Tuesday, December 31, 2013

Embracing stereotypes

As we come up on the end of another year, there are plenty of blogposts, info graphics, and videos summing up the best moments of 2013.  I wrote something similar myself last year, and I generally love these entries and find them quite useful in reflecting upon the previous 365 days.  However, this time I'd like to distill my various significant moments of 2013 into just one scary realization I have had from this year:  Stereotypes are (mostly) true.  

I hate to say it, I really do.  I love nothing more than proving people wrong, going against the grain, not submitting to popular opinion.  However, I have recently crossed a lot of borders, both literally and figuratively, and after changing industries, moving halfway across the world, traveling around Asia, starting a business, hiring a team, and meeting countless entrepreneurs, I have spent quite a bit of time looking in the rearview mirror and getting some real perspective.  It is impossible to see something for what it really is when you are entrenched in it.  You just can't.  It's too real, too close, too nuanced to draw conclusions relative to the rest of the world.  But with every new experience comes a new vantage point, a different context, and a wider angle lens with which you can see the past, present, and future.  

When I worked at Goldman Sachs, sure I had read Liar's Poker, I had seen Boiler Room, and I had heard plenty of people bash the world of finance and the myopic, testosterone-fueled personalities that had made it what it was.  At the time, these opinions gave me a twinge of mild offense and resentment, and I brushed most of it off thinking that these people didn't really understand how Wall Street worked and if they did, they would see it differently.  Please let me caveat what I am about to say by pointing out that, of course, there are always exceptions to the stereotypes, and these extreme views are not true for everyone that works in the industry.  There are plenty of very intelligent, down to earth, morally centered individuals who I have had the pleasure of working with in my time in finance.  However, now that I've spent time on the outside, I have realized that quite a bit of what is said about the trading world is (gasp) true.   A typical day at work did start with copious amounts of caffeine at 6 am, followed by co-workers putting their feet up on their desks, drinking Monster energy drinks and taking prescription drugs.  There was a lot of shooting the shit with clients on the phone and screaming at traders or brokers for (debatably) messing something up.  There were plenty of mini footballs being thrown around the trading floor, and superiors would regularly motivate people by employing frat-boy antics that were centered around challenging people to improve by constantly putting them down in front of others.  Then, we'd often end the day with drinks and fancy dinners in Midtown.  Of course, if that's all you know, you intimately understand the immediate motivations for each of these equally ridiculous rituals and truly believe that anyone who criticizes them is simply taking them out of context.  But that's just it -- then you venture out into the real world and realize your definition of "context" is highly limited.  It becomes clear that you've been seeing the world without peripheral vision.

After moving to Hong Kong, I've also been able to see both America and China with fresh eyes.  Looking backward and reflecting on my own upbringing, my own habits, priorities, and experiences, I have come to believe that what most of the world believes (and either vehemently mocks or earnestly glorifies) about Americans, is absolutely valid.  Indeed, American portions are unnecessarily large, and as a consequence so are many of our waistlines.  We produce awful, degrading reality TV shows, as well as the majority of the world's pop music and films.  We are also innovative, creative thinkers, who tend to be quite open to new experiences and ways of thinking.  We're friendly and largely welcoming to others, even if we don't like them, and unless we're deliberately taught otherwise, we don't really know or care that much about the rest of the world.  Yes, American suburbia is big and boring, lots of people own guns, and we consistently rag on our own government.  All of that is totally okay, and there are plenty of reasons why that is the way things are, but unfortunately the rest of the world is relatively on par with all of their American jokes.

I would also venture to say that China, too, is in many ways what people think it is.  It's loud, it's crazy, and it kind of feels like everyone is yelling at you all the time.  There are a hell of a lot of amateur photographers, even more Hello Kitty enthusiasts, and people really do eat chicken feet.  In Hong Kong, the majority of people work in finance, there are quite a few white men dating Asian women, and there are luxury cars around every corner.  If you go to Mainland, it is true that someone will shove you in front of a bus so they can be first in line (and I use the term "line" loosely), there are kids who open the flaps on their onesies and squat and take a shit in the street, nothing is exempt from forging, copying, or faking, and all agreements are subject to revision.  I don't mean this to be offensive, but simply an outsider's observation of the various ways in which images of China map to the way things really are.

Moving onto the startup world, there is no better place to observe tech culture than San Francisco.  Though I have spent time in the city twice before (once for an internship in 2005 and for another brief visit in 2011), this is the first time I'm here with the eyes of an entrepreneur, and an expatriate one at that.  Much of Asia sees The Silicon Valley through rose colored glasses; SF is a magical land of opportunity, where millionaires are made overnight, entrepreneurs run the show, being a geek is cool, and eager investors abound.  It is the epicenter of the entrepreneurship movement, and as such it is symbolic of the start up world at its best.  My first impression is that while much of the glorification is justified, there are also downsides to being the epitome of the entrepreneurial mindset.  

