I Could Be a VP and Why I Never Will Become One

I am at the point in my career where I know the exact traits and skills required to climb the corporate ladder. And, despite seeing a clear path to the top, I’ve looked down to see I have no feet and I don’t have the strength or energy to continue climbing upwards. I look back down at the steep hill of my 20’s behind me and feel my legs buckle beneath me as I slowly slip and begin to roll back down the hill. I’m scared and sad and partially so excited to jump fall all the way down and lie there at the bottom in a pile of my own failure, staring up at this giant hill I once climbed, seeing my feet appear on my ankles again and, for the first time in years, I can stand without feeling myself falling.

Here is what it takes to become a Vice President in my field, and why I’ll never be one:

  • Develop achievable goals, create a plan for yourself and a team to perform to achieve those goals, hit the goals or manage them for minimal slippage in delivery, and report on success; rinse, repeat.
  • Negotiate with C-level executives for budget, resources, and other support to achieve these goals. Convince them these goals are the right ones. Hit or exceed them.
  • Hire and fire. There is nothing more important to your success than hiring the right people. This means being someone that good workers want to work for. This means not being socially inept. And, you can’t be afraid to fire people fast if they aren’t performing. You should be empathetic, but at the end of the day your job is to manage resources.
  • Be extremely sociable. Have charisma. Sell. Sell. Sell. When you’re a VP, you’re a salesperson, no matter what team you’re on. Be able to work a room. Don’t suffer from social anxiety. Network, network, network. Be the kind of person that people are drawn to without effort. Every presentation of yours is like a TED talk. Be magnetic.
  • Don’t let the ups and downs get you down. Be solid. Business is tough. Not every quarter will be a good one. There are some things out of your control. There are some things out of your control that you will get blamed for and that may even get you fired. But you can’t let that hurt you. You need a very thick skin.
  • Connect with your peers at the senior level and develop a network of senior mentors. Figure out how to navigate the mostly male-dominated world of business as a woman, somehow making friends with men without any sort of non platonic scenarios occurring (which is impossible because there will always be a guy who thinks your inquiring about meeting for drinks is your asking them on a secret date). Find the good guys out there (they exist) and bond with them in a way that men do with other men, even though you have no idea how to do that.
  • Show up early and prepared. Don’t have ADHD. A CEO is the only executive that can be successful and have ADHD. A VP is hired by the CEO to be detail oriented. A VP gets shit done.
  • A vice president will get on an airplane last minute to meet with a client half way around the world to smooth over an issue. A Vice President is trusted by the CEO to be put in front of tier 1 clients and partners, not hidden from them out of embarrassment.
  • A vice president knows how to look the part – she is dressed professionally and, ideally is decent looking and has perfectly-coifed hair and somehow managers to always look so put together despite not having time to do anything other than work. She’s just the right about of sexy, but not too sexy. She wears makeup, but not too much makeup. Just the right amount. She always looks naturally flawless, despite that it took her a long time to maintain the look. She has an amazing personal trainer and works out at 5am because when else would she do it?
  • A vice president has been able to successfully deal with unconscious biases about her gender or color or any other thing that makes people judge her more harshly than other employees. She is likable yet firm. She has figured out the exact personality to create that others like and want to work hard for – she is constantly perfecting her public psyche. She is no longer herself.
  • She enjoys being the person to review and sign off on everything, or to give a small amount of feedback to improve projects, versus being the person who is executing on the details.
  • She doesn’t care about work-life balance. Work is her life. She works because she loves it. She loves the power of being in charge and she loves to generate business results. She doesn’t mind rarely seeing her family or waiting until she is retired to have a life again outside of work. She makes a lot of money but doesn’t have time to spend it. But her family has a nice house she never sees and her kids go to a great school district that she never visits and she is the “success story” of the town she grew up  in because she has truly made it.

Even though I’m not a Vice President today, in order to be successful in my current role I have to do most of these things. If I were able to do all of these, I’d undoubtedly be promoted soon to a VP role – which would lead to other roles at the same level with greater pay and responsibility. I’d be well on my way for a long executive career. I’d be one of the few women to have make it.

