Category Archives: Management

Mozart in the Management Jungle

mozart-in-the-jungle

After a weekend of binge watching Amazon’s Golden Globe-winning Mozart in the Jungle, I felt equal parts saddened and inspired. Saddened, because the show follows the lives of artists — musicians — who dedicate their lives to creating. Their madness is enhanced for comedic purposes, yet the madness of a musician is something I mentally relate to far more than that of a CEO. However, I also found the show offering lessons in leadership, and a reminder that the conductor, while expected to be versed in numerous instruments and able to step in to play if needed, is considered successful as a leader, a director, an – orchestrator – not a musician, i.e., an individual contributor.

I’ve always wondered why conductors were considered so important — all they do, it seems, is wave a stick and keep everyone playing at the same pace. Perhaps they would make a bigger motion to increase volume, but it seems to be largely for dramatic effect. What does the conductor actually do? Why do orchestras — filled with musicians who can read music as well as most of us can read the English language — need a conductor to begin with?

My challenge as a manager is stepping away from my nature to be an individual contributor. Although in a small company, I cannot walk away from the individual contributor role entirely, my value is in being the conductor. With this in mind, I return to examining the value of a conductor – not as someone just waving a stick in the air in a marvelous rhythmic dance, but someone who is leading a team, interpreting the “best practices” of the music and adjusting with their vision, keeping everyone together, guiding them through to the final product. The conductor’s work and value, I’ve been reminded, largely is contributed before the product release (aka the performance.)

I think I’m actually a very good manager as a conductor, but when I’m trying to play the proverbial violin and trumpet and oboe at the same time, it makes it nearly impossible to conduct successfully. Although the conductor may step in to fill missing seats, it’s her responsibility to hire the right musicians and then inspire them to follow their greater vision. A manager must do the same thing. She must hire the right team members and determine what role they should play, how loud they should play it, and otherwise orchestrate the score of any given quarter’s objectives.

While business isn’t art, it’s still an orchestra of creation, and still needs to be conducted. Without a conductor in an orchestra, perhaps experienced musicians could play music – but they wouldn’t know which music to play, or how fast to play it, or what to do should one of their violinists get sick for an extended period of time. In romanticizing the life of an artist – which I do frequently – I find myself feeling most alive when I approach my own work as practical art. I can still bring the passion which a conductor brings to the stage in front of a large concert hall during a sold-out performance. I can inspire people to be excited to play their instruments from start to finish, even if they’ve played this score a million times. I can inspire them to think differently about the music, to hear subtle shifts in rhythm and composition, to try new things, take risks, and ultimately learn and grow and make the great music of increasing ARR.

In orchestrating a team, there is a musicality to the work, a rhythm which must be established, an ecosystem of players who must all come together to accomplish a common set of goals. So, while I likely lost the chance to live the life of the broke artist, I’ve gained the opportunity to make a new kind of music – one that 10 years ago I didn’t know existed. When I feel overwhelmed or frustrated or scared, I now close my eyes and imagine myself with a baton in front of an orchestra, and I examine by players as well as the notes written on the page, and with a deep breath, I lift the baton, and my team begins to play.

The Gender Pay Gap from the Top and What to Do About It

Last week, Salesforce CEO Marc Benioff announced that the company paid $3 Million dollars to correct gender pay imbalances across its organization. Although this isn’t a huge number for a company of it’s size, it’s still telling that the firm found $3M in imbalances to fix in the first place. This means that when they ran the numbers they believed that women were earning less than men in the organization for roles of a similar level, and they decided to publicly fix this. But why was that the case in the first place?

As I approach my job negotiations for a senior-level position, and I’m incredibly uncomfortable with doing so, I remind myself that I have to negotiate because any male in my position would. As one woman, I’m not representative of all women, but I can say I find it incredibly hard to negotiate. As a woman, I may read negotiation advice and bring a request to the table based on research from online websites that give some idea of pay ranges. And, as a woman who doesn’t like to shake the boat, I’d typically pick the average to ask for because it feels uncomfortable to ask for anything more.

But I’m not an average woman, and I try to push myself to ASK. This gets harder and harder as the numbers get bigger. I always like to state that it is a PRIVILEGE to have this problem, but it is an issue nonetheless. According to this Harvard Business Review article, the Gender Pay Gap Widens as Women Get Promoted. Basically, the higher up in the organization a woman is, she is likely earning less than her male counterparts. A female executive earns 6.1% less than a male, compared to only a 2.2% gap in an individual contributor role.

