Thursday, September 26, 2013

Taking what's yours... or not

When I was in grade school, once a week a small group of us loaded up onto a big yellow school bus and headed over to a different grade school for our district’s “Gifted Resource Program” (aka GRC).  As you can imagine, being lumped into this category and forcibly separated from all the “normal kids” did not exactly bolster my third grade reputation.  My tortoise-shell prescription glasses, plaid fleece-lined overalls, meticulously organized Trapper Keeper, and shameless passion for homework didn’t do much for my social status either, but such is the price we must pay for being ahead of our time.  In spite of inducing social isolation, GRC taught me many important things about being successful in school and in life.  Our teachers encouraged, if not demanded, endless curiosity and creativity.  We acted out famous historical scenes in both puppet form and in live plays, invented our own new products, brainstormed how to market them, conducted chemical experiments, and learned new –ism words every week.

The program opened my eyes to so many new things, such as the fact that the word ‘ignorant’ does not mean that you are brave and ignore your obstacles (it’s more like another word for stupid) and how a hot air balloon works -- but what I will never forget is when I learned what it meant to take initiative.  I'm not sure what the dictionary says, but what I figured out was that taking initiative means doing something productive without being asked.  This involves understanding and anticipating others’ needs and then being thoughtful and savvy enough to produce something that meets those needs. 

In social terms, this is often seen as being ‘thoughtful’ or ‘conscientious’.  I take great pleasure in this in my personal relationships – one of my favorite things about myself (usually favorite, sometimes I hate it) is my ability to sense others’ emotions and understand what is meaningful to them.  Whether it’s a minor logistical decision or showing up to a certain event or simply making myself available to listen, these are the things that I do for others that make life feel meaningful. 

In the work world, taking initiative is more of a matter of being prepared, aggressive, and seizing opportunities that are not necessarily explicitly offered to you.  Working as a summer intern on the trading floor, it was a quick lesson that the only way to stand out was to take initiative and deliver things beyond what was being asked of you.   I took great pleasure in observing the world around me, taking note of where I could add value, and getting creative about how I could do that in a way nobody else had thought of.

So, no matter what the context, this process of anticipating needs and goals and then working to surpass them is usually both fun and relatively natural.  However, there is also an art to knowing when you are in a good position to do that and when you are not. Taking initiative is not the same as telepathy or magic – it requires skilled information gathering, contextual understanding, and situational analysis.   When you’re in an unfamiliar environment, or for some reason you are without a clear picture of the situation at hand, taking initiative is no longer enjoyable, it’s fucking scary.  Without the proper information, doing work that wasn’t asked for or sharing a sentiment that isn’t going to be well received can be detrimental to all types of reputations and relationships. So, basically, this whole taking initiative thing can really backfire.  Well, fucking great.  Instead of feeling empowered to take the reins and move forward on my own, I'm left cowering in fear of the fact that anything I do could be misinterpreted as carelessness, misunderstanding, or straight up ignorance.  

Many have said, Nobody will hand you great opportunities, you must seize them.  Indeed, it is true that in many situations nobody is stopping you from taking what is yours – but how do you know what that is or what it looks like, let alone that it is there or that it could be yours?   It would be unrealistic to think that the people around you are thinking about what would allow you to perform at your highest level, wondering what they could to make you feel informed, challenged, and confident.  Nobody else is considering what you need to take things to the next level.  It is on you to speak up and clearly articulate what you need to deliver above and beyond what is expected of you.  But how do you know when and what to ask for?  

In an industry like finance, where roles are generally well defined, career paths are clear, and hierarchy is beyond question, it is relatively easy to identify what to ask for because you see people all around you doing the same thing.  However, in a start up, where processes, roles, and responsibilities are constantly in flux, it is much more difficult to properly anticipate the needs of the overall business and deliver in a manner than meets those needs within the window of time while they are still relevant. There are so many great things about a start up culture, including the ability to constantly carve out and create new responsibilities for ourselves – but this also creates a moving target for identifying what tools and scenario analysis should be done to justify action.  This is true for any entrepreneur - when do you look to your customers to tell you what they need, and when do you take it upon yourself to understand the market and deliver what it is really asking for?

In the interest of widening the scope of this pontification (hello to whoever is still reading!), I think this applies to relationships as well.  When should your partner be able to understand your needs and wants and when should it be your own responsibility to articulate them?  This is particularly hard for women because men have a notorious reputation for an inability to anticipate needs (sorry, guys).  I have struggled with this in every relationship I have ever been in.  How could he possibly know what matters to me unless I made it explicitly clear?  He isn’t a mind reader, after all.  You’re such a bitch for expecting him to know when you don’t even know yourself sometimes!

I mean, sure, being clear about needs works well when it involves providing instructions on the acceptable amount of time to wait for a response to a text, how to introduce me to his family, or how to include me in weekend plans.  It doesn't work so well when it comes to providing the emotional support, advice, or guidance I need to feel safe, secure, and self confident.  When is he supposed to listen, when is he supposed to solve, when is he supposed to probe?    Especially when it comes to processing emotionally charged subject matters, it is exceedingly difficult to identify what you need from someone, let alone how to ask for it.  But then, how can you expect it to be delivered?  Where do you draw the line between someone knowing you, understanding, and anticipating your needs, and your own personal responsibility to do all of those things and ask for what you need to be happy?

