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.

Combating Perfectionism to Survive

My childhood was spent painting. I learned early on that mussing around too much with color on top of color eventually turned a beautiful painting brown, and the only way to fix this horror was to let it dry and paint over it again. If only I just stopped while I was a head – when it was “good enough” – and moved on. But I couldn’t, because stopping before it’s perfect in my mind was a relative impossibility.

Perfectionism is ironically the worst enemy of success. I oft forget how much of a perfectionist I am until someone else points it out. For example, the other day, a family member saw me working on details of a poster with a designer and said she would never spend that much time on such an item. The most successful people, I’ve learned, are not necessarily the ones who dot their i’s and cross their t’s, but the ones who quickly move from one thing to the next, covering the most ground.

Of course, that’s not the case for some fields – like medicine or physics – where anything less than perfection can result in failure. But in most aspects of life, perfection doesn’t actually matter. Let’s just ignore the fact that in most aspects of life it doesn’t even actually exist, for a moment. As a whole, most people aren’t going to notice if your colors or spacing is slightly off. Most people don’t notice quite as many details as I do on a daily basis to begin with.

Yet with my distracted, ADHD mind, I’ve yet to find a way to ensure that the important details do not slip without obsessing over the many that no one should care about. Even then, I find I somehow miss the big things that others will notice, while all the details that probably won’t get any mindshare in a person’s busy day are flawless. Clearly, I’m doing this all wrong. You know, existing.

The thing about perfectionism is that over the long term to accomplish anything near perfect you need repeatable processes to maintain such perfection, and then you need to, as in the words of the immortal Disney song, Let it the fuck Go. (Ok, I added two non-Disney words in there.)

But the reality is, I’m not saving lives with my job, I’m not saving the world. In the grande scheme of things what I’m doing doesn’t matter. As an INFP, I’m an idealist, and I pour 100% of myself into everything I do. It’s just my nature. And I have a lot of trouble detaching work from the rest of my life. The truth is, I’m as passionate about my work as I am any other aspect of my life, if not more so. Which is probably the problem to begin with.

That said, I’m the type of person who fades if the passion isn’t there, so I’d much rather be wholly passionate in each project, at least at the broader scale picture, than just getting through the day. How do I trick my mind into not caring so I can just get shit done? How do I make myself acknowledge that it doesn’t matter if the poster’s alignment is slightly off, but still catch that the word in the bottom left is misspelled?

This is my little dilemma. It sounds silly, but it’s the reason why I’m yet again struggling with my job. Deep down, I realize that my calling may have been a more creative field — cinematography, for instance — where such perfectionism, at least in terms of visuals and story flow, is actually a benefit to your success, vs business, where you’re expected to churn out results at an impossible speed, where “Minimum Viable Product” (MVP) is what you always want to be aiming for. You’re never creating something you’re proud of then, you’re just constantly rushing to create whatever works to achieve your goal with the very least amount of effort. That, on it’s own, over time, is soul crushing.

But it’s just work, right? And it’s the big wins that should fuel you. At least in business, al the little things are done to accomplish a very measurable, tangible goal. What is your annual revenue? That is the result of a lot of people’s hard work and little, non-perfectionistic successes.

I haven’t had a good New Years resolution yet, but I think this year mine will be to Let it (the fuck) Go. Because, let’s face it, if I don’t I will be unemployed again soon, and more deeper in the rut of unemployment than I was before. On the other hand, I have a very real opportunity to do extremely well in my current role. I have maybe three months or less to make it or break it, which may feel like a marathon, but in the grande scheme of things is actually a sprint.

The Challenge Meter

Remember when life was all about getting good grades? When, generally speaking, there were right and wrong answers, and either you solved for X or you didn’t? Ah, how I failed to appreciate those days, dreaming of the time when I’d be free of solving right-or-wrong questions, trading this in for the freedom of creating in a world of no actual correct answers. I didn’t appreciate life back then at all. It seemed like it was all this trick leading up to reality. So I held my breath and waited.

But it’s become increasingly clear to me that I’m not cut out for certain aspects of adult life. I can try. I can fake it for a while. It is a fight every single day, every second of the day, to get just to passable, if I’m lucky. More often then not I’m failing to do even the most basic things right, I’m being belittled and disrespected, perhaps for good reason, by my superiors and peers, and ever little dig eats away at me until there’s no fight in me left. I’m weak and sensitive. That’s how I roll. I fall apart too easily. I’m lucky if I get through an entire day without a top-secret breakdown.

