Fantasy Millionaire: How Far From Reality is It?

One of the “benefits” that comes with working for a startup is stock options. I put benefits in quotation marks because stock options end up being worth nothing, or in the case of NSOs that you exercise early, end up costing you money. But along with the risk comes that little glimmer of hope that as the months go by, you’re quietly collecting what, in the future will be worth hundreds of thousands, if not millions of dollars.

At the same time, I’m still living in my $600 a month shared apartment, feeling depressed looking at basic homes in the area that cost $1M, and feeling like I’ll never come near to affording a home and stable life until my 50s or 60s. I’ve managed to save $170k thanks to the stock market returning and a weighted investment in Apple,  but that still is a long way away from the type of money you need to live a comfortable life in Silicon Valley. Meanwhile my boyfriend has saved absolutely nothing and will likely be enrolling in graduate school and taking on debt before we get married in a couple of years. Saving enough money to lead my dream life is all on me.

The possibilities of what stock options could be worth are exciting, but the reality of life is a bit of a mindfuck. It feels like all my chips are on red and the roulette is spinning for a half decade before I see where the ball lands. Luckily there aren’t too many great sacrifices because my life is pretty simple now. But in a few years when I want to have a family, that changes. I’m absolutely terrified of the future, and spend everyday wondering what if, or what if not.

At least there’s a tiny chance that my reality could be my dream reality — one where I reach financial independence before I have a family, where I can go back to school for art or film, and not worry about the financial implications of creative failure. I have so many dreams for this life, and with a little bit of luck, patience, tenacity, and hard work, maybe dreams can come true.

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The Sun Fades on Another Weekend

My first free weekend in a long time is coming to an end. I need more of it, but I won’t get more of it until next weekend. Granted, it’s only 4:30, there’s still plenty of time for productivity in the day. And productivity is what I need to accomplish the long list of items I need to catch up with before the week starts again.

I’ve been thinking a lot lately about my mental health (not to mention my physical health) and how important it is to focus on improving it.  There just isn’t enough time to seek help, as much as I need it. The question I have lingering on my mind is whether traditional help could ever really help. All the psychological drugs in the world can’t help me get me to where I should be going if I’m on the wrong path. But what is the wrong path?

The truth is that I have such deep-rooted ethical values and beliefs that it is difficult for me to be a marketer. On one hand, I think I’m really good at marketing. Marketers need to be a little crazy in order to do good work. They must be a little narcissistic (everyone should be thinking about their company in a positive light and if they’re not then they need to make that happen), they must be a bit borderline (fear of customer abandonment), and perhaps even a bit sociopathic (natural charmers, but even if you believe in the product and company at times your charm is going to be fake.) You are hyper sensitive and aware of reactions. You have anxiety about anything that might cause a poor representation for your brand, and also about your competitors. You must have black-or-white thinking, your competitors are bad, you are good. Yes, no wonder I am a good marketer.

I do believe in my company, 100%. I just think deep down I like to help people vs sell to them. That’s it. I’m not a selfless person either, but I’m happiest when I feel like I am actually helping someone. It’s not like I’m the type of person that wants to change the world and save the whales. I’m not ready to join the Peace Corps and leave my dream of wealth behind. I’m just not so sure I’m cut out to be a marketer. Fortunately I know that my company by far has the best product on the market, so I can easily say that and mean it. Still, my passion is and will always be creating quality and innovative user experiences. I’m so far removed from the product as a marketer that I just become this megaphone of everyone else’s creativity and ideas. Perhaps a pretty good megaphone (I’ve realized lately that it is actually pretty hard to do what I do, especially writing-wise, and I’m good at it) but I don’t want to look back on my life, one which was supposed to be filled with art and creativity and creation, and say I was one damn good megaphone.

Two weeks ago I took two Adderall to help me stay awake (I know, not the best idea when I hadn’t taken them in a while) and suddenly everything was so clear. It felt real, all the direction in life, to just do the best job possible now, really contribute significantly to making my company worth as much as possible (which I can do in my role, one great part about it, I can at least help a team that know what they’re doing) and in three to four more years, apply to art school, and — even if I’m not that good — spend 2-4 years just painting and drawing and getting better at it. It wasn’t even something I was considering at the time, I was just sure of it, that it was the perfect plan, and in that time I had decided I needed to push back having kids until I was 35 so I could dedicate a part of my life, before I got too old, to becoming a better artist.

Then the meds wore off an reality set in. It didn’t really make sense at all. I mean, maybe, if I can save enough money and I really think I could make a career as some sort of artist or art educator, but I’m not really that good at it. And I have such a good career right now. I mean, somehow or other I managed to line myself up for a really solid professional life as long as I can keep improving, fix my issues with time management and leadership, and really be a rockstar marketer. I mean, nothing is easy, but compared to just seven years ago when I was at my rock bottom, completely depressed post graduation, and hoping for a full time job doing just about anything, I’ve somehow landed on my feet. It really wasn’t that long ago when I was sending out thousands of resumes per month, applying for just any job, hoping someone would bite, and finding it extremely difficult for anyone in Silicon Valley to give someone without an Ivy League degree and heaps of internship experience a chance.

God knows I don’t want to mess up now. It’s very possible that I’m just so mentally unstable (ie bipolar and/or borderline) that I’ll never truly be content in my life as much as I want to be. There is a part of me that loves exactly where I am right now, and wouldn’t change it for the world. I was just telling my boyfriend that of all the jobs I’ve had thus far, this is definitely my favorite. I finally have some autonomy and responsibility. Still, what does this actually lead to professionally 10 years down the line? Do I want to be VP of Marketing when I’m 38? Or would I rather be a product manager, or psychologist, or artist, or…?