Obviously, I have no fucking idea.  But what I have realized over these past few months is that in these situations, just start talking to your peers.  For me, it’s all too easy to drown in my inner dialogue, to lose myself in that endless mental struggle to figure out what is right or wrong or, at least, optimal.  The older I get, the more this frustrating routine seems inevitable and uniquely painful, and the more alone I feel.  However, every time I open up about it to someone I know, trust, or love – I realize I’m not so special.  Almost everyone has gone through these issues before, work-wise or personal-life-wise.  Granted, whatever worked for them may not always work for you, but at least you can get some more data points as to understand what and where are the right pathways for taking initiative.  Everyone has different methods, different analytical processes, and different standards.  So it’s important to remain true to your own feelings and morals in this process – but either way, it can only make you feel better to have a broader picture of where and how to stop questioning and move forward.  Because that’s the whole point, anyway, right?

Monday, September 9, 2013

Bringing it all together

The further I go down this road of entrepreneurship, the more I am seeing the various parts of my life converging.  This, in and of itself, is a significant departure from what I once hoped my life could be.  When I started working on the trading floor, one of the most appealing parts of the job was the ease with which I could compartmentalize my personal life, my professional commitments, and my passion projects.  Unlike traditional banking or consulting jobs, the financial markets open and close at the same time every day.  They aren't open on the weekends.  When there's a holiday, they're closed, so you are truly forced to walk away at the end of the day and come back the next day to pick things up where you left off.  This regularity provided a much-needed structure that meant I knew when I would be busy and when I would have free time for relaxation or other adventures.  

However, after a few years of strictly scheduling my friendships, romantic relationships, art and film classes, travels, and everything else, I felt like I was doing a lot, but I still wasn't happy - it still felt like something was missing.  I woke up every morning looking forward to the end of the day, anxiously awaiting the next activity I had on my agenda. I'd go to that class, or catch up with that friend and temporarily feel better, but then I'd go to sleep and I'd have to wake up and do it all over again.  It felt empty, pointless, and tiring.  This is when I started searching for new jobs, but only after many weeks of wallowing, and wishing very hard that the next day I would wake up and this feeling of my life not being "enough" would go away and I could live happier ever after.  But alas, the emptiness persisted.

As I started looking for other jobs and new opportunities, the thing I started to realize that the sense of "freedom" that had originally attracted me to finance - the ability to compartmentalize and the resources to live an exciting life outside of work - was not really freedom at all.  I thought being able to leave "work" at the office when the markets closed would allow me to be present in the rest of my life.  Instead, it mean I spent 12-13 hours per day at work occupied (sure, sometimes even entertained) by things I didn't really care about, desperately looking forward to whatever was next.  I was relentlessly busy and still unwaveringly ambitious, but also distracted, sad, and lacking the time and the tools to see a clear path forward.   It's hard to be able to find the answer to that critical question, "What do I want?" when all you can say is, "Not this."

I still don't know the answer to that question, but what I did start to understand is that I wanted to feel useful.  I wanted to be able to draw upon my personal experiences to make me better at my job.  I wanted to always be looking at the world with open eyes, ready to learn, and ready to apply whatever I was picking up in all different contexts of my life.  I wanted to want to wake up in the morning and go get work done. I wanted to enjoy what I was doing so much that I had no choice but to take it home with me at the end of the day because I would be so excited about accomplishing things and moving forward.  

I realized what all this meant was that I actually no longer wanted to keep my work and life separate.  Not necessarily in an obsessive, work-a-holic type way, but more of in the sense that I wanted to break down the walls and open up the doors for seeing and experience life as an individual, free of the definitions and various identities required by living in several different worlds at once.  There are lessons to be learned from how we deal with our best friends that can be applied to our clients.  The discipline required to streamline and organize one's personal finances is the same discipline required for budgeting time, money, and resources at work. There is a level of confidence and independence required to ask for what you need from your personal relationships as well as from your job.  It's really all the same, because you're the same no matter where you are (if you in fact are the same no matter where you are).  And in order to get to that point, I needed to start seeing and experiencing these parallel worlds in a unified fashion.

Now, for some very strong individuals, perhaps this is simply a mindset and doesn't require actually switching careers.  I have spent a long time wishing I could be that way, but I have always been the type of person that has had the ability to float between friend groups, to fit in and blend in a lot of different contexts.  I've always been the one that's pretty good at a lot of things, but never amazing at just one.  I generally enjoyed this because it allowed me to connect with and learn from all different types of people and experiences, but it also meant I never really felt validated or at home with any of them.  I always figured this was a result of my basically introverted qualities, destined to seek independence as the only means of regaining my energy and sense of self.  Now, I see that it's me that has always seen these worlds as separate and perhaps they don't need to be.  I'm still not sure how they will all come together, but now I definitely believe that they will, and I'm looking forward to figuring it out.