Monday, December 29, 2014

No silver bullets in education... except maybe this one

Someone recently asked me about red flags for investing in early stage companies.  Particularly when it comes to education, a red flag for me is anyone promising that their product or service will “revolutionise education” or “disrupt the educational system as we know it.”  We all know entrepreneurs are prone to hyperboles, and I certainly appreciate a bold vision, but I usually find these type of statements to be overly dramatic, simplistic, and short-sighted.  In fact, by believing that you are single handedly revolutionising education, you’re missing the potential for revolution entirely.

I have been thinking about this concept quite a bit and have been mulling over how to write about it for way too long, so I was delighted when I was looped into a conversation around this video “What will revolutionise education?” by Veritasium. The author posits an interesting point that many technologies have promised to “revolutionise” education, yet none have.  At one time, Thomas Edison was so excited about the potential for motion pictures to revolutionise education, he is quoted as saying, “Books will soon be obsolete in schools… scholars will soon be instructed through the eye.  Our school system will be completely changed within ten years.”  That was in 1913.  So, what happened?

Veritasium points out that the motion picture did not successfully revolutionise education, and neither has any technology since, because when it comes to education no technology is inherently better than the other.  I don’t disagree entirely but I would add a qualifying factor that no technology is inherently better than the other at scale.  For certain concepts, for certain students, some technologies are actually better than others.  Everyone learns differently.  For me, I remember pictures much better than moving images.  I remember words that I see much better than words that I hear.  (Fun fact, I had a grade school teacher who thought I had a photographic memory.  I don’t, though that would be awesome.)  In any case, each person is different, which makes a revolution nearly impossible given each person wants and needs different things when it comes to their education (I mean that on micro, macro, and meta levels).  So the what we need to do would be figuring out a system that allows for scalable individualisation, mass customisation of content, delivery, trajectory, and motivation.  Clearly, no silver bullets here.

Suspending our disbelief for a second, let’s say there were some silver bullet technology that could “fix education” — scaling it to any sort of “revolutionary” level requires cooperation of a diverse group of people and systems, which is exceedingly difficult.  When people are so different, how can we convince them that any one thing is the answer? In fact, the comments section of this Youtube video embody this challenge.  Let me share some highlights:  
  • Everyday, millions of children march to school with drudgery and resistance.
  • It is the teachers job to try to inspire their students, but let's be honest, they don't. Most don't try or fail miserably at it.
  • Kids are without homes, and without clothes. Teach these first and you will revolutionise education with full stomachs.
  • For you to personally accuse me of thinking I'm better than them just shows how irrelevant your train of thought is.
  • Stop wasting your time criticising my ideas when you could be thinking of your own. Get a grip.
  • Everyone is being a total bitch?

Clearly, it is all too easy for a productive conversation around education to devolve into a virtual pissing contest.  My point is that the challenges with education are incredible, astonishing, diverse, far reaching, and incredibly complex.  Given all of these competing factors (egos included), it is all too easy to throw our hands up in the air and say, “Forget it!  It’s impossible!” 

But here’s a thought.  Maybe the truly revolutionary concept is simply embracing that there is no revolutionary concept.  By acknowledging that there is no “one size fits all” solution, no single technology that will change the system forever, we are liberated to pursue a multitude of different strategies that solve different problems for different learners in different markets around the world.  We will never have the answer because there is no one answer.  That’s not discouraging, either.  It’s incredibly empowering.  It frees us to stop talking and start creating solutions (or in my case, investing in them).  That’s why I truly believe that empowering engaged and passionate entrepreneurs with the resources and networks they need to succeed is the only thing that even comes close to a silver bullet in education. 

Tuesday, September 2, 2014

Getting real about gender issues

There’s been a lot of talk recently about female founders, discrimination in the start up world, and what we can do about it.  There have been countless articles, studies, and op-eds talking about what are the challenges for “female entrepreneurs”.  Those who have the courage to express their opinions and personal experiences are simultaneously praised for their bravery and viciously criticised for their skewed interpretation of the issues at hand.  There is no obvious answer for, “Why do only 13 percent of venture-backed companies have at least one female co-founder?” or “Why do women make up only 4.2% of partner level VC’s in the US?”  It’s dumb and unfair, and I want to be part of changing those numbers.  In order to do that, though, I have to stop walking on eggshells and own up to something important.

Regardless of my opinion on these issues, I must admit I often find myself holding my tongue and not saying what I really think. Not because I’m afraid of disagreement - I’m fine with that. It’s much more shameful to admit than that.  Mostly, I am afraid to let go of the idea that I can be totally objective.  That’s the ideal, isn’t it?  I don’t want to be seen as “biased”, “sexist”, “unsupportive” or “overly supportive”.  Especially when I am making decisions to invest or not invest on behalf of our partners, the last thing I want them to think is that my analysis may be skewed by prejudice.  

However, it is precisely this fear that is keeping these unbalanced statistics firmly in their place.  Forget the numbers themselves, the conversation about minorities and entrepreneurship is not going anywhere until we all get real, acknowledge where we are coming from, and start saying what we really think.  

Let’s face the facts — absolutely every single person is biased when it comes to gender issues.  Except for a very small subset of the population who have experienced the world as both genders at different times (who we should all pay close attention to because they can provide the most accurate description of the differences between society’s perceptions of men and women), we are born either a man or a woman.  You can’t help how you’re born, or how you grew up, or the set of experiences that have formed your current mindset.  So, guess what?  You are biased.  I am biased.  We are biologically hardwired to be biased.  So why is everyone pretending that they’re not?  

Instead of striving for complete objectivity, we should all take ownership of our biases so we can fully embrace and benefit from diversity.  Diversity of experience, mindset, and purpose is a competitive advantage, but only if we allow it to be by being honest about where we're coming from.  Hello, I am a white American female in my late-20's. I went to an Ivy League school, worked on Wall Street, then at a VC-backed education start up in New York and Hong Kong.  I now live a privileged life of an expat in Asia.  Does that define who I am?  No.  Has it shaped how I see the world?  Absolutely.  

As a woman in VC, I want to support female entrepreneurs.  I really do.  But yes, sometimes I am unintentionally harder on them than their male counterparts.  I have experienced the disadvantages of being a woman in male-dominated industries like finance and tech.  I believe I have had to fight a little harder than a male in my position would have, and sometimes I take that out on other women by expecting the same from them.  I am very aware of this bias.  I’m owning it right here, right now.  I hope I can change that, but I’ll never have the chance if I don’t acknowledge it.  

As part of a team of two at Fresco, we come from different backgrounds, life experiences, professional capacities, and personal interests.  We communicate well, but most certainly approach problems in different ways.  Being aware of our differences and open to new ways of thinking has been a huge advantage for us in the investment process.  Out of our 28 companies, 50% have at least one female co-founder.  We don’t have quotas, and we never set out to encourage female co-founders, it simply happened as a byproduct of owning our biases and staying open to new possibilities.  I hope that through continued awareness and honesty, we can continue to peel back the layers of our own prejudices and create the space for diversity to truly flourish.

Monday, September 1, 2014

Starting from scratch

Logic will get you from A to B. Imagination will take you everywhere. – Albert Einstein

In classic Hong Kong fashion, I have spent the last year living in an apartment that is cozy, convenient, and compact.  Yes, just like a shoebox.  Naturally, as I hit my two year mark in this bustling metropolis that I love so much, moving to a bigger apartment that can actually fit furniture inside of it feels like a rite of passage.  As much as I love my Murphy bed and the cabinets that are pre-built into my walls, I'm thrilled to finally have enough space that I can actually choose what it might look like.

Well, I was thrilled until I realized that "possibility" also means "responsibility", which really means "work".  All of a sudden I have to figure out what fits where, how big it can be, what it will look like, whether or not it will match everything else, what if it gets spilled on, how much of our budget can we allocate to it, when it is available vs. when we need it and how the hell we will get it to the 17th floor. Starting from scratch starts out feeling like the ultimate freedom of a blank canvas, but shit starts piling up pretty quickly, and all of a sudden you don't feel so free anymore.