Boo hoo. I’m so fortune. I’m so grateful. I’m so tortured by wanting to do amazing work and somehow running into walls. My 20s were all about figuring out how to get jobs with a bigger paycheck. I lost sight of what I actually enjoyed and instead just chased wherever I could finagle my way into an opportunity. I learned that once the ball is rolling, as long as you keep your head up and eyes on the prize, there is always someone who will give you chance. It’s up to you to take it and run for as long and fast as you can, unless you explode, fall to bits, and wait for someone to pick up the pieces and shove you back together for the next go.

I hate being so weak. I’m most comfortable in any situation where I’m made fun of and shot down, because that’s all I know. And I can’t stand up for myself to anyone who is certain they are always right, especially when I’m never certain in any of my own suggestions. I’m yet again tempted to disappear as I am staring at this impossible mountain to climb where there is no possible path to success, only a few ridges along the way to precariously balance on before I fall over or just keep climbing.

How long can I hold on? I don’t know. I’m really starting to stop caring about money. I like money, sure, but I’m over buying shit. I’d love to be able to get to $1M before I simplify my life and move to bumblefuck the middle of nowhere and enjoying pseudo retirement (i.e. do work that is meaningful and low paid) – but what if I don’t, does that matter? In the grande scheme of things maybe happiness is just a small house with a backyard in some town no one has heard of, spending a long, slow-moving life with my love of choice, who I happen to have, thank the dear lord.

I’m fairly certain I can’t go on like this for much longer. Suicide doesn’t seem like a sensible option. But packing up and trading in someone else’s dream for defining one of my own may be a better bet, before I’m tumbling down a jagged cliff with nothing but jagged ice to catch my free fall.

 

Tenacity and Intellect, the Perfect Combo

For the longest time, I believed that people were either smart or not smart. Either you could easily figure out how to do something or it just wasn’t meant for you. Now, to some extent, that’s true, as some people find certain things easier than others naturally. But one of the things I’ve come to appreciate in life today is that intellect only gets you so far – it’s tenacity that gets you the other however many miles you need to go. But everyone can get there as long you try hard enough.

It has been interesting getting to know my friend better over the last year as he has been preparing for a major exam for graduate school. The amount of focused studying, both self-study and via outside tutors, he put into the exam, showed me how even for a very smart person, the amount of practice required to get a great score takes a lot of work. In fact, even after taking the exam once and scoring very well, but apparently not quite as high as he wanted, he went back to the books, studied even harder, and walked away with one of the best scores you can get on his second try.

Most of my anxiety stems from not knowing how to handle being challenged. When I was a young child, I loved math, doing multiplication workbooks over dinners out waiting for the food to be served in first grade and probably kindergarten. I loved it when it came easy. Then it got harder and I gave up too quickly. My father would get frustrated at me for not understanding things fast enough. I grew distracted and antsy and sad that I couldn’t just get everything as easily as I once did. I gave up way too soon. I gave up because I figured most things in school were irrelevant to my life.

Fast forward X # of years and – I’m still that person who gives up too easily. Who freaks out over every minor imperfection. I’ve never actually witnessed the work it takes to succeed at the highest levels of intellectual performance. And for everyone, even the most intelligent people out there, it takes work. But it’s the work, and the efficiency of that work, that defines their intellect. Focus (to keep attention on one problem until it is solved, even if it has multiple steps), creativity (the ability to think outside the box for answers to problems that are trick questions or don’t have obvious answers), processing power (how fast do you compute?) and memory (how well do you store and receive information) and determination (how quickly do you give up when it gets hard?) are the five core tenants of intellect, IMO. As a person with ADHD I struggle with all except creativity. Every person can become smart is they can fix those four tenants of themselves. Not everyone will be Einstein but we can all get good scores on exams, or be loved by our colleagues for the work we produce, if we try hard enough.

I’m thankful for being able to get to know this friend better over the past year, as his refusal to give up on what he wants, and ultimately walking away with a major victory en-route to the prize, has shown me the truth about being the best person you can be. In 2015, I want to be the best person I can be. I feel inspired. And I know this is going to be a trying but great year.