The Weight of Should
…Reclaiming Choice in Retirement
“I should be more grateful.”
“I should be happy to help.”
“I should just go with the flow.”
Sound familiar?
For many individuals stepping into retirement, “should” statements seem to multiply. The external structure of work may disappear, but internal expectations can grow louder than ever. In the absence of a job title, routines, and deadlines, we often lean into inherited beliefs, outdated roles, and old scripts about how we’re supposed to show up. And while “should” might sound harmless, it can quietly drain energy, agency, and joy.
Why “Should” Feels Heavy
In Cognitive Behavioral Therapy (CBT), “should” statements are classified as a cognitive distortion—a way of thinking that adds unnecessary pressure and often leads to guilt, shame, or frustration. According to Dr. David Burns, author of Feeling Good, “should” implies obligation rather than choice. It’s a subtle inner voice that says, This isn’t what I truly want, but I have to anyway.
In retirement, that voice might show up in decisions about how time is spent, what roles we play, or what expectations we try to meet:
I should be available for the grandkids every time they need me.
I should downsize because that’s what people do.
I should say yes—I’m not working anymore, after all.
It’s easy to fall into the trap of thinking retirement is supposed to look a certain way. And when our lived experience doesn’t match the expectation, we might assume the problem is us.
The Should-to-Choice Shift
Here’s a simple way to cut through that noise:
Replace “should” with “want” or “choose”—and see how it feels.
Let’s say you’re thinking, “I should join that volunteer board.” Try rephrasing it: “I want to join that board” or “I choose to join that board.”
If it resonates, great—you’ve just named a value-aligned action. If it doesn’t feel true, that’s valuable data. It might be worth exploring where the “should” came from. Was it a habit? Pressure from others? A fear of being seen as unproductive?
This small shift creates space. It puts you back in the driver’s seat, where you can examine whether a decision is rooted in desire or duty—and whether it’s still serving you.
Why It Matters in Retirement
In our working years, we often have guardrails that help filter decisions—deadlines, job descriptions, limited time. But in retirement, there’s more room—and ironically, more room for “shoulds” to creep in.
When you find yourself feeling resentful, stretched thin, or disconnected from joy, chances are you’re navigating life through a lens of obligation rather than intention.
This isn’t about saying no to everything. It’s about pausing long enough to ask: Is this truly what I want?
Try This: A Week of Noticing
This week, try a simple reflection exercise:
Catch the Shoulds – Every time you say or think “I should…”, write it down.
Ask Yourself – “What do I truly want in this moment?”
Dig Deeper If Needed – If you’re backseating your own needs or desires regularly, journal about what’s underneath. Is it fear of judgment? Desire to please? A sense of lost identity?
The goal isn’t to eliminate every “should”—some are based in shared responsibility or personal values. But noticing when “should” is driving your decisions gives you the chance to course-correct.
Reclaiming Your Voice
Retirement isn’t about conforming to a new set of expectations—it’s about designing a life that reflects your values, energy, and aspirations. And that starts with reclaiming your voice, one should at a time.
So the next time you feel that weight creeping in, take a pause and ask yourself: What do I truly want?
You might be surprised what surfaces.
Conflux Retirement Coaching is about merging the best of who you are with who you want to be. Retirement can be a time of expansion, fulfillment, joy and excitement. However, if we allow the “Shoulds” to take over, we rob ourselves of these opportunities, experiences and more. So take some time to notice when you use the word “should” to understand if the action you’re taking is reflecting your voice and your choice.