I hate to admit it, but this is an uncomfortably familiar feeling.  Graduating from college initially feels like the ultimate freedom - no classes, no semester schedules to juggle, no reason not to live anywhere you want.  Leaving a traditional career path for a start up initially feels like the ultimate freedom - you can create something new, craft your own product, team, and vision.  Oh, but what about paying your bills?  Generating revenue?  Wanting to live close to your friends?  Need to find the right people to hire?  People keep talking about this Lean Start up thing and agile methodology, aren't you supposed to work that in somehow?

When faced with such an overwhelming challenge, a natural first step is to start gathering information.  In the tangible case of furnishing my apartment, I gained a new appreciation for how much money furniture stores must pay brand agencies, because they seem to have successfully manipulated me into believing that where I buy my furniture really says something about what kind of person I am.  Seriously, I have used way too much of my brain capacity wondering if I am still an IKEA person, or does that mean I have commitment issues?  I'm drooling over the clean lines, translucent smoked glass, and trendy gray felt fabrics at BoConcept, but the price range is slightly above my means.  Or, maybe I should stay true to my inner scrappy entrepreneur by scouring GeoExpat (Hong Kong's functioning version of Craigslist), where I can bargain my way to underpaying for high quality, only gently used items that may or may not fit together.  Do I care more about my money or my time?  Go ahead and try to analyze that.

Then the hunt begins - gathering information, comparing dimensions, weighing priorities.  Nothing fits quite right - if the dimensions are perfect and we love it, it can't be delivered until 2015.  Maybe the fit isn't quite right, but it's within our budget, and available immediately, but what if the color doesn't match the other things we have picked out?  No matter what the context, it's excruciatingly frustrating to have a vision of what you want things to be like, but the path to getting there is cluttered with a million uncontrollable variables blocking your way.

Frustrated and teetering on the border between a panic attack and completely shutting down and giving up, we finally stumbled upon some furniture stores in Wan Chai.  We wandered in and started asking about the pieces they had in the showroom. We braced ourselves to mentally prioritise delivery time vs. design vs. price.  The little team working in the shop, a soft spoken yet quietly eager young man and an older more portly Cantonese woman with a designer's eye, patiently watched us debate the numerous variables.  The English speaking young man quietly interrupted and suggested, "Well, we can make it any size you want."  I was so dumbfounded, I asked for clarificaiton multiple times.  Apparently, you can choose literally everything about the furniture you order: the color, dimensions, wood, glass type, door type, fabric color.  It would then be manufactured just across the border in China and delivered to our doorstep for literally one third of the cost of any fancy, Scandinavian furniture store.  Fuck you, IKEA.  Ah yes, I fall deeper in love with Hong Kong every day.

The scariest and most empowering part of this particular metaphor is that when faced with unlimited possibility, we are the ones holding ourselves back.  In some ways, we need these restraints to avoid the sheer panic that comes with truly starting from scratch.  So instead, we search from the existing set of options, trying so hard to fit everyone else's designs and specifications into our own space.    Sure, you can have this job, use this type of methodology or job description template, go to this or that type of furniture store.  Price points, salaries, dimensions, hours, office locations may vary, but really it's all pre-determined.  We just assume that these are the only options available to us, because subconsciously, we think it will be easier that way.   But is it?  As Einstein so wisely put it, we resort to logic to get us where we need to go, but what we really need is just a bit of imagination.

What we forget to embrace is that literally anything is available to us.  Don't see it at the store?  Doesn't matter.  You can decide exactly what your life, your business, your home will be like.  It may take some work, you may have to go to Hong Kong to make it happen, but there's no reason why you can't have things exactly how you want them to be.  You may just need to stumble upon this store in Wan Chai to realize that it's actually possible.  So, there you go.  For Forrest Gump, life is like a box of chocolates.  For me (right now, at least), life is like an unfurnished apartment.

Tuesday, August 19, 2014

Keeping the lights on

I was recently asked to speak at the opening event of Baker & Bloom, an innovative education center in Hong Kong that aims to empower young people with confidence through courses like social entrepreneurship, creative writing, and many others.  The topic was, “How can we create entrepreneurs and innovators?” A pretty powerful question that I am sure millions of people would love an answer to.  If we could just figure out how to effectively teach our youngsters to be gritty, driven, creative, and innovative, we could transform generations!  No pressure at all...

I started racking my brain for an answer and initially found nothing by a bad case of impostor syndrome.  What could I possibly have to add to this conversation?  However, as I reflected upon my own journey, it occurred to me that perhaps this problem of "creating entrepreneurs and innovative thinkers" is actually a false choice.  Perhaps we don’t need to create them at all.  I would argue that all children are born with a natural light inside them.  A natural penchant to create, to innovate, to affect positive change in the world around them.  Our job as educators, investors, parents, friends, and members of society is simply to figure out how to keep that light from dying out, to fan the flames of entrepreneurship within each child, and to empower them with the tools and the confidence to pursue their unique passions.   

Of course, I’m not going to even pretend that I know how to do that, because I do not.  But I can share my own experience of how that light of entrepreneurship within me died out, how I was able to turn it back on again, and what I am doing now to keep the lights on for as many people in the world as possible.

When I was a child, I was incredibly creative, eager to try new things, and always trying to find a way to be different.  In second grade, I boldly proclaimed to my friends that I LOVED homework. I wrote a series of books about a cartoon aardvark named Dixie and her best friend, Missy the Chicken. I started a custom pillow business where I sold basketball shaped, heart shaped, and animal shaped pillows to literally anyone who would buy them, from my extended family, to my neighbors, to my computer teacher, Mr. Gilhooley.  

But somewhere between the social pressures of trying to fit in, wanting to look cool but also wanting be successful, between attempting to work hard, play sports, be editor of the Yearbook, and study for the SAT’s, between getting into Harvard, wanting to be the “perfect student”, daughter, friend, or girlfriend, I forgot how to be weird, crazy, and to try new things.  Instead, I simply learned how to be the best according to other people’s standards.

As a sophomore at Harvard, I was recruited to work on Wall Street, within the Sales & Trading division at Goldman Sachs.  I had no idea what a “derivative" was, but I knew that it was an exclusive world that was very competitive and fast-paced, filled with smart people, and that I should be grateful for such a sought after opportunity.  Throughout my four years at University, in spite of career counselling, academic advisors, and a diverse group of friends, I can honestly say it never even once occurred to me to do something else.  So, after graduating with a degree in Economics and Film Studies, I joined the Equity Derivatives team at Goldman in New York.  

My parents were extremely proud, people were always impressed by my business cards, I was able to support myself and even save a little money, and a lot of people wanted to have my job.  I felt lucky, but I was sad.  I was busy, but I was stressed.  I absolutely hated myself for not just being grateful for what I had, but there was no spark. I had no idea what it was, but something was missing.  Somewhere along the way, that crazy pillow saleswoman had closed shop and that little light inside me had gone out. 

In 2012, I decided to do something about it.  I took a leap of faith and left Goldman to join an early stage education start up in New York City called General Assembly. I was an early member of the team and saying I got thrown into the deep end is putting it lightly.  I was tasked with building out their long-form courses for practical digital skills for entrepreneurs - programs to teach people how to code, digital marketing, data science, user experience.  All amazing skills, none of which I knew how to do.  It was completely overwhelming, but all of a sudden it was like someone turned on the lights and the world had gone from black & white to full colour.  I was learning new things, solving problems, creating completely new possibilities for myself and for others, I was engaging with other incredibly talented individuals in ways that came very naturally to me, but I had completely forgotten how to do.  

