Asking the Hard Questions

To say I've been unhappy recently would be a gross understatement of the fact. Anybody who follows me on Twitter or has seen the exceedingly rare Google+ post would know that underneath the calm demeanor that I typically exude is a very, very angry person who is not happy with how much time is being wasted for the sake of paying the bills. What's the reason for all this bottled rage, you ask? It's Merlin Mann, of course.

I first became aware of Merlin Mann and his work through his 5by5 podcast with Dan Benjamin, Back to Work. On this podcast we get to hear Dan and Merlin work through a number of very difficult questions. These questions are never answered, though, because there is no perfect answer. The questions are put out there for people to ask themselves and answer themselves. Because these questions are hard, the answers are equally difficult.

Some of the questions that Merlin Mann has had us ask ourselves include:

  • why are you buying a pedometer before putting on your shoes?
  • is failure really not an option?
  • what does success look like?
  • why is it that we become scared about our job when we feel like we're going to lose it?
  • what will it take before you stand up for yourself?

And some of the things he's said that have stuck in my mind since hearing them:

  • Everything in life is a goddamn tradeoff and if you don't accept that, you're a child.
  • Leaving the burning building is more important that finishing your TPS report.
  • Sometimes the best thing that you can learn is that you're wrong.
  • The more you try and please everybody, the more likely you are to sort of disappoint everyone.
  • You don't let the guy with the brooms decide how many elephants can be in the parade.
  • No one's ever gonna be satisfied with how quickly you're becoming the person they expect you to become.
  • Everything seems reasonable from one's own point of view.
  • It doesn't matter to strangers what you care about. It really doesn't. If you think it matters, you're a hippy. Nobody really cares. Because they've got plenty to care about on their own.

The man has helped me look at the decisions I've made over the course of my adult life and see that I've been heading in the wrong direction (almost) the entire time. The question I have now, though, is whether the new course of action I have in mind is correct, or more of the same.

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