The problem with negotiating as a woman is that you can’t win. There is plenty of research that shows women pay a higher social cost for negotiating. I’ve experienced this first hand. In my last role, I negotiated very well (in my opinion) but the I was reminded pretty much every single day from my boss that I was making “so much money” and this made me insecure and ultimately defeat myself in the role. I would have been more comfortable had I been earning less and not rocked the boat.

But what I come back to is this – my role is one that generates clear revenue for the business (well, if it doesn’t, I don’t get to stay for all that long.) I’m working for a for-profit organization in a revenue-generating role, and I deserve to be paid for it. Even then, I have no way to know if I’m overstepping — a man in a senior role can ask for anything. He may not get it, but it’s accepted that he’ll ask. A woman in a senior role worries she’ll offend someone. That’s just how it works.

The HBR article notes that while it’s not clear why female executives are paid less than men, it appears that women need sponsors in organizations more than they do mentors. My strategy has been to change jobs relatively frequently in order to move up and earn more. I would not feel comfortable negotiating for higher pay once I’m on a successful track within an organization. It’s at least a little easier to negotiate at the start — but the big question is, how often do men negotiate throughout the year when women do not? Do men ask for bigger raises each year, or do they request salary increases at a more regular frequency than women? Are the raises of similar frequency but just more substantial due to executive sponsors? These are questions no one seems to have a good answer for, so we’re all left in the dark.

In order to solve this problem, organizations need to be provided training from the top down and bottom up about negotiating. It’s tough to do this because it’s in the best interest of the organization to pay each employee as little as possible to keep them engaged and working as hard as they can. If one employee will accept less than another, this is good for the business, at least on paper. And if no one knows how much everyone else i making, how much can it hurt? But wouldn’t it be crazy if a business actually taught people how to negotiate and encouraged it, making typical negotiation timelines around promotions (official and non-official) more transparent? I wonder if anyone would do that. What Salesforce did is a good first step – but also a good PR move. How long will it be before those salaries are unequal again? And what can we do to fix that?

To start, I’m always going to ask for more, even when it makes me sick to my stomach, and even when I know that my likability factor is dinged, because in the long run to be successful, if you’re a woman, you can’t be liked. You can only be respected.

 

 

 

The Jobs. The Offers. The Decisions. The Lack There Of.

It used to be getting a job offer was a huge challenge. It’s not exactly easy today, but I find myself in a place where I have three serious offers (well two offers and one offer if I wanted it) and I’m trying to figure out what to do.

Both offers at this point are somewhat equal in terms of compensation. Base salary is identical in the initial offers for both. One has a bit more stock, the other, a bit more bonus / cash earning opportunity. I haven’t accepted any so theoretically there is room for negotiation. I hate negotiation. Last time I negotiated I got the salary I wanted but then I was reminded over and over again by my boss how overpaid I was (btw, I wasn’t, given the offers I’m getting now are even more than what I was paid there, so clearly market rate wise I was fairly comped in my last role.)

The reason I hate negotiation is that I have no one at my level in a comparable role to talk to about it. At this level of compensation and given my relatively frugal lifestyle, even for this area – on one hand, when numbers get this big, I feel just downright silly negotiating for more money. On the other hand, I think – if I were a dude or someone with confidence, I’d negotiate anyway. Ultimately, my role in either firm is one that indirectly generates revenue for the business – it’s pretty cut and dry if I have generated revenue or not (granted, I’m not closing business, but I’m still generating it) and thus I think a bonus compensation structure makes sense, and that structure should be more or less unlimited as a percentage of sales, or at least substantial in a tiered structure where maybe base stays about the same but total compensation is based on how well I do my job. If I do my job well – then I’m “cheap” – if i’m not, then I’m – “gone.” Low risk to the company either way, given they plan to hire me (or anyone else for this role.)

But I hate that awful taste of negotiating for more – and ultimately I want to pick the job where I can do THE BEST job. And I don’t know which that is right now. I’m not at the point in my career where I can get an offer at a company that has its shit together. That means either I get an offer at a new, young company where it’s still figuring things out, and where it needs someone who can deal with the ups and downs of startup life — OR I get an offer at a company where things are probably more systemically dysfunctional due to years of poor management decisions, but one that has managed to sell enough of its product/service to still be alive either private or public, it doesn’t matter as both come with their own challenges.