Not only was I experiencing a change within myself, but by creating education programs that empowered others with the same experience, I was watching that light turn on within each and every student we had.  Our programs were geared toward adults, toward working professionals who, just like me, had been jaded by the real world and somewhere along the line, their lives had lost their spark.  I could see their eyes light up and their worlds turn to full color as they found themselves building their own websites, launching their own marketing campaigns, making their own dreams a reality.  All things they had always said they wanted to do, but had forgotten were completely within their reach.

Once I got a taste of my childhood back, the entrepreneur within me came back with a vengeance and I haven’t looked back since.  People tell me I am crazy all the time, but I can’t help that I just keep thinking bigger and bigger.  After seven months building out the education programs and team at General Assembly in New York, I decided I was going to move to Hong Kong and launch their business in Asia… they just didn’t know it yet.  I pitched the founders on why they should let me give it a try, they told me I was insane, that I was completely inexperienced, but I didn't care.  I wouldn’t take no for an answer.  They finally said yes, and in 2013, I incorporated General Assembly Hong Kong.

From nothing, we started launching all types of education programs to empower entrepreneurs in Hong Kong. After just nine months (and very little sleep), we had dozens of amazing teachers on board, 2,000 students had come through our doors, we had formed countless partnerships, and I even had a full-time team of six people.   Then, in January of this year, I took on a whole new challenge when I handed off the business to a new Director and joined Fresco Capital, a seed stage fund investing in entrepreneurs around the world. 

I have been learning a lot as an early stage investor but I just couldn’t stay away from the power of education and the magnitude of the work that needs to be done to make sure that everyone has what they need to keep the lights on and to see the world in full color.  Again, I can't pretend to have any idea how to do that, but I know I can contribute.  So, now, we are raising a new fund at Fresco specifically to invest in entrepreneurs who are starting businesses in education technology.  The goal of this fund is to scale our impact as much as possible - to leverage our capital, experience, and network to help change the system, one business, one entrepreneur, one student at a time, one light at a time.  

I share my experience here to highlight that the challenge of encouraging innovation and entrepreneurship is not about shaping our children as individuals.  They are already filled with infinite capability and wisdom.  Our challenge is banding together to shape the system so that it fuels their passion instead of stiffing it.   

Thursday, July 24, 2014

3 Life Lessons from a Hong Kong Summer

When I decided to move to Hong Kong, there were plenty of things about this lovely little place that had never occurred to me.  In particular, my Midwestern pea-brain did not fully comprehend that although it is part of China, Hong Kong is technically in Southeast Asia and it is a tropical climate.  I’m not sure what I expected, but oh boy was I surprised by what I got.

I may brag about the 70 degree and sunny December days, but now that it’s July, I’ve got my tail between my legs.  Don’t get me wrong, I still love Hong Kong, but after two summers here, I figured it was time to stop complaining. I’m finally ready to face the heat and the humidity with humility and see if I can find meaning in my temporary physical suffering.

Perhaps it is just my deluded desire to take the negative and turn it into something productive, but I realised that dealing with summers in Hong Kong actually has taught me a lot about life.  I thought I would share a few key lessons I’ve learned recently and what they might mean outside of the weather forecast.

1.  Just because the sky is blue doesn’t mean it’s not raining.

First of all, I mean this completely literally.  Summer in Southeast Asia is rainy season, which means no matter what colour the sky is or how many days in a row it has been raining, there are absolutely no guarantees.  The sky’s determination to secrete water is unpredictable and undeniable.  The clouds move swiftly and vindictively, so if you aren’t prepared with an umbrella at all times, you will get soaked.  The good news is, there are 7/11’s on ever single corner and every half block in between, and there’s a Circle K across the street from every 7/11, so there’s usually a solid backup plan if you get caught protection-less.

What has this really taught me?  Never take things at face value.  Always be prepared.  And if you’re not prepared, know what your options are (7/11 or Circle K?)  Just because things are going swimmingly now, doesn’t mean there isn’t a T10 typhoon waiting for you around the corner… 

2.  You don’t actually want it to be sunny.

Having lived through a lifetime of brutal winters in Chicago, Boston, and New York, I have been conditioned to believe that sunny = good.   What could be bad?  Summer sun evokes romantic images in my mind of playing in the sand on the beach, frolicking in the grass, soaking up rays with friends, laughing over picnics and bonfires and sunsets.  

Early in the erratically cloudy Hong Kong summer, I found myself resenting the rain and yearning for blue skies and sunny days.  Then, I got what I wished for and I learned my lesson:  When its 100 degrees fahrenheit and 100% humidity, you do not want it to be sunny.  A day at the beach in the HK summer sun is a recipe for skin cancer, multiple days of dehydration, and intense fatigue.  

Especially when it comes to startups, traveling, and relationships, we always have romantic notions in our mind of what the ideal experience would be like, if only the conditions were perfect.  Sometimes, we are lucky enough to get what we want, only to quickly discover the reality is far from what we had imagined.  

3.  You may think you don’t smell, but you do.  I 100% guarantee it.

I don’t care if you have never been “a sweater” or if you use investment-grade deodorant.  I don’t care if you just showered, or if you took a taxi here.  It is summer in Hong Kong, and you smell horrible.

I can say this because it is completely true for myself.  I used to be one of those people who could run for miles and barely break a sweat.  I never understood the difference between antiperspirant and deodorant, I just bought whatever had the best perfume.  Consequently, I spent one year in Hong Kong assuming that smell was not coming from me.  I spent another year thinking I was probably the only person that could smell myself.  Now, I’ve come to terms with the fact that I stink and everyone knows it.  And guess what?  You do, too.

I recently read a great post on the importance of facing your ego and acknowledging your own motivations for doing a startup (check it out here).  Besides our sometimes savoury scents, there are a lot of things about ourselves we are afraid of facing: we are selfish, we are mean, we are scared of failing, we want to be needed, we need to be valued.  The beautiful things about admitting these otherwise shameful realities is that you’re not the only one.    

Accepting your body odor, your vanity, or your selfish motivations won’t cure you of them.  It will, however, liberate you from dwelling upon them and wondering if they’re good or bad or relevant at all.  It will free your mind to move onto more productive tasks.  It will also remind you that sometimes if you want to get things done in Hong Kong during the summer, showering three times per day is just plain essential.  

Tuesday, July 22, 2014

Why education? Because I am selfish... but I'm not an asshole.

Several years ago, I was tentatively toying with the idea of leaving my job on Wall Street and someone forwarded me a job description for something called an ‘Education Program Producer’ at a young, venture-backed, NYC-based tech start up.  Not only did it not make sense (at the time, education + tech start up = oxymoron), I almost immediately deleted it mostly because I never saw myself working in education.  

Sure, I believed in education and I valued education, but I most certainly didn’t want to work in education.  The word conjured up images of slow-moving organisations, underpaid teachers, inefficient practices, endless paperwork, cruel bullies, and overly demanding parents.  Being a teacher requires being patient and kind, two virtues that were not exactly valued in my then current line of work on the trading floor. As someone who had come to love the fast-paced, no bullshit attitude of the finance world, education is the last place I saw myself going. 

I’m glad I didn’t let my obnoxiously judgmental attitude get the best of me and gave that job description a second glance because my experience at that NYC-based education start up changed my life forever.  Now, several years later and halfway across the world, I find myself doing everything I can to be involved in education.  I brought an education company to Asia, I joined a seed fund because they were involved in education, I am making investments in early stage education companies, and now look - I’m even writing about education.  

Since my obsession can, at times, feel out of character for an efficiency focused, mildly foul-mouthed, impatient individual like myself, I recently started asking, why the hell do I care so much about education anyway?  I mean, sure, if you ask someone if they care about education and they say “No,” they’re either ignorant, full of shit, or a psychopath.  But believe me when I say, I really fucking care about it.  True education is all about asking why, so I decided I would dig a little deeper and try to figure out what about it resonates so much for me.  

The word “education” itself comes with a myriad of connotations, but what I seek to do here is to minimise the emotional implications and figure out logically why it is so relevant and powerful.  Here’s what I came up with.  Three reasons: it is personal, it is sustainable, and it is scalable.  Hear me out.

