How to Tell the Difference Between What You Want and What You've Been Told to Want
And why it matters before you make any career move.
There's a word for the invisible pressure that shapes most mid-career decisions.
The scary part? It doesn't feel like pressure at all. It feels like your own voice.
It’s called “should.”
You should be further along. You should want the next title. You should be grateful — the comp is good. You should stop being restless, you worked hard for this.
Those shoulds don’t announce themselves. They just quietly move in. A parent’s definition of success. An industry benchmark. A version of yourself that made sense at 28 but hasn’t been updated since.
And after a while... they reshape your thoughts.
If you read Monday’s post, you know the feeling I'm talking about.
By the time you’re mid-career, those shoulds don’t feel like outside pressure. They feel like your voice. They’ve been living in your head long enough that they’ve redecorated the place.
Most of us didn’t lose direction because we made bad decisions. We made a long series of perfectly reasonable ones... ones that we were praised and rewarded for and somewhere in that chain, the question “what do I actually want?” stopped being asked.
Here’s the Framework That Changed How I Think About This
I spent a year studying happiness on my joint podcast What’s On Your Bookshelf. Really studying it — reading the research, going deep on the philosophy, talking to people about what actually makes them feel like their life is working.
One of the most useful things I came across was from the book Solve for Happy by Mo Gawdat.
The idea is simple. Happiness is a balance scale. When what you have equals or exceeds what you expect, you’re in a good place. When expectations outweigh reality, you’re not.
But here’s where it gets interesting.
When you load the expectation side of that scale with shoulds — expectations that were never really yours to begin with — you tip the scale toward unhappiness without anything in your actual life changing.
Your title is still there. Your comp is still there. Your accomplishments are still there.
The scale is just off... because you’re weighing yourself against a benchmark someone else set.
That’s not a career problem. That’s a weight problem. And that weight isn’t yours to carry.
(I went deep on this during a year of studying happiness — you can find those episodes at woyb.substack.com if you want to go further down that rabbit hole.)
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So How Do You Know Which Shoulds Are Actually Yours?
This is the work I do with every client before we touch anything tactical. Before job searches. Before positioning. Before next moves.
Because if you don’t audit the shoulds first, any next step is just trading one set of inherited expectations for another.
Here are the six questions I walk people through.
1️⃣ Where did this expectation come from?
Not in the abstract — get specific. Did you decide this was the goal, or did you absorb it? A title, a salary number, a timeline for where you “should” be by now... trace it back. If you can’t name the moment you chose it, that’s worth noticing.
2️⃣ Would I still want this if no one could see it?
Strip away the LinkedIn announcement, the dinner table conversation, the reaction from people whose opinion you respect. If the outcome were completely invisible to everyone else, would you still want it? This one question does a lot of heavy lifting.
3️⃣ What am I actually afraid happens if I let this go?
Most shoulds are held in place by fear, not desire. Fear of falling behind. Fear of looking like you gave up. Fear of what it means about the years you already put in. Get honest about what’s really keeping the expectation alive.
4️⃣ Does pursuing this drain me or energize me?
Not the outcome — the pursuit. The daily work, the conversations, the direction of effort. If the path consistently feels like swimming upstream, that’s information. Not every hard thing is wrong, but sustained depletion usually means misalignment.
5️⃣ If a close friend described my situation back to me, what would they say?
Sometimes you already know the answer. You just haven’t given yourself permission to say it out loud. The outside view cuts through the noise faster than any internal debate.
6️⃣ What would I want if I wasn’t trying to prove anything to anyone?
This is the deepest one. Underneath the titles, the comp benchmarks, the career arcs that look good on paper — what actually matters to you at this stage? Security. Autonomy. Impact. Connection. Something else entirely. The answer to this question is where real career direction starts.
This Isn’t a One-Time Conversation
These questions aren’t a checklist you run through once and file away.
They’re worth returning to, especially when a decision is in front of you and something feels quietly off.
The goal isn’t to abandon everything you’ve built. It’s to make sure what comes next is actually chosen... not just inherited.
Because when you stop carrying the weight of someone else’s expectations, something shifts. The next move stops feeling like an escape and starts feeling like a real decision. One that’s actually yours.
That’s a different kind of clarity. And honestly? It’s where the real work begins.
If you want a starting point, the Next Move Diagnostic is a quick way to find where the real gap is right now — between what you have, what you think you should have, and what you actually want.
🎯 It takes about a minute and tends to surface things worth thinking about.
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💌 Know someone stuck in the same loop? Send this their way.