You should totally read this...
...if you start sentences with "you should."
“You should just tell your boss you want a raise.”
My (self-employed) friend said this with the kind of confidence reserved for people who’ve never actually told their boss they want a raise.
I’d been venting about work. As you do. Not looking for a solution, just… airing it out.
And that’s when she hit me with it. The “you should.”
The moment those two words leave someone’s mouth, my brain shuts down. Because rarely does anything that follows “you should” turn out to be helpful.
Here’s what I hear after “you should”: I’ve thoroughly assessed your situation in the 90 seconds you’ve been talking, determined you’re handling it wrong, and I’m about to tell you the obvious thing you’re too dumb or too weak to think of yourself.
“You should” is the advice-giver’s usually well-meaning way of saying they know better.
They’ve boiled down your complex situation into something neat and tidy. Something that fits their experience. Something that - if you were just a little smarter or a little braver - you’d have figured out on your own.
“You should have your neighbor cut down the tree that sheds leaves all over your yard.”
“You should read your husband the riot act.”
Or - the best of the bunch - any variation of:
“You should tell them to go pound sand.”
Yeah, well. “They” sign my paycheck. Or babysit my dog when something urgent comes up. Or sleep in the bed next to me.
“Go pound sand” tends to have lasting repercussions.
People who say “you should” operate from the safety of not being in your situation - and not having to deal with any fallout.
I’ve also found that “you should” is almost always followed by something grossly oversimplified.
Something you thought of immediately and dismissed based on those pesky-but-real nuances.
As if something like the complexity of my relationship with my boss - the politics, the history, the fact that I actually need this job - don’t factor in.
“You should just ask for what you deserve!”
Sure. Right after I “just” figure out how to phrase it so I don’t sound entitled. And “just” time it right so it’s not during a hiring freeze. And “just” make sure I’ve documented enough wins to justify it without sounding like I’m bragging.
But yeah. Super simple.
I should have thought of that.
And then there are the people who follow up “You should...” with “I would...”
No, you wouldn’t.
Not if you understood the full situation. You wouldn’t if you were standing in my shoes, with my mortgage and my team dynamics and my proprietary blend of anxiety and people-pleasing tendencies.
You think you would. Because from where you’re standing, it looks easy.
It always looks easy when it’s not your problem.
I really want to call people out when they hit me with an unsolicited “you should.”
Explain why their advice isn’t helpful. Help them understand that maybe - just maybe - I’ve already thought of their stunningly obvious solution and dismissed it for reasons they don’t know about. That my problem cannot be so easily and cleanly resolved. Like an episode of Modern Family.
But I don’t.
I generally just weather it, then move on.
Which, of course, doesn’t teach them anything. They walk away thinking they’ve been helpful. I walk away feeling no closer to a solution, but with an added serving of irritation.
It’s taught me, though. If I ever catch myself saying “you should…” I immediately shut up. I’ll ask a few questions, and I’ll commiserate, but unless someone asks me “what would you do?” that’s as far as I’ll go.
So what’s the productive response to “you should”?
I don’t know. I’m still working on it.
Maybe I should just tell them to pound sand.




Nice post. I usually reply back, "are you shoulding on me?" Their reactions is priceless :)