Category Archives: Career

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.

I Need a Makeover. Stat.

Before you judge me and my piles of clothes on the floor and my “nothing to wear” conundrum, hear this — my wardrobe says more “college student who hasn’t slept” than “marketing director.” Every day, I wake up, look in my closet, and on my floor, and find there’s few items that reflect my position, and the rest of my life’s aesthetics aren’t supporting the cause (case in point, my busted car with Styrofoam instead of half a bumper.)

There have been times over the past few years when I went through this “makeover” shopping splurge, which usually lead to buying too much overpriced, dry clean only clothes at Banana Republic that don’t even look good on me and end up getting wrecked a few times after I wear them. The purchases I’ve made at Express, despite being more suited for “just out of college” than my professional status, at least last me. But that leaves me with a closet of “Editor” stretch pants in black and a few short sleeve, button down shirts in various cheap materials that still look young and unpolished. Hey, at least they’re machine washable.

But what’s a girl to do? When the interns dress better than you do, it’s a reality check. As more and more employees of the female species join our company, I’m quickly becoming the worst dressed. And I don’t want to be on that list. But I also don’t want to spend a fortune on outfits that will inevitably make it into the share pile quicker than you can say “how on earth did I gain five pounds?”

My closet, however, is just not cutting it. I’m tempted to do the Banana and/or Anne Klein splurge — find some clothes that manage to be trendy and hip enough for the startup culture, but formal enough to put me at the head of the figurative class. It’s a tough splurge to swallow, since I’m determine to LOOSE those five pounds, plus another 30, in the coming months.

Beyond clothes, i’m questioning my hair style (it’s now long, layered, but hard to manage) and just tinted with a “glaze” — somehow expensive highlights make people seem more put together and worth more. Marketing is 10% product and 90% sales. Sales is polish. And on that spectrum I’m always leaning towards scruff. Clean, but lacking in the shine that can take a girl places.

Tonight, I’m tempted to toss all my old clothes for good, and start from near scratch. But what will that cost me? Seems like such a waste of money, as I’m getting on with my Express clothes just fine, and the Banana clothes I do own are sitting in my dry clean only bag collecting dust.

How often do you buy new work clothes and where do you shop?

Overwhelmed at Work: For Better or Worse

My job isn’t nearly as high stress as a career as an emergency room surgeon, but it has its ongoing stress nonetheless. The stress comes from carving a path that is not clear, and the responsibility that comes with both carving it on your own, while also the pressure of not trying anything too far out in left field, as there isn’t enough time to waste on something that doesn’t work. And you can still mess up quite a bit, even while keeping your work fairly ordinary.

I love the challenge that comes with my current job. I truly have the opportunity to make a huge difference in my company. I also have the opportunity to really hurt my company (not on purpose, of course, but if I just can’t meet my commitments for whatever reason.)

My confusion is when I am fairly overwhelmed and when I’m not organized/focused enough to get things done as they should be. It’s hard to say because I know I do have a tendency to procrastinate, but I’m still working 60+ hours a week, barely sleeping, staying up all night to get projects done. So I might not be the most productive at the office straight through the day, but I’m still putting in quite a lot of hours into this job. I can’t imagine – even if I could manage to retain focus from 8am to 7pm – that I’d be much more productive. I might sleep more, but my output would likely be around the same. Continue reading

The Currency of Time: Life’s Most Precious Commodity

Lately I’ve been trying to compute the currency of time.

Not every second holds the same value as the next. And value is relative — sleep seconds, for instance, are highly valuable cohesively, yet alone they are nights of insomnia dosed with fissures of awareness. The same goes for time to spend with family, friends, or even yourself, outside of your daily work hours. What is the value of that time? High, surely, but how high? What if you spend four years of your life dedicated to work, almost every minute of your life, to build a successful company, so the rest of your life requires less stress over earning and the ability to appreciate time more — making time more valuable.

At this very moment, I’m sitting on a plane (in first class again – yeay, elite status upgrades) and — after two bloody marys — am quite introspective. God, I only had one and a half bloody marys — they make these very strong in first class! Regardless, I’m once again pondering time as currency, because time itself is the most limited commodity, therefore it’s the most valuable. I also owe you all a post, since I’ve been incredibly busy with — work (and rewarding work at that) — and haven’t had time to write. Or haven’t known what to write about. But now, sweet readers, I impart my thoughts on the most valuable currency of all, the limited moments we have here on this earth between birth and death that are quickly flying by as we sit at our desks, stressing over something that in the grand scheme of things, as far as the meaning, or lack of meaning, of life itself, is not that important, beyond purchasing for more “time” with an investment in today’s time value.

My job doesn’t need to require all nighters, but I do my best work at night, and need to be at the office during the day to handle the thousands of little things that come up — an interview to schedule, a event to coordinate, a new graphic to manage the design process for, and so on. I’m completely overwhelmed by my role and terrified I’ll be replaced. There’s the alcohol truth serum speaking up. I like drinking, occasionally, on flights, because it gives me time to think, straight or crooked I’m not sure, but at the very least, I feel calm, and can process simpler important matters without worrying about the bigger picture.

