In a previous post, I shared questions that can help in overcoming fear of failure. But sometimes, there's an even more basic problem that can stop us from pursuing bold challenges and ambitious goals: not knowing which challenges or goals to pursue. These days, you're urged to "follow your passions" and "lean in"—but what if you're not sure where your particular passion lies? What if you don't know which way to lean?

This can be an issue not only for those starting out in a career, but also for some who are established, even highly-successful, yet unfulfilled. It's easy to find oneself on a path determined by others, or by circumstance (i.e., the job offer or project that comes along unexpectedly and is too good to turn down, then becomes a career).

Whether you're starting out or considering a possible change in direction, asking yourself the right questions is critical. The following eight—shared by a noteworthy lineup of entrepreneurs, innovators, consultants, and creative thinkers—can help you figure out where your heart lies and what you really ought to be doing.