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.