My Blog Title - Can you guess what it means?

The title of my blog carries a significant meaning.  It was uttered a handful of times to me by a mentor of mine.  Can anyone (that is any of my three followers or random internet surfers who might have stumbled upon my blog - both of which probably sum to -2 viewers) surmise what this line means?

"Keep chalk on your heels."

Rewards will be awarded to the closest and most creative submissions.

The awards will include 5 minutes of uninterrupted eye contact and a scratched "The Office" dvd (season 4, disc 3).

(I need a new job - too little to do and too much time.  It sounds appealing, but is a dread.)

Stay Classy