The fact that these jobs require 24/7 commitments and contributions is fine in my 20s, but could I really do this in my 30s as I hopefully start a family? And am I even cut out for any leadership roles? I’ve already written on here that I’m terrible at leading and managing. I could get better, but some people just aren’t natural leaders. Those people who excel in business, especially in the softer side, are people people. And I am not good with people. I’m good at understanding people, I’m good at observing people, I’m good at listening to people, but I’m not so good at all the other social skills that are so valuable in life, especially in business. The only way one can get away with that and still be a leader is if they are a brilliant engineer, which I am not.

Anyway, I probably shouldn’t be writing this all publicly because one of these days someone who knows me is going to figure out who I am and take all of this the wrong way.  I hope I’ve made it clear that I really, really like my job and even more so I like my company and the people I work with, there is just a fundamental concern I have regarding if I’m in a career where I’ll never actually be good enough to get ahead due to my poor social and leadership skills.

That said, maybe I do this for 3-5 more years, and focus on really doing the best I possibly can, just deal with all of the painful criticism when I am not perfect, hang in, hold tight, sit back, and try to get better at the things I’m not that good at, or focus on improving what I’m already good at, and when that time is up, I can make a decision about where I go next. Maybe that is really dropping everything and going to art school. Maybe that’s an MBA. Maybe that’s going to school for user experience. Maybe that’s going back into journalism (which I miss and think I’d be much better at now than I was when I didn’t understand the business world at all.) Maybe that’s just leaving work and becoming a full-time mom. I don’t know, but what I do know is that I need to wake up every morning and commit to where I am at now. It’s a great place to be. And I really do have the ability, everyday, to make a difference. Ultimately that’s all I really need to be happy, as long as I’m succeeding more often than failing.

 

 

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The Never-Ending Job of Managing Stress

Stress can be a good thing. No stress in your life and you’re stuck on a plateau where motivation is neither welcomed nor refused. Too much stress, however, and you end up frazzled, producing sub-standard work, and watching your life disappear before your eyes. I’ve realized that the trick to happiness is finding the perfect balance between the two extremes. It’s not easy.

Lately, I’ve been working over 12 hours per day, and still the amount accomplished is so much less than I need to get done. Given there is no real set beginning or end to the day, it’s admittedly easy to get caught up in a less important task or other distraction, as I know I’ll be working well into the evening and night regardless of how productive I am during the day. The more productive I am, the more I get done, the more I need to get done. It’s the nature of my job that there’s no “finishing” and there’s never “enough.”

A part of me loves that kind of stress, and thrives on it. Some of my best work is created when I’m exhausted, when I’m so tired I can’t even find the energy to worry, and I sit down and just write. But lately I’m even more exhausted than that. I don’t think I’ve been this constantly stressed out before, feeling like I am having one ongoing panic attack.

I’m trying hard to prioritize and focus on one project at a time so I can feel a sense of accomplishment at the end of the day, and thus tone down the stress level a bit, but there’s too much going on that is a priority to stop and focus on any one thing. I’ve been reading a bit lately how multi-tasking, despite what resume-writers might want you to believe, is actually a detriment to productivity.

I prefer to work hard for success and praise, but there must be something I can do to make all of this stress more manageable. Do you have any tips?

 

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The ever unwinding journey to selflessness.

The only time I’m every happy is when I forget myself and give something to others, so why is this so hard to do? My overarching ego gets in the way of satisfaction; I’m no better or worse than everyone else, and there is no reason I have to be.

I don’t want to give out of some subconscious desire to receive in return, whether through admiration, boomerang generosity, or karma. I want to let myself be happy making other people happy. After all, no matter how much I ramble about my selfishness, my freak outs, my quest for millions of dollars, I just want to make people smile a bit and feel not so alone in this world. Then again, is wanting that selfish too?

Today, I took a minor step in the right direction. I receive a quarterly bonus based on my performance and if my team succeeds it just isn’t fair for the entire bonus to go to me. I can’t fairly accept that entire bonus (if it is offered) without splitting that with my team. I’m not doing this to buy back the respect I lost, I know that it’s fair to use this bonus as a way to reward my team, not just myself. It’s still selfish of me not to split the bonus 50/50, but I have reason to believe my team members, who are supposedly my subordinates, make a higher salary than I do, and if the entire bonus is received the amount offered is still substantial enough that it will be noticeably absent from my bank account, and hopefully and more importantly noticeably present as a bonus where it was earned. Continue reading

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Effectively Managing Time, People, and Happiness

It’s 2am and the only thing I’ve effectively managed to do is stay up way past what should be my bedtime. Somehow official work hours disappear in the blink of an eye, somewhere between meetings, interruptions, and small tasks requested of you that end up taking longer than anyone else might expect, not to mention your daily distractions.

There must be a much more effective way to successfully manage all aspects of life; if there’s anything I fail at most it’s management. If someone gives me a project to do with some sort of general framework, I can get it done. The second I’m tasked with competing priorities (personally and professionally) things go to shit. And that is why I’m still awake at 2:16am.

I’m also thinking, and concerned, about a conversation I had with the one person I manage at work. While I’m bad at managing myself, I’m absolutely terrible at managing other people. To be honest, I haven’t had a lot of experience in this area so I have to learn somewhere, but some people learn management skills from their parents and others don’t. I’m in the don’t camp. I’m in the “get beaten and degraded until you do what they want” camp. Not to say good managers couldn’t have been put through that sort of upbringing, but I can’t imagine it helps the case.

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