Taking a Break

Let's step back to the time when I graduated college, which would be June 2002. I landed a job post-graduation at a tech consulting company called Appian Corp. The recruiter encouraged me to begin my orientation on June 18, about two weeks after I graduated. My older and wiser friends (who were a year or two out of college at the time) suggested that I take some time off and enjoy myself before throwing myself into the working world. I took the August 5th start date, and had a great time hanging out with my college girlfriend, living in my parents' basement, and visiting some friends in Alaska. It was pretty glorious, and probably the last time that I had two whole months off.

In fact, I think it was the last time that I took any deliberate time off between jobs. When I left Appian a couple of years later to join Google, I had just a week in between, and that time was spent moving cross-country. I left Google about a week before I started grad school at MIT, and that also involved a cross-country move (and a four day long cross country drive). By the time I finished grad school, I had already started working on InstantQ and had received seed funding from YCombinator. InstantQ is a bit more complicated, because when it failed, I tried a number of other startups before giving up. But, if I remember correctly, I had a new job at Zecter about a week after I finally gave up for good.

Moving forward to 2011, by the time that I left Zecter, I had already started working with Sam on SpeakerGram/Scaffold. Moving forward to last summer, when we finally decided to call it quits, I lined up a new job within two weeks. Well, I had originally decided to take some time off to reflect and enjoy the summer in New York City, but I began to feel anxious and depressed after about a week. So, as soon as Jason called, I was pretty much ready to go.

So I left my most recent job a bit over a week ago. Things weren't working out for me, and it made sense to move on. Overall, it was about as amicable as such a thing can possibly be, and I don't feel like there are a lot of regrets (maybe I'll write more about this later). My normal move would be to jump immediately to the next thing, but I had a sense that this might not be the right play this time around. So, I decided to try something new, and pledged that I would take thirty days off before starting to think about what I would do next. 

I have noticed that whenever it comes time to figure out what I'm going to do for work, I jump to make the first reasonable choice that comes along. This has happened with jobs, but also with picking startup ideas to work on. It's just so easy to say, "that will do," rather than having the strength to wait for the thing that's actually right. Paul Graham once said something to me along the lines of "It took a lot of time and effort to kill your startup idea. You might as well take your time when deciding what to work on next." While that seemed like pretty good advice, I jumped into the next thing that came along, and the next, and the next. Until I was finally willing to listen.

What am I going to be doing during the next month-or-so? Well, the short answer is basically nothing. I've been going to a lot of Bikram Yoga, spending a lot of time hanging out with friends, and taking regular long walks to Ocean beach. I'm also resolving to write something in my blog every day (today is actually the first such day), and I'm going to come up with a bucket list of things to occupy my time. I have a trip to New York planned for the end of the month, and maybe I'll take another trip somewhere else. But, most importantly, I'm trying to commit to as few things as possible, and to enjoy every day for what it is. More on this later...