From where I'm standing, San Francisco is certainly a city almost exclusively consisting of hipsters, hackers, and the homeless.  The countless indie coffee shops are filled to the brim with people typing away on their Macbook Airs, surfing the web, writing their blogs, and working on that epic idea they have in the works while they search for that perfect CTO to help them build it.  Nearly every single male individual in the city has an ironic beard of some kind and is wearing flannel shirts and skinny jeans, craft beer is the drink of choice, and composting is commonplace.  It is the status quo to think big, think outside the box, and try new things.  Failure is accepted, if not encouraged, and people really do believe anything is possible.  There are also plenty of overly idealistic entrepreneurs who can speak with falsified confidence on any topic and truly believe they exclusively understand "the way things are" and "what people want".  And though this is a topic for another post, they're actually pretty fucking convincing, as I have spent a lot of the last week feeling vastly inferior in almost every way.  Which very well may be true, but I'm not sure yet.

In any case, seeing rumors match up with reality in so many different contexts is actually quite upsetting.  It feels like giving up hope that individuals can create their own identities independent of their environment.  It also scares me because it means that maybe what other people think about me upon first impression, the conclusions they may draw after learning I am from Illinois, went to Harvard or worked at Goldman Sachs, are actually true.  For so many years, I have been carefully curating my first impressions so as to make sure others know that I don't fit into any mold, that I cannot be defined by any of these preconceived notions.  But lately I've had to accept that I actually do fit into some stereotypes: I do pronounce my a's funny, I do like intense, philosophical discussions and cocktail parties, and I do believe that derivatives are interesting and serve a real and valid purpose in financial markets.  If you want to judge me on that, then… well, at least I judged me first?  Recognizing that I conform with the norm in some ways, however, doesn't mean that there aren't a lot of interesting things about me, or that I don't have a unique point of view, or that I'm not worth getting to know.  

The intention of this post is not to declare that it's okay to limit one's view of the world to sweeping generalizations, nor is it to condone prejudice or discrimination based upon said generalizations.  For starters, I was hoping this post would be kind of funny since many of these things have given me a solid chuckle, but I also intended for this to serve as a public acceptance that stereotypes are actually relevant and they exist for a reason.  That is, they exist as data points to help guide us based on aggregated knowledge and experience.  Stereotypes exist because a lot of people have observed similar things, they talked and drew conclusions, probably made some inappropriate jokes about it, and before you know it word had spread around the world.  There's no point to denying these time-tested observations when we can benefit by accepting them and looking beyond them. 

Embracing stereotypes as mostly true allows us to see the world as it is, and consequently liberates us to find joy in searching for the reasons why things are. After all, you can't dig beneath the surface and appreciate the nuances without first acknowledging the surface itself.  As we move forward into a new year, my resolution is to accept reality while also remaining open to new possibilities, welcoming exceptions to the rules, and persistently encouraging the world to prove you wrong.  So, in conclusion, cheers to continually evolving perspectives, and to the new and exciting things an ever expanding mindset can help us create in 2014.

Tuesday, November 26, 2013

Getting real... I'm still getting started.

It's been a little while since I posted, and there's good reason.  Writing again has been simultaneously desperately needed and desperately dreaded, but I've finally had to embrace it and get real with myself and with whoever the hell is reading this (oh, hey!)  Part of the reason I started this blog is because I wanted to be honest about my personal and professional challenges and my insecurities about facing them.  I found strength in acknowledging those challenges and insecurities and sharing them with others.  Of course, part of that is selfish - you put what you are feeling or experiencing out there, and you realize that a) it's not so bad once you say it out loud, and b) you're not alone.  But it also isn't necessarily so difficult to put it out there when you're just getting started in a new career and a new place because you don't really have much to lose.  I was able to start out on an honest foot because I felt far enough away to be frank, but also because I was in a place where I felt safe enough to not be afraid of what people thought of me. I took solace in the promise that seeing the world as it is, acknowledging reality, and dealing with it is the only way to break through to great things and I still felt a certain confidence that I could be on the verge of that.  I still felt confident that I was on an adventure, that I was working on building something that mattered, and I would be able to find myself in that journey.

But now I have an embarrassing confession to make.  I'm over one year in Hong Kong, well over one year into this "entrepreneurial adventure", GA Hong Kong has grown into a community of several thousand students and a team of nearly six... and it's fucking scary because I still feel like I'm still just getting started.  I'm still struggling with all the same things I wrote about over a year ago - climbing all those steps but not sure where they lead, knowing things are hard and somehow being surprised when they actually are fucking hard, highs and lows, trusting my gut, taking responsibility, knowing who I am and what I am good at, blah blah blah.  I certainly didn't leave finance and leave "the known" expecting to get it all figured out in a year, but shouldn't I have some things figured out?  It's scary to look yourself in the mirror and acknowledge that maybe I just might be no further along than I was before.  (Note that of course, this does not mean I regret anything for one second.  I wouldn't trade what I have experienced over the past few years for anything in the world.)