I seem to be a perfect fit for those environments, maybe thanks to a very turbulent childhood. But I also think a positive, healthy, rather successful work environment would be nice. My challenge is that I’m not so great at maintaining the status quo. I’m someone who comes in and creatively solves problems. I fix things or build things but I certainly don’t inherent the same old and run with it as such to collect a paycheck. I like moving fast and getting in and making a difference. But then, as history has proven, either I do that really well for short bursts or I can’t manage to figure out how to fix things fast enough and I’m out.

My last job was a trainwreck from the start. CEO who sexually harassed (in a joking way, but nonetheless, it was sexual harassment) most of the women in the company and heck, even some of the men if you were to ask a real HR department. I learned a lot in the role but there were just so many things wrong with the company that I felt lost at what to do. Too many things to fix. Too many holes to fill as water would start leaking out another opening I didn’t even see.

If I go to the smaller company, my main priority will be to hire a small handful of really great people really fast. Hiring is hard. People have to want to work with you and the rest of the team. You (me) have to be a leader. A true leader. In my mind I like to think I’m a leader but what I see in leaders I admire I don’t see in myself. They are very strong, determined, and once they pick a route they don’t chance course (and if they do it certainly doesn’t appear they did this because they realized they made a bad decision.) Leaders have a very clear vision and get everyone aligned to common goals. I have a hard time getting myself aligned to a common goal, let alone a team.

The larger company would immediately have me managing a decent-sized team. It’s a huge opportunity in that if I can successfully manage a team and help them become more productive, that’s a metric I can take to the bank for the rest of my life. I can also build a team at the smaller company and have a similar outcome, but at the second company I would’t have to hire immediately. I’d have something to work with. That can be good or bad, depending on the contributions of the team today and what I figure out needs to be done to hit goals. It likely involves being able to come in and, if anyone isn’t holding their weight, being that bad guy and letting people go early on and replacing them. You know – typical management stuff that I don’t like to do because I’m an INFP and I can’t handle hurting people’s feelings, only letting them down.

I still am most excited by the smaller company… if the larger one was a bit more stable, or selling a product that I could get extremely excited about, it would be a different story. But I have some good opportunities here and I just need to finalize what I’m going to do… it’s a good problem to have, for sure. I just am at that point where I really don’t want to make the wrong decision… and I’m not sure there’s a right one to make. Because – when it comes down to it, I’m in the wrong career overall – but it’s a hot market and people keep throwing money at me and it’s hard to say no. It’s easy to say – one more go, let’s see if I can make it happen… I’ll try my absolute best… and in the meantime, keep on putting away $5k a month to attempt to reach my goal of $500k in networth before I give birth to my first child. After that, I feel like I have a bit more flexibility/freedom to maybe switch jobs and earn less, or consult part-time at a higher hourly rate, or… anything other that continuing on this trajectory which can’t be forever.

 

The Reality of My Professional Apptitude

As I review my next steps, I have many, many, many variables to consider. Above all, I want to take on a role where I can be successful *long term,* not just for a few “burn myself out” projects — OR, take on a role where “burn yourself out” projects are the norm. I’d be much better off in a creative industry working on television shows or movies, but it’s a bit too late for that, especially given my massive fear of change. I’m trying to work with what I’ve got here. And, at the least, I have options. And good ones at that.

Ten years ago at about this time, I was getting fired from a marketing internship at a non-profit. It was my first year out of college and I didn’t know what on earth the future held or what I wanted to do. I applied for hundreds if not thousands of jobs and rejection emails gave me a warm, fuzzy feeling that someone or something out there reviewed my experience, or lack thereof, and decided to personally not give me a chance. Since the full-time job thing wasn’t working, I applied to a pretty-much unpaid reporting internship and, when I found a place to live, found a part-time admin job which was never a good fit for my ADHD self. I survived the entirety of the internship, but the part-time admin gig was, well, a predictable disaster.

Although I moved on and continued to apply for job after job after job, I didn’t know what I wanted in life. I had no friends in the area, very little family, and the only reason to live was to try to make money… to save a little bit… to build something when everything around me was crumbling. I somehow impressed a magazine that I was a worthwhile hire for an editorial assistant role and I stayed for a year, writing articles and attempting to become a better reporter. But my social anxiety really got in the way of that. I did the blogger thing for a short while, which was even worse, because bloggers need to be super aggressive and not let anxiety get in the way of getting a scoop. My journalism career practically ended before it started.

