The Challenges of Being an Effective Leader

To be an effective leader, perhaps the most important ability is being able to hire well. As I’ve said before, when directing a theatre production, 90% of your success is achieved by casting the right actors. You have one chance to get that right – because you can’t really fire actors (especially if you are not paying them), so you better make your picks count. You can hire great actors and do nothing and still have a reasonably good result, or you can hire poor actors, try hard to direct them, and still end up with a mess. It’s exactly the same with management.

The challenge with hiring though is the quality of your employees trickles down from the top. As a manager, you are tasked with bringing in A players. Your success depends on it. But if you aren’t the best at recruiting or hiring others, and your firm is not, say, “Apple” or “Google,” you have to figure out how to recruit great people. Getting heaps of applications isn’t the hard part — getting the right people to apply, move them through the hiring funnel, and closing them is. Every manager must be great at marketing and sales, especially those who are at companies whose name does not yet do all the sales before the candidate walks in the door.

I know if I’m going to be successful in my current position I need to hire fast, but not too fast that I bring in the wrong people. In order to attract high-quality candidates, I know I’m already handicapped. This is the case of many newer managers, especially in innovative industries that naturally attract candidates who were genetically modified for a high IQ since residing in utero, who also are only interested in working for Ivy League-esque graduates. Just as a talented actor won’t audition for a play directed by an unproven director in a local theatre which has yet to make a solid name for itself, talented professionals are weary of working for companies and managers that don’t have a long list of gold stars on their C.V. Not only do you have to sell your company, you have to self yourself as a great manager. It’s a lot easier to sell a company you believe in — harder to sell yourself when you don’t even look like a great manager on paper.

The only way I’ve managed to scoop up one great talent, at least part-time, is due, strangely enough, to him knowing everything that goes in my mind, as he is pretty much the only person I know IRL who has access to this blog. It’s my one success story, but I need to hire more talent like him, and that’s proving very hard. At the end of the day, I have to hire fast, but also get the right people in the door. I admit I’m not doing a good job at it. I’m also in that hard place where I’m a young manager, so I’d be better off hiring talent older and more experienced than myself, but then I don’t know how I’ll actually remain the manager. At some point I have to ask if the person I should be hiring for is someone to manage me.

This opportunity is so remarkably huge that I don’t want to screw it up, but I just don’t know if I have it in me to do this. With the opportunity comes the weight of needing to move oceans fast in order to succeed, and my success = helping many others be successful as well. If I fail, I am not only failing myself, I am failing my team. I feel infinitely stressed and terrified. I love so many of the pieces, the industry, the people, the intellectual side of telling the right story, and much more. But I also see myself crumbling yet again. I am trying to be strong. I am watching the opportunity disappear before my eyes as I fail to effectively lead.

Then, when I do have resources, managing them just doesn’t come naturally to me. Growing up not playing team sports, I never learned how to be a team player. In the arts you are pretty much in it for yourself. But when it comes to business you are not important. You must be a machine, making your part more efficient and productive. You must be clear on objectives, and once you’ve hired the right talent, make sure they have what they need to be successful. You also need to know if said talent isn’t delivering, and if it’s your fault or theirs, and if it’s theirs can you provide guidance to help correct this, or not, and are you even capable of providing the right guidance?

Maybe leaders – mostly men – are better at faking it until they make it, especially when it comes to management. I feel as a woman I already have less natural respect statistically. As a young female leader it’s worse. Then I show weakness just once or twice and I’m done for. I wonder often if it’s already too late.

What does the ideal manager look like? Is she flawlessly dressed, hair with an “at home” professional-looking blowout, body toned from daily pre-sunrise workouts at the gym, protein shakes, and weekend 8-mile hikes to ensure her body is in tip-top shape? Does she spend thousands of dollars a month on clothes and accessories to look fashionable without trying too hard, each item in her wardrobe tailored to fit her toned physique? Is she so organized that every day she creates a list of “to dos” and knows exactly what her team is working on at all times, so she effectively communicates this up the line of command and motivates the best work in her direct reports, while always being one step ahead of any potential fire drills? Is she a duck smoothly gliding across the executive pond while kicking furiously underneath, moments away from drowning?

