Category Archives: Career

Girls Just Want to Have Fun

When I was filling out the “10 financial commandments for your 20s” post, one of the commandments said that you should be focusing on having fun in your 20s. That one bullet sent me into a bit of an identity crisis. I started to try to remember what I consider fun… and it was really difficult to find something. I’m struggling to find anything outside of my job that is fun in my life.

I’m turning 28 next month, and while the birthdays before this one haven’t felt significant, I am starting to feel, well, old. Now, I know some of you who read my blog are much older than I am, and I don’t mean that you’re extra old. I’m just saying that — as the world around me ages — I question not just what I’m living for, but also what I’m not living for. One thing I’ve realized lately is that I’ve died a few times so far in my life. For instance, the young me that I once was died a long time ago. She doesn’t exist any more. She might not be buried under ground, but she’s just as dead as a corpse. And although I never loved her, I still miss her and need to take the time to morn her passing. I also need to remember what made her happy, and try to bring some of that back into my life. Continue reading

10 Financial Commandments for Your 20s, Part 2

This is part 2 of a series inspired by Give Me Back My Five Bucks, based on a Kiplinger article of the 10 commandments for finances in your 20s… I’m grading myself on each one of the commandments. Read Part 1 here.

6. Establish credit. In order to qualify for the best interest rates on a credit card, auto loan or mortgage, you need to start building a solid credit history. In fact, a good history can also save you a bundle on your auto insurance or help you land an apartment or a job (see Why Your Credit Score Matters). Building a good credit history in your twenties will ensure it’s ready when you need to use it. If you didn’t have a credit card in college, one way of getting credit now is to apply for a secured card: You make a deposit — usually $300 to $500 — in a savings account as collateral, and you can get the money back after one year of using the card responsibly. You can also start building a credit history through, an alternative credit bureau that gathers data on regular payments for rent, cable and other recurring expenses. (See Rent Your Way to Good Credit to learn more.)

Score C. I’ve never made a big purchase on a credit card and paid it off slowly, so my credit score is not as great as it could be. That said, I’m totally opposed to how you need to carry a balance in order to build credit. I do have a credit card (ok I have a lot of credit cards) but I don’t have a lot of recurring expenses. Continue reading

10 Financial Commandments for Your 20s: Part 1

The other day, I was reading Give Me Back My Five Bucks, one of my favorite personal finance blogs on the web, and came across a series on 10 Financial Commandments for Your 20s, based off a Kiplinger article written a few years back. As Krystal, author of GMBMYB, detailed how she’s doing with the commandments in a two-part series, I thought I’d do the same. If you’re in your 20s, you should too!

1. Plan ahead. To get where you want to go in life, you need goals and a plan to reach them. Having neither is like driving a car without a steering wheel — with your eyes closed.  Start by asking yourself what you want in your future. Think about the short term (five years or less), medium term (five to ten years) and long term (20-plus years). Now you’re driving with your eyes open. Then take hold of the steering wheel to reach your goals.

Score: C. My idea of planning ahead is trying to not spend all of my income for the month. Some months I succeed, some months I don’t. My planning is less itemized as it is general, ie “hit $150k in networth this year.” That isn’t a bad goal for someone who is 27, but when I look at the big-picture purchases/expenses (house, new car, retirement, etc) nothing seems possible without some big exit at my current company. While I have faith my company is going to be huge and feel very fortunate for the opportunity to be a part of it, nothing is certain, and I’m doing terrible at having a real plan for my 30s and beyond.

2. Live within your means. Can’t afford something? Don’t buy it. Sounds simple, but too many people have a heck of a time following this one and get in over their heads in debt. Borrow sparingly, and only for those things that have lasting value, such as a home or an education. Continue reading

Why Steve Jobs’ Death Hit Home

Since Steve Jobs passed away on Wednesday, there has been an outpouring of articles, memorials, tweets, status updates, blog posts, etc, on the man’s life and his impact on the world. I wanted to wait until I had time to write a meaningful post on the entire situation instead of a gut reaction. Although I never met Jobs, I think the reason that his death hit us all so hard is that outside of celebrities, he’s the closest to a living god that we’ve had in our secularized society.

For someone who seems immoral, dying at 56 is a fast blow to the face of reality. I look at my father, also suffering with cancer, also in his last years of life, and see the world moving faster than I want it to. All of our days keep ending, the world keeps spinning, and we’re all just specks of energy that take our first breath and last breath in a pinprick moment compared to eternity.

