Thou Shalt Not “Should” on Thyself

Some people look to their business or career coach for the kind of conditioning they might receive from a drill sergeant: “Drop and give me 20!” That isn’t my style: I’m a kinder, gentler coach. However, I do have one hard and fast rule when working with my clients. I insist they follow this commandment: “Thou shalt not ‘should’ on thyself.”

I received my inspiration for this rule from my friend Linn Billingsley, an accomplished healthcare executive who shared a patch of my career journey with me when we both worked for Humana Hospital-Phoenix. One day I came into Linn’s office to share (read: vent), bemoaning some foolish choice I’d made. “I should have done this! I should have done that!” I wailed. Linn stopped me cold. “Vickie,” she said. “It sounds to me like you’re ‘shoulding’ all over yourself.”

The double entendre is what makes this so funny, of course. But there’s nothing funny about living in the Land of I Should Have. Here are just a few observations about why we need to catch ourselves from using the word “should” whenever possible:

  • “Should” is usually based in the past. Maybe we should have done something differently, but we didn’t. There’s nothing we can do about it now other than learn from our mistake. If we focus instead on what we could have done, next time we’ll know better.
  • I’m no etymologist (that’s someone who studies words, not bugs) but I think “should” somehow is closely linked to the word “shame.” Whenever we “should on ourselves,” we’re usually beating ourselves up for either doing or not doing something that we now know would have been a better idea. There’s shame around our decision and it’s a fruitless, wistful kind of longing for having had better judgment. Sometimes the only way we learn to make better decisions is the memory of having made some bad ones. Or, when the “should” is coming from someone else, as in “You should have done this…” there’s judgment and blame. Never a great way to build a relationship.
  • There’s no grace or forgiveness when we “should all over ourselves.” In business and in our careers we need a huge amount of grace, both for ourselves and for the people we work with. Yeah, maybe you should have… but you didn’t. Forgive yourself and move on.

OK, I admit, there are a few hard and fast “shoulds” and “should nots” in the world. Example: You should NOT stick a knife in the toaster to stab your toast while the toaster is still plugged in. For issues related to safety and health, “should” is there to protect us. But listen to yourself this week: how many times have you used the word “should” when you’re either berating yourself or someone else?

Language is powerful. Once I heard my friend Linn say “Quit ‘shoulding’ all over yourself!” I never heard the word “should” in quite the same way. I invite you to substitute the word “should” whenever you can with the word “could.” The word “could” is future-based, filled with opportunity, possibility and grace. You deserve that grace, and so do the people who work with you.

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