I stopped by my boss’ office to debrief her on the lunch meeting she was unable to attend.

Before I could get a word out, she looked me up and down and said:

“You know, next time you really SHOULD wear a suit.”

SHOULD is a word we hear so much.

Well-meaning people believe they have the perfect advice for how we can “do better next time.”

The thing is, their SHOULDs are based on THEIR perspective and are usually more indicative of expectations they have for THEMSELVES rather than the best choice for you.

I’m sure my boss wanted me to make a good impression. And for her, a suit was the way.

But my meeting was at a quick service restaurant with the founder of a small startup on a tight budget – who showed up in jeans and sneakers.

I was relatable in business casual and that’s how I made a good impression. Anything more would have been out of sync with the nature and purpose of the meeting.

Still standing in her doorway, I thanked my boss for the feedback, but I knew better than to second-guess my intuition.

Next time someone SHOULDs on you, think before taking it to heart.

It’s most likely meant to help, but make sure it’s helping you be a better YOU – not them.

Feeling overwhelmed by other people’s SHOULDS? Please reach out, I can help.