Shoulding All Over Yourself

I was talking with someone the other day who kept saying what he should have done. Last week. Last month. Last year.

At one point, I joked that if he believed in past lives, he probably had a few should’ves from those, too.

The truth is that most people don’t realize how often they should on themselves.

It’s not always bad — sometimes it’s simply regret, or a quiet reminder that something still matters. The trick is to use it instead of repeating it.

Here are three ways to move from Should’ve to Next:

1. Catch it in real time.
Most of us use “should” so often it becomes background noise. Start noticing when it slips in — during a meeting, on a walk, while replaying a conversation. Awareness is what turns a habit into a moment of choice. You can’t change what you don’t catch.

2. Look for the lesson, not the loss.
Behind every “should” is a clue. It might be telling you what matters, what you value, or what you want to do differently next time. Instead of criticizing yourself, pull out the insight. That’s how regret becomes direction.

3. Turn it into immediate action.
Every “should’ve” has a next step. “I should’ve called” becomes “I’ll reach out today.” “I should’ve worked out” becomes “I’ll walk after dinner.” If you don’t turn it into something you’ll do today, you’re just adding another “should” to the list.

But not every “should’ve” needs action. Some just need to be released. They’re one and done.

This week I’ve been down with bronchitis. Talking with my wife, I started shoulding all over myself — about what I didn’t finish, what I should have started, who I should’ve followed up with.

She looked at me and said, “You know you’re sick, right?” She was right. I laughed, wiped that should’ve away, and moved on.

Every “should’ve” can become a step forward — or something you finally let go.

What if, instead of shoulding on yourself, you simply acted on what you learned — or released what no longer needs your energy?