I don’t care about money anymore.

For the last almost 15 years of my life since I graduated from high school, I’ve felt overwhelmingly lost. I may as well have been wandering blindfolded through Siberia with my hands tied behind my back. Somehow or other I’ve managed to float from one job to the next, things I never really wanted to do, but it all just happened. I got really good at faking it enough to get hired in only the things I didn’t actually want to do.

I always return to my $325k+ networth, because that’s my one heaping achievement at this point in my life. I don’t own a house. I paid for my used car outright. I live in a relatively modest one bedroom shared with my boyfriend. I have no kids. I barely have a social life. I spend most of my time working or thinking about work or doing something related to work, despite not being nearly as productive as I should be. And I’ve given up on all of my dreams for fame or fortune. Right now, I just want to find my calling. I don’t need a six figure job. Ironically I find the more money I make the less I want to spend, the more I want to save – and I’ve figured out I can get away with about $3k a month in expenses, or less if I was desperate.

Part of me thinks I’m absolutely crazy. I should be fighting for my current life, my current job, with every ounce of my being. It may not be enough – I may just not be intellectually capable of doing a good job in this specific type of role – but I should at least be trying with all my might. I don’t feel like I have the right to be burnt out at this point – it isn’t burn out, it’s just the wrong fit. My whole life has been the wrong fit.

But I see a light at the end of the tunnel. I’m not completely on the wrong path. There are elements of my role, the industry I am in, which are more than fulfilling. I just know that the only thing that stands between me and a life I can be proud of is the GRE. Yes, there’s graduate school as well, but the GRE is the big giant monster standing in my way. When I say this out loud it sounds like I’m throwing a pity party but I’m really not that intelligent in the book smart sense of the term. While I need a billion hour of study on quant to score decently on that section, I feel like I have a chance to master quant if I put my mind to it. I’m terrified of verbal, surprisingly enough, because my comprehension skills are limited.

Clearly I’ll need to study a lot for the GRE. With an undergraduate GPA of 3.2 (barely, it’s a bit all over the place) I don’t know i fan self-respecting graduate program would seriously consider my application without some crazy stellar GRE score. I’m talking top 95%. Or, you know, I just don’t go to grad school, and I figure out something else. But the longer I think about it… you know… 10 years or so… the more it’s clear that I need to go back to school to get where I want to be. There are specific programs I want to apply to, and all of these are at top schools to where I wouldn’t have dreamed of applying for undergrad. And I still think it’s rather funny I’m considering applying to them for grad school. If I were to actually get in, I think that would be the first actual accomplishment of my life that I’d be proud of.

At the moment I’m trying to figure out how to arrange my studying. I’m not opposed to putting $1000+ down on a class, but I feel like it would make more sense to TRY to study on my own and take the test first – see how I do after seriously studying on my own for two months or so, and then go take a class or get a tutor to hone up on the parts I couldn’t learn on my own. The whole prep class thing reeks of scam — the GRE is supposed to be the type of test one can learn themselves. And would 8 weeks of classes really get me where I need to be? Tutors are crazy expensive though. I realize compared to a $100k graduate program spending $5k on getting in is really not that insane. I just don’t think a one-size-fits-all type of program would really work. So I’m going to see what I can do on my own first… probably. I’d like to double down on quant first. Answering verbal questions is frustrating because I can’t go back and “work” them and figure out what I did wrong – other than memorizing words. And I SUCK at memorization.

In any case, the next 4 months of my life = intense GRE study. I need to approach this like a game. The game is the GRE. And I want to win it.

Absolutely Terrified of Making the Wrong Decision

All my life, I’ve been a jill of all trades, master of none. I’m at the point in my career where I want to invest significantly in becoming an expert in one area – but I’m still perplexed as to what that one area is. I always come back to the fact that my current savings of $325k, growing at 5% annually for the next 30 years, gets me to a $1.4M nestegg in retirement. That assumes, of course, that I’m not touching any of that money until retirement – but that’s quite a reasonable expectation if I can manage to make enough yearly to at least cover my expenses.