But back to the point of this point — what is the value of time, and does it make sense to trade in time now for time later? As the company that acquired my former company announces its IPO, I realize that, although I’ll never see a dollar of that success, wealth is within reach. Wealth, not as in becoming a billionaire, but as in earning $1M before I turn 32. Granted, this isn’t a requirement by any means, but it’s more of a possibility now than ever. There are days I believe — despite my ardent atheism — that there must be some great screenwriter above writing my life story. It’s too funny how things work out, or don’t work out, but if you keep pushing, keep going, eventually something works out.

Two bloody marys and a red wine into this 1 hr flight before I have a stopover and get on my next flight, I’m, admittedly, extremely intoxicated. Not to the point of feeling sick, but to the point I love, occasionally, on extremely rare occasions, by myself, when the rest of the world just disappears, where I’m in my mind, in a place where I can examine what matters and what doesn’t.

Red wine, done.

I don’t want to be a billionaire. I’d like to have a million dollars at 30 or 32. To invest most of it and live a simple life. To pay rent off my boyfriend’s salary. To have a family — three kids — we’ve already named them, go figure — and to love them more than anything. I want to paint, to write, to do all the things I have absolutely no time for right now. I want to kick ass in my current role and be a leader in helping this company be extraordinarily succcessful. On one hand, that sounds ridiculous. On the other hand, it’s possible.

It’s so possible it really seems like it’s scripted. I invested $20k into my stock options because, quite frankly, I’ve been blessed (in a non religious sense) with a CEO/boss who is brilliant, who I trust, who knows how to build an extremely valuable company. I don’t know what my place is in that company, as I think I’ll be replaced, or “superior-ized” as a VP is brought in to manage me once it really matters — but I really want to prove I can do that. I can kick ass. I can help our entire company be successful. I love that. For the first time in my life, I believe I have the opportunity to make a difference in the company. If we’re ever to be worth billions of dollars, I’m going to own up to the fact that there’s a good change I’ll have something to do with it. Incredible. That job of mine is not being done well now. I need time to focus. Time to read and learn as much as possible. That time is not available. That time is spent worrying, and then working through the night. I love the night. I wish I had the day to read books about marketing and analytics and the night to work. But I can’t have that — I just need to be amazing at what I do have. The opportunity is there. I don’t want to fuck this up.

Which brings me back to — time. I am more than willing to give all of my time to work now, so I can live the life I want later. I don’t know what that life is — maybe it’s painting, having a family, starting my own business, volunteering — whatever it is — I know money is the only answer to that end goal. It isn’t the answer for everyone. I don’t want to be a billionaire. I don’t want a big house. I want time. How much does time cost? Maybe more than a big house. But that’s what I want. How can I get it? How can I help my company succeed? That is all I want right now.

My $20,000 Bet: The Biggest Risk I’ll Ever Take

Given that my largest one-time purchase ever has been on my $7,000 car, it was difficult for me to write a check today for $15,000 to “early exercise” the majority of my mostly pre-vested stock options. Perhaps I should have sought out more advice before doing this, but I feel like my life has a way of working out and this was a smart risk to make.

Worst case scenerio — I find out that over the long run, this risk has cost me $15,000 plus whatever interest I would have made investing that money elsewhere. Best case, I could become a millionaire, or even a billionaire. Most likely outcome is somewhere closer to the first option, but why not take the risk now when I’m young and can handle the set back.

The whole equity situation at startups is so tricky. You really can only get the best value out of your options if you’re able to exercise early, at the strike price, before the stock value is raised in a later funding round. But early is also when it’s not very clear how the company will do over the long run. It’s exactly like buying a lottery ticket, except maybe you know that the winning lottery ticket was sold within one specific town. You have some insider information that within this “town” someone is going to win big. Everyone else, still, is going to lose. But if you were able to pinpoint the town, or even the exact street the store is on, would you buy a ticket?

That’s what I’ve done. I wrote out my check, stared at it for a few minutes before handing it off to my boss to exercise most of my stock options. I believe that of all the companies I may work for in my life and have in this past, this is the one to bet on. The team is great, the product, while early, is solid and something that companies are willing to buy and spend quite a bit of money on. I’ve been involved in many aspects of the business, enough to know the market and believe we have a shot at really building something special.

My last startup — where I never bought the stock — never had a business model. There, it seemed silly to buy the stock. And even they managed to get acquired for a small sum. No one besides the founders got rich off of it, but at least anyone who exercised their options got their money back plus a little pocket change.

Still, as I drive around in my busted car with no air conditioning, I can’t help but think… should I have taken that $15k and spent it on a nicer car vs. exercising my stock options that a few years from now could very well be worth nothing. I guess I’ll just have to wait and see. My dream is to have a million dollars by the time I’m 30, and given I’m half way to 28, this is really the only possible way.