AM on March 17, 2014


That's a really good point. It's probably partly geographical, and partly demographic (skewing young vs older). I was super curious after posting this, because I'm not in the thick of recruiting for startups right now, and this strikes me as something that probably changes pretty rapidly. So I asked a couple of friends who've been actively recruiting for tech startups in the last few months. One is an SVP for a company with solid funding, competitive salaries and benefits, a big name PR firm, and lots of TechCrunch buzz, etc. His description of hiring is
- they were desperate for really good iOS and Android developers, so they basically looked at everyone who applied
- first, they looked at resumes for relevant employment experience
- then they strongly favored people with high performing apps already on the market (note: I think this was individual hackers with their own apps)
- finally, they did look at GitHub, "if they are industry experts, say, on the level of conference presenters"
Note: almost all of the senior people (VP and CxO) were former coworkers who networked their way into the position

The other is a CTO for a prefunded bootstrapped company with no salaries, part time sweat equity employees.
- #1 recruiting: people she met working in coffee shops
- hackathons
- GitHub "doesn't hurt"
- cofounder meetups
- LinkedIn, especially for mid to senior level people (she was recruited from LinkedIn)

So when I answered in my messages above, I was mostly thinking of the first type of startup, who generally network their executives before/while setting up their first round or two of funding. Of the tech execs I've known since before they were execs, I'd say they are roughly divided between
- hired on as dev or senior dev, started their own company as a spin-off of the company they previously worked for
- hired on as less-technical (e.g., UI, QA, etc), worked their way up to VP or SVP in the same company
- were college-aged cofounders of very small companies acquired by a larger company; 5-10 years later left and founded unrelated companies (with strong business and funding networks in place from people at the parent company)
- worked their way partly up the ladder of a company (say, chief architect or senior director), then were wooed away to a new company, generally based on the network they'd built at their first company

After watching somewhere between fifteen and thirty (?) friends or friends-of-spouse go from mid-level to exec, I'm left with the overwhelming lesson that biggest part of the puzzle is who you know, not what you know. About 80% of these execs came from within one very fertile startup company, which was practically its own incubator. In large part because the founders of that startup supported a lot of former employees with angel investing or networking assistance to help them get off the ground.

But on the other hand, I'm in a tech-startup-friendly region that is NOT the Bay Area, so it may be very different for you. For something as important as a massive career strategy change, you shouldn't go on an educated guess. Ask people in your network what they recommend. Preferably someone in a position to hire you in a year into the kind of job you'd like. "What can I do to become more marketable in the next couple of years? Does it make sense to quit my job at WidgetCorp and focus on GitHub projects for a year?" (And then please come back and update, because I am desperately curious.)
posted by instamatic at 5:12 PM on March 17, 2014


1. Those founders you admire do still have some social life. They still spend time with friends and family, and have fun.

2. Right now, social activities seem unbelievably addictive to you, because of novelty. Eventually they will become the same as other things you enjoy but aren't obsessed with, like watching a movie or eating good food. The first time you jump over a fence and social engineer into a party might be unbelievably exciting, but the 7th time is boring.

3. You sound like someone who got 99% of their information on what it takes to succeed through secondhand sources, like Hacker News or reading Paul Graham's essays or living vicariously through strangers at a hackathon. A large portion of what you said is misguided.

Honestly, I think that part of your brain wants you to become a shut-in again. It concocted this semi-believable reason: "You need to study hardcore for one year so you can be in a position to make gigabucks so that you can _then_ experience life!" But really it's just trying to get you to go back to being a shut-in. If you ignore this, it'll probably then devise a theory that the best way to have wild sex with women you love is to become a shut-in for a few years and watch every episode of The Bachelor repeatedly.

If you really want to propel a tech career, go find a job at the most world-changing company you can. Then you'll learn that figuring out which shade of color increases clickthrough happens at every company, including the ones run by your idols, Tesla and Facebook. You'll be able to figure out the right direction, instead of blindly coming up with a direction based on misinterpreted secondhand facts and then running as fast as possible in that blind direction.

You seem to revere Paul Graham. Remember he said that you can only build products for usage cases that you understand. If you shut yourself in for a year, the only products you'll be able to build are products for shut-ins. Even if you build the world's best Product for Shut-ins, that's not a large market.
posted by cheesecake at 7:02 PM on March 17, 2014 [6 favorites]


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