In the journey thus far, I have released myself of many different parts of my identity.  I left a promising and stable career in finance, I left a city that I loved and knew (New York), I left the clarity and safety in my close friends and family, I left the reinforcement of being part of a larger team at GA in New York where I felt supported, seen, and appreciated.  In a funny way, in the process of letting go of all those things, I thought I was peeling back the layers.  But what I have realized recently is I was also layering them right back on as I actually just started growing attached to a whole new set of things.  I was meeting hundreds of new people, I was getting entrepreneurial and technical education off the ground in Asia, I was facing the challenges of co-habitating and being in a committed relationship… basically, I started identifying myself with the fact that I was "getting started".  I know, I'm getting meta here so please forgive me. Or, stop reading and decide I'm totally full of it and I totally over-think things and give up on me.  As Britney would agree, that's your prerogative.

In August, I acknowledged that I had personal needs that weren't being fulfilled in my relationship and that I did not feel supported in my current journey in the way I needed to be.  I'll write more about that in due time, but leaving a three and half/four year long relationship, which brought me to a new part of the world no less, is fucking terrifying.  At the same time, General Assembly was just starting to take off in Hong Kong.  We launched the first full-time web development bootcamp in Asia, our team started growing, we started commanding more respect, resources, and responsibility from headquarters, and I started empowering others outside of myself to take ownership over what we we were building here.  I started getting messages from people saying, "There's someone from General Assembly at this event and it's not you… what's going on?!"

So, on one hand - awesome!  Isn't that the point?  On the other hand, there you go -- or rather, where'd I go?  I'm no longer the committed girlfriend that moved to Hong Kong for love.  I'm no longer "the General Assembly" person in Hong Kong, I'm no longer just that aspiring post-corporate entrepreneur.  It's all bigger than me now, which is awesome, but it is also a whole new process of letting go.  Once again, I can't help but feel like I'm starting over -- tackling a whole new "management" role, building a new home for myself, heading off on what feels like yet another new adventure.

I guess the point is that "getting starting" isn't something you can do in a year.  Or two years.  Or more.  Or, ever? Perhaps in order to take a leap of faith and start over, you have to momentarily believe that there's something else on the other side.  Once you jump, you slowly realize there isn't necessarily anything solid to land on… Or, maybe there is, but once you get to the other side you see that it's not at all what you thought it would look like, and there's just a million more rivers to cross.

Tuesday, October 15, 2013

Who, me? Taking responsibility, for better and for worse.

I always had an awareness of the concept of "taking responsibility" but it wasn't until just about two years ago that I realized how powerful it really could be.  We're conditioned to believe that anything that is wrong with our lives is not our fault.  It starts with our parents, afraid of their adorable little kids being perceived as anything but perfect, who are quick to believe that it was the other kid that started the fight.  This misappropriation of blame in a little schoolyard squabble quickly evolves into knowingly deceiving our parents that the only reason we didn't get an A was because the teacher hated us, or that it totally wasn't my bottle of rum that you found in the trunk.  Then it becomes internalized and we start to genuinely believe that the only reason we didn't get that job was because the interviewer was jealous of our outfit, or that our friend is mad because she's just completely crazy, or that we can't keep a boyfriend because we're just too good for all the men out there.  It's just too easy to think that all the bad things in our lives are happening to us and not because of us.

The funny thing is that this mindset plays itself out with both the bad and the good.  In the aftermath of Lean In, Sheryl Sandberg's modern manifesto for the ambitious female, there's been a lot of talk of something called the Impostor Syndrome.  Impostor syndrome is, "when one does not believe that one’s accomplishments came about not through genuine ability, but as a result of having been lucky, having worked harder than others, or having manipulated other people’s impressions."  This is basically a symptom of the same disease -- not taking responsibility or, when it comes to the positive stuff, taking credit for what happens to you. I have also been guilty of this, and I don't think it's just because I'm a woman.  

When I was packing up my childhood room when my parents moved house, I found a copy of our high school newspaper.  Someone had interviewed me about getting into Harvard and my quote was something like, "I'm sure everyone that applied deserved to get in!  There are a lot of factors in the admissions process we don't understand..."  I remember quite clearly the feeling of "I tricked them somehow" or "Clearly, someone was having an emotional day, and something I said mattered to them."  I felt the same way about getting a job at Goldman Sachs -- it might have had a little to do with me, but c'mon, not that much.  

