Why do we need so much encouragement to do what we love? If we love to do it why aren’t we doing it already? Too often we get stuck thinking that it’s just not that easy, but is that really true or is it just a cop-out on our parts? Maybe when I say “not now” I’m really just too scared of what might happen. It’s no surprise then, that those same keynote presentations very often tell us to take incredible risks.

It’s one thing to be risky, but it’s a very short step to being reckless. “Taking risks” doesn’t mean doing something stupid without thinking of the potential consequences, it means doing something with a high probability of failure with a potential for great success. You have to know what that failure can entail and you have to be prepared for the worst-case scenario, even though you might not know what success will bring. In her keynote presentation at this year’s CUSEC, Leah Culver talked about dropping everything and moving to San Francisco. “What’s the worst that could happen?” she asked. Her answer was “Well, I go back to Minnesota and live with my parents.”

Before you even get to the point where you’re ready to take risks to do what you love, you have to know what it is you love, don’t you? You have to put your heart and mind into it, focus on it, and when the time is right make your move. And therein lies the challenge. How do you know what you love? Every job is going to have its share of grunt work, whether you’re working for yourself, or a startup, or a mega corporation. It could be dealing with bureaucratic overhead, your clients or your mom. Po Bronson phrased this sentiment very well:

The right question is, How can I find something that moves my heart, so that the inevitable crap storm is bearable?

That’s a lot easier said than done. The very first step lies in figuring out who I am, what I like, what I don’t like, what I can grin and bear and what will eventually lead to breakdown. Only once I’ve got enough of that nailed down can I really start looking at where I belong and what I should be doing with my life and my career.