No matter who much money or fame you accumulate throughout your life, eventually it will end. Today, tomorrow, a year from now, 50 years from now — as Jobs’ put it so eloquently in his speech to the Stanford graduating class of 2005, “Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.”

Steve — how could you forget his face and spirit? Despite being one of the meanest managers, he knew what he had to do to get HIS job done, and done well. A lot of us aspire to be like him in business, to be relentless, to not settle for ok, to revolutionize the industry through a perfect melding of science and artful design. Not only did he change the world with Apple, he also changed the world by building Pixar into the most successful animated film business of today.

I remember back in college when I rolled my eyes at Apple — what a hipster company — and today I own an iPod, iPhone, a macbook air, and covet my boyfriend’s iPad. I’m iObsessed. How Steve Jobs, in his last few years of life, turned the company from a computer company focused on designers to the world’s most valuable company that sells extraordinary new products that change all of our daily lives is the result of pure genius. Granted, he had an incredible team working for him that came up with many of these ideas and details, but it’s clear he had a pretty big say in which of the ideas were going to be seen to fruition, and how to market those ideas.

The whole college dropout story is enviable (Jobs, Zuckerberg, et al) and reminds us that genius and passion can’t be taught. In fact, traditional, formulaic teaching might actually hold us back from making the larger changes in the world. It reminds me that perhaps business school isn’t the ideal option for growth in my career, and that working in a fast-growing company is actually the place to learn the best lessons day in and day out.

The night before I found out about Jobs’ passing, I watched the episode of Mad Men when Marilyn Monroe died and all the secretaries were crying, because they all aspired to be her. She was their hero. I felt the same way about Jobs. He was my hero. He was unafraid to think different. His inspiring quotes live on. If you haven’t yet seen his speech to the Stanford graduating class of 2005 (which you probably have because everyone and their mother has posted it), I leave you with the transcript and video from this speech. Let’s all remember life is short, and no amount of money can change that fact, so live each day like it might be your last. Stay Hungry. Stay Foolish.

“I am honored to be with you today at your commencement from one of the finest universities in the world. I never graduated from college. Truth be told, this is the closest I’ve ever gotten to a college graduation. Today I want to tell you three stories from my life. That’s it. No big deal. Just three stories.

The first story is about connecting the dots.

I dropped out of Reed College after the first 6 months, but then stayed around as a drop-in for another 18 months or so before I really quit. So why did I drop out?

It started before I was born. My biological mother was a young, unwed college graduate student, and she decided to put me up for adoption. She felt very strongly that I should be adopted by college graduates, so everything was all set for me to be adopted at birth by a lawyer and his wife. Except that when I popped out they decided at the last minute that they really wanted a girl. So my parents, who were on a waiting list, got a call in the middle of the night asking: “We have an unexpected baby boy; do you want him?” They said: “Of course.” My biological mother later found out that my mother had never graduated from college and that my father had never graduated from high school. She refused to sign the final adoption papers. She only relented a few months later when my parents promised that I would someday go to college.

And 17 years later I did go to college. But I naively chose a college that was almost as expensive as Stanford, and all of my working-class parents’ savings were being spent on my college tuition. After six months, I couldn’t see the value in it. I had no idea what I wanted to do with my life and no idea how college was going to help me figure it out. And here I was spending all of the money my parents had saved their entire life. So I decided to drop out and trust that it would all work out OK. It was pretty scary at the time, but looking back it was one of the best decisions I ever made. The minute I dropped out I could stop taking the required classes that didn’t interest me, and begin dropping in on the ones that looked interesting.

It wasn’t all romantic. I didn’t have a dorm room, so I slept on the floor in friends’ rooms, I returned coke bottles for the 5¢ deposits to buy food with, and I would walk the 7 miles across town every Sunday night to get one good meal a week at the Hare Krishna temple. I loved it. And much of what I stumbled into by following my curiosity and intuition turned out to be priceless later on. Let me give you one example:

Reed College at that time offered perhaps the best calligraphy instruction in the country. Throughout the campus every poster, every label on every drawer, was beautifully hand calligraphed. Because I had dropped out and didn’t have to take the normal classes, I decided to take a calligraphy class to learn how to do this. I learned about serif and san serif typefaces, about varying the amount of space between different letter combinations, about what makes great typography great. It was beautiful, historical, artistically subtle in a way that science can’t capture, and I found it fascinating.

