I had missed every single Brazen Careerist webinar… until today, that is. I thought, hey, if I were going to squeeze one in, it definitely had to be the one with Seth Godin, right? Yup. You betcha.

I was only able to catch a small chunk of the interview, but just like what some people would say about cutting the Bible or picking out a random tarot card, it was like The Fates really wanted me to catch that particular part of their discussion for a very good reason.

Before I continue, I would like to make a disclaimer and say that it’s past midnight and, as much as I had wanted to take down notes or TiVo-ed the webinar (like that’s even possible), I was in such a hurry that time, and right now, I’m relying solely on memory and my own interpretation of what I had heard. I’m not going to quote anyone, but in the event of inaccuracy, please feel free to correct me.

Brazen CEO Penelope Trunk was then rummaging through visitor questions, and there was one that almost got booted out of the pile. Seth chose to talk about it though, and he started off by saying (and I’m paraphrasing here) that perhaps we all had to re-think the questions we were asking. The visitor wanted to know what tools he needed in order to achieve a particular career goal. His question, ultimately, was a How question: How do I become a bestselling author? How do I finish what I’ve already started? How do I get there?

Sounds familiar? Personally, I thought it was spot on. Although the question almost got the boot, I was glad Seth decided to dissect it, because secretly I knew that I would’ve asked the same question too.

The challenge was to re-think the How question and transform it into a Why question. To me, asking the Why question is just like taking the road less traveled — I knew that the whys in life are the ones that most practical minded people like myself choose to avoid, simply because it pushes the thinker to think even deeper than he already is. The whys supposedly breed philosophical, profound light bulb moments that ultimately help us understand the essence of things. And why do we avoid these things? Because it takes too much precious time. We just want to dig into the tool box and get on with it.

The concept of role models was then brought up. In the simplest terms, people have done it already — your seasoned marketing professionals and human resource managers and life coaches, etc. You want to know how to publish a bestseller? Talk to a bestselling author. You need the proper tools to become a successful entrepreneur? You can easily get an e-book on that.

The point is that the tools are already there. We’re all in a candy store and you can easily grab whatever suits your taste. But if you don’t know why you’re in that particular candy store in the first place, you wouldn’t know which aisle to choose and, God forbid, you might even come home with a whole bag of useless.

We could really learn from a 4-year old who asks Why? all the freaking time, don’t you think?

It’s hot.
Kid: Why?
Because the sun’s completely out.
Kid: But why?
Because it’s almost summer.
Kid: Oh… but why?

And this goes on until you yourself can’t find the answers to the kid’s questions anymore.

From the kid who’s simply inquisitive about the world around him, to us Gen-Y folk who could turn this inquisitiveness onto ourselves, as individuals. Why do I want to be the next Steve Jobs? Why do I want to be a teacher? Why do I want to retire at 40? From what I had gathered from that small part of the webinar, it’s about being completely honest with yourself, with what you want and need, and what you believe is best for you. Once you’ve established your true purpose, then go ahead and gorge away in your candy store of choice.

Photo courtesy of Flickr Creative Commons.