So – I could move to somewhere super cheap, take on a few side jobs to cover housing, health insurance, et al – and whatever I have left over use for travel or taking art classes. Kids will be expensive, that’s for sure, but my boyfriend would also be working – we would never be rich, but we should have enough to have a decent retirement. Heck, if it 325k compounds at 10% year over year then in 30 years when I’m 62 that would be worth over $5M.

Why bother spending $100k now on myself when I don’t trust the investment will pay off. I just don’t have much faith in myself and for good reason. Even now as I browse the help wanted ads for a variety of different positions I return to how today I’m qualified only for roles people are desperate to fill, if that. I started to put together my resume and I couldn’t think of one valid accomplishment in my current role to put on there. Not one. Clearly I deserve to be laid off. In the meantime, I’d like to actually add value that I can talk about later. As a trusted mentor once told me – no job is forever, focus on doing the things that will help the company but that will also be the achievements you’ll put on your resume. I ought to get to that asap, if there is still time left.

There are so many different things one can do in the world – but it’s hard to imagine what would actually make me happy over the long term. If I was already a millionaire and money wasn’t an issue, what would I do? I’m not the type who actually wants to sit around all day, or who wants to spend years traveling the world. The funny thing is – I like to work. I like to work a lot. I like to feel like I’m actually contributing to something greater than myself. So I don’t want to just sit on my ass and waste my life away. But then, money aside, what is it that I would actually be able to do? I’m really awful at so many things. I’m pretty bad at responsibility overall – which is pathetic, but true. I’m forgetful, unorganized, and while I tend to do a lot of things at once I’m a terrible multi-tasked. I’m pretty much the antithesis of who anyone would want to hire today. I should be doing whatever it takes to keep my job because god knows it is going to be awful hard to get another one.

But then I come back to my frustration with myself, and acknowledging that maybe I’m not ready for this position. Every role I’ve taken on in my career I’ve started from scratch, pretty much. New field, new industry, everything new. I liked that – it was exciting and kept me on my toes. But it’s also been really hard. And I’m just not good at certain parts of my job that I don’t think are trainable, it’s just either you are good at it or you’re not. Needless to say this is not a long-term career. I give myself 60 to 180 days at this point. Maybe less. Not by choice. And given my performance, I wouldn’t blame them.

It’s just I don’t see myself ever succeeding at anything. I’d be wise to quit while I’m ahead, hibernate my life away, invest my cash and wait until it compounds enough to actually see the light of day again. That’s a bit dramatic, but it is actually an option. There are things one can do for little money to entertain themselves. One laptop or pen and paper if you really want to rough it and you have all you need to write the next great american novel. A few colored pencils and a sketchbook and you can draw your days away. Reading is pretty cheap, so is going to the occasional movie or watching television. Exercise is free. Food can be affordable if you cook yourself. Really, work doesn’t have to be the central part of one’s life once you have a decent savings. I’d never want to quit work entirely – but I don’t want to have to rely on it. I want time to live.

On the other hand, I am completely the type who lives to work. I can’t not think about my job – ever. I’m always thinking about what needs to get done, the overall industry, and creative ways to tackle problems. I don’t actually go on to execute these well, but I know I am happier when I have a job I can throw myself into 110%. So if money wasn’t an object I’d probably still work. I’d still want to get really good at something so I can finally feel successful and productive. But what is that one thing? I’ve always been interested in too many things. Too many interests left me with no direction. I don’t know how I got where I am but it all feels like a giant sham. And it is. I’m tired of the charade. I just can’t fake it, and everyone sees it. When you’re in a field where results are easy to quantify, there’s no place to hide, for better or worse.

When I invest in the stock market I always invest in what I think is stable or is solving a key market problem that will only get worse over the coming years. In other words, I’m smart about my investment choices. If I were a business and I knew everything I know about myself, I wouldn’t make the investment. That’s why I’m so scared. I don’t think it’s worth it. I don’t actually believe in myself one bit – not to do anything I actually want to do. Be an accessories designer. A photographer. A film editor. An interior designer. I don’t know. Be something that has nothing at all to do with enterprise software. To create something tangible. To spend my life on projects that have a clear beginning, middle and end to them. And to reach some level of creating something that is well received by others. That others want to see or buy. To actually create that said thing. If money were no object, I’d be a maker, not a marketer. But the grass is greener and I had my time in life when I was studying the “making” side of things. That didn’t go over so well either.