None of this had even a hope of any practical application in my life. But ten years later, when we were designing the first Macintosh computer, it all came back to me. And we designed it all into the Mac. It was the first computer with beautiful typography. If I had never dropped in on that single course in college, the Mac would have never had multiple typefaces or proportionally spaced fonts. And since Windows just copied the Mac, it’s likely that no personal computer would have them. If I had never dropped out, I would have never dropped in on this calligraphy class, and personal computers might not have the wonderful typography that they do. Of course it was impossible to connect the dots looking forward when I was in college. But it was very, very clear looking backwards ten years later.

Again, you can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.

My second story is about love and loss.

I was lucky — I found what I loved to do early in life. Woz and I started Apple in my parents garage when I was 20. We worked hard, and in 10 years Apple had grown from just the two of us in a garage into a $2 billion company with over 4000 employees. We had just released our finest creation — the Macintosh — a year earlier, and I had just turned 30. And then I got fired. How can you get fired from a company you started? Well, as Apple grew we hired someone who I thought was very talented to run the company with me, and for the first year or so things went well. But then our visions of the future began to diverge and eventually we had a falling out. When we did, our Board of Directors sided with him. So at 30 I was out. And very publicly out. What had been the focus of my entire adult life was gone, and it was devastating.

I really didn’t know what to do for a few months. I felt that I had let the previous generation of entrepreneurs down – that I had dropped the baton as it was being passed to me. I met with David Packard and Bob Noyce and tried to apologize for screwing up so badly. I was a very public failure, and I even thought about running away from the valley. But something slowly began to dawn on me — I still loved what I did. The turn of events at Apple had not changed that one bit. I had been rejected, but I was still in love. And so I decided to start over.

I didn’t see it then, but it turned out that getting fired from Apple was the best thing that could have ever happened to me. The heaviness of being successful was replaced by the lightness of being a beginner again, less sure about everything. It freed me to enter one of the most creative periods of my life.

During the next five years, I started a company named NeXT, another company named Pixar, and fell in love with an amazing woman who would become my wife. Pixar went on to create the worlds first computer animated feature film, Toy Story, and is now the most successful animation studio in the world. In a remarkable turn of events, Apple bought NeXT, I returned to Apple, and the technology we developed at NeXT is at the heart of Apple’s current renaissance. And Laurene and I have a wonderful family together.

I’m pretty sure none of this would have happened if I hadn’t been fired from Apple. It was awful tasting medicine, but I guess the patient needed it. Sometimes life hits you in the head with a brick. Don’t lose faith. I’m convinced that the only thing that kept me going was that I loved what I did. You’ve got to find what you love. And that is as true for your work as it is for your lovers. Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it. And, like any great relationship, it just gets better and better as the years roll on. So keep looking until you find it. Don’t settle.

My third story is about death.

When I was 17, I read a quote that went something like: “If you live each day as if it was your last, someday you’ll most certainly be right.” It made an impression on me, and since then, for the past 33 years, I have looked in the mirror every morning and asked myself: “If today were the last day of my life, would I want to do what I am about to do today?” And whenever the answer has been “No” for too many days in a row, I know I need to change something.

Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Because almost everything — all external expectations, all pride, all fear of embarrassment or failure – these things just fall away in the face of death, leaving only what is truly important. Remembering that you are going to die is the best way I know to avoid the trap of thinking you have something to lose. You are already naked. There is no reason not to follow your heart.

About a year ago I was diagnosed with cancer. I had a scan at 7:30 in the morning, and it clearly showed a tumor on my pancreas. I didn’t even know what a pancreas was. The doctors told me this was almost certainly a type of cancer that is incurable, and that I should expect to live no longer than three to six months. My doctor advised me to go home and get my affairs in order, which is doctor’s code for prepare to die. It means to try to tell your kids everything you thought you’d have the next 10 years to tell them in just a few months. It means to make sure everything is buttoned up so that it will be as easy as possible for your family. It means to say your goodbyes.