But, do I really want that?

It doesn’t seem to matter, because I can’t do any of the items above. I can perhaps focus really hard and get myself to check the box on a few of them for a week or two, but it’s just not sustainable. I’m not a vice president. I’ve never been cut out for business. I didn’t grow up wanting to go into business. My mother was a fashion designer before I was born and I thought that I should probably do that (even though fashion design is a business job, it’s at least creative.) My father did something with math and I had no idea what it was until I was an adult. He wore a suit and went into the city and came home late and was always angry and obese. He wasn’t a VP because he didn’t want to be a senior manager, but he had an analyst type job which paid well enough without moving up in the org. He once told me that he was offered the opportunity to move up but he turned it down. Knowing my father’s stubborn attitude and horrible temper, I’m sure his colleagues were glad he didn’t move up into more senior management.

I want to work. I like working. I like solving problems. I don’t want to sit home all day and do nothing. I enjoy adding value. I really like working.

And it upsets me that so few women are in senior leadership roles – and upsets me more than I should be helping the statistics. I don’t want to be one of the women who just doesn’t desire to be a leader. Men are  promoted to “first” managerial positions 30% more often than women. And 80% of C-suite executives are male.

Are all women really bad at management? Are we “leaning out” as we want to take less all-encompassing jobs in order to have a family? Do we just not have the same drive to have a seat in the boardroom? I know that am not a good fit for upper-level management… but surely more women should be leadership material (especially given that I’ve managed to come so far despite my poor social skills and ADHD.) But women just getting stuck.

Here I am, so close to climbing to the top, and all I want to do is roll backwards. I want to just wave my flag of surrender and to give up. I want to walk out of the office and say I CAN’T DO THIS and never return to a business role again. I want to move to some super cheap location and get a job answering support calls and feeling like I’m helping people without having to convince a giant team upwards and downwards to follow my lead. I want out.

Out, but where to go? There is no where to go. The jobs I get are more of the same. I certainly don’t get jobs easily, but the ones I do get are at that senior, “right before you’re a VP” level. I’m too senior to be a manager, they say. Too overqualified. I need to be a manager and an individual contributor because that’s why I get hired. I move the needle. I am a transient professional sadist, floating from one draining role to the next, until I can’t take it anymore, until my manager sees I am useless and throws me out.

I like the money. I still can’t believe how much I take home each month. I know it won’t last. I can’t handle the anger from my boss about my compensation. I don’t like the feeling of being his biggest regret in the business to date. I try to show my value. I fail. Even when I do add value, he doesn’t see it. He sees me as a high-priced recurring expense. A line item to cut as soon as a better one comes along for a lower rate or for the same price in a fancier package. He may have thought that I could be all he wanted to hire me for to start, but quickly he lost faith in my abilities. Did I trick him? I didn’t lie in my application. But maybe I was a bit too slick. A bit too confident and convincing. Maybe he feels he was lied to and hates me for it. Who knows. It’s not really an issue with just this job. It’s my life story that needs a new chapter – yet every time I turn the page I see one that looks exactly like the start of the last. Welcome back to your recurring hell – a little better paid, if you’re lucky, but undoubtedly headed towards the same result.

More than anything, I want to start a family. I never wanted to be a professional businesswoman. It all feels like an act. I’m terrified of becoming a mother, but it just feels like who I am meant to be. I’m sure it will be hard. I’ll probably write a blog post one day about how horrible I am at being a mother. But I trust that I know how to be a mother. I won’t be a perfect mother – but I know how to care about people. I know how to love. And, in a lot of ways, I know how to manage a team and how to motivate people to do their best work – something I can certainly leverage in my future as a mother should I ever have children.

I don’t know if a career ever can feel as natural… after all, having children is a biological draw, whereas marketing software is not something that’s part of our organic instincts. Making money is, but only in the sense that it  enables us to secure food and shelter for our family. Moving up the corporate ladder requires not just the desire to make a lot of money, but it also requires enjoying being in charge and being responsible for something highly unnatural – one piece of capitalism – one business or business line.