I feel constantly I’m not strong enough for this. I don’t know when I should push vs pull, to chase vs accept, to strive for perfecting the important details vs just let them go. I think maybe one day I could be a decent leader but maybe I’m just not ready yet. It’s only I don’t want to blow this opportunity. I really want to fake it until I make it, to at the very least ensure we hit our numbers to provide time to fix what’s broke and to grow into the leader I would like to be. I may be on the verge of a mental breakdown, or professional breakthrough. It’s too soon to tell. But as I comfort the chaos in carbohydrates, I fear I’m quickly aging and falling apart, trying to hold myself together so no one would guess just how broken I am.


What Did You Want to Be When You Grow Up?

When I was a little girl, I never for a moment envisioned myself as a grown woman. I’m not sure how many kids actually picture themselves as grow ups, so maybe this isn’t that strange. I could easily imagine myself as a teenager, but not any form of an adult – not a working woman, not a mother, not anything other than an awkward child.

Maybe if I had some vision for myself as an adult, this all wouldn’t be so hard. If I had grown up watching a mother put on a suit each morning and go into the office, coming home with stories about her own boss and sharing her tactics for handling adult life. My mother, like many mothers of babies born in the 1980s, was a stay-at-home mother.

She was a helicopter mother because she didn’t have anything better to do. Her entire life consisted of bragging about the accomplishments of her children. Every tiny win was a huge victory the world needed to know about. Every struggle was ignored. Emotions outside of anger and anxiety were not allowed in the household. No one knew how to handle such an emotional, insecure child. I never learned how to handle myself.

This weekend, I saw the movie Birdman, which is a film about a man who has basically lost his shit because life didn’t turn out quite the way he expected. While his psychological illness is one of delusion, I could relate to the feeling of hopelessness and angst surrounding all aspects of life not particularly epic. Perhaps it was the two-drink brunch and stresses of my work that brought me to tears through the film, along with my own compulsive self obsession, but I felt as if I were drowning. The film tossed many personally uncomfortable themes together – regarding life, parental misguidance, and the need to be not just loved but admired.

Gasping for air as I shoved a bag of drunkenly purchased move theater candy into my mouth, I didn’t want my friends who were also at the movie to my right to notice that I was having a minor emotional meltdown. I escaped to the woman’s restroom once the credits began to roll and muffled my overly dramatic tears with a few fraudulent flushes.

I’m far too sensitive. Both my boyfriend and a friend have said this in a different combination of words and looks of concern. Despite getting myself into professional situations where I take the brunt of deprecation, it is my own fault for allowing others actions to push me down so quickly and so hard. My boyfriend, like my last therapist, reminds me that so much of ones mental state has to do with their own internal monologues. He says that I need to actually believe that. I believe that if I believed whatever it was I was saying to myself – but just switching the talk track in my mind from “god I am so terrible at this” to “I tried my best and I think what I provided was actually good” is not going to change the fact that I believe I am so terrible at it.

Or, I have no ability to gauge what good enough is, since the only good I’ve ever learned is the one which can be paraded about for the neighborhood to see. It was artwork which wasn’t extraordinary but pretty good for a teenager. It was performing a solo at the school talent show despite being partially done deaf, and all of the photos which could come from the occasion. When one is not rewarded for being average or being just as good as the next person, it can effect a child in different ways. For some, they work harder, always feeling better than everyone else, but never quite being fulfilled. For me, I lost the tastebuds for the modicum of success that one must survive on in adult life.

The advice I received is not to let things said to me at work effect me at such a deep level. If my boss is not going to be happy with the work I produce, then either I figure out how to produce better work, acknowledge no amount of work will every satisfy him and do my best, or I look for another job. There is no point in just wallowing in self hatred because despite how much effort I put into my job I feel like I can’t produce what is needed for success. And, while I rarely discuss my emotional turmoil with those I know outside of those who read this blog, I can’t let myself slip into the land of suicidal ideation. Even though I’d never actually kill myself, it’s not at all productive to spend the remaining minutes of my life when I’m not at work or doing work fantasizing about the beauty of just being done with the world, since that’s the end result of all this anyway.