I lived with that diagnosis all day. Later that evening I had a biopsy, where they stuck an endoscope down my throat, through my stomach and into my intestines, put a needle into my pancreas and got a few cells from the tumor. I was sedated, but my wife, who was there, told me that when they viewed the cells under a microscope the doctors started crying because it turned out to be a very rare form of pancreatic cancer that is curable with surgery. I had the surgery and I’m fine now.

This was the closest I’ve been to facing death, and I hope it’s the closest I get for a few more decades. Having lived through it, I can now say this to you with a bit more certainty than when death was a useful but purely intellectual concept:

No one wants to die. Even people who want to go to heaven don’t want to die to get there. And yet death is the destination we all share. No one has ever escaped it. And that is as it should be, because Death is very likely the single best invention of Life. It is Life’s change agent. It clears out the old to make way for the new. Right now the new is you, but someday not too long from now, you will gradually become the old and be cleared away. Sorry to be so dramatic, but it is quite true.

Your time is limited, so don’t waste it living someone else’s life. Don’t be trapped by dogma — which is living with the results of other people’s thinking. Don’t let the noise of others’ opinions drown out your own inner voice. And most important, have the courage to follow your heart and intuition. They somehow already know what you truly want to become. Everything else is secondary.

When I was young, there was an amazing publication called The Whole Earth Catalog, which was one of the bibles of my generation. It was created by a fellow named Stewart Brand not far from here in Menlo Park, and he brought it to life with his poetic touch. This was in the late 1960’s, before personal computers and desktop publishing, so it was all made with typewriters, scissors, and polaroid cameras. It was sort of like Google in paperback form, 35 years before Google came along: it was idealistic, and overflowing with neat tools and great notions.

Stewart and his team put out several issues of The Whole Earth Catalog, and then when it had run its course, they put out a final issue. It was the mid-1970s, and I was your age. On the back cover of their final issue was a photograph of an early morning country road, the kind you might find yourself hitchhiking on if you were so adventurous. Beneath it were the words: “Stay Hungry. Stay Foolish.” It was their farewell message as they signed off. Stay Hungry. Stay Foolish. And I have always wished that for myself. And now, as you graduate to begin anew, I wish that for you.

Stay Hungry. Stay Foolish.

Thank you all very much.” — Steve Jobs, 2005

Do you deserve a raise?

One of the best conversations I had at the Financial Blogging Conference was a brief chat over dinner about how men and women differ at finances, and how women are generally more afraid of asking for a raise. I consider myself a solid negotiator when I’m first hired and setting an initial salary, and when it comes to negotiating for other people — or even my company (I’ve saved us thousands of dollars through negotiations with various sponsorship opportunities) — so why does it seem so unfathomable to ask for a raise in my current work environment?

After listening to folks like Ramit Sethi talk about how to go for the big wins, and just ask with confidence to get what you want, I felt a big kick to my stomach for my fears of moving up in the work world. Other than my “fear of conflict” boyfriend, do men — as a generalized group — have as much trouble asking for raises or believing they’re worth more than they’re paid?

It’s hard for me to fathom asking for a raise in this economy. My company could probably afford to give me a raise, but I feel guilty and selfish to ask to be paid more when my current income is enough for me to live a modest lifestyle as a single person in a shared housing situation and even occasionally splurge on a tech toy or two. The question of how much do I “need” to live on is so subjective. Right now I make $90,000 a year and that’s an odd place to be. To many people in the country right now — it’s a HUGE salary. But then there are lots of people making $100,000… $130,000… $150,000… $170,000… and how did they get there? It doesn’t really matter. Shouldn’t I just shut up and be happy with what I’m getting and try to improve myself so maybe, just maybe at some point down the line my boss will decide I’m worth more than that for a permanent salary adjustment?

Oh, right, that’s not how raises work. I don’t want to be greedy. I don’t feel like I deserve to have a job given that I’m not perfect, so it’s hard to even contemplate asking for more money. Yes, I think I add value to the organization. Yes, I’ve been the only person in a department that could probably use a team of at least five people to be run successfully — even though deep down I believe that I’m just a failure and that my inability to have superhuman powers and never sleep and do a perfect job 100% of the time is really all about me just being rather dumb. How could a dumb person ask for a raise? I feel like I should ask for a raise for my coworkers who are clearly deserving of it…

But what does “deserving” have to do with getting a raise anyway? I don’t know what I’m worth or how to improve what I’m worth. Does going back to grad school and getting an MBA or masters in something or other suddenly make me officially worth six+ figures? I don’t want to be unreasonable. I already feel unreasonable thinking about asking for more money.