1. Education is personal.

“It is personal.  That’s what an education does.  It makes the world personal.” - Cormac McCarthy
Everyone has either had an education, or not.  Formal or informal, public or private, too much or not enough, your education has had an undeniable impact on where you are today.  For these reasons, everyone cares about education, everyone has an opinion on education, and everyone knows how important it is.  When you ask someone what their education was like, they will tell you with words but more than anything, you will see it in their eyes and feel it in their heart.  Engaging with individuals on this level is powerful and incredibly energising.  The connections I have made with people when discussing this topic have moved me to my core.   
Education is personal for me, too.  I may be selfish in my desire to change the world and not waste any time doing it, but I’m not an asshole.  I am infinitely grateful for all the opportunities I have been given, and I believe everyone deserves not only the opportunity to get what they want out of life, but also the privilege of being able to figure out what that is.   
 2.  Education is sustainable.

Give a man a fish, you feed him for a day; teach a man to fish and you feed him for a lifetime.”  - Proverb
I care about the world I live in, mostly because I have to live in it for my entire life (unless space travel takes off, but that's a different topic).  I want the world to be a better place, because then I get to live in a better place.       
I also value my own time.  Call me crazy but I’d much rather teach someone to fish and then move on with my life, than have people bugging me every day to give them fish.  
The beauty of education is that it never goes away.  Its presence, or lack thereof, impacts an individual's every thought, word, action not just now but forever.   
 3.  Education is scalable.

“Give a man a fish, he eats for a day.  Teach a man to fish, he eats for a lifetime.  Teach him how to learn, and he’ll own a chain of seafood restaurants.”  - Someone on the internet
Creating a sustainable solution is great, but sharing it with as many people as possible is even better.  Education is the most scalable solution to any problem simply because it empowers the individual.  This means its impact is not just lifelong, it can be worldwide.  
It’s very simple math, actually.  If I teach three people to fish, they each teach another three people, who teach another three people, who teach another three people, now 121 people know how to fish.  Definitely a lot more people will be eating fish than if I had just spent all day catching fish myself. And, selfishly, I don’t have to spend all day on a fishing boat.  Win, win.

The word “education” is socially, emotionally, politically loaded.  It means different things to different people and is undoubtedly scary and dangerous to try to tackle.  I don’t intend this post to make light of the weight of education, but instead to look at it from a practical standpoint and understand why it is a good place to focus one’s efforts.  Whether you’re a teacher, a student, an investor, or a business person, it’s hard to deny that education is the most efficient way to change the world.  And for what it’s worth, it sure is a hell of a lot of fun, too.

Monday, June 30, 2014

Pivoting... but still getting started.

Someone said to me once, “Everyone has one good blog post in them.  After that, well… it rarely lasts. One Post Wonders, I call them.”  At the time it made sense superficially, but I was determined that it would not apply to me.  I have always loved writing and this was my chance to challenge myself to be open, connect with people from afar, and feel the rush of being creative on a regular basis.  

Recently, however, I have found myself thinking back to this comment as I must admit that I’ve been finding harder and harder to write.  I spent a few weeks wondering why this is.  Is it because things are stable, so I find myself boring?  Do I not feel like I have anything to say anymore?  Have I simply gotten lazy and stopped questioning myself?  Should I just give it up and try starting something new?

When I began writing this blog, I was facing a tremendous amount of uncertainty.  Given the alternative was crawling up in a hole and not coming out, I decided to approach my complete lack of knowledge and experience as a journey of self discovery.  I was figuring out what I was good at, what I cared about, how I could relate to others and the world around me.  Almost completely overwhelmed by all the things I didn’t know, I felt the only thing I had the authority to write about was myself.  Having an opinion on anything else seemed uncomfortable, almost arrogant.  So I chose to put my questions about myself out there first.  And it has been an amazing process sharing those questions with anyone who cared enough to read what I had to say. 

But simply writing about myself has gotten harder because, well, let’s face it... I’m pretty damn boring these days.  But also because as I am diving deeper and deeper into the angel investing world, my confidence is growing.  The number of informative experiences are piling up, data points are accumulating, and I’m starting to form stronger and stronger opinions on what I am doing.  I want to share thoughts on these topics, but I’ve been holding back because I actually believe sharing what I think about the world is a lot scarier than sharing what I think about myself.

Many have told me it is bold to be as uncomfortably honest and open as I have been on the blog.  Sure, I get a little nervous about it sometimes, but overall I actually think I’ve been taking the easy way out.  Writing about myself is easy because even if I reveal too much, if you don’t get it, or you disagree with my approach…. you can’t really tell me I am wrong.  It’s like when mature people tell you to use “I feel disrespected….” statements instead of “You disrespected me ….” because the other person can’t tell you that you are wrong (tricky, right?)  

Semantics?  Maybe.  But my point is that I feel I’ve come to a point where I’m ready to start thinking and sharing about topics that are much bigger than just me.   I no longer want to be afraid that people might discredit me or disagree with what I am saying.  

So, in the interest of always getting started, this post is marking a pivot away from writing just about myself. From now on, I'll be blogging about bigger topics such as what it's like to be a young angel, why we believe in female founders, why I care about education, and lots of other things which will certainly continue to involve my regular rambling, lack of conclusions, new beginnings, and self questioning/reflection. 

When we invest, we look for entrepreneurs who love what they do and feel they are on a mission.  That means that they’ll keep going even if they see a bump in the road or things get a little harder.  Nobody likes a hypocrite, so here I am, refusing to give up.  Refusing to be a “One Post Wonder”.  I love to write, and I cherish nothing more than the connections I have made and strengthened through this blog thus far.  So, yep.  I’m still getting started.  Just in a bit of a different direction.  Stay tuned!

P.S.  To mark the occasion, I also bought my own domain name.  #booya #bigtime #thelittlethings

Tuesday, June 24, 2014

Working hard... whatever that means.

I have been formulating this post for way too long in my head, so let me just shut up and get started right with the point.  How do you know if you are working hard?  

Now, maybe you have a healthier answer to this question than I do, but I know I am working hard if… I feel exhausted.  I don’t have time to get enough sleep.  Even when I do, I probably can’t because I obsessively think about whatever I am working toward.  I don’t have very much time to spend with my friends, let alone by myself.  When I am alone, I crave an escape - a mental vacation.  In short, I’m basically miserable.  

But even with all of that, there’s something about that state of voluntary distress feels so fucking good, right?  The masochist within me smugly smirks at the fact that there’s no denying that I am pushing myself to the edge, being everything I can be. The narcissist within me also feels rewarded for the reinforcement I get for how hard I am working.  Friends and family take one look at me and say, “Oh, wow, you look so tired.  You are such a hard worker!”  I’m offended, but I also feel validated.

Whether or not we like to admit it, we glorify this state of working hard and the misery that ensues.  Whether it is comparing how many hours we spent on our homework in high school, how many all nighters we pulled in college, how little sleep we get as adults, emphasising your self sacrifice tells the world that you are disciplined, diligent, and driven - all positive indicators that you are on your way to being successful, or at least you have what it takes to get there.  This is especially true in the start up world, where all nighters and success seem to go hand in hand.  There’s no surprise there are lots of issues with founder depression and burning out.  

I’ve often heard it asked - If a tree falls in a forest, but nobody hears it …. did it really fall?  In other words, if you’re working hard, but you’re not miserable… are you really working hard?  

I have been asking myself this question for the past several months.  When I was at Goldman, I worked 12+ hours days in an extremely high pressure environment.  I was in the office at 6am every day, reading the overnight news so my superiors wouldn’t have to. Starting General Assembly in Hong Kong, I barely slept.  I only had three months to prove the business would have traction here, and I was doing anything and everything I could to make sure that happened.  There was no one in the world who could claim I wasn't working hard.