In any case, I do need to figure something out. It won’t be the end of the world to go on unemployment and have six months to get my head on straight, but that isn’t forever. I just hate feeling like I’m back at square one, yet again.

Am I a Writer?

I write an awful lot, but unfortunately it’s all redundant non-fiction bullshit about life and admittedly rather benign. If you were to read any of my attempted academic content you would might have a good guffaw over my inability to successfully support a thesis. My college teachers, much like my high school teachers and middle school teachers before them, were vehemently confused over the nonsense I turned in for reports, which would often be rewarded a C at best, and the long musings which poured out of me in opinion essays, which most often received the highest mark, always punctuated with a +.

There is a musicality to language which I adore. I wouldn’t say I’m a great writer – my vocabulary is limited and often used incorrectly – and any content of mine that has been published in print has been thoroughly edited. But of all the things in the world one can do – if I’m inspired, writing comes the most naturally. I wish I could turn my little writing hobby into an actual career. Well, I have turned my little writing hobby into a career – and unfortunately that career required other talents which I do not have – playing well with others, maneuvering my way through corporate politics, maintaining relentless, unbridled enthusiasm for some product which, based on my experience, I will likely long outlive.

I’m angry at myself for not being able to write anything worthwhile. Even a memoir would be impossible – my life is yawn-inducing with the exception of a few non-memoir-length moments of my youth that shall be reserved for a never-to-be-printed appendix. I haven’t done anything special enough to merit a memoir – and the only illness I suffered through as a child put me in the hospital for a week and then I was fine. My own neurosis aren’t tragic enough to be considered art, they’re just cumbersome.

It seems, if I’m going to be a writer – a novelist, a screenwriter, a short story creator, a playwright - well, I need an imagination. You know those people – who you grew up with, who were just constantly inventing stories and ideas? Yea, I wasn’t one of those people. There was a story about a magical peacock I wrote in third grade, I think that might have been my last dose of sheer inspiration to date.

The challenge is I’m not much of a reader either. I’ve tried to get into fiction and I always return to reading the news. I watch a ridiculous amount of television so perhaps that is my calling, but attempting to generate believable dialogue when I barely interact with humans proved futile in my few attempts.

Maybe I just need to do a shit load of drugs.

Who am I kidding? Getting high leaves me sitting indian style on the floor noshing on a bag of avocados. That’s not quite the right writing nudge.

It’s just all those people out there who have managed to write – who love to write – who just fucking write, I am so envious of them. For their wild imaginations. For being able to close their eyes and envision whole new worlds, new people that never existed in real life – you know, the way they speak, move, and their own fears, hopes and dreams.

I have ideas, of course, but they don’t go anywhere. They’re not plots, they’re themes, concepts, visions of future worlds in which my story might live. I haven’t yet imagined one believable character, and I’m too terrified about pissing of people anyone I know to borrow them for inspiration.

So maybe I’m not a writer. Or, maybe I could be one. Some novelists do start out in their 30s. But how to even get started? I should have written that damn 50 Shades of Grey book. I’ve dabbled in erotica, but my erotica has been much less mainstream, even compared to that. And 90% of it was written before I so much had been to second base. So that’s out of the running.

I would love to write strong female characters for film – because they’re sorely needed. But I’m not sure where to begin. I have this one idea for a romcom – it’s actually a cute idea, one that could be quite mainstream, or indie if the jokes are a bit wittier – I’d like to start with that. Still, I just waste away my little free time writing about how I can’t write here versus actually being productive and churning out a few pages a night.

A few days ago I had an interview for a certificate program I’m considering applying to, and they asked me what is one accomplishment I am most proud of over the last 10 years. I had to stop and think because I’m really not proud of ANYTHING I’ve done over the last 10 years. I managed to talk about a few work projects and then the first show I directed, which was now seven years ago. The only thing I will ever feel proud of is my creative work – my completed creative work. Nothing else – I don’t care about my title or how much money I make or save – feels remotely rewarding.