As a side note, there's also a large chance that my response to that question, and my subsequent lack of taking credit, that has to do with wanting people to like me.  Part of this is the fact that I wasn't exactly awarded the "Coolest in school" award for getting A's and loving homework, it was generally a detractor from my social capital.  I hid the fact that I was on the math team in high school, but still won the "Brainiest" award at my Senior Prom.  Additionally, I don't think I am the one that hates people that walk around parading their accomplishments like they're the only ones that have ever done something great.  In reality, nobody does anything completely on their own.  We are constantly subjected to external forces beyond our control, it's just what we do with them and how we work with other people that determines our success in the long run.

Anyway, back to this concept of taking responsibility (getting people to like you is a whole different story, something I have talked about before and will certainly address again in another post).  As for the bad stuff, it wasn't until a few years into finance, a series of eerily repetitive relationship patterns, and the feeling that everyone was out to get me that I started to think about what role I could possibly be playing in these various factors contributing to my own misery.  Well, that's not true - I have always been a pretty self reflective person, which has caused me to incessantly and relentlessly question myself, my intentions, and my capabilities.  But, ironically, it was also the fact that I identified myself as "self aware" that made it even more difficult to really see how much I was contributing to my suboptimal state of being.

After you get over feeling like shit, the cool thing about realizing that you're an active participant in your own failure is that it's completely within your control to turn things around.  If you spent years complaining that people don't talk to you in bars, and you just realized that your dismissive attitude and constantly crossed arms might have a little something to do with it... chances are that you can just start wearing a friendlier facial expression and before you know it, people will start talking to you.  That's the empowering part.

But for me, particularly in the context of entrepreneurship, empowerment can quickly turn to exhaustion.  When you're in a big corporate environment or you're working with a big team of people, it's easy to see that there really are things that are out of your control.  However, if you're a one person team and something does not get done, there is literally no other reason than you did not do it.  The proverbial buck really stops with you.  If you don't reach your goals or hit your targets, there's nobody else to blame but yourself.  So then isn't it inevitable to constantly arrive at the conclusion that if you're not successful, it's because you didn't try hard enough, or worse... you just suck at what you're doing?

That seems awfully sad, depressing, and disempowering.  There must be more to the story.  Or maybe there isn't.  Maybe we just need to really look at ourselves and separate ourselves from any preconceived notions and judgements about our own capabilities so we can find that line between what we deserve and what we've fallen into.  One person can't do everything.  If you can't move mountains, it may be because you're not strong enough, but nobody is.  It's physically impossible.  So then, the empowerment comes from reconnecting to reality, accepting what is and is not possible and instead of sitting around beating yourself up because you're not Superman (or beating your chest because you think you are Superman), knowing when and where you need to ask for help.  Conversely, recognizing, accepting, and embracing your strengths can allow you to understand what you deserve credit for and where you have responded positively to the benefits of working with other talented people and within certain positive circumstances, and adjust accordingly.  Then, once you know when and where you need reinforcement, you can go out and find other people to move the mountains with you.  Or you can just hire a construction crew that can go get some dynamite and blow up that fucking mountain.

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.

Monday, July 29, 2013

Settling in and looking up

I can't even begin to comprehend the fact that I have been in Hong Kong for nearly nine months.  Everyone always cites "time goes by so quickly" as a general truth, but now I understand that there are actually certain points in your life where you feel like you're moving so fast you're bordering time travel.  That said, I think it's established pretty early on in human life that it takes nine months to create something new and fully functioning.  After that point, your creation continues to grow but it remains fundamentally the same.  No, I'm definitely not pregnant, but that's exactly how I feel about my life in Hong Kong.  I'm fully functioning and finally ready to really grow again.

When I was a sophomore in high school, I stopped checking my work before I submitted tests.  My teachers remarked (and even mocked) my exceptionally efficient test taking abilities, but the reality was that I did much better if I didn't check my answers.  If I went back to review my responses, I would talk myself out of my initial instincts.  I might not have been able to rationalize exactly why I thought my first response was right, but I would end up convincing myself another answer was better.  If I went back to check, I'd think... "Well, how do I really know that's right?  I could actually rationalize this other response as being correct, so it must be better."  It turned out most of my erased/replaced answers were wrong.  So, relatively early on, I resigned to tricking myself into following my intuition.  It consistently turned out for the better.

I have applied this purposefully deceptive methodology to my broader life as well.  I have specifically sought out new and different experiences as a means of avoiding over-analysis and just experimenting on myself.  I craved situations where I didn't have time to do anything except react from my gut.  Just as I had felt with the tests, I was surprised by the accuracy of my own thoughtless reactions.  I realized that it was in these moments that I could see my "true" motivations, capabilities, and desires -- because I didn't have the time to try to control them or convince myself of anything other than my natural instinct.  Sure, maybe I could have just learned to "trust my gut", but I didn't even trust I could do that.  That's what drew me to sales and trading in the beginning.  If someone yelled at you, you didn't have time to analyze it, you just yelled back!  Similarly, this is why I love to travel.  Take away all your familiar surroundings, your habits, and life's other common denominators, and you are free to see what really makes you you.