Now, since I joined the angel world, there’s not too much that is traditional about my job.  We are a start up, too — a distributed team of two, constantly in and out of meetings, in the process of setting our fund’s goals and metrics, creating our processes and scaling our modes of communication.  I still wake up for 6:30am conference calls with our teams in the States, answer emails on the weekends, spend time thinking about the infinite projects, meetings, teams, and tasks to take on.

But, the typical stressors, motivating “or else” factors inherent in any job are missing.  I am often too self conscious to admit this, but I occasionally go to yoga classes at 10am, I work from home, I run errands in the middle of the day, I meet friends for coffee or lunch or dinner.    I have the opportunity to spend time learning about areas that I am interested in.  For the most part, I get to proactively choose who I work with.  All of this is fucking awesome, and as I’ve said before has created the space for me to be happier than I have ever been before.

But I would be lying if I didn’t share that every day I go to sleep and wonder, am I working hard enough?  Shouldn’t I be trying harder?  Sometimes I imagine other people’s voices saying, “Oh that Allison, I saw her going into the office at 11am the other day.  Does she even work?!  She must be so lazy.”  Even after I force myself to forget what other people think of me, silencing my inner critic is difficult.  I don’t know if I will ever feel I am working hard enough.  I can’t help but think if I were really on my way to taking things to the next level, I should be way more miserable.  

But maybe not.  What if feeling happy and balanced is part of the long game?  As evidenced by the things that we let fall by the wayside when we are busiest, listening to your instincts, trusting your limits, and taking care of yourself is hard work in and of itself.  Maybe dialling things back and taking care to not burn out is what allows us to push ourselves to the limit in a macro sense.  Someone told me the other day that balance is actually about living the opposites.  Perhaps there are just times in life where we push ourselves to our limit and are a little less happy.  And that allows us to get to a place where we can recover and reboot and get ready for the next sprint.  

Or, maybe I’m just making excuses because deep down I’m actually just a lazy motherfucker who doesn’t have what it takes to change the world in the way that I aspire to.  I really, really hope not.  I suppose only time will tell...

Sunday, April 6, 2014

Nothing is wrong?

You may read this post, immediately hate me, and never read my blog again.  In the past, that's probably what I would have done.  That's why I don't usually write about these type of things, because I've always thought happy people who talked about being happy were delusional and annoying.  Well, maybe I am.... so, proceed with caution.  I wouldn't blame you for telling me to shut the fuck up.  

For the last two and a half years, my life has ostensibly been incredibly chaotic.  In early 2012, I basically cried every day out of sheer frustration and misery with my job.  A dramatic turn of events on the trading floor led to the firm abruptly firing the people that sat directly to my left and to my right.  I, myself, quit only a few months later to join a start up. My first day on the new job, my boyfriend told me he was transferred to Hong Kong and would be leaving in a matter of weeks.  I moved apartments four times in six months.  My parents sold the house I grew up in, then moved into separate homes and ultimately separate cities. I decided to move to the other side of the world, where I started General Assembly in Hong Kong with exactly zero contacts and zero idea where it would lead.  I moved in with my boyfriend.  I broke up with said boyfriend. I moved out and started living alone for the first time in my life.  My parents got divorced.  I hired a team of six, then left General Assembly HK in their capable hands.  I traveled on my own for the first time, then I started an entirely new job and career in angel investing, an area I have no experience in whatsoever... I think you get the picture.  There's certainly no denying that my recent past has been rather noisy.

Funnily enough, however, things have gone quiet lately.  Sure, things have been busy and lots of change is always happening, but today I stopped for a moment.  I looked around, sipped my coffee, checked my phone, and then realized that nothing is wrong.  I am now two months into what can only be identified as the best job ever.  I'm reeling from how incredibly fortunate I am to be working with early stage startups in the way that I am.  I am constantly learning new things, working with people who are both intellectually and emotionally intelligent, meeting passionate and talented founders, investigating all different kinds of industries, products, and businesses.  I'm clarifying the things about which I am personally passionate (education becoming the more and more obvious choice).  I feel acknowledged, appreciated, and valued by my teammate.  I have a huge amount of flexibility over my lifestyle, my schedule, and my goals.  My typical day is mostly self directed and I have nearly unlimited opportunities to delve into whatever I find interesting.  I get to help identify problems and find creative solutions.  I play a role in empowering others.  All those things I've always said I wanted to do.  For now, it feels like I am doing them.

The rest of my life is pretty good, too.  I have healthy communication channels with my parents, I am eagerly rooting from the sidelines as they move forward in their new and separate lives.  I'm learning how to actually let go of myself in a relationship and support someone else unconditionally instead of constantly trying to have the upper hand (yeah, I tend to do that.)  I have been doing more yoga, sleeping well, maybe still drinking too much caffeine but overall I am feeling healthy, stable, and motivated.  I feel... incredibly grateful.  Might I even feel happy?  What the hell is this?  

I can't believe how unusual and shocking it is to actually feel okay.  In fact, as stated above, I have always found happy people to be incredibly boring.  Since a young age, I have not only prided myself on my cynicism, it has become an integral part of my identity.  Being cynical makes me interesting, real, and I like to think it's even kind of funny sometimes.  Whether I’m aware of it or not, I’m used to leading with the negative as a way of disarming others and relating to them.  Look, I even did it in this post.  

Sharing about things that are wrong with your life is much, much easier than simply talking about how great things are all the time.   First of all, it signals that you're not full of shit and that you're not faking perfection for the sake of your own image.  It makes you much more interesting and approachable.  It proves you're not blinded by optimism and therefore cannot be easily taken advantage of.  I will also admit that presenting the worst also means people sometimes end up feeling sorry for you, which can also occasionally have positive externalities.  Indeed, it's pretty frightening to truly realize how much being moderately dissatisfied has become such a big part of who I think I am and how I relate to the world.  Will people still find me to be authentic, interesting, and funny if things are generally going well and I’m open about it?

Not only that, but I suspect that a nagging disappointment with the way things are and a corresponding fear of contentment have kept me moving forward for most of my life.  Being constantly focused on what’s next because what is now is never good enough is a pretty strong motivational tool.  In my previous post, I admitted that one of my factors of success thus far in my life has been perpetuating an endless cycle of negative self talk.  Similarly, I think that as much as I may say I want to be happy, the promise of "I'll be happy when...." has kept me working hard for a long time.  I tell myself, All I need is to get to that next step and I'll feel better.   I just need a little more money, a new environment, a shorter commute, more support from my team, and then I'll be able to sleep better at night.  

Well, Allison, here you go.  You're lucky as can possibly be, you're in a great spot, you've got what you were looking for (at least recently) and it feels damn good.  Now what?  How do I remain motivated in the face of actual satisfaction, contentment, and genuine optimism?  Will I be able to keep moving forward if I'm not running away from something?  Am I losing my edge?  

I hope not.  This really deep guy named Robert Frost once said, "Nothing gold can stay.”  Things surely won't be this great forever, but for now I'm just going to embrace it and worry about it later.  I'm scared of happiness translating into stagnation, but I know I am still moving forward because I'm still learning.  How else can you define moving forward, anyway?  And as for relating to others...  if you don't like me when I'm happy, then as another prominent wordsmith of our generation, Cee Lo Green, once wisely stated, “Forget you.  Oo ooo ooo."  I guess we'll just have to see how it goes.

Tuesday, March 4, 2014

The secret about being hard on myself

As a sort of Type-A, driven personality, the top 3 pieces of passively judgemental and massively unuseful advice I have received over the course of my life are:
  1. Don't worry so much.
  2. You just need to relax.
  3. Don't be so hard on yourself.
Most often delivered in an unsolicited fashion, these all deserve a sarcastic and repugnant reply on par with, "Ohh.... I hadn't thought of that, but now that you mention it, sure! I’ll just go ahead and do that.”  Okay, sorry, that's just me being an asshole.  But seriously, I wish more than anything I could do all three of these things but thus far in life it has been basically impossible.  Lately, I have struggled with number three the most: "Don't be so hard on yourself."  Ah yes, if I had a Bitcoin for each time I have heard this piece of advice, I would be filthy rich by now.  

