Too Late to Start Over?

Get me out of here. I’ll miss the microclimates, the waterfronts, the overly-gentrified streets with a variety of boba, fro-yo and ice cream shops, the security of pretending like I fit in here, that I’m one of them, that everyday I get on the train and wear my company with pride like I’m part of a cult where a job is so much more than just a job, the fantasy that somehow if I just work hard enough I can somehow afford a $1.4M starter home with a tiny backyard and raise a family here, and pay for pre-school for 1-3 kids and manage to see them enough to feel like a damn good mom.

It is so torturous to be so afraid of stepping back a thousand miles to get ahead a few feet, should you manage to make it back to where you started years later. Adulthood is not the time to romanticize potential – college was the perfect time for that and I genuinely fucked it up but not figuring out fast enough what it was I wanted to be when I grew up. I didn’t understand how it felt being in the same office day in and day out, or that I’d be able to do anything worthwhile in the world where someone would be willing to pay me for my contributions. I graduated, but I wasn’t ready to — I am not sure anyone is, or if that is what college is for, but 12 years ago when I received my diploma it didn’t feel like an accomplishment, only a big lie in which said I was somehow certified for life, yet I wasn’t at all ready for my future. I was suffering from a terrible depression and I was falling apart.

If I could do it all over again, I’d probably still fail to get the value out of school — there isn’t enough time, enough credits, to become a master at anything. Extracurriculars enable more time to focus on specific skill sets, as do internships, but I feel like I did a lot of those and yet still ended up with few skills and a whole lot of WTF am I doing with my life? And, it’s such a fucking privilege to even have the opportunity to make something of myself, and I blew it big time. Well, maybe I didn’t, I found a few jobs, I saved some money — but this isn’t at all sustainable.

There are so many things I hate about my current career, I want to just walk away from it entirely. I hate feeling so out of control over the success of projects. I hate having to use data to back up every single decision when I prefer to make choices largely based on intuition, because generally I understand people’s motivations and don’t mind the idea of testing things but data is a crunch in Silicon Valley when people are too scared to think for themselves since you can’t truly fail if the data told you one thing and you listened to it. I hate how everything seems so damn important and life-or-death where you’re being suffocated by stress when in the long run all the small things that felt so enormously important don’t matter – when even your “big” mistakes don’t really make a giant different in whether the company succeeds or fails because you aren’t at all involved in the product itself therefore even if you make it sound great in the long run no matter what you do, the success of the company is not at all in your hands, the product has to be great, and remain great, or at least better than other options on the market, and whether it is or isn’t your job is to make people think it is, to make sure everyone knows it’s the best. Your job is to tell the truth or to lie, it doesn’t matter, you just have to make sure that everyone wants to buy your product. You have to take data and massage it so it tells the story you want to tell, you have to constantly be manipulating everyone and everything with your fake smiles and astounding interpersonal communication skills, and pseudo-empathy and heaps of politics that get in the way of just getting your job done. And you probably don’t actually know what the hell you’re doing because no one teaches you this shit and everyone is making it up but some people naturally are good at sounding like they know what they’re doing by testing things and follow through and some results which maybe make them good at their jobs or as good as anyone can be at a job that has no actual success metric that one can achieve that is meaningful, as you aren’t building on top of work done previously most of the time but instead constantly trying to scale a mountain but starting back at the beginning every quarter and looking up at a peak that is getting increasingly taller and further away. And you have to organize your projects that you think based on data will have the appropriate impact needed and delegate this work to other people and motivate them to work their asses off to make a dent in the sea of impossible victory and you somehow have the ability to get your employees to want to work 24/7 on being part of this “team” and making an impact and doing the best work of their lives that in the end, again, is virtually meaningless, albeit potentially helpful in the short-term and that’s the best one can ask of themselves in a role where success is defined by how good of a bullshitter you are tied to some serious project management and political skills namely the ability to lie with the most brilliant poker face because that’s what great managers do best.

Can I go back to that? I know long-term success in this role is impossible, but short-term stints of holding my breath and trying to play that role are becoming easier each time – but they will never be easy. I can’t do work when I don’t care, even when they pay me a lot, and I wish I could because life would be so much easier that way — I’d be a millionaire in 5-10 years, which isn’t rich but it sure is a nice number en route to serious financial security. But. I. Just. Can’t. Do. This. Anymore. It’s not good to ask oneself if it would be better to jump in front of a train than to go to work one more day as a clear failure… if the embarrassment of failure is worse than the pain of disappearing.

Part of me wants to just say fuck it – to say fuck it because I don’t care if I spend all (some) of my money on – who knows – getting a second bachelor’s degree in something more interesting and maybe more practical… or, taking expensive classes to get certified in something or going back to grad school and getting a master’s degree in something that I can do everyday without wanting to jump off a cliff… even if it doesn’t pay that well… even if it never will pay that well.

