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...