It might be the outcome of narcissistic parenting, but maybe it’s my truth, and I ought to listen to it.

My hope was that my stock from my prior company would be worth enough to free me up to lead a creative life, but instead that turned into a loss. I’ve saved aggressively but it’s not enough. If I were to hit $1M in my 30s I’d be perfectly satisfied working part-time to break even on a monthly basis and allow my savings to compound while I pursue whatever art I find myself actually getting good at. But that $1M is so far off. Even if I were to keep my current job for the years to come, or one like it that pays as well, assuming an average of $50k savings per year, that will take me another 13 or so years.

That’s not horrible – at 44 I could retire and maybe by then I’d actually have something to write about. But I know I can’t mentally maintain work like this for long. I’m falling apart. I see the schizophrenics wandering all day on the streets of San Francisco, babbling to themselves, screaming at the world, and I think to myself — how far away am I from that, really? I often want to just grab a shredded blanket, wrap myself in it, and wander the streets screaming, maybe even sobbing – I think I’d fit in more with them than the people I work with who are far more civil and far less insane.

 

 

Leadership lessons they don’t teach in college…

Being a great leader, no matter if you’re a politician running for office or a manager moving up the corporate ladder, requires one skill that no one will teach you in school. It is a particular art form which there is no course for, even in an MBA curriculum. That skill, the most important of all, is the art of lying.

It’s a matter of semantics, you can say, as the ability to hide the truth or fib or changing the subject is one of the most vital character traits of a leader. It is why many great leaders are sociopaths – lacking empathy helps in business, especially if you have the rare ability to convince others you care. Needless to say, I don’t do this well. As an INFP and enneagram 4 and Johnny Appleseed’s third cousin once removed, I’m partial to full-on truth. Luckily so far I haven’t been faced with anything challenging to keep under wraps. But I’ve seen leaders who I know, and even respect, flawlessly execute weeks without hinting at what is discussed behind closed doors.

Maybe college should offer a course on lying – lessons in leadership: the lost, but secretly never actually lost art of perfidy.

Except colleges already know that the best leaders already intimately know how smile and handshake their way through any looming storm. The less you feel, the better you can lead. Pick your poison regarding your favorite leadership style and you’ll find charisma synonymous with the ability to smooth any cracked surface. It’s a talent which you’re either born with or beaten into you in some way. Most leaders are men because most men are taught to not have emotions from day one. Women are typically expected to be openly emotional and thus, for some, when we enter the workforce the culture of deceit can shock our systems and leave us riding on empty.

Is it possible to be a leader and never tell a lie?

Only if you refuse to accept its definition.

Definition of LIE

intransitive verb
1
:  to make an untrue statement with intent to deceive 
2
:  to create a false or misleading impression

Leaders are liars and liars are leaders. It is quite simple. But not all of us, men or women, are cut out to live a life of caring more about cashflow than people. And in capitalism we create this vicious cycle, this pyramid scheme from top down, with everyone clawing to get up and few ever making it to the tippy-top point where all you can do is lie – to others and yourself – in order to handle any remnants of feelings you once had for the sanctity of human life. It is up to us to perform the roles in the machine that cannot yet be performed by robots, but to think much like a robot, to make all decisions on communication and action based on a clearly calculated call on risk.

Maybe I’m just ravenously dissatisfied with our world today, a sentiment fueled by my marathon Mad Men watching and a general acknowledgement that no matter what firm you’re in, no matter what era, it is a dog eat dog world, and in this world I’m more or less a pescatarian.

More Thoughts on Ambition, Depression, and An Otherwise Ambivalent Life

When I was a child, I was remarkably judgmental. My parents raised me as such. For them, having grown up in households with parents who were not college educated, who were bluecollar workers or clergy, who lived only slightly above the lifestyle afforded by poverty, I understood their hatred of all things they worked so hard to escape. Although my town was quite diverse, as a child I always felt better than many of my peers. My parents created and reinforced this notion. I never felt better in the sense of actually liking myself or better in that I was able to make and maintain friendships, but I was told time and again that there is a large faction of others in the town, and while I was allowed to be friends with those people they were not like us.