But pay that well… I don’t know what that even means. IVF costs $50k+ and I can only “afford” that now because I have (had) a good job. If I don’t have kids by choice or by fate of my messed up hormones, then maybe it all doesn’t matter — I can live on next-to-nothing and just make art, make documentaries, tell stories, feel like my passion doesn’t have to be my professional Achilles’ heel… I just want to find a job where being passionate is not only accepted but desirable. When I get hired people think my passion is an attribute but they learn soon enough that bold and honest passion causes more harm than help in a role where sociopathy is the true required skill for success. I need a job where I can be myself… if that exists… one where my dry sense of humor and wild desire to live ethically and empathetically based on my own moral code will enable me, and ideally those around me, to thrive. I’m exhausted trying to be someone I’m not and clearly failing. I want to start over.

I’m talking to a career counselor now but not sure that will help. I went to a psychiatrist and they gave me a prescription for Zoloft which I haven’t started taking yet (and I may not because there’s a risk for minor birth defects and should I get pregnant I’d never forgive myself if I harmed my child, kind of defeating the purpose of an anti-depressant…) and I’m trying to see a psychologist but all of that is just more bullshit when I know the only thing that will help is taking some sort of action to just change everything about my life, or at least the parts which need fixing (mostly my career.) My husband is awesome and he’s my rock and I love him more than anything but having a husband certainly complicates things as these choices are not my own, they impact him as well, especially if my next steps require me to move to another part of the state or to another state. But he’s pursuing his dreams now and I think I at least deserve the opportunity to pursue mine, if only I knew what those dreams are… if only I knew what way to point my glistening arrow of optimism in an unproven satisfying future before I blindly and clumsily shoot in the wrong direction.

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8 thoughts on “Too Late to Start Over?”

  1. It is NOT TOO LATE!
    Think about it: you are in your 30s. “Typical” retirement age is 60-ish. That’s 30 more years (as in MORE YEARS, same amount all over again). What were you doing 30 years ago? Couldn’t walk, couldn’t talk, couldn’t wipe your own behind. You went through all that, plus preschool, elementary school, junior high, high school, college, grad school (?) and then worked some! 30 years…you can literally start COMPLETELY over from birth to now…and lucky you: you already have those walkin’ talkin’ wipin’ activities down pat (hopefully!) – head start baby!

    But we moved from the Bay area to the south about 5 years ago. (this is me dragging my husband and dog around) Bought a cheap-a$$ house and lived there for 3.5 years. it totally sucked – the people were awful, it was hot and humid, and I couldn’t find a real job (ended up teaching/tutoring – pay sucked but it was cheap to live there, so it wasn’t so bad). We moved back west-ish (to CO) and we both make more than we did in the bay area, we have a rental property that brings in some money each month (that house we bought in the south), and our net worth is heading up (at a nice clip too – woohoo!). But it’s amazing what a few years of exploring will do – to your psyche and your wallet. Now’s the time to do it, before you have to drag kids all around with you too.

    But 30 years – you can do it all over again and still be ahead of the game.

  2. My observation is that it is very difficult to really build a career as such in Silicon Valley. In most places, one job builds on the previous one so hopefully you advance at least a bit in your career as you move from one job to another. However, in the Valley two factors change the dynamic a bit–the high cost of living coupled with the possibility (not achieved by most but definitely achieved by a few) of becoming very very rich. So everyone is focused on becoming very very rich because that is the only way to have a comfortable life given the very high cost of living. People move from job to job not with the hope of advancing their career but with the hope that the next job will be the one to make them rich. Getting fairly rich seems to also be the primary and best way to advance in career in the Valley. If you get rich, certain career options–such as angel investing or serving on the boards of hot startups–open up that just don’t seem to be available until you have your first successful exit. Succeeding financially–rather than building a resume–seems to be the primary way to advance in the Valley.

  3. I hear ya, I feel ya. I totally relate. Stuck in a job with no movement, but fearful of unknown to leave. The greatest irony is my net worth is in the 7 figures, I don’t even depend on my job for a living (just keeping it for the medical insurance, and sounds better to have a long term stable job whenever I cross the border instead of declaring “unemployed” when asked by boarder officers)

    yet I can’t bring myself to be where I truly want to be because it would cost me half my net worth. I am already financial free, but I’d rather be somewhere else and instead am where I am now. Have you heard of a depressed millionaire? I’d be one of them.

    1. Wow – where do you really want to be (that would cost half your net worth?) I understand the wanting to have stable job for travel and such.

      1. I’m Canadian but my boyfriend is a permanent resident in the states as engineer in silicon valley but he isn’t a citizen. It takes 5 years to become a citizen and sponsor me or sponsor me now but would be a lottery system for immigration.
        Unfortunately he’s already mid30s and spent a long time in school getting a PhD so now he wants to have kids sooner. We are perfect together but immigration keeps us from living together. See, millionaires have problems too

      2. Have u considered going back to freelancing for less stress and more flexibility before diving back into full time employment? Might be a good temporary situation to have a bit of accountability while more time for yourself

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