Since a very young age, I have had myself convinced that I am a constant disappointment, that I'm not living up to my true potential, that I am pathetic, and that I might not be good enough.  Seeing these statements in writing, they look like something that a mildly psychologically abusive parent might tell their children.  But that is not where I learned to be so mean to myself.  Au contraire, I am so fucking lucky that I grew up with wonderful, loving parents who overlooked my cliche rebellious high school years when I crashed our car, snuck out of the house, snuck boys into the house, drank gin out of water bottles and occasionally cheated on my AP Euro homework. Through all of that, they have always told me I am great just the way I am. Somehow, though, I never believed them.  I still don't.

I may have grown up in a lot of ways over the past ten to fifteen years, but when it comes to my inner dialogue not much has changed.  I still beat myself up, I still drown myself in guilt and shame over the tiniest of things.  I shouldn't have eaten that cookie, or had that last glass of wine, I am absolutely disgusting.  I shouldn’t have skipped the gym today, I am so lazy.  The email I sent to my parents wasn't long or thoughtful enough, I’m such an ungrateful brat.  I can't believe I didn't spend the last hour working, What is wrong with me? Why am I so apathetic?  How could I possibly lose my keys, I'm such an incompetent fucking loser!  

On the bright side... this constant sense of self disdain allows me to brush off criticism from others because nobody can say anything meaner than I have said to myself.  In light of this all, trust me, I want nothing more than to be nicer to myself and I have tried many different tactics to quiet my inner critic.  Inevitably, nothing seems to work and I end up more frustrated and ashamed than ever before.  

Something clicked for me recently, though. The other day, I listened to a pitch from a company who is interested in creating a smart tool to help people quit smoking cigarettes.  As they presented their idea, I could relate because this struggle is all too familiar to me (and much too fresh in my mind than I'd like to admit.)  What I realized throughout the process of quitting, however, was that there's only one reason why people can't stop smoking; They don't actually want to.  Seriously, that’s what nobody is willing to say.  If you absolutely can’t, it’s because deep down you don’t really want to.  

Here's the dirty secret I haven't admitted before:  even though I have been saying otherwise, I haven't actually wanted to "go easier on myself".  Though the entire routine regularly makes me feel like absolute shit, often leads to extreme behavior, undermines my confidence, and is probably giving me premature wrinkles, I still indulge in it.  You might ask, why not, you crazy masochistic person? Well, it’s because this intense self hatred has served me quite well.  The worse I make myself feel, the harder I am willing to work to prevent it.  If I didn't dread that burning shame, that self-imposed guilt, the endless stream of insults that run through my mind when I don't follow through, maybe I wouldn't have worked as hard as I have.  I motivate myself to work hard out of a fear of failure, a need to prove myself, a desperate desire to achieve my way to happiness.  If I really were kinder to myself, I'm terrified I might not be as motivated to succeed.  Of course, this sparks a whole new round of disappointment with myself... shouldn't I be able to work hard for the right reasons?  How pathetic that I need to motivate myself via negativity instead of a pure desire for success.  And the cycle continues.

So here's the key realisation I’m trying to share: I haven't been able to stop being so hard on myself because I haven't really wanted to.  I have been too afraid of what might happen if I let it go and chose to work hard out of a genuine desire to change the world and not as a desperate attempt to escape my inner Mean Girl.  Not to worry, I still have some pretty stinging insults lined up in the back of my head, but a lot of my recent experiences have given me more confidence in myself.  I left Goldman Sachs, I left my friends and family back home, I started a business in an unknown place, I worked alone from my apartment without anyone telling me what to do... and I'm still doing okay.  I think it's time to move on and start working toward my goals from a place of love instead of one of fear.   It's all so much easier said than done, but I just hope that admitting that I haven't truly wanted to do that until now is the first step in the right direction.

Wednesday, February 12, 2014

Crisis of confidence?

I have been told I seem like a generally composed and put together individual.  However, what you might not know is I have this bad habit of absolutely hopelessly breaking down into a teary eyed, whiny, self loathing, pathetic mess the day before I start anything big and new.  (Attractive, yes, I know.)  Unfortunately, try as I might to resist it, I have always been this way.  It has proven to be a time honoured tradition across time and space.  It happened the night before I left for college, the eve of of my first internship at Goldman Sachs, the day before I started in Equity Derivatives, the night before my first day at General Assembly, the day before I moved to Hong Kong...  I think you get the picture.  Any efforts to prevent it have proven futile and I have found I have no other choice other than to simply brace myself for the breakdown.

With that as my track record, I suppose I can’t be surprised when, most recently, it happened the day before I started my new job in the space of angel investing. Per usual, and especially due to the fact that I have exactly zero experience in this field, I felt hopelessly terrified that I might not be able to contribute in a way that would be useful to my colleague, our investors, or our investments. Ah yes, yet another venture off into the unknown.  It certainly didn’t help that all of my household appliances had broken concurrently, and my inability to overcome the extreme inconvenience of getting them all fixed was making me feel like a totally incompetent adult human being.  My mind and heart were overflowing with fear - both rational and irrational.

Many people have tried to offer me advice on how to avoid these situations, but most conventional wisdom just makes it worse. In fact, I fucking hate it when people just say, “Just be confident.”  “Just be bold and act like you know what you’re doing even if you don't." "Fake it ’til you make it.”   Well, sorry but, I could absolutely never do that because I don’t think I know everything and I am simply not capable of faking it.  I’ve always been one of those people who readily admits when I don’t know, don’t have all the information, or don’t have a strong opinion.  Except for very special circumstances (like I know you’re full of shit, or I’ve had a tad too much to drink), I don’t like to argue just for argument’s sake.  Perhaps part of me assumes that other people are the same way, so if someone is willing to push vehemently for one side of the argument, they must know more than me in order to have so much conviction.

This certainly doesn’t mean I’m a wallflower when it comes to debates or confrontation.  If I do truly know what I am talking about, sense that I know more than the other person, or that they’re running on the fumes of false confidence, there is no stopping me.  I’ll only push hard for things I genuinely believe, and I’m not one who gives up easily on things I really care about.  This means that if I have genuine confidence in myself and what I’m doing, I can go very far.  Unfortunately, this only serves to fuel my crippling self doubt because I am acutely aware of the fact that in many ways, I am the only thing holding me back.  If I could “just be confident”, I would be completely fine.  God dammit, I suck.

Settling for nothing less than authentic confidence may feel respectable, but the reality is that this “all or nothing” view of conviction just doesn’t work.  At the end of the day, I will never have all the information.  In many cases, I will never have enough to feel comfortable having a strong opinion.  Now, it’s actually my job to have an opinion without all the necessary information.  Part of investing in early stage start ups (part of starting anything new, frankly) is to have a strong view, move confidently in that direction, and do whatever you need to do to validate it.  The key is not being blindly bold, but being sure in not knowing enough, not knowing everything — embracing and owning the uncertainty.  It’s not false confidence because I know and readily admit there is plenty I don’t know, but that doesn’t mean I can’t take action.  If every opinion is simply a hypothesis, and then the only respectable thing to do is test it.

And, as I have discovered, there’s no better way to test things than by just shutting up and getting started.  I may have my semi-regular break downs, but as soon as I make it through to the other side, I feel better about things.  I’m one week in to the new job, I’ve stopped questioning, stopped worrying, started learning new things, started asking questions, started thinking of how things could be different or better…. and in the process, my confidence is growing (I think.)  Actively participating means there’s no more room for the self doubt or fear of embarrassment or disappointment.  The more things I do, the more lists I make, the more emails I write, the more people I meet, the more problems I start to solve, the less I wonder what I can do and the more I show myself what I can do.