Without rehashing my C.V. for the thousandth time, the point is that I haven’t really massively succeeded in any one role. There have been pieces of roles where people have seen my strengths, and there have been times in the past 10 years where I’ve really poured my heart and soul into projects, and they’ve been considered significant successes. But nothing has ever been sustainable – you can say I just need to suck it up and work, but when you have ADHD and bipolar disorder, it’s not that easy. My mind doesn’t work that way. I have the potential to do great things, or not so great things, but very rarely anything in the middle. I seem to be failing at acceptable.

When it comes to my two or three job opportunities that are getting closer to being real, I consider all of the elements of the role and companies. A few of you long-time readers have warned me that it would be absolutely idiotic to take on a role at a smaller company again. But – there are reasons I failed at those companies that #1, are unique to the companies (not due to their size) and #2, there are similar issues that would happen at a company of any size. If anything, I am more suited for smaller companies because I need to move fast and get things done, or else I get bored and demotivated, and that’s when I do my worst work. If I’m just a cog in a corporate machine, I might keep my job longer just due to HR policies, but I certainly won’t be helping myself or my firm.

The smaller company job is exciting to me right now because I can see many things I can do in a very short amount of time to make a huge difference. I want to compare this opportunity to my past failures at smaller firms to try to hash out the difference, and realistically explore why a smaller company is or isn’t a good idea…

My past two companies, which have ranged in size from 20 to about 100 employees, had significant challenges unique to each opportunity.

Upon leaving a smaller firm where I stayed four years without getting fired(!), I took on an opportunity I knew I wasn’t the right fit for. The head of the company was an expert in my field, and while it’s his fault for hiring me without asking some basic questions to establish if I actually knew what I was doing or what he expected me to do, I also had a boss who had a very set way of how he expected me to get my job done. I really didn’t know what I was doing and it became clear pretty quickly that I wasn’t the right fit. If I were to take on that job now I’d actually do  much better at it. I still wouldn’t be the right person for the position, but I now know enough that I could have lasted longer. I was just clueless and five months in when I was let go, it was the right decision for the business. Given the industry the company was in, I couldn’t even do the things I do best there because of the industry. It was just a very bad fit from the start.

My next job, where I stayed a year (which is respectable in startup time), I picked a company in an industry that I care about. Yet again I found a CEO who was starry eyed about me and recruited me so aggressively I had no time to discuss my strengths and weaknesses. I was thrown into the fire, but at least was given a reasonable budget to work with. But everyone at this company would agree – there are some serious management issues teetering on schizophrenic. Another trend – the head of the company had a background in something similar to my role, so he had a lot of strong opinions on how to do the job, and would basically force me to do a whole bunch of things that didn’t make sense at the expense of time to do the things that had to get done. I did fail to hire a team for a number of reasons, some of which were out of my control – the biggest problem was that the company had a lot of fundamental issues and it still does (lots of people have quit by choice over the last few months and the trend seems to be continuing.) Beyond the basic issues of the core business, the head of the company’s behavior teeters on sexual harassment (anyone working at the firm would agree) and everyone working there is so stressed and upset that they end up taking it out on each other.

Despite the challenges at the company, and it being the right time to leave by choice or by force, I learned a ton in the last year. I worked with an outside agency who taught me a lot about how to do my job. I learned how to not waste money through a bunch of trial and error and how to do things faster. I also discovered a bit about the types of people I like to manage and the types of people who I cannot manage. I learned how important recruiting is and how challenging it is at any company but – it’s actually easier at a hot young company than a big corporation or a startup that has been around for years and is on the verge of falling apart. If you can’t attract the right candidates to your firm, you’re pretty much fucked (or you’re spending a whole lot of time on recruiting that you should be spending on getting your job done.)

Ok, so why even think about going to a smaller company again? Haven’t I learned my lesson!?! Well, as you can see, a lot of the issues had at these companies were company-specific, or addressable by the fact that now I have about two more years of experience and I much better understand the bigger picture. I understand how much things should cost so I’m not freaking out every minute about budget and wasting too much money or not spending enough. I’m not saying I’ll be perfect at my next job, no matter where I go – but I do know I do my best work when I care about the product my company is making and respect the people who are making it.