If we work to work and make money to support our lives, then why does it matter if I care about it or like it? Maybe men perform these roles because they enjoy making money – money means more power, more women (replacing first wives for second wives and so on), more travel to escape their homes to live in a fantasy (but very real) world of fancy food and drinks and fancy people. Why do men want to be managers so much more than woman? Is it just because it’s expected of them? I think to the male senior executives I know, and I couldn’t be like them. Many of them I do respect, but their version of executive is so far removed from anything I could ever be:

  • The Playboy: very successful male, 50s, beautiful wife, home, salary of at least a half million, travels the world, rarely sees family, so charismatic he could sell a paper bag. He may not have the highest IQ, but he’s successful because he can inspire groups of people and gain consensus.
  • The Asian Achiever: very successful male, late 40s or early 50s, seems to have moved up the corporate ladder because of cultural expectations for success – seems to enjoy status more than power. He has no other choice.
  • The Player: very successful male, late 50s?, much younger wife, travels the world, fidelity questionable (he clearly hit on me once when we were both drunk at a business event), a player type who loves power, has built his career around his charisma and likability, and he is a nice guy
  • The Sociopath: male, late 40s, clear sociopath, power hungry, will manipulate anyone for his own success or profit. Trumpesque. Will make you feel like a rockstar if you are feeding his needs, will cut you off and slice you if you are no longer useful to him anymore.

Compare these profiles to the few female leaders I know…

  • The Failed Husband: married to someone for love, but the woman made more money, and moved up in her career. The husband took a lot of risks in business, likely made a series of bad investments. For her family she stayed working to make sure they would be taken care of. She became a VP because she had to. She might be divorced, or about to get divorced, or considering a divorce.
  • The Sociopath: there are some female sociopaths. I’ve encountered one, who I heard screaming at my male colleague through the thin office walls many times, berating him for his stupidity and failures. Meeting her she seemed like a nice, competent woman, but you don’t want to get on her dark side. These women are challenging types because they actually are horrible managers and people, but you don’t want to call them out on it because they’re female. It’s also just more socially acceptable to be a sociopathic leader if you’re a male.
  • The Power Trip: often a lesbian (*based on what I’ve seen), the power trip actually enjoys power and being in a more masculine role, so it makes sense that she wants to move up in the professional world. Nothing wrong with the power trip, but she can be scary to work for because she overcompensates for being a woman by being really strong. She can be a great boss if you get on her good side, but you have to play her game by her rules.

This is totally sexist and only based on my 10 years of experience, but these are not just individuals but types of people I’ve seen in leadership roles. What’s noticeable is that men in leadership roles tend to enjoy them more as the player or playboy, whereas I don’t know any women who are the female equivalents of players or playboys. I’m sure there are some, I just haven’t worked with them yet.

Now, I think certain types of professional paths do not fit these types. Generally speaking, the VP of Finance / CFO is a very sane, rational, and friendly person of either gender. The people I’m talking about are in front-of-house business roles.

I’m not any of these types of people. I don’t want to be.

Who am I? Any of the below. None are VP profiles.

The Problem Solver: I like to see problems holistically, to listen to many different sources and understand all aspects of a problem before coming up with a recommended solution. But mostly I like to use my intuition to solve problems, I don’t have the patience for thorough research or analysis.

The Empathetic: I care about people. I like to listen to their problems and provide advice. I enjoy doing research and planning things to do or ways to resolve issues. Customer support is enjoyable for me because I feel great joy when I can help people, even if it’s providing a simple answer.

The Storyteller: I like to come up with ideas and tell stories. Non-fiction only (I’m not creative) but I like to approach stories journalistically – to find out what really drives people, to tell their stories, to edit and put together something that didn’t exist before.

I am not a vice president. I never will be.

So what am I doing here? What should I do? Where should I go?

It isn’t about just getting another job. I can get another job. But I need to get out of this path. I need to move far away from it. Who knows if there is anything out there I can do permanently that pays money – but clearly it isn’t this.

So, I’m sorry, but not sorry, that I won’t be fixing the stats on gender equality in the senior-level workplace… because soon I will be leaving. I just don’t know where I’m going, yet.



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