To be clear, this was not a racial issue, as my parents looked down upon people of all ethnicities – though, of course others “like us” – Jewish families, typically got a pass. It was horrible, and yet at the time it made sense –  was our shared values of education and working hard to achieve goals, with a general disrespect for cultures that, by stereotype and outcome, didn’t have the same type of lifestyle. It wasn’t their fault, or at least it certainly wasn’t the fault of the children, and yet there was still this sense of sameness and otherness that pervaded our view of our town. It is how I, despite being miserably depressed and empty as a child, was able to find some solace in going shopping with my mother and purchasing hundreds of dollars in Nordstrom Brass Plum shirts and pants and skirts and dresses. It is how I managed to push myself harder to get where I am today, because deep down I was terrified of becoming one of “them.” I could never truly envision myself a starving artist or struggling parent. It wasn’t in the vernacular of my limited foresight. It was the only truth I knew, which now I know to be no more truth than any other dream or goal.

We were never rich, but my mother dreamed of great wealth and my father wasted away his life eating himself fat and working long hours to provide for our family so we could maintain our illusion of happiness in the shape of comparative success. My mother would frequently go on and on about how she wished she had married someone richer, not once considering returning to work herself. That was somewhat normal of a train of thought at the time. My father, meanwhile, earned a rather high salary for his middle management consulting role, and we lived a very comfortable life. My father liked to purchase “nice” things, although I didn’t always agree with his taste. My mother, for the most part, liked to purchase whatever QVC or the Clinique woman happened to be selling her. And I grew up with this painful sense of privilege compiled by the guilt of knowing none of it was deserved. Through each year, that guilt grew stronger. When my mother made an off-putting comment about a friend at school whose parents rented instead of owned, I cringed inside, knowing that criticism was completely unjust, especially against a child who had no choice to whom she was brought into this world.

I do believe that so much of your ambition is tied to how your parents wired you for reward. My reward came from meeting and surpassing expectations of this illusion of our stability and relative superiority. If I wasn’t to be a math genius, I was to be a great painter. I had to be something better than the others. I had to be special to matter to my parents at all. They certainly didn’t appreciate when that special came with a fragmented mind and a hyperactive, mess-creating child who longed so desperately for the attention and approval of others, unless, of course, this need for approval resulted in something they could brag about.

As an adult now, having been through enough sociology classes and life to know that everything that I thought was real as a child is a complete clusterfuck of a post-war generation and immigrant family mentality tossed down through the ages, I want out of this. Out of trying so hard to prove something to someone when no one is even listening anymore. Sure, my mother still shares every thing I post on Facebook as if I had won the freaking Olympics, with pride acceptable for a 12 year old daughter, perhaps, but not a 31 year old. And in my little puddle of psyche so empty and ambivalent I kick myself together trying to find the shape of a person who has some motivation, some drive, some reason to exist beyond merely existing or earning a paycheck. And I can’t find it. I can’t find anything that tastes real anymore, except the incredible and overwhelming love which my alter-ego of a boyfriend – warm, quiet, sensitive, needing no attention or approval – bequeaths to me in ample supply.

But one cannot live on love alone. And I often think if I didn’t have this love right now, I would be so fragile, I’d have nothing to keep me going. Thank god for his kind heart, his deep compassion for all the people of the world and all that is unjust and cruel. I am happy to have a safe place to go, wrapped in his arms, far from the judgmental warfare of my suburban family home.

I don’t want to just set out to help others when I’m not ready for it yet. One can easily do more harm than good. If I fuck up in business it’s terrible for sure but, at least in the communications side of things, a fuck up here or there never killed anyone. But to dedicate my life to helping others, I don’t want to do it for selfish reasons, because that won’t go over well. I need to find something deep within me, something so true, which I can become passionately obsessed with, something which can become my intention for life. It could be motherhood. It could be psychology. It could be design. It could be writing should I ever muster up a plot, realistic dialogue and the tenacity to draft more than eight pages. For someone who writes so much as I do it should be easy, but my stunted empathy has made it quite impossible to dream up others. I’m still trapped deep within myself, this little, weak, shell of a human being who attempts to claw out of her flesh to find her guiding light.