The smaller company I am considering is SMALL, don’t get me wrong — there will be challenges for sure. But the founders are a bit younger – closer to my age (I think the head of the firm is maybe 2-3 years older than I am) – and this makes a huge difference in team chemistry and respect. I’ve always worked for teams where the execs are in their 40s/50s, and much older than I am. I’m fine being the only woman in a senior leadership role, but it helps with the others aren’t all dudes who are going through their personal mid-life crisis while making the younger women of the company feel uncomfortable.

What’s great about the small company is that I believe in them. I see that their product is already getting a lot of traction, and I see a lot of ways I can quickly help – and I’m super excited to jump in and do just that. I know I have some hiring to do – but I also have the momentum of the company and it’s early stage to help source the right talent. There are really two types of employees in Silicon Valley – the ones that like early stage startups and want to be part of growing something — and then the ones that want to work for a very late-stage startups or public companies that are big and somewhat stable and come with that fancy brand name and cult-like culture. It’s really hard to hire for the middle ground… the companies that are not hot, sexy startups but that haven’t made it… the ones that are dying a slow and painful death, who often have second or third CEOs who are brought in to “save” the company which had about a .00000001% chance of actually saving.

So, in short, not all small firms are created the same AND my experience today is vastly difference than my experience from a year ago. I have a fairly strong opinion on what to do and who to hire, and I won’t be floundering quite as much for the first six months on the job. I’ll certainly hire a detail-oriented person to be on my team, who balances out my big-picture strategy style. And I just think I can knock this one out of the park. If I didn’t, I’d never even consider it. But something tells me this is a really good opportunity. But I could be delusional. I could be lying to myself because it’s the most exciting opportunity, but not actually the best fit. I’m trying to sort that out.

The larger private firm is also a really good option. What I can’t figure out is how much is broken right now and how much is working. It’s not a stable public company and it’s not a small, early-stage company with the fun moments of cherishing each win and feeling part of that with the whole team (I really love that about smaller companies.) My role would be very vital to fixing some of the pieces that aren’t working right now… and I can see what those are and have some ideas how to get things in order… but once I get the basic stuff functioning, I’m not sure where I’d go from there. The role seems a bit more limiting. The company’s product, while useful and needed, is not something I can get super excited about. Maybe that’s a good thing? But I’m an INFP and I really need to feel morally connected to my work. I told myself I’d never work for a company selling to marketers again, and, quite frankly, the two larger opportunities I have are selling to marketers. I’m not sure that’s the right fit for me either. Yes, it may be more stable and it may be closer to home and the salaries may be higher (don’t know that yet) but… if I’m not feeling passionate about the product I’m just going to crash and burn pretty quickly.

There are other jobs out there — but so much of the business technology lacks the human side. I like to have that human piece to spin stories and generate buzz. The smaller firm has so much going for it around the stories I can tell, and that’s what I do best, with the right company and right stories. I think I could help all three companies but I see my value being most at the smaller firm. I think what they’re looking for and what they value is a lot more in line with what I do best — they very much appreciate that I can do all the other stuff, but I do feel like they’re hiring me for the skills I actually have, and will value my ideas and contributions in those areas vs constantly debate me and tell me I’m wrong.

So… I am most enthusiastic about the smaller opportunity, but I’m also not 100% on it. I think that the feedback from my readers warning me to not go to a small company again has merit. I hope the above explanation shows why I’m not just jumping into any smaller firm, and that this one specifically excites me for a lot of good reasons. It will be hard and a lot of work… but I want to feel inspired and work hard. I want to go to work everyday thinking that I feel good about building something great with people who deserve to be winners. Good people who aren’t sociopaths or narcissistic or delusional or suffering from borderline personality disorder. Just people who want to build something great. That’s where I want to be, and that’s why I’m excited about this opportunity, history be damned.

 

 

What on earth should I do?

Two companies are about 24 hours away from giving me official job offers. Meanwhile my old boss has a consulting project for me to start Monday – if I want it. I’m on unemployment now and the messed up thing about unemployment is if you take a side project that’s short-term you can end up losing your unemployment earnings (which aren’t that much at all but still) — I mean, I make about $1800 a month on unemployment so theoretically I would work one week a month and make that at my going rate… so it’s not like, the end of the world if I lose unemployment, but it would still rather suck if I can’t find consulting work and these full-time ops don’t pan out.