So, of course, I have no answers, nor do I have any semblance of a cure for my habitual crises of confidence.  Maybe I don’t want a cure.  However, I feel good about the fact that once I get the ball rolling, I don’t need to fake it.

Wednesday, January 22, 2014

Privacy, Public Perception & The Circle

After confessing in my last post that I had barely cracked open a book, I proceeded to binge read the new David Eggers novel, The Circle.  It had a little bit of a chick-lit feel to it, which may very well be why I couldn't put it down, but it also seemed remarkably relevant for a myriad of reasons.  When you boil it down, the book poses a very important question about the value of complete honesty and accessibility vs. the value of privacy, control, and truly personal interaction. You can probably see how this applies but I'll get to that shortly.  To sum up the plot, "The Circle" is the ultimate tech company - a conglomerate of Facebook, Google, Apple, and everything else remotely relevant these days.  As such, it has a complete monopoly on everyone's personal information from search, e-mail, social networks, online shopping and anything else that composes our online identities.  The company has guaranteed ultimate convenience by centralizing all user information, but that also means that they have nearly unlimited data on every individual that uses the internet.  As the company grows more powerful, it pledges to use its omnipotence for the betterment of the world, but even so there is an undeniable question of what if... where are the boundaries and who draws the line?

I am probably not unique in that I found myself relating to the protagonist, Mae Holland.  She's a classic Millenial seeking success, acceptance, and everything good for the world but simultaneously crippled by her own underlying insecurities and loneliness.  She initially struggles with the Circle's pledge of allegiance to complete and unconditional openness, but after she is caught red handed in the act of theft (and lying about it) and is perplexed and troubled by her own behavior, she decides to go all the way and commit to "total transparency".  This means she wears a camera around her neck all the time so anyone and everyone can access her conversations, activities, and behaviors.  She finds that knowing she is being watched makes her more accountable, a better and more balanced person.  She's relieved of the difficulty of wondering (and knowing) what she would do "if no one were watching", because people always are.  Anything she has felt compelled to keep hidden, she has been forced to share, and the reaction was always overwhelmingly positive.  She felt reinforced, validated, and less alone than if she had kept it to herself.  The more access she granted, the larger following she commanded, the less alone she felt, the more she wanted to share, and the circle perpetuated itself.

What it all boils down to is: How do we deal with the trade off between honesty and privacy?  How much should we, or do we want to be, in control of how we are perceived by the world?  When I was in finance, I had a manager sit me down to tell me that people didn't think I was logging in enough hours.  I didn't look like I was working hard enough, he said.  I insisted I was simply being efficient.  I was getting all my work done and my clients were happy, but he looked me in the eye and very seriously said, "Allison, that's great.  But you have to realize that perception is reality."  I'll never forget that, and I change my mind pretty regularly on how much I agree with that statement.  I don't want to agree with it, but it's kind of true (for better and for worse).  The scary part about that truth is that if you read this blog, you most likely see me differently than you would have otherwise.  Maybe you see yourself in what I am debating, maybe you like to read it and laugh at me with your friends taking shots every time I say "I don't know".  But maybe, just maybe, it coincidentally struck a chord and has helped you feel okay in a strange and unexpected way.  The point is that I don't know.  I put it out there and that's it.  Nothing more I can do about how you are reading it, and I have to be okay with however you decide to perceive it.

When I was in college, social media was still relatively new and I had no idea how (and definitely not enough confidence) to use it any real or substantive way.  When I graduated, I went straight to Goldman Sachs, which is basically a beacon of total privacy.  We weren't even technically allowed to publicly state that we worked there (obviously LinkedIn threw a wrench in that rule) but not on Facebook, nor on Twitter was it okay to comment at all on GS or its inner workings.  (And then there was @GSElevatorGossip, which you should follow if you don't because it's hilarious.)  Anyway, I digress.  Looking back, I can still understand their reasoning which is their #1 concern is that clients come first.  'Clients deserve their privacy and as GS employees, we are not in any position to share information or activities on how we serve them because it isn't completely ours.  Public commentary or opinion on what we do day to day (which is, serve our clients) is not relevant to our success - our success lies in the hands of our clients.  We are much better off putting the energy into serving our clients and being the absolute best at what we do.'  OK fine, it may very well have been bullshit, but I bought it then and I still think it makes sense.  Either way, the point is that during my time at Goldman Sachs I barely posted on Facebook, I forgot my Twitter password, and anything else was simply an afterthought.  

However, once I left GS and entered the start up world (a small subset of what some might call "the real world"), I was quickly exposed to the fun, the danger, and the value of social media. It still didn't have much personal relevance until I left for Hong Kong and felt a strong hankering, very undeniable need for connection to those that understood me.  A great friend looked me in the eye before I left and said, "Start the blog."  As I looked up at the seemingly insurmountable challenges of starting a life in a new place, starting a business in a new culture, starting over and getting started yet again, I needed to share it all to make it real and to make it okay….  but more than anything, I wrote so that I could be honest with myself.  Like Mae, I needed some bullshit barometer that held me accountable and kept me from getting completely lost in my own thoughts.  So I started the blog.

I wrote a post the other day about traveling alone and the challenges of actually being myself vs. trying to be someone I want to be.  Clearly that, as well as most of my posts, are quite personal and I am very open and honest about what I'm thinking about or struggling with.  Why do I write these things?  What's the point of sharing this, of putting myself out there?  Though many may not understand it, there are plenty of reasons.  It's incredibly cathartic - and revealing - to actually put my fears into words and explain why they are there. I learn about myself, I figure things out as I write, and ultimately I find that I don't actually need an answer.  Even if I do, I end up with some decent thoughts that I can share with other people.  Not only does writing scratch my itch for self expression and exploration, but it also facilitates me connecting to random people from my past, from my present, and people I didn't even know yet.  I have found myself having the most real, open, and candid conversations I have ever had with somewhat strangers, and it feels really fucking good.  When I think about what it means to be human, what it means to really live, I think it comes down to connecting with others over the things that make us human.  

To be fair, putting it out there can also be very personally validating.  Constantly thinking and questioning can feel incredibly lonely because it's all too easy to look around (and scroll through Facebook) and see everyone's happy pictures and think that everyone else in the world has some secret that I'm just not in on.  That secret is apparently not worrying about things and just being happy.  Maybe some people really have found this secret -- or worse, they don't even need to look.  If that is the case, I'm still getting over my resentment of them (just kidding, but not really), however, I have almost always found that vocalizing whatever I'm agonizing over results in people saying they feel that way too.  
I find that I'm not so isolated, I'm not so alone.  Knowing that allows my incessant self doubt to take a pause and I'm periodically free to enjoy myself and the world as I perceive it.  So yes, it's also selfish, but I think we all knew that already. 

But going back to the power of perception, there are a million and one reasons why I should not be posting this shit.  I don't know what my previous employers think about my online persona, but luckily it hasn't affected my ability to be successful at my work thus far.  When I began writing like this, I had a steady significant other and I don't think this type of honesty made him see me differently.  But now that I'm on my own and I'm about to embark on a new professional endeavor, I can't help but stop and think…. "Oh God, what have I done??"  There aren't that many people reading this, but anybody can search my name on Google and find this blog.  Even if we've never met, you now know some of my most personal struggles, you know nearly everything I don't like about myself, and certainly now you know that I'm far from put-together person I can seem.  The fact that I have put this all out there has very real implications for meeting new potential employers, employees, investors, friends… it's really fucking scary to think about who might think what about me, and what opportunities it could close off without me even knowing.  And why? Simply because I felt the self indulgent need to express myself in a public forum?  