It would be nice if I made enough to put more money into savings and live on my own. Not a necessity. It would be nice if I made enough to buy a “new” used car. Not a necessity (yet.) It would be extra nice if I could go to Bloomingdales and Nordstrom and buy Trina Turk and BCBG and all the fashionable brand name clothes each season, even though that is definitely NOT a necessity. It would be lovely to have the money to spend on a personal trainer and weight loss coach, but do I really need that?

I could live on less and I could live on more. All I want to do now is save money so I can feel ok about having kids a few years down the line. While I can certainly cut back on my spending, the only way to really save significantly more money is to make more money. I can either push for that additional income at work, I can find a side income stream (not that I have time for that given how many hours are focused on my day job), or I can just be happy with what I have now, which is much more than most people in America currently make. I should be happy with my shared three bedroom apartment, my about-to-fall-apart car, my very slow networth growth which isn’t being helped any by the gloomy stock market… I should be happy with some sort of semi-consistant middle class life. If anything, I don’t want to give my supervisors a reason to ask me to leave. Maybe I’m not the cheapest employee, but the second I become too expensive for what i’m worth, I’ll risk losing my job and being replaced with someone else.

So I’ve been with the company for a year and a half now, and officially full time for a year. If my boss wanted to give me a real raise, he would. And clearly he doesn’t. And it’s not like I even successfully got through every single one of my projects for the last quarter. I just look at all the other people in the company and feel so insecure about my work and my mind. I mean, I just feel incredibly stupid and like I don’t fit in. All I want to do is contribute enough so that people say, wow, she’s worth x dollars more because she is a huge help to this company. Right now, I feel like my ideas aren’t worth a dime because they’re rarely any good. So I can’t ask for a raise, all I can do is try my best to somehow be smarter, sharper, funnier, more witty, more spot on, more in line with what everyone wants. To mold myself into the perfect form to help fill in whatever voids exist until someone better comes along to fill in that space, and then like jello nudged over I slither into the next hole.

I just wish I knew if other people, specifically other men, have this sort of mindset to begin with… is it that people who are confident are just amazing, smart, and know it — or do some people just know how to fake it better than I do? How often do people… my colleagues past and present… really ask for things they want, like raises and other additional benefits? If I could just see into the transparent world around me of the politics that underly the corporation I’d at least know what’s reasonable to want and to ask for. Meanwhile, all I can do is think how my current role is setting me up for a decent salary jump at my “next” job, so even sticking it out in this current spot for a while is a good move. I really love my job, the people I work with, but it’s also stressful, difficult, and I have no idea how much a guy or anyone else in my position would be making in this same exact role (other than what says, and that information is too vague to be relavant.)

The Dream Taste of Success

Although I graduated college just six years ago, I’ve already been through a handful of careers — admin, journalist, customer service, marketer — in a heaping handful of companies. I’ve often been involved in projects that failed, and were fairly clearly destined to fail from the start for one reason or another. This took a toll on the quality of my work, and the overall enjoyment of work on a daily basis.

Then, I joined my current startup as one of the very early employees. We were so small when it started, and I wasn’t sure where it was going. Today, our company has pretty much exploded — in a good way. Of course, anything can go wrong, as we’re still super early stage, but I have the taste of success in my mouth. It’s crazy, being part of this, and feeling both part of it and like an outsider looking in, all at the same time. There are many days, hours, minutes when I wonder what I contribute, but then I look back and see just how much I have contributed. Sure, I’ve made mistakes, I haven’t contributed as much as someone with a brain that processes information at top speeds, but I think I’ve contributed as much as I can. Now, it’s not clear if that will be enough going forward, but I’ve made it this far, and the whole situation is surreal.

Time flies on the wings of a successful venture. I’m watching my company grow incredibly fast, and there are people here that I haven’t had a serious conversation with yet. I travel to a conference for a week or two, come back, and there are new faces who wonder who I am. It’s a totally different company than it was just 12 months ago.