I’m trying to be really smart about this next job thing. And I’m really not sure what to do. I wish I was comparing apples to apples here but I’m really not. I have so many things to take into consideration. The logic side of me says to go work for the slightly larger company that is more stable and get a solid name on my resume that people will know. The passionate, excited, wants-to-do-something-i-love side of me is really interested in this opportunity to run a department at a very small company (<20 people.) One thing I would do for the second opportunity is make sure to negotiate in specific headcount before I accept the job. I’m looking to build a team, not be a one-person-machine masochist. Which is what I normally am.

I could also feasibly convince everyone to hire me as a consultant, but I’m not sure that’s an ideal route either. I mean, I’m not sure what my rate would be. My friend said I should bill $125 an hour. I think I’d try $150 and see if people would go for that. Compared to FT salary it isn’t that much w/ self-employment taxes, health insurance, buying supplies, non-covered transportation, loss of unemployment income in the future if needed, PTO & maternity leave (if provided by company), et al. Those costs add up fast. I figure if I could work 40 hours a week for $150 an hour, though, I’d be doing very well for myself. And I’m sure I’d be a whole lot happier and way more productive in those 40 hours. But I really don’t think these companies would be open to hiring me PT, or for that rate.

The problem with the small company is that it’s far away from where I live again — big red flag — but I’d also really focus on negotiating remote work before I sign on the dotted line (like 2x per week remote plus occasional longer periods to work from east coast.) If they really want to hire me, I’m going to make sure it’s on my terms. Otherwise I’ll go to the bigger company which is closer to home and that probably has better benefits since they can afford them at this point.

But — there is a part of me that’s thinking this is my last big shot to do a startup and really run with it. Yes, I’ll prob be a young mother at some point in this journey — but I can get a good year in before I have a kid right now (i mean, it takes 9 months to have the kid even if I get pregnant at some point in that year.) I can do a lot in a year with the right team. When I have a kid I’m def going to want a job closer to home and such, and there will always be those opportunities out there. But now… I just want to go somewhere where I can make some magic happen.

 

Do I Choose to be Stressed?

A friend of mine, a stay-at-home mother who is married to an engineer who is likely earning over $200k a year, has told me to stop making choices that make me so stressed. I should go to a mindfulness class, she says, as this helped her resolve the majority of her own anxieties. They aren’t rich by any means for this area, but they do have a small condo that the husband’s parents purchased and they are renting the unit from them. I agree with her that I put myself in stressful situations and even when I don’t I have a tendency to stress about every little thing, but it’s hard to have a conversation with her about the stress I feel about money and the ability to live a comfortable life. I hear my mother’s voice, someone who doesn’t really want to understand money or retirement savings, but who just assumes it will all work out. And maybe it will for her. And maybe it will for me. But maybe not.

In the case of my life, I just don’t see it all magically working out. I have to make it work. And,  yes, that is stressful. I am literally making the choice between jobs that will pay over $150k and jobs that would pay $60k — and the crazy thing is it’s easier to get hired in the former right now. Those well-paid jobs come with a heaping dose of responsibility and the corresponding stress.

Here I am, one month from turning 32, and — this is the year I’ll get married and when I want to try to have children. I know having children will be challenging due to my health issues, and I also know that stress can contribute to infertility and miscarriages. I need to focus on being healthy and stress-free right now, but that’s hard to do when I am staring down these startup jobs that I’ll always feel under-qualified for and incapable of any sustained success. And just logistically these companies don’t have paid leave for maternity or anything, so I’d basically have to quit when I have a kid, if I have a kid. Which really sucks since I’m currently the breadwinner (well, at least prior to getting the axe!) I don’t know how I can make this work. It works FINE now – living in a one bedroom apartment and being ok with having to move if our rent goes up too much… but I can’t do this with kids. I mean, people DO do this with kids. But if I’m stressed now… then I can’t imagine how I’d feel then. And I don’t want to be a stressed out mother around my future children.

Today, I’m trying to decide whether to do COBRA for health insurance or to purchase it on my own. Neither option is great. For $550 a month I can have a $1500 deductible plan… or I can buy my own and do something like $350 a month for a $5000 deductible. In either case, it’s just a catastrophic plan and any other health needs… like… pregnancy stuff… wouldn’t be covered (well, it would go towards that impossibly high deductible or not at all.) My fiance doesn’t have insurance through work so it’s not like I’ll be better off when married. We’ll just be paying more in tax (if we’re both working) as our big reward for tying the knot.