While I never pictured myself as an adult, today the picture I have of myself as the adult I hope to become has nothing to do with professional success. Today, my only sense of satisfaction comes from seeing my networth increase towards my annual goal. I do not find happiness or satisfaction in anything else, except perhaps exceeding my clearly quantifiable quarterly goals at work. Since when did I become so boring? I can’t make small talk because I have no hobbies. I don’t have time for hobbies beyond occasionally pouring my heart out in an anonymous psychological illness journal disguised as a personal finance blog. I tried to sign up for a club in the evening during the week after work but then my boss required me to meet in the evening and so I was unable to go to the club. So much for trying to build some sort of non-professional “life” for myself.

I fully acknowledge that I’m getting paid extremely well at this point in my life and I don’t want to fuck it up. I’m learning a lot and even though each day brings its meltdowns and takes weeks off of my life due to the stress that I let build up in my chest, I am in a very good place for many reasons. If I screw this up, I don’t know if I’ll ever have such a good opportunity again. I keep reminding myself this is not a forever thing, this is a focus and just move mountains now thing so I can open doors for the rest of my life and have options thing. I know I’m so fortunate to be in this place, yet I seek to find some resolution to the emptiness, the wanderlust for the epic, the acknowledgement that after all these years of thinking life was more exciting on the other side of the great youth-adult divide, the reality is that life is just a series of repetitions until our bodies fail to reboot for yet another go at it.

Is it so horribly wrong to want my parents to be impressed with my accomplishments? My father constantly reminds me that I can’t hold down a job, even though I’ve informed him time and again that spending 2-4 years in one company is completely normal for my industry. There are days when I just want to tell him exactly how much money I’m making because perhaps that would be enough to impress him, but that would open up a whole new can of worms. I’d forever regret having explained to him how I’m making the same if not more than most MBA graduates my age, despite having only an undergraduate degree in something unrelated to business — it would turn into some guilt session about how I should buy them nicer gifts, or how I should be purchasing a house now instead of renting. Worse yet, when the day comes that I leave this role, and if I was to decide to pursue something that pays less, which would be likely, I’d never hear the end of it. So I keep my mouth shut. I think to myself, every time I receive a paycheck, how proud they’d be if they only knew how far I’ve come.

Then I think to myself, damn, it’s sad that your parents aren’t proud of you for, you know, being in a stable relationship, or being “happy,” or having a job in the first place, or that you even care so much about what they think, even though you’re now a living specimen of a grown woman.

The whole overly dramatic depressed rambles aren’t very productive, but they’re what goes on in my mind day in and day out, nonetheless. I wish I could turn all of this energy into something useful. I think of all the great authors who have suffered with their own inner demons, who feel deeply enough to express the intricacies of human joy and suffering, yet create fiction with lessons for humanity that far outlive their demons. It is wrong to romanticized the disturbed creative mind, but it is at least calming to acknowledge that most of the world’s greatest poets, painters, and writers would probably feel just as tortured attempting to neatly fit into the box of corporate executive #280258019.

For all my incapacity for embracing the lull of routine, I’ve managed to force myself into a box in which I clearly do not fit. Every morning of everyday I roll out of bed, wipe my eyes wide open, and fold myself into myself until I look halfway presentable as some grown up woman going about her day. And I fight through my life with the hope that maybe someday, somehow, I’ll no longer feel so far removed from the world around me, that I’ll wake up and know what it’s like to be “normal,” and not waste so many precious seconds drawing out a romantic fantasies where either I’m some great savior or gone.

