Inspirational quotes are about as useless as they are annoyingly trite. Taken out of context, they often send the wrong message. But stories can provide powerful lessons that can change your life, if you experience them at just the right time in the right state of mind.

I’ve had several such transformative experiences that forever changed my perspective on life and altered my career trajectory in very big ways. This is one:

There have been times when my career seemed stalled and it wasn’t unusual to find me up in the middle of the night watching reruns of old TV shows. About 25 years ago I had a major epiphany watching an episode of Dobie Gillis from back in the 60s. I know how crazy that sounds; just go with it.

The show takes place in college and Dobie is learning about Robert Browning in Mr. Pomfritt’s class, most notably the famous quote “a man’s reach should exceed his grasp” from the poem Andrea del Sarto. In modern terms, it essentially means that, when you’re after something that seems unattainable, you should go for it.

Never mind that Pomfritt is a play on pommes frites or French fries.

Anyway, the quote inspires Dobie to consider going after a girl who’s out of his league and risk losing his steady girlfriend Zelda. Pomfritt councils him to go for it while his dad takes a more conservative view. Caught in a classic risk-reward tradeoff, Dobie ends up in Pomfritt’s office asking how he ended up as a teacher, being so gung ho and all.

At that point, Pomfritt pulls a huge manuscript out of a desk drawer and explains that he did reach, big-time, but was rejected enough times to realize that becoming a great writer wasn’t in the stars for him. So he fell back on teaching and now he’s cool with that because at least he knows he fought the good fight.

On its own, Browning’s quote would have you reach for the stars regardless of the tradeoffs or the message the universe is sending you. But in context this story, provides quite a bit more nuance that helps clarify a classic tradeoff, i.e. how to know when you’ve reached far enough and maybe it’s time to pull back a little and be happy.

That story – that episode of Dobie Gillis, strange as it sounds – changed everything for me. It’s been a guiding light throughout my career and hasn’t failed me yet. That’s why, after the dot-com bubble burst, squashing my startup CEO gig, I was cool with segueing into management consulting and writing, which is working out pretty darn well.

Here’s the thing. Sometimes, facing reality and letting go of a dream frees you to find what may turn out to be your true calling. Go figure.

Image credit Eva Rinaldi via Flickr