I have learned a lot about myself by observing those instantaneous reactions, such as the fact that if you scream at me, I will fucking yell back (this tends to surprise a lot of people, which is also entertaining.)  Or the fact that I'm surprisingly okay with multiple days of not showering, but terrified of swimming in the ocean.  Sure, these things are interesting and relevant in certain contexts, but now I realize that constantly forcing yourself to react can actually prevent you from seeing the bigger picture.  These situations may be useful to observe, but they are really just distractions from doing the deeper digging.  Maybe it's just that I'm older, but I'm now much less afraid of asking myself, "What am I actually good at?  What do I really enjoy doing?  What do I need from life?  What can I give back?"

When I first left finance for the startup world and my boyfriend moved halfway across the world, I was in reactionary mode.  But after a few months I got used to it, and I have to admit that I kind of found my groove.  I developed my routines, I made myself comfortable in my new surroundings, I found a place where my basic needs were met so I could start truly observing myself.  Sometimes, the way that we react when we're truly comfortable is when we learn the most.  Where are you drawn when nothing is pushing you in any given direction?  Though I'm not strong enough to truly not care what others think of me, what am I like when I am at least aware and accepting of how I am viewed by those around me?    What happens when you really let your guard down?

I think I have finally gotten to that place in Hong Kong.  I have settled into my life here, I have accepted my general place in this foreign context, and now I am itching to get back to looking past the immediate.  What truly matters and what is only a reaction to my present surroundings?  Where do I find myself taking initiative and where am I simply scraping by?  What do I do when I have nothing to do?  These are much scarier realities to face, but I think I'm finally ready again.  I'm not sure how that applies to test taking, though....

Sunday, July 21, 2013

Structural dissonance

Until now, my daily life (and general life path, too, I suppose) has been very structured.  You might even call it regimented.  Sure, it was partially by default.  When I was in school, classes started and ended at the same time every day.  When I was on the trading floor, the markets opened and closed at the same time every day.  But ever the creature of habit, I sought out routine as well.  Even when I entered the start up world and schedules became a lot more flexible, I still woke up at the same time every day. I still had a schedule for going to the gym. I still wrote a to do list every night before I went to bed. I even picked up the same breakfast every morning (god I miss New York bodega breakfast egg wraps...)

Then, I moved to Hong Kong and completely threw away anything that had any semblance of a pre-established guideline.  When I embarked on this adventure, my inner rebel took over and I thought... "Routines?  Please.  I don't need no stinkin' routines." (film reference, anyone?)  My day started and ended when I wanted.  I had meetings whenever I decided to schedule them.  There weren't any restaurants around that had my regular food choices, I could eat anything that sounded good.  I could do my work from wherever I pleased. I could go to the gym whenever it fit into my schedule, even if that was 2pm.  Hell, I could wear my pajamas all day if I felt like it and nobody could say or do a thing about it.

At first, I was in heaven.  I felt totally liberated, empowered, and independent.  I had broken free of all of the "defaults" that had dictated my days for so long.  It seemed I was cheating the game of life, and it made me feel giddy.  Like a kid who had effectively managed to stay home sick from school, though feeling completely fine.  But soon, the honeymoon period ended and the fog of indecision slowly settled in. I began to obsess over when and where to do things.  What would be the optimal schedule for that particular day?  Which coffee shop did I really feel like working at today?  When would it be most efficient to drop by the gym?  No, I can't respond to this e-mail right now... I'm not prepared to write the response it deserves.  I can do it later.  I have to wait until I'm in the perfect 'honest and personal e-mail writing mood.'  There was plenty of time open in the week, surely it would strike me when the time was right.

Well, you probably see where this is going.  Those honest, personal e-mails never got answered.  I wasn't writing as much.  I often skipped the gym, or waited until just before a meeting to go, forcing myself to cut my exercise short.  No matter what I did, I could only think about the opportunity cost.  What if doing this at another time or in another place would have been better?

Worst of all, I was chronically late.  For some reason, I felt as if this elusive bolt of productivity only struck when I had but few precious minutes left before I needed to rush out the door.  I had no choice but to take advantage. I had to get this or that done before I could be on my way, otherwise I'd miss the opportunity to check it off the list.   I don't know if people really minded me being consistently 7 minutes late for meetings, but it sure bugged the hell out of me.  I felt like a really fucking annoying person.  A weakling who was constantly paralyzed by overanalysis, indecision, and regret.  Gross.

I finally had to look myself in the mirror and admit it.  Yes, I need structure in my life.  I crave routine.  I had been terrified of admitting this to myself, not because I didn't think I had the self discipline to create my own framework for daily living.  But more because I was afraid of relying on said framework. I thought I was weak for needing to outsource my decision making to a predetermined set of defaults.  But this time, it's different.  Because I'm choosing structure.  I'm not choosing it over freedom, I am choosing it for freedom.  So that I can stop obsessing over the little things and liberate my brain to think about the productive, creative things that really matter.  I don't need to wait for the "optimal time" to do something, I can make it the optimal time by just doing it now.