I’ve been waiting for this opportunity, and here it is. I won’t get rich off of it — wealth in startups is reserved for founders, investors, and a few very high-level executives, but if I can focus on kicking ass for a few more years, and just hunker down on what that exactly means, and execute, maybe I’ll have enough for the downpayment on a decent house — maybe I’ll have enough to feel comfortable having children in my early 30s instead of feeling guilty and terrified of not having the money to support them. Everything seems so far yet also within reach. I can taste my life finally working out. It tastes sweet and refreshing, like cool, wet watermelon on a warm summer’s evening dripping down my throat. It opens up my sinuses and relieves all the pressures of the world. It’s just a dream right now, but it’s the closest I’ve ever been to that dream. I long for freedom to live the life I want — to be a mother, to be an artist, to start my own company, to start my own non-profit, to sleep in late, to get up early, to spend a day lying in the sun in the middle of the week, whenever I feel like it, and to spend time with my family, my loved ones, my friends — that’s the dream I long for. That’s the dream I can’t get out of my head.

what goes on in everyone else’s mind?

I love talking to people. I hate conferences. I’m a marketing director. I’m an introvert. It’s the oxymoron of my life. I’m currently traveling for a work event, and went to an evening mixer at this conference, with an open bar. I’ve had three drinks; after two and a half I was able to talk to people, but probably clearly seemed a little tipsy. Without that I hide in a corner. I hate my social anxiety and introversion. I feel like my insecurity, my social anxiety issues, and my lack of any sort of confidence in myself leads me to this downward professional spiral.

Yet who know what people see from the outside. I feel like I’m a huge mess. I feel like, I believe, I don’t deserve success. I try to fight that. I want to believe in myself. But I see myself as a huge joke. I’m not good enough, I think. I’m not smart enough. I’m not ___________ enough.

It’s sickening how lost I am in this business world.  I don’t belong here, but I am here, incredibly awkward, trying my best to generate interest for my company, to talk to people, to drive leads, and I don’t know how to relate to people. Small talk? What to talk about? I am only interested in talking business or about the deep psychology of humankind. Not appropriate subjects for business conversation. I wish I could work a room, to come off smart, not slutty or drunk. I don’t know how to relate to people. Maybe it would be easier if I was a man, but I’m not. I’m a  27=year-old woman and now I’m young and soon I’ll be old, and I’ll always be female, and that seems to make everything all the more challenging.

The Next Steve Jobs? Most Definitely Not a Woman.

The other day I read an article in the Mercury News titled “Who will be Silicon Valley’s next Steve Jobs?” This photo sums up the article:

That reflects the industry I work in. Thinking back on my past jobs, everyone in the C-suite were men. White men. My first startup was founded by four white men. My last job was at a large, international public company, where all of the C-level executives were male. My startup now — of 32 employees, four are female. For a long time I was the only woman. We’re adding on our executive team, and not surprisingly, the employees brought on for the high-level positions are all men. Is it just that there aren’t enough women working in tech, or is it something more than that? Even at my last company (the large international technology company) there were many female mid-level managers, but they were all stuck in middle management.

And even if women are few and far between in Silicon Valley, isn’t there one that deserves to be in the running as the next Steve Jobs? How about Sheryl Sandberg, COO of Facebook? Heck, it was only a few months ago when the same man who wrote the “who will replace Steve Jobs” article wrote an entire piece on the Top 10 Women of Silicon Valley — I guess he forgot about them when capturing the key execs to highlight in this piece (oh, wait, Sandberg is mentioned down below as one of the reason’s Mark Zuckerberg is so brilliant — for hiring her.)

Watching the leaders of companies I’ve worked for — especially the ones that I think are really GOOD leaders — I see that these leaders can come off (like Steve Jobs) as assholes at times. It’s not that they are assholes outside of the business world, it’s just that they don’t care about much other than what is best for their business. And if someone isn’t going to contribute to that, then they are worthless to that leader. But — the leader will also go out of his way to motivate and reward people who are actually contributing to making the business run well and succeed. I don’t think I have the asshole in me. At least, if I let her out, she’d come out at all the wrong times, and it wouldn’t help anyone or any business. It’s rare to find a woman who is able to stand up for herself and her ideas that much, especially in an industry that’s primarily men. Women are taught to compromise. I think there’s truth to that as one of the reasons so few of us rise to leadership positions in technology or in any industry (though it’s worse in tech and other male-dominated industries.)

