One of the great gifts that comes with the work I do is that people share some big and tender questions with me. I’m always humbled by the experience of hearing them, because it’s such a vulnerable thing to open up and share the stuff we are wrestling with.

I received an email recently from a reader who is working with a question that I know is shared by a lot of people – and at its heart, the question is this:

How do I know when it’s time to start following my dream?

This reader has a vision for a business she wants to start, and she is weighing the possibility of starting it now, or pursuing an opportunity to return to the corporate world, where she could sock away some cash for a couple of years and start her business with a bigger financial cushion.

I think all of us can relate to the question on some level – whether we have a dream for a new business, a project, or a big life change, there comes a time when we need to decide when to take the leap into the unknown.

Something about this reader’s question prompted me to think of Elizabeth Crook. Elizabeth is a strategist and advisor to entrepreneurs – I worked with her at my last company – and she is both an incredibly brilliant businesswoman and one of the warmest, most big-hearted people I know. She’s also got a whole website dedicated to “Discovering your yippee,” which is all about finding work you love – so I know she’s been thinking deeply about this question.

So I hopped on a Google Hangout with Elizabeth, and we recorded our chat for you to watch. We share some key questions to ask yourself if you’re facing a similar dilemma, and frameworks you can use to evaluate your options.

(That third thumbnail you see below the video is the fabulous Heidi Hartman, who sat in with us to help us through our first recorded Hangout… obviously we didn’t realize the thumbnails would be shown!)

This is our first time doing this by video (and as you’ll see, it’s a little rough around the edges), so we welcome your feedback. And if you have ideas or questions for next time, please feel free to leave them in the comments, or email me at lb at laurenbacon dot com.

Your turn: How did you know when it was time to follow your dream? I welcome your thoughts in the comments.