Obviously (if you're making fun of me, this one's for you… get ready to take a shot), I don't know if the good outweighs the bad.  Every time I hit publish, my heart races.  The night after my last post, I couldn't sleep because I wondered if I had said too much, revealed too much, shown too many of my imperfections.  Would it compromise relationships, jobs, transactions, friendships?  Sharing openly means I can't control what people will think when they objectively observe my online identity. But I guess I'll just keep my fingers crossed that what I do share will help me cut through the bullshit and weed out those that think I'm crazy and don't respect a desire for self discovery, or that the personal validation I feel now is worth any negative consequences I may experience in the future.  Or maybe it doesn't really matter and I'm just worrying about nothing.  I don't think so, but what's the point anyway?  As they say in The Circle, I can't delete it now!

<disclaimer> For the record, there are plenty of things I don't share and never would share, because I respect the privacy of others and particularly those I care about.  In terms of the question posted by The Circle, I believe that total 100% transparency would be nothing short of disrespectful and dangerous… I'm not a complete idiot.</disclaimer>

Monday, January 20, 2014

Traveling solo: The good, the bad, and the ugly

As I find myself saying over and over again, it's been a crazy few weeks.  I last blogged from San Francisco and now I am writing from the north of Thailand where the traveler's scene is ripe with stereotypes of its own kind.  You might ask, why am I here?  Well, after a lot of contemplation, a prolonged period of indecision, and a hell of a lot of emotions, I made a really difficult (but exciting) choice to officially separate myself from being "Allison from GA" and accept a new job opportunity in Hong Kong.  It was, as expected, extremely difficult to step away from a team and a community that I spent the last year and a half of my life pouring my heart and soul into, but in a way that's why I felt I had to do it.  After surviving several separations of a more personal flavor last year, I felt like it was time to actually make my own life in Hong Kong, and not just one that was inextricably tied to my job.  Ultimately, I'm not sure how intertwined I want those those two things to be - of course I see my job as integral part of my identity, and I want to always (or as often as possible) be in love with whatever I end up doing… but there's got to be some sort of healthy balance out there, right?  Maybe not.  Anyway, I'll still be working with startups of all kinds, and as the second member of an angel investing team I will very much continue to be an entrepreneur myself.  

I knew this change was going to be a doozy so I decided to get away from Hong Kong for a bit to clear my head and physically force myself to disassociate from work.  As much as I'd love to be able to finish up my duties and then hit the mental and emotional reset button myself, I'm just not that strong and I'm okay with that. I chose eight days in Thailand because the weather is ideal, it's cheap, and it is generally safe to travel alone.  The last one is big and is both figuratively and literally my biggest challenge for this little adventure.  

I've done a fair bit of traveling in my adult life thus far, but it's always been with a partner or friends.  This is a completely different story.  Of course there is the element of physical safety to consider; where and when can I wander around alone, when to talk to strangers and when not to.  But what's more is that especially at a time where I'm finding myself unnervingly scared of being on my own - without a relationship or a job to define me - traveling solo is simultaneously intimidating and liberating.  There is absolutely no one to answer to, nobody to compromise with, nothing keeping me from doing exactly what I want to do and when I want to do it...  Or so you would think.  It's only been a few days so far but I still have some thoughts to share on a few interesting positives and negatives about my experience traveling alone so far.

First, the good:  You get to pick where, when, and how much to eat or drink at all times.  If I want dessert for lunch or beer with breakfast, I can.  I can plan as little or as much as I want to.  I can plan, then decide I'm feeling lazy, and not follow through.  I never have to wait for anyone.  I can sleep as much or as little as I would like.  I can walk as fast or as slow as I want to.  Nobody is nagging me to wear sunscreen (I know, I know, I should).  If I mess up the directions and end up hopelessly lost because I thought I recognized some sort of landmark but turned out to be wrong… it doesn't matter!  Love it.  

But then there's also the bad:  Things are more expensive because you're not splitting things with anyone.  If you forgot something, you're shit out of luck because there's nobody to borrow from.  If you order dessert, there's nobody to share with to prevent you from eating the entire thing. If some weirdo asks for your phone number, there's nobody to step in and deflect.  You sort of always have to be looking over your shoulder to make sure you're safe, and when night falls, there are real limitations on where you can go alone.  In fact, I find the evenings the most difficult anyway.  Especially when you see couples and friends joking around everywhere around you, it can feel a little sad, even a pinch pathetic to be sitting at the dinner table alone.  Though, I have to say, as a loner you find yourself doing a lot of high quality people watching and a good 80% of people eating together are just on their smartphones not talking to each other anyway.  

This leads me to the ugly part, and it's not just that I'm not wearing any makeup at all.  No, the ugly part of traveling by yourself is the fact that you also actually have to be with yourself.  If you are still reading, then you probably have read my blog before, or you know me and you are aware of the fact that I can be a rather intense person.  I think a lot, feel a lot, question a lot and it can frankly be quite exhausting.  I have a newfound respect for anyone that has spent a good deal of time with me because I can be really fucking annoying, so thank you to anyone that has stuck around for awhile.  Sure, Thailand feels exotic and far way, but there's absolutely nowhere in the world I can go to escape my hyper aware and overly analytical self.  

To first paint that in a constructive light, I can't help but view this all as a mini experiment.  In my little quest of "getting started" and seeing what I'm really all about, I am eager to place myself in completely new situations and see what happens.  What choices will I make, how will I react to things when I have no other limitations to consider?  It's a laboratory for self that I hope will help me understand myself better and allow me to make better and more deliberate choices about how I want my life to be.  As I observe what I really want to see and do, what kind of traveling I enjoy the most, it's sometimes fun to listen to where my cautious, type A, planning and list obsessed self ends and where my adventurous, spontaneous, romantic self begins.  They're always battling and sometimes I really don't know which side will end up winning.  

However, I am also finding myself stuck in an endless spiral of comparisons.  Having primarily traveled with others previously, I am constantly comparing my preferences with and without other people around.  Am I choosing to do something because I really want to or is it in reaction to what I did in the past?  This also applies in a larger sense as I am finding I have a lot of subconscious guidelines for myself for "how I want to be" as a traveler and as a person.  Though I purport to be out here "figuring myself out", "on my own", and "listening to what I really want", that's also a bunch of bull shit.  In all honesty, I know very well how I would like to be, and I can paint a pretty good picture for you about what I would like to discover.  I'd love to have this amazing vacation on my own where I come back newly confident in the fact that my self awareness is a good thing, that I am a fearless, independent, friendly, mindful, thoughtful, appropriately adventurous, and open person.  I'd like to find myself writing, engaging with the world in new ways, truly relaxing, and relishing in every moment.  If that's who I figure out "I am", I'd think that person is fucking awesome.  I'd want to be friends with her.  She sounds cool, right?  

Unfortunately, that's not exactly what I'm finding.  Nope, I'm still pretty damn scared of actually listening to my seemingly endless stream of anxious, stupid, fearful, sometimes judgmental thoughts.  Even in Thailand, I am finding it kind of difficult to meet other travelers (except for one overly persistent and creepy Russian gentleman) so I guess I don't give off such friendly vibes after all.  Plan-less evenings make me nervous, sometimes I feel like staying at home instead of venturing out, I have barely cracked open a book, I keep checking my email, and I still don't feel totally relaxed (obviously).  Indeed, there's a lot about me and my experience that I'm not so proud to admit and feel like insurmountable impediments to me being "the real me" - or at least the version I'd want to hang out with.  Even on my own, it feels like I'm still traveling with someone else - the actual real me, and the me that wants to be a certain way.  So it turns out that even when I'm alone, I'm still negotiating with someone else.  Whoever at some point in time threw their hands up in the air and excitedly exclaimed, "I have nobody to answer to but myself!" forgot to mention that "myself" actually counts as someone to answer to.  Go figure.

So anyway, in conclusion, as usual there is no conclusion except that traveling solo is every bit as hard as I thought it would be.  I guess the point of all this "getting away" and "relaxing" business may seem like it is to "figure out what kind of person you are", but maybe that's not the point at all.  Maybe the point is to embrace the good, the bad, and the ugly so you can be with your actual self, and see what happens.