Tuesday, October 5, 2010

Risky Business

It is raining today and I love it.

I have a large bay window in my office and I am just staring out of it – listening to the raindrops and the busy Barham traffic sloshing through them.

Work seems to distract from my enjoyment of the rain, so instead I am getting caught up on my reading: The Chronicle of Philanthropy, a New York Times article about LinkedIn and my favorite blog, Penelope Trunk’s Brazen Careerist. (For my job, this is considered working, but I always have a hard time justifying it).

I haven’t read Penelope’s blog for a while – I think she took a break from writing over the summer and I’ve been slow to catch up on her new posts. But she is an excellent writer and reading her blog inspires me to want to do the same. I have felt this way throughout my life: when I read something really good, it makes me want to write something really good. Which makes me think that I want to be a writer.

But getting that going often seems like a huge challenge – and counterintuitive to my nature.

Writing is risky. Ideas go from inside your head and out into the world. People read them and may judge you, or not agree with you, or know too much about you. You may spend hours on something that never finds the light of day. You may spend a weekend on something that no one likes. You might miss the window of relevance because you needed to prepare for the staff-wide business development meeting.

Writing also takes a lot of self-discipline. In order to be good at something, one must practice it again and again – and usually on some kind of regular basis. In theory, the idea of a prescribed writing agenda sounds really good to me - but something else usually comes along to throw it off: dinner plans, a much-needed Spin class, The Closer.

So suffice it to say: I am not a huge risk-taker and I have a very hard time practicing self-discipline. But I would really like to capture both of these ideals… as we all know, there is little reward without risk and few results without a little self-discipline.

Penelope has recently written about both of these challenges. In last week's, How to Take Intelligent Risks, she concludes that trying something new isn’t really all that risky since humans are quite adept at positively rationalizing an outcome - even if it’s not the one we expected. And that taking risks comes with only a small emotional cost: others are so concerned about what’s going on with them that they have little time to worry about whether or not you are suceeding.

For a year Penelope also wrote extensively about what makes people happy. Interestingly, having self-discipline tops the list. But its elusiveness can also drive people mad. So her advice is to “find an easy re-entry point” and to give up on perfectionism, “the enemy of self-discipline.” For a Virgo, this line of thinking is also very risky. But this astrological attribute also comes with a gift for making plans and outlining beautiful to-do lists, which for me is a starting point for any project.

Based on circular logic, this all means that writing will help me take risks, realize self-discipline and achieve maximum happiness. Not a bad gig! So with my writing tool box packed with a finely crafted road map, a fantastic skill for rationalizing, and an impeccable to-do list, I will give it a whirl.

And if it doesn’t work out, I will find a really great way to tell you why. And then make a list for how to achieve my next venture.


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