Letting Unimportant Tasks Go: Declaring Job Bankruptcy

I've had an interesting couple of years; today I just left my 4th job in 18 months after working at the same company for the first seven years of my career.  Most of this was unplanned; one was a failed startup, and two were related to an unexpected move from Boston to San Francisco.  Leaving each job always comes with a certain amount of sadness when leaving behind co-workers you enjoyed working with and not being able to see your product vision to its conclusion.  However, each departure has also brought this wonderful feeling of being able to let things go that I never seemed to find time to do.  You know what I'm talking about; I'm sure you've been putting off replying to that pesky email that's sat in your inbox for months just like I did.  This is work that I know is not important, yet I'm never quite able to let it go until I finally have no choice. The relief one feels by letting go should not be underestimated.  In fact, it's a shame that one cannot enjoy this relief without having to leave a job.  I think that twice a year taking an honest look at everything on my plate and assessing the items that truly can be forgotten will allow me to recharge and focus on important items.  In effect, I'm going to declare bankruptcy and get a fresh start.  Getting the mental weight of these items today makes me feel like a million bucks right now; I am super excited to start my new job next week with a clean slate.

Is it better to specialize or generalize?

I've been doing a lot of soul searching lately about where I see myself in the next five years.  In almost all aspects of my life (work, school, recreation) I seem to come back to the realization that I'm really good at many things, but not truly great at any one thing.  Taking sports as an example, I'm better than average at tennis, baseball, soccer, running, skiing, biking, etc., but I'm far from being truly exceptional in any of those.  Or in my career, I have experience in a number of specialized areas such as web development and UX design, but my best skill is probably connecting and leading those with the specialized skills to deliver successful projects.  I'm now at a cross road where I'm trying to figure out if I want to pick a skill and specialize in it, or if I want to continue to generalize.XKCD Cartoon Nora Dunn, a writer at Wisebread.com created a great pros/cons list, especially the cons of each such as:

  • You have less job security if your area of specialty becomes obsolete.
  • If you are too specialized, the company can’t use you for other tasks or jobs, thus decreasing your overall flexibility as an employee.
  • Less focused job searches are more difficult to endure.
  • Employers might not know how best to place you in their organization if your skills are too spread out. They may not view you as reliable or tenacious enough with any one job or skill set to be worth hiring.

I think great companies realize the need for both.  Without specialists, a company can never separate itself from the competition with truly amazing or unique products/services.  If a company could only exist with one or another, there is no doubt that a company of specialists would become more successful.  But, with too few generalists, a company risks a few things.  First, their vision and focus might become too narrow if everyone is an expert in specific types of trees, but nobody knows how to navigate the forest.  Second, the role of a successful generalist is in many ways that of a "Connector" (as outlined in The Tipping Point by Malcolm Gladwell).  They understand enough about the problem at hand, the skills of the specialists in the company, and they understand possible solutions for the problem enough to be able to connect the right people to bring about the best solution. The toughest problem with being a generalist is trying to measure your impact and convince others of the value you bring to the table.  I know that I would be a tremendous asset to many teams.  It warms my heart to hear former developers I led say things like "When you were there was some fun while developing apps.... Day by day that fun deteriorated... ".  My struggle remains convincing someone that hasn't worked beside me before have confidence that I would be the best decision they could make.

What makes Boston such a special city?

An iced over Charles River that thousands of Boston Marathon runners likely spent many hours running next to Over the past few years I've had many discussions and given lots of thought to specific reasons why I love Boston so much.  It's hard to quantify what makes me love a city so much despite the cold winters, bad drivers, and unfriendly people (compared to other regions of the US).  Despite all of this, it is a city that so many people furiously defend as the only place they ever want to live.  So what is it that makes Boston so special?

Many great cities have a core competency or passion that is usually a source for jobs, government policies, and overall spirit.  Boston's is health care and education; it is the home to many of the world's best hospitals and colleges.  When you contrast that to what other cities revolve around (Technology/entrepreneurship in SF or Wall Street in NY), health care and eduction both center around helping others above all else.  As a result, Boston attracts and retains people that want to share their knowledge with others and treat those who are unhealthy.  It attracts the best of the best for education and medicine, along with thousands of people in supporting roles.  It is this focus on two of the most humanistic industries that I believe is what makes Bostonians so special, even if they won't say hello when you walk by them.

It is also this spirit of caring for others that is coming through in how Boston has so far responded to the horrific tragedy yesterday at the Marathon.  The typical Bostonian might not come off as the most friendly person, but deep down Boston is a city that truly cares.  I really wish I could be there with my friends and family now, but I know next time I step foot in Boston the spirit of the city will only be stronger than I left it.