Time After Time After Time

Our childhood is like the first lift of a roller coaster, the very first time you experience a thrill ride of this scale. It takes what seems like forever to get to the top. While it’s scary, you’re headed up the entire time, and while you can’t see much past the peak, the drop is inevitable and even desired, in a twisted sort of way. Adolescence is that brief moment in time when you’re at the top of the first peak, manically exhilarated by being at the top of this massive hill you’ve slowly trounched up — having absolutely nothing to do with your own momentum and everything to do with a lift in place before you even got there — and ready to the point of obsession to free fall into adulthood. And then, well, then you’re on the ride.

Up, down, down, up, upside down, and around, and around, life flies by and your stomach drops with every unexpected jolt. And then, the ride comes to a halt, slowing down briefly before pulling into the station, and you’re done.

It would be a lie for me to say I miss my childhood immensely, because I was miserable during my childhood and wanted more than anything to escape that first long lift hill and experience some kind of freedom. I was always intimately aware of the coming fall, so I didn’t have much patience for the tender slowness of youth. Let’s get on with it, I thought, let’s just jump to the spirited part of the ride instead of trudging along on this godforsaken lift.

And here I am – miss early 30s – miss life is melting away as I fling from side to side; trying to keep up with the pace of this coaster without being flung off, I do my darnedest to be good enough to maintain the pace. Today, my life is all about work. “Tomorrow,” maybe it will be all about my own “children.” Yet not until that brief pause before the end of the ride, if I’m lucky enough to have one, will it be about that slow, vaguely tormented experience of gluttonous time. The all-you-can-eat buffet of seconds ticking ever-so slowly around the clock. That’s over with. You’re an adult and you’re in free fall until the very end.

There is the good of it all as well – there is no limits beyond gravity, origin and capital to sourcing opportunity – there’s an infinite number of paths one can take at any given moment, none really right or wrong. There is the moments on the ride when, despite it’s chaotic forces shoving you around, you feel like you’re flying, and finally free. Those are the moments life is worth living for, it seems, yet they are fewer and farther in between. Who has time for moments when life keeps you busy with the details?

So, the depression of mine lingers on, this year taking the shape in the form of overwhelm – of acknowledgement that I am not suited for what it is that I do, yet also trying so desperately to succeed as in the pit of my stomach I know yet another failure would be futile. I make mistakes constantly, yet occasionally there is a sliver of success which buys me another day to sort out the variety of misgivings I may have in my career and daily production. But this polish does not buy much time at all. It is a never-ending race for quantifiable results, these small wins, to plug the holes in the eternally seeping bucket of success.

The true question here is – how long can I actually last before the next drop on this ride? Some of this is in my control, but not much of it, as I’m limited by IQ, focus, and resources, though mostly IQ. I can’t solve for my own incoherance or inability to communicate concepts. I can only work hard, get to work early and stay late, try to solve for that which I can effectively improve, and hire the best talent to understand all the many things I do not.

What I wonder, though, is if any speed of life would soothe me – if living in a sleepy rural town would bore me to tears yet being caught up in the urban vines of a metropolis brings me close to spontaneous self combustion, maybe there is no source of satisfaction beyond awareness and pushing forth down the path I’ve already forged, to see how long I can hang on to this crazy, uncomfortable, yet thrilling life.


L is for Leadership

You know that quote about how leaders are made, not born? I’m not sure I believe that to be the case. Sure, anyone can become a “B” quality leader, but the best leaders are people who just have something in them that I’ve never had and I never will have.

The hardest part is being able to so easily break out the qualities that I believe it takes to be a leader and look at why I can never achieve these qualities.

1. A Great Leader has The Ability to Say Exactly What She Wants to Say… in as few words as possible
I’m naturally, howdoyousay, verbose. While in writing this verbosity can come off eloquent, in person I am a rambling mess. While I can certain optimize my speech and communication skills, it takes all of my energy, as someone with ADHD, to be able to follow my own train of thought, store relevant comments, and hold them for just the right moment to share them, while also following what everyone else is saying. Typically the scenerio is that I have so much on my mind that either I hold it all in, say nothing at all, and feel frustrated about it — or more often I just blurt out what I feel needs to be said. The thing is, in my world, there is never a good or right time to talk. Unless I literally raise my hand and wait my turn to be called on, I don’t feel comfortable jumping into conversations. I acknowledge that 50% of the time I’m oversharing or overasking, but sometimes I do have good, relevant questions. The problem is that once you’ve shown that you suck at communication, no matter what you say, you’ll never really be listened to again. A great leader never runs into this massive road block in the first place.