It's only been a few weeks of this newfound acceptance of needing some sense of regularity.  But I'm feeling a lot better about things.  It feels like a weight has been lifted.  There's less paralysis by analysis and a lot more of just getting shit done.  When setting my new daily schedule, I need to walk a very fine line between holding myself responsible but not being too rigid.  Much easier said than done, of course.  I'll let you know how it goes.


Tuesday, July 9, 2013

Taking the first step

I think it is just beginning to dawn on me how significant of a step I took when I decided to leave my job at Goldman.  I'm a year and half into my P.F. (post-finance) life and, for a variety of reasons, it's just hitting me now.  It seems sufficient time has passed such that the public has deemed me beyond the point of no return and they are starting to marvel at my apparent insanity.  I've been asked with increasing frequency: "How did you do it?  How did you figure out how to leave and not look back?"  There's also the fact that my bank account is dwindling and I'm marvelling at my own apparent insanity.  I still don't regret it for a second, but the reality of changing my lifestyle has certainly settled in.

Additionally, as the buzz around the startup community in Hong Kong grows, I am talking to more and more people who are working in finance, consulting, or other corporate jobs, and secretly dream of one day leaving to pursue some other passion.  Though many credit money for being the primary reason for not taking that leap, I think it's something else -- or at least a combination of factors.  For me, it was both a lack of direction and a lack of confidence in my own abilities.  I thought, if I did leave my job ... what is that 'other' passion that I would pursue?  I have always been interested in a lot of different things, but I never had that one thing that I loved so much or that I couldn't live without.  I am not obsessed with one industry, one product, one activity that would make it glaringly obvious what I should pursue.

And from a practical standpoint, what would I even be able to do? I've always been kind of good at a lot of different things, but never excelled so much at one thing that I had no choice but to go after it.  If anything, my strength would be general business skills, which is why I dream about starting or running a company one day.  Even still, the only jobs I had in my adult life were... bank teller, smoothie/sandwich girl, tour guide, a little data entry, and Equity Derivative Sales.  Not really the most applicable background if you want to start a company.

When I would share this frustration with people, their answer was always, "Why don't you just go to business school?  You can figure it out there."  But I didn't want to take two years to go to business school to "figure things out."  My frustration with my then position was that I didn't feel like I was really doing anything.  It felt like I was just spinning my wheels every day.  If I went to business school, I was only delaying the inevitable.  It wouldn't actually solve my perceived lack of productivity.  

I really believe this is a fundamental desire that lies within every one of us.  A desire to break free of our constraints and get to a place where we can truly contribute, where we can build something bigger than ourselves, where we actually matter.  It is natural to seek the satisfaction that comes from seeing tangible results of something real that you did, an idea you came up with, connections that you made -- that satisfaction is indescribable.  I think it's fundamental because it means you have a sense of agency -- the ability to contribute, to create, to choose is precisely what makes us human.  So, I suppose it's ironic that so many of us are waiting around for someone to tell us it's okay to take control of our lives and to make a conscious choice to be free.  We don't actually need to rely on other people to get a taste of creation.  It's ours for the taking, we just have to go after it.

So, then, how did I get started?  It didn't happen overnight.  But, even though I had no idea where I was going to end up, I did take some small steps to set myself on a different path.  Here are some little things I did that I'd recommend for anyone lusting after a change.  These seemingly minor changes are what allowed me to subtly, passively, subconsciously formulate my escape plan.