I know I’m fortunate to even have these problems… but the next few years of my life are legitimately terrifying. These are the years when I either become a mother OR become a woman who never has kids. Either is a major, major life-defining situation. I want kids, even though I’ll never feel ready. I don’t want to watch my 30s go by and have just let work become the only thing that matters in life. And I’m the type of person that is all or nothing — it’s so hard for me to be just enough, but not too much, especially when in the startup world the general unspoken agreement is that you should work 14 hours a day, 7 days a week (give or take.)

Becoming a contractor would be ideal – for the flexibility – but then I’ll really have to deal with the health insurance situation… I mean, after rent, health insurance, and car insurance … that’s about $1800 a month right now. I just don’t think I can – for the long term – do the consultant thing. I think, even though the stability kills my drive, I need it. I just don’t know WHAT to do. It’s not like I can bring up the whole “hey… so I may get pregnant in the next year or two… and also, I may need to take crazy hormones and take time off of work in order to get pregnant because my body doesn’t work so can I negotiate some of flexibility into this contract or you know what just go hire some woman who doesn’t want kids or who already has them at least or just someone who probably won’t have substantial medical issues trying to get pregnant.”

My friend would tell me that I shouldn’t be stressing over this. But, I guess, I would want to ask her if she’d be stressed if she didn’t have a stable place to live and a husband with such a well-paid, high-stress career. She says she doesn’t care about money but I know she likes nice things — she has good taste — and I know she says she doesn’t really care about money because that would be too stressful, but that’s because at this point, perhaps, she doesn’t have to care, or she chooses not to think about it or be involved in her financial future.

There really isn’t anyone I know who is in a similar situation either — my friends here (the female ones) are either married and stay-at-home mothers or part-time self-employed types with husbands who have high-paid tech jobs, or they’re in a situation where they’re making about the same as their significant others and will probably leave the area since their careers don’t provide the salaries needed to last here. I don’t relate to (or have any friends to people who are) powerful women who have high-paid jobs. I mean, I’m not that type, I’m just faking it… for now. I really want to just tell these companies I’m interviewing for all the reasons they shouldn’t hire me… because I’m so tired of being a good interviewer but then feeling like I just don’t know what to do or how to do it when I start – or especially after I get through the few things I know how to do… and am left with a whole bunch of “figure it out” that never goes so well when I’m in charge.

 

 

 

 

 

 

 

 

Not The Best Year Yet.

Shortly after I was given a new boss said new boss announced that he wants me to leave the company. The company is, from all appearances, protecting themselves and providing some sort of a performance plan to document any and all mistakes, but it seems that no matter what I do right now I’m dead man walking. Needless to say, such a feeling isn’t exactly the most inspiring when it comes to driving further engagement and one’s best work.

At the moment, whether it’s my paranoia or accurate analysis of said situation, I’m hypersensitive to each criticism flung my way by my boss who is not at all supportive and who clearly wants me out. Yesterday. I’m pretty sure he’s overreacting to every tiny error on my part just to build his case to throw me out the door, and there isn’t one person willing to step up and protect me. To be fair, I am not the ideal person for this role, and I’ve struggled with the position both from the day-to-day tasks of the role, as well as in building a team (let’s just say the few hires I did make ended up embarrassingly failures before they even started… and then they never even started!)

Right now I’m in this pickle of a predicament where the only type of roles I’d be considered for are more senior level roles in my particular field/area of my field – yet, those are the jobs where I feel like I’m not the right fit. Sure, I can brainstorm strategy and come up with some good ideas – but I’m not a good team builder and I’m certainly not the best when it comes to ongoing detail-oriented execution. Clearly I can do well enough in an interview(s) to convince certain types of executives that I’m the IT girl that is going to skyrocket their business to success. Then reality hits. And it’s only a matter of time before all the shit hits all the fans. And I’m back to square one.

Then again, I tell myself – maybe this time, it will be different. After all, I’ve learned quite a lot in this role, many things that looking back I could have been much more effective doing if I had such insights before playing a fast-and-loose game of trial-and-error. Maybe I wouldn’t be any better at the execution but I’d be better at staffing up early, hiring for people to do the things I’m not good at (vs trying really hard to prove to myself I can do everything when clearly that’s a recipe for absolute disaster.) Maybe with a fresh opportunity and a growing company I can actually do a good job.

That is the futile optimism that continues to lurk relentlessly in the crevices of my foolish skull. My mental illness, inability to sleep on a regular basis, and general existential emptiness ensure that I run blindly off cliffs in any which direction all while telling myself “I CAN DO THIS.” (No, I can’t. And, fuck it, that’s ok to admit.)