Everyday I switch back and forth between dreams of being a truly innovative person in Silicon Valley — who happens to be a woman — and having absolutely no confidence in getting anywhere near accomplishing that feat. It’s frustrating because I feel like a many times as I’ve failed thus far, I’m still on a trajectory that could lead towards success. I’m turning 28 in a few months and I’m already at a Director level role within a fast-growing startup, I have a book deal on the table (though that’s far from a sure thing right now), and I’ve become fairly known across a few key industries in technology (I could do a better job at promoting myself, but for what I’ve done, I’m always surprised how many people have heard of me.) Still, going from where I am today to VP level or C-level, just, well, it seems impossible. I certainly don’t represent all women, but if the picture above signifies reality, I also feel I fit in that picture — as in, not in the picture at all.



When You’re Not a Natural at Meshing Well with People

There are days I sit at my desk at work, looking at my colleagues, my daily acquaintances, and wonder how many of them see me as the girl who sat alone during recess, never quite understanding how to fit in. I imagine it’s pretty obvious — I’m far from a natural at people skills — and struggle with this every single day.

It’s not an introvert vs. extrovert issue, though that plays a role. It’s not even about my social anxiety, per say, because I feel comfortable around people I work with – generally speaking – and still, I’m at a loss for how to keep up with the pace of normal socialization. Who knows what disorder I actually have — I only know that some things are overwhelmingly challenging to me that come natural to others.

For example – management. I received one hell of a very deserved critique session today for my handling of managing the summer interns. While a large part of the issue was my lack of time management skills (hello ADD), another huge portion was clearly my lack of people skills. One thing that my boss does so well is know how to reward his employees. This isn’t with monetary prizes usually, instead, it’s with recognition. Everyone at the company respects him. He works hard, he is willing to get his hands dirty, and he seems to know exactly when to step in and push for something and when to step out and let the team work their magic. He seems to have been born with the gift of knowing exactly what to say at exactly the right time to make everyone do exactly what they should.

Which no doubt frustrates him about me — I don’t seem to react to feedback the way a normal person would — though I carefully listen and try my best to improve. And by try my best, I mean my unmedicated best, because I really want to be able to do this on my own without adderall or an anti-depressant.

What hurts the most is knowing I’ve sunk down in the totem pole of respect. The only thing that motivates me – for better or worse – is having someone who I hold in high regard think of me in almost equally high regard. The moment I lose that respect, the moment I start to crumble. And I ALWAYS lose that respect due to my people skills. Words slip from my mouth when I ought to stay quiet. And then, when it’s the perfect time to say something, I freeze. So I revert to being the jokester, after all, I’ve figured out a way to get most people to at least find me amusing through self deprecation and letting myself and my ideas get pushed around like the wind. Because deep down I rarely think my ideas and contributions are any good. Because deep down I feel like a complete failure day in and day out, and no therapist or drug can get me out of that one.

Looking at my colleagues now, I see all the kids on the playground. The popular kids, the nerds, the jocks — all working together, all grown up. They all talk to me now. The nerds are either shy and say hi when I say hi to them, or they have some form of Aspergers and are glad to talk to me. The popular kids talk, but only to make small talk, and it always feels somehow politically oriented, even though there is likely no such motivation prompting the conversation. Am I still the weirdo? That’s my part in this story, or at least it was for the first 15 or so years of my life. (No wonder I was depressed.)

I know I don’t have to be the girl on the playground who everyone made fun of — I don’t have to let fear and insecurity rule my life. But it still does, and it is reflected in my many reviews with my boss where he is clearly disappointed. I leave them thinking I’ll do better next time — I’m going to prove that I can do better — and somehow my ability to remain consistent, even with the most positive intentions, just dwindles.

There are many, many things I love about my job, and I don’t want to lose it. I’ve learned how to hide my issues with people for longer and longer each new job I have, but once they’ve surfaced, can I ever change someone’s mind about me? I feel like I need to get a whole new wardrobe, focus on straight ironing my hair in the morning, dressing like a person who is put together, and then somehow acting the part, to show I’ve changed — but I have absolutely no idea how to maintain that for longer than a few days. I want to be different and I want to be perfect.

The reality is it’s best to be “normal” and allow for imperfection so things can get done. Or, maybe I’m just not that smart, not quick enough, and ought to find a career and industry that doesn’t put me up against some of the brightest minds in the world. But that, right there, is what drives me to begin with. That’s what actually makes me — happy. So how could I ever give this up? I just wish I could change.