  1. Expose yourself to your other options in the corporate world by signing up for notifications for job listings.  I had never looked for a job outside finance, I had no idea what was even out there.  There's a lot of riff raff, but at least you'll have a sense for your "practical" alternatives and the skills/background they would require.   
  2. Sign up for Escape the City.  This was first thing I signed up for after all the traditional newsletters.  Getting exposure to non-traditional options will open your mind and help you consider something you'd never even thought of before.   I didn't think I'd move to sub-Saharan Africa to work for an NGO, but who knows?  It got me thinking out of the box.
  3. Make sure you subscribe to both of these things using your PERSONAL E-MAIL.  Or, maybe don't, and your employer will find out and make your choice for you.
  4. Beef up your LinkedIn profile.  Add your experience, your background, ask for recommendations.  This puppy is pretty powerful and recruiters spend hours trolling for candidates with certain backgrounds.  You never know who might reach out to you.  I got my first startup interview for a role at ZocDoc after someone randomly contacted me through LinkedIn.
  5. Talk to your friends.  Tell people you trust that you're looking for a change and that you're unhappy.  If you're still unhappy and complaining years later, they'll hold you responsible and subtly push you to make a change (if they're good friends, that is).
  6. Start writing cover letters and doing interviews with start ups or other random industries you've vaguely been interested in.  Telling you now, you probably won't get the job (I got lots of rejections before I joined GA) but you'd be surprised how much value you get out of talking about your skill set, listening to how you sell yourself to others, testing how far you're really interested in taking things.  That way when the right thing comes along, you'll have a clear picture in your head of why you want it and how you can contribute.
  7. Sign up for Meetup.com, commit to some random activities, and meet some people in different industries.  Try out some new things, listen to other people's paths and stories, expand your realm of possibilities.  It's so inspiring to meet other people who are passionate and eager to share their interests.
  8. Go to a class or sign up for a course at a place like NYU School of Continuing Ed or General Assembly (I'm not just saying this, I'm serious.  I did this before I worked there).  You'll gain a practical insight into other industries, you can make some solid connections with the instructors and other leaders in the field, and perhaps most importantly, you'll get exposed to other people that are searching just like you are.  You may think you're special -- and you probably are -- but that doesn't mean you have to be alone.  Because the reality is you're not alone.  There are so many other people out there looking to make change but aren't ready yet, or don't know how yet.  There are also a lot of people out there that have made the change, and they'll make it seem a lot less scary.
  9. Get involved in a project, whether it's through friends, through a hands-on/project-based course as mentioned above, or even through Craigslist.  It doesn't have to be your own, it doesn't have to be your dream passion project, but you'll get to exercise your mind, test and come to understand your own capabilities, and you'll feel amazingly empowered to see that you can accomplish something meaningful out of your office.  It will remind you what human agency tastes like, and you'll have no choice but to go looking for more.

So, there you have it.  It's a long list, but it's pretty easy to do.  It won't force you to do anything you're not ready for, but it will help you passively prime yourself for success.  You're just warming up your muscles for your leap so you don't sprain, tear, or break anything.  Before you know it, you'll find yourself at an impasse where it feels natural to just jump.  I can tell you from experience, it will still hurt, but as long as you're properly prepared it'll be a really good kind of sore.

Sunday, June 30, 2013


This weekend, I climbed a waterfall.  Literally.  Admittedly, I didn't totally know what I was getting into, but I am still giving myself credit for being adventurous and mildly crazy.  I've been making a conscious effort lately to get away from the computer (obviously not now) and commit myself to relaxing, enjoying life, and not worrying about e-mails, students, or anything else work-related.

I've realized in the past few months that when you work primarily from home, this is basically impossible.  Thus, the best way to accomplish this so-called "un-plugging" is to get my ass outside and into an environment where the digital world is wholly inaccessible.  And while I'm at it, I figured why not throw in some potentially life threatening rock climbing to really drive the point home?  Yes, I fully acknowledge this is a sad thing to have to manipulate yourself into relaxing, but so it goes.  And I have to tell you, it works quite well.  There's nothing like plopping yourself in the middle of nature to remember how insignificant most of our troubles are -- in a good way, not in a depressing "nothing matters so what's the point" type of way.

As I was looking for the next way to unplug, I was sifting through Hong Kong's many fun outdoor excursions and I came across this hiking blog which recommended a hike to Wang Chung stream (橫涌石澗).  There were several warning signs that this would be a new flavor of adventure, all of which I failed to notice.  My ability to read quickly sometimes results in a compromise on the comprehension of the details.  For example:

  1. I should have noticed that Waterfalls was a separate category on his blog.  He refers to it as "stream trekking" which is "more challenging than regular hiking".  
  2. I did read the note that said "Do not attempt to climb directly into the larger falls.  People did lose [sic] their lives there."  I thought, 'Um I'm not a fucking idiot... who walks directly into a large waterfall and tries to climb up it.  We'll be fine!'
  3. The directions begin with, "Take the steps down right by the sign that tells you not to enter."  
  4. Next, he says, "You will walk along the stream for a few meters then enter the stream proper."  

Anyway, hindsight is 20/20, but I'm glad I didn't fully process the potential danger of the situation
Green river.
because if I had, I might not have gone and it was pretty damn awesome.  We started out wandering along Bride's Pool Road trying to find previously mentioned "Do Not Enter" sign.  Should have been another warning sign that there were actually quite a few of them, and we ventured the wrong way a few times.  One wrong turn brought us to this dam and smaller waterfall where the water was so green it looked like an optical illusion.  I've never seen anything like it before.

There were several moments where we were tempted to just explore on our own instead of continuing to find this guy's directions, but ultimately we both opted to minimize the unknown and look for the beginning of the path.  Once we found the entrance he described (after a lot of debate and probably an hour of back and forth), we ventured down the steps and saw the falls and thought, "This can't be right.  There's no path."  We turned back, debated some more, and decided that indeed that was the correct entrance so it must be right.  Maybe we just missed the path.  This is when we realized that the directions actually did say, "Enter the stream proper."  And so it began.