2. A Great Leader Can Say No with Authority and Doesn’t Have to Explain Why
The best leaders are so confident that they can navigate the complex world of office politics and prioritization with ease, or at least it seems so “above the water.” When she says no to a project or ask, it’s clear that she has done so for a long line of really good reasons. Simply said, she has her shit together, and whenever she’s asked to explain something she’s able to quickly process her thoughts to output a very clear, simple statement that is taken and accepted as the way it has to be.

3. A Great Leader isn’t an Artist
Leaders cannot be perfectionists — unless they are Steve Jobs and even then there’s a balance of business savvy and communication skills that makes that level of OCD-ism acceptable to certain followers. But 99.999% of leaders are not setting out to create art everyday in everything they do. They do the bare minimum possible to reach the best possible results and move on. Quite frankly, they do not invest so much of their heart and soul into everything they do, because if they did, it would crush them. On the Myers Briggs scale, they rank low on the “Feeling” type. They rule their world by logic, efficiency, and the fastest, most acceptable route to success.

4. A Great Leader Loves to Delegate and Take Credit for Other’s Work
The best leaders know that their success is built on top of the shoulders of an amazing team. Sure, they may have hired and motivated that team to do their best work, but ultimately the success of any given leader is the result of all that work going on behind the magic curtain. I mean, just look at politicians – while they have a natural ability to speak with confidence and to only say the bare minimum, they also have a team of experts advising them on what to say, what to wear, how to move, et al. Leaders are only as effective as they are in convincing people to do a lot of work for them and to then take the majority of credit / reward for that work, all in the name of being a “great manager.”

5. A Great Leader Doesn’t Care What Other People Think
When you’re raised day after day that your opinions are wrong, that anything you think or do that conflicts with your fathers one take on every thing in the world, you get to a point early in life when you become so neurotic about what everyone else thinks and how everything you think or do is wrong that you have no hope of coming off remotely confident. What’s worse, that horrible relationship between you and your parental figures gets played out time and time again in your life, whether that’s a boss who treats you like you’re worthless or worse, you’re set up to return to that sort of mildly abusive type of relationship. It’s the only thing that feels safe and completely awful all at the same time. A great leader would never get caught in such traps. She would immediately showcase her charisma and confidence, and handle any conflict with ease. And if she messed up a small thing, she wouldn’t obsess over it for hours, letting it ruin her day. She really doesn’t give a shit what people think, unless it effects the primary goals she is aiming to achieve.

Here’s the thing. I’m not a leader. I am an operations type person as I see inefficiencies and patterns and can creatively come up with ways to fix them. I come off overly critical of others when in reality I’m much, much more critical of myself, but I can’t for the life of me provide constructive criticism without it coming off like I’m some distant cousin of satan once or twice removed. Either I’m too apologetic or too bitchy or both. I don’t know how the fuck I manage to be both but I do. And every time I hear myself speak I want to fling my fist at my face and run out of the room.

So why write about all this? How does it help? I guess I keep coming back to the question of – do I HAVE to be a leader? Yes, leaders make more money, and yes, I like being in charge (to an extent) and yes, I prefer to lead then to follow bad leadership, but — I’ve never really been a leader even in leadership type roles. I’m always some peon who speaks out of turn and accidentally misses a typo in an email that was blasted out or who can’t multi-task a dozen projects at once and effectively delegate/complete them all without feeling like I needed to have my hand in everything.

