In our careers most of us aspire to go up the corporate ladder (with varying degrees of zeal), but most wishing for greater responsibility, autonomy and visibility.  So I was surprised when in a recent discussion with my father he told me about the Peter Principle which says that everyone eventually gets promoted to their level of incompetence.  Taken to its logical conclusion it means that in steady-state every non front-line employee, i.e. every manager, is incompetent.  Great.  Glad I’m a manager.

Recently our CEO Brian Halligan said during an employee gathering that there are only two jobs worth having at a company – either building the product or selling it.  The blunt statement has seemingly obvious wisdom, particularly in our tumultuous economy where jobs come and go at an alarming speed, but it left some people outside of engineering and sales feeling queasy about their career prospects. 

For the latter half of the twentieth century the path to a solid middle class lifestyle was to get a college degree, join a Fortune 500 firm and work there for the next forty years or so, banking away a pension for a healthy retirement.  That path ceased to be "safe" about a decade ago given the dramatic swings in the fortunes of big companies due, in part, to trends like globalization that have seen jobs come and go with alarming speed.  Job security is an oxymoron and I suspect in a few years, if not already, no matter what you study and what practical skills you gain there will be no guarantee for a “safe” career path anymore.

One of the most humbling realizations as I’ve progressed through my career is how big a role luck has played in where I am today.  Many of the pivotal events in my career happened more due to a lucky break than my own doing.  When I tell this to colleagues and friends they think I’m being falsely or unduly modest and indeed I have been told that I undersell myself sometimes.  Well I’d like to recount the biggest break I’ve had in my career and you can decide for yourselves.

A Masters in Business Administration (MBA) degree has become quite popular in the last two decades with applications and enrollments exploding at hundreds of schools worldwide.  When awarded by a top school the degree is often seen as a reliable filter for identifying top talent and even otherwise it is seen as a way for professionals with any prior background to get a well rounded understanding of business.  Both of these are legitimate reasons to do an MBA - finding a good job and advancing up the career ladder - as well as my personal reason which was to allow flexibility in changing fields or at least provide insurance for doing so in the future.

At a previous company I faced a crucial decision a couple years into my tenure.  My boss was leaving the firm and my job was being redefined by the recently appointed CEO.  As my scope of responsibilities was being dramatically changed I was faced with a question – should I go for my boss’s job or accept the fate of whatever role I settle into?  The answer proved to be my undoing and I learned the most valuable political lessons of my career here.

When I recently joined HubSpot as a VP I was excited for a number of reasons, particularly the chance to work with a phenomenal executive team whom I'd met during the interviews.  I knew the role would entail long hours but I did not realize exactly what kind of commitment I had signed up for then.

With Steve Jobs stepping down as CEO from Apple, the Wall Street Journal put together some of his very best quotes.  The whole collection is beautiful - inspiring, insightful, legendary.  But there are 8 that are particularly special to me and that I hope will move you, the reader, as well.

When I finished my undergrad degree in computer engineering in 1999 I got a job paying $54,000 a year, based in Seattle.  This seemed like way too much money for a new grad and indeed I was able to save 15-20% while living well.  My calculations at the time said if I reach that clichéd milestone of a six-figure salary I'd have more money that I would know what to do.  Well, 12 years later I've surpassed that milestone but financial bliss hasn't transpired; on the contrary I spend less time doing some things I love outside work and more time worrying about saving for the future.  How did my financial finish line move and how much salary do I need to be happy - now and for the future?

Perhaps the most alarming statement an Indian-born adolescent can make to his parents is that he is going to study liberal arts at college.  "What was that son?!"  "You're not choosing from the holy triumvirate of engineering/medicine/economics?" (the last one only recently gaining popularity with the rise of investment banking but still somewhat looked upon suspiciously).  When asked why one would make such an incredulous choice the answer "it's what I love doing" is almost certain to be met with a smack upside the head.  Yet growing up in America choosing a career you love is exactly what you're taught to search for.  Which is right and when?