We thought this was the top.
I've never experienced a place where it was so loud and yet so quiet.  The only sounds around were the stream, the distant, more violent falls, and my occasional whimpering.  There wasn't another soul in sight.  We started up the first set of falls.  Unlike my previous post about climbing the stairs, where you can't help but look up and marvel at how far you have to go, this type of climbing had a distinct requirement of only focusing on where you are right now.  This is because a) you can't see that far ahead because there are giant rocks and water crashing down right in front of you, and more importantly b) if you aren't paying attention you will fall over and into the waterfall. Sure, there is the occasional need to brace yourself and look ahead in order to avoid dead-ends and strategize which path will allow you to keep climbing, but you get what I mean.  As you can imagine, this is the perfect remedy for an unrelenting anxiety about life.  At some point when someone was trying to counsel me on how to "just relax" (good luck with that if you haven't tried it), it was said that fear is living in the past, and anxiety is living in the future.  Well, here you go: no choice but the present.

Although there were a few points where I looked down and said, "What the hell am I doing?" or "If my parents knew what I was doing right now, they'd kill me," I was generally pretty uninhibited by the task at hand.  It brought me back to the hours we used to spend as kids playing "hot lava" where you couldn't touch the ground.  It was so fun and carefree, hopping from rock to rock, trying to devise the most efficient and least life threatening way to climb higher.  No tactics or strategies were off limits; there was crawling, scaling, pouncing, grabbing onto moss-covered branches, using your arms to hang on as you swung between slightly too distant stones.  There wasn't a "right way" to get from one point or another.  It was about doing whatever worked to keep moving forward and upward.

But actually, that's the top.
My boyfriend provided the perfect amount of support, testing the water (literally, at one point) so he could turn around and provide me an extra hand whenever necessary, but also letting me climb ahead when I was feeling confident.  When I thought I had finally reached the top, I hoisted up onto a flat rock where I could comfortably relax and let my guard down, I looked up and was shocked to see... there was more.  Way more.  It was already a wonder to marvel at the medium sized fall, and even more breathtaking to look up and see something ten times as big.  It was just like reaching a different level in a video game, it remained hidden until you were at a point where you thought you'd conquered the game.  And then, there it was, a challenge that loomed aggressively above you, reminding you that you can never "win", and just how tiny, weak, and insignificant you are.

We obviously decided this was the end of the line for us, so we stopped for a minute for some water and to soak in the epic atmosphere.  Though my boyfriend had no problem relishing in the experience, after a few short minutes and a couple photos (included here), our little adventure finally caught up with me and my sense of self preservation kicked in.  How had we come this far, and how were we going to get down?  What if it starts raining?  Those clouds look dark, it would be better if we started our descent immediately.  Yes, the falls were great, but they were also scary and it was time to go.  My boyfriend wanted to relax for a few minutes, but I couldn't be convinced.  I went ahead and started the descent.

OK that was fun, can we go down now?
It's amazing to me to reflect on how genuinely I had enjoyed that climb to the top.  My mind was at once completely free and also wholly focused.  I was experiencing everything in real-time, instead of the delay that usually results from my habitual over analysis.  I was playful, joyful, and totally present.   There was no real "destination" or "goal", there was a drive to get to the top but a lack of clarity on what that looked like.  Yet, I instinctively knew when I had "arrived" and it instantly ceased being enjoyable.  On one hand, it is validating to realize that I had truly embraced an "It's about the journey, not about the destination" mentality, but shouldn't I also revel in the destination, even a little bit?

To take the analogy further, I am truly enjoying the experience of living abroad, of establishing a new business in a foreign place, of navigating the challenges that come along with it.  Though I have a vague idea and a motivating vision of what "ultimate success" would look like here, the fun part is figuring out how to get there.  I don't think "success" would necessarily make me any happier than I am now.  If anything, the pressure of that sort of "achievement" would ruin any corresponding sense of enjoyment.  In some ways, I have already fallen victim to this, as I don't think I have paused to properly acknowledge or celebrate even the little milestones I've reached in the past six months.  Sure, after each accomplishment there was a brief moment of relief, but then came the subsequent flood of new goals, concerns, and problems that were suddenly within reach.

Part of this lack of pause is simply my personal drive to "achieve", but perhaps another part of it is a bit of the "impostor syndrome" -- not believing I deserve my own success, but that I have merely tricked the world into thinking I am capable and as a result of my deception, I have accidentally landed in a good place.  So, I better keep going, keep taking things to the next level before anyone figures out that I'm not actually good enough to have done all this.

Whatever the reason, my new goal is to change this mentality (though I'm still a bit unclear on how) and try to step back once in awhile and feel good about what I've accomplished.  Enjoying the journey shouldn't mean the destination can't be great, too.