It’s challenging to go from being raised focusing on art – where the details matter and you’re supposed to spend time to make things the way you want – to a life where the real world is all about just good enough, not giving a fuck, as my friend puts it, and just getting through another day. It’s sad to me if that’s all life is. I want to care. I know at the end of the day certain things don’t matter… and certainly at the end of the year who will even remember whether something was flawlessly executed or just a step above half assed? I’m not sure. I just know that I have entered a level of stress I haven’t experienced before because this time around I really do care. I care and I love the opportunity on a lot of levels and I want more than anything to be successful. But without having this innate ability to be a leader, I’m not sure how long I can last faking it.

She Quit Her Job to Become a Porn Star…

Before you get all excited, I’m not talking about me – though that would make an excellent storyline for this blog. I’m talking about Veronica Vain, who decided to leave her blossoming cushy career as a Wall Street intern to instead, well, be cushed. Repeatedly. On camera. Over and over again. She’s competing in a new reality tv series hosted by the “one and only” Duke porn star. Apparently, “Veronica’s” rational for leaving Wall Street and getting into the Adulty Industry was that if she’s going to get screwed for the next decade she might as well get into the hall of fame for it. Fair enough.

While not everyone is going to leave a stable career for one so fickle and disrespected, and mostly not everyone has a desire to become a porn star, there is something to be said about following your dreams and going after what you, deep down, feel most natural doing. Of course, for a job like that, it’s the rare few who get to stardom levels where their salary would be comparable or better to that of a financial analyst. Even with 15 minutes of fame, the longevity of a porn career is short in most cases. What next? That said, if she’s smart enough to be a financial analyst she’ll be fine, if not permanently sexually harassed at jobs filled with lots of nerds.

For everyone else out there, what would it take to leave what you’re doing to today to do what you love most? Do you know what that is? I think I’m actually very close in a lot of ways. I love creating, and being a leader in a young company teaches me a lot about entrepreneurship and business. That said, I think my long-term goal would be to come up with a product idea that can be pitched on a show like Shark Tank. Something that could be useful but also innovative. I want to be an entrepreneur, but I’m not cut out to the a tech entrepreneur. Tech requires too much up-front capital and it takes too long to build something really useful that by the time you have a product the market needs, it’s a few years too late. That’s just the nature of the tech industry. And it’s on marketing and sales’ shoulders to convince everyone what you have today is what they actually need. That’s the case in 99% of tech businesses.

As I think more about myself and what I really like about my job/career/industry, there is a lot of good there. I just realize that while I fell into technology and feel so fortunate for my time in the industry, as well as in learning more about business by being part of companies selling to other businesses, I don’t feel quite comfortable here, and I never will. I do enjoy being in Silicon Valley — finding myself feeling the epic rush of being smack dab in the middle of the innovation world is something I’ll never, ever regret. But I still wonder if this is sustainable, and if this is where I can add the most value.

I’ve been thinking a lot about getting an MBA, then reading lots of blogs that say do not get an MBA. Most suggest that if you want to change careers, though, an MBA can be useful. I would want to have a very solid goal before enrolling in any such program. I’d also have to be accepted to a top 10 school – which on its own is unlikely due to my schizophrenic undergrad transcripts and my test-taking challenged mind. That said, I don’t need an MBA to be a real entrepreneur.  I need some chutzpah and an affinity for risk that was zapped from my psyche by an actuarial father whose entire life’s work was to reduce any uncessary risk.

But I have realized that money doesn’t drive me. I mean, I like money, and I like having money, and building my networth. And I spend money reasonable well. So I guess it does drive me. And this month when the stock market sharply shot down and I lost a good $3000 in networth, that was mitigated by earning and not spending enough so my networth stayed flat. I would like to get to $500k in networth because while it’s not enough to pay for the rest of life,  it is enough cushion to move somewhere with a much lower cost of living and, I don’t know, focus on building a life that is a bit less stressful.

Maybe these women who leave their stable jobs and lives for a short-term, financially lucrative career in pornography have it all right. I’d never do that for a multitude of reasons, but perhaps there is still time to change careers, at some point, and find something I’m more naturally equipped to do – whatever that is.