How many times a day do you catch yourself saying “I should”? I should be further along. I should want something different. I should have this figured out by now. That one word quietly runs so much of our lives, and most of the time, it isn’t even coming from us.

In this episode of What If It All Goes Right?, I’m breaking down the language of “should.” Where it comes from, why it feels so heavy, and how it keeps you stuck chasing expectations that were never yours to begin with. We talk about how comparison, family pressure, old timelines, and past versions of yourself shape your choices, even when they no longer fit who you are now.

I’ll walk you through how to spot when you’re operating from obligation instead of desire, why resentment is such an important signal, and how small language shifts can help you move from autopilot into choice. If you’ve been feeling behind, boxed in, or disconnected from what you actually want, this episode is your reminder that you’re allowed to choose yourself.

What's Discussed:

(00:05) The word “should” and how it quietly runs your life

(01:20) Why “should” isn’t your voice and where it actually comes from

(03:15) How “should” creates anxiety, pressure, and constant self-judgment

(06:39) The hidden cost of building your life around external expectations

(09:43) How to tell when you’re operating from “should” instead of desire

(11:23) A simple exercise to identify the “shoulds” keeping you stuck

(12:42) Replacing “I should” with “I choose” and “I want”

(22:00) Building a life based on your values, not someone else’s timeline

➡️Watch my TEDx talk, What One Pull-Up Taught Me About Resilience, for a deeper look at how small, uncomfortable actions build confidence and reshape identity over time: https://youtu.be/CNEdft5lDMs

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