In 2022, I wrote a post called Shoulds and Social Contracts about my growing awareness of one small but powerful word: should.
Back then, I realized how often I used it; mostly when I was talking to myself. That reflection was the start of my journey toward letting go of “should.”
- I should work this weekend.
- I should eat fruit instead of ice cream.
- I should do another 30 minutes on the treadmill.
Each time I said should, I felt a little guilty, like I was telling myself I wasn’t doing enough. I realized this was a form of self-sabotage. That word held years of ambition, pressure, and comparison; habits I picked up from long hours, moving for work, and always trying to get ahead.
When I finally walked away from that cycle, I thought I was done with should. I promised myself I’d stop living by what I should do and start listening to what I needed. Better still, I was going to focus more on what I truly wanted for once. I call it my “Era of Yes”.
Fast-forward to this week, when I came across a Forbes article by Nicole Lipkin about that same word.
She wrote that replacing should with want can boost motivation and well-being. There’s actually research that backs this up.
It was perfect timing. I may have quit the 80-hour weeks, but I haven’t entirely quit the mindset that fuels them. Should still sneaks into my internal monologue.
- I should network more.
- I should post on LinkedIn.
- I should be further along in growing my business.
This small shift from should to want reframes everything. It turns sacrifice into choice, self-criticism into agency. Three years ago, I broke the social contract that tied my worth to work. Now, I’m just trying to be kinder to myself and stop letting self-judgment call the shots.
I still catch myself falling into old patterns. I wrestle with the expectations (real or imagined) about growing my business.
- I should be doing more lead generation.
- I should have more clients.
- I should be ready to hire a team.
- I should be making more money.
I’m not sure if these expectations are internal or external, perhaps both. But it’s difficult to ignore them. The truth is, I’m not even sure I want those things. I’ve spent my entire life working toward “success.” Now, I’m realizing success might mean something completely different to me. Maybe it’s working less, not more. But it’s hard to set down those long-held ambitions and expectations. And harder still to admit that I don’t yet know what to pick up instead.
So for now, when I hear the word should, I try to pause and ask: Do I actually want to? Sometimes the answer is yes, and that yes feels honest and powerful. Other times, the answer is no, and that feels like peace. The hardest moments are when the answer is both. It’s confusing and thrilling at the same time.
I guess that’s what letting go of should really looks like. It’s not a one-time decision; it’s a daily practice of noticing, learning, and choosing what matters most. I’m trying to remember that my goal doesn’t have to be to do more. It could be to live more intentionally, more truthfully. To build a life around what I want (whatever that turns out to be), not what I should.
I’m still learning. But I think that counts as progress.
