Andrew Chen Archives

After staring at the 320 hours of paid vacation on my pay stub for months, I finally decided to take a week off of work. Now, why did I allow such an enormous amount of vacation to accumulate? Well, basically because I usually think of vacation as unnecessary and unproductive :)

So when I did take vacation, of course I used it to catch up on reading, go through an introspective bent where I evaluated where I was in my life, and other fun things like that. I’ve come to the realization that taking time off is actually very productive, as long as you are using it for the right thing. In general, it helps break up the time between long stretches of work, and forces you to think about the meta things, and meta-meta things, rather than get stuck too close to the weeds.

Rob, a wise and all-around nice guy, challenged me to think of the following, in regards to my professional life:

1. Am I getting challenged/pushed on a regular basis by my current job?
2. Am I continuing to develop new skills or augment my current skills?
3. Am I broadening the number of interesting people with whom I interact with and who will be valuable for networking as my career progress?

He also noted that within these questions, he specifically left financial rewards off. He said, for someone who is young and thinking through these questions, financial rewards will come – instead, focus on learning.

The idea, I think, is that like all "assets," people go through an "investment" phase and a "collecting money" phase. At the beginning, young people often have negative net worths because of school debts, and spend all their time learning how to be productive human beings. Now, it is true that some 20 year-olds actually create value in addition to sucking it out of the system – otherwise we wouldn’t have 28 year old billionaires – but the norm is to only start adding lots of value back into the system once you become a responsible 30 or 40 year old. Either way, the important part is to be investing when you are young, and hit your peak later on.

A corollary to this is that if you find yourself "harvesting money" too early, you are probably in the wrong job. The reason is that for most 20 year olds, you don’t have that much to give back, so harvesting money at that stage is just another way of saying "dead end job." So don’t do that.

Another way to ask Rob’s questions above, in a less systematic and formal way, is to ask, "If you had $50 million dollars, what would you be doing right now?" (Of course, substitute $50 million with whatever your "number" is – and yes, I know this question was in Mike Judge’s brilliant Office Space) Asking yourself that question frees yourself from financial constraints, and removes social status as an issue – and instead, it focuses on your "true" goals.

Then the second step of this question, of course, is that even if you don’t have 50 million dollars, as young and resourceful lads, you should be able to figure out a way to work towards that goal, regardless of your current income. This is especially true for Ivy League Microsofties, who an get a "real job" anytime they want, but somehow view their world as trapped behind a desk in Redmond.

Now hilariously enough, many people I’ved asked this question to really answer "I’d invest it," which tells you they are altogether too responsible :)

My friend Tim Higgins, whom I admire greatly, has his answer and his current life aligned completely. He worked in the financial services industry, saving money over 4 years to fund 2 years of golf. Tim’s attempting to be a pro golfer, and he would be doing this regardless of the money situation. I remember in a conversation I had with him about it, he said, it’s better to try now than when I’m older, and also that it’s better to try and fail rather than regret what "could have been" years later.

Anyway, my life is not 100% aligned right now, but will be quite shortly. But from now on I’m taking vacations more often to think about stuff like this :) Better to risk a week of productivity than a year heading towards the wrong direction.

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