Managing people is it’s own skill and personality type. It’s rewarded handsomely with much better salary and benefits than just managing yourself. It also means that you have to somehow have the ability to take pride in your team’s success and take on some of that success for your own bragging rights (which are necessary to keep you employed vs having a younger, faster, better and eager employee who earns significantly less than you do take your place) and manage to buffer team members who are not performing as well from the powers that be, falling on the sword, so to speak, for those who aren’t performing, and/or figuring out how to jump in and fix shit that you may or may not have any idea how to do. Management sucks.

All of the mind games of corporate life – even in a startup – are too much for my INFP psyche. I’m just a sensitive sap who should be an artist or novelist but instead is writing a series of entertaining yet unfinished whitepapers and shaking hands at conferences silently begging her social anxiety to shut the fuck up. It’s no longer just a cute recurring nightmare of my 20s, this is my life – my career – the entirety of the next however many years I face ahead of me until retirement, and I don’t know what it is that I can do, in a stable sense, to have some kind of sane life where I’m not desperately looking for a new job every 6 to 12 months and ending up right back where I started.

You know?

 

 

 

 

Leadership lessons they don’t teach in college…

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

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

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

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

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

Only if you refuse to accept its definition.

Definition of LIE

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

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

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

Point Made: Improving Communication Skills

When I was a freshman in high school, I took a class called “speech and drama” where half of the year we focused on public speaking skills. One of the things the teacher would say to have us focus on being crystal clear in our speech was “point made.” It was something everyone in the class would get told on occasion, but it practically became a running joke every time I had to talk. Succinctness, if you can tell from the lengthy posts on this blog, is not my strong suit.

Being verbose might be beneficial in a social situation when you’re in a room full of introverts who would prefer not to speak or at a table of people who culturally like to talk a lot to and over each other, it’s not ideal for the board room. While I’ve gotten to the point in my life where I actually believe in my points that I’m trying to make, I’ve yet to uncover how to turn my mush-pot of a brain into quality communication. My boss pointed out the other day that I was verbose and sounded defensive over a project I was in charge of that didn’t go over so well, and speaking of points I agreed with his. Yet I find no matter how hard I try I just cannot in the moment figure out how to produce words that say exactly what I want to say without babbling. It’s especially hard on conference calls as one cannot quickly see others in the room zoning out.

I know I need to focus on improving my communication skills if I will ever be a successful executive. But how do I do this? Yes, there are things like toastmasters and such, but those are more for getting up in front of an audience and presenting. I could use help there as well, but my bigger problem is just general conversational communication. I did not learn this from my parents as my mother is the type who will just talk your ear off and my father, while he’s better at debating, is so convinced that he always has the right answer that he taught me that I’m always wrong (unless, of course, I agree with his POV.) I wasn’t taught that it’s ok to stand your ground or believe in your point so much that you don’t need to constantly defend your point. The more you defend it the weaker you seem, the quicker your conviction foils.

So I have good ideas, just as good as anyone else, yet some people with good ideas get others to buy in and stand behind them and others just get lost to the wind. I can take my ideas and execute on them and then finally people see that they were good ideas. I’m not the type who can just speak with great charisma and get others to join alongside me. That’s what I need to be if I’m ever going to become a successful executive. But is that something that can be learned, or is it just not in my personality? And where could I go to learn such a skills, if it is learnable?

Life Lessons from X-Men: Days of Future Past

It’s nice when mainstream action movies attempt to present a very eloquent message about the state of our world. The X-Men series doesn’t shy away from prothletising its own ethics code. Of course all of our famous stories of good and evil do this somewhat, but X-Men Days of Future Past specifically touched on how everything we do, even in an instant, is a choice that can dramatically shift the course of the entire future.

Two days ago, sitting in my psychologist’s office, we had a very good session. She recently moved to a new location where there is a large open glass wall behind her chair overlooking somewhat wild nature. One could almost forget she was smack dab in the middle of bustling Silicon Valley, where the suburbs are about as urban as many other small cities. I’ve been seeing this therapist for over a year now — which is a first for me… I usually go to a therapist/psychologist et al when I’m going through a massive depression and have them talk me out of it for a month or so and then I’m back in my own wilderness. Not so in this case. It’s surely isn’t cheap but the routine of going to see her weekly is helpful. Continue reading