Episode 23: The “Should” Trap: Who Said You Have to Do It This Way?

How often do you tell yourself you "should" be doing something? You should be further along. You should stay in your job. You should want certain things. You should have your life figured out by now.

9/10/2026

✨ Just because you think you should doesn't mean you have to.

In this episode of Reinventing Life After 40, we're exploring how the word "should" can quietly shape your decisions, create guilt, and keep you from pursuing what you actually want.

Many of the expectations we carry in midlife came from family, culture, work, or ideas we developed years ago. But not every "should" reflects what you value today.

In this episode, you'll learn:

  • How "should" thinking contributes to guilt, self-doubt, and feeling stuck

  • Where many of our expectations come from

  • How to recognize when you're following someone else's definition of success

  • Why asking "According to whom?" can change the way you think

  • A simple exercise to help you make more intentional choices

If you're feeling stuck because your life doesn't look the way you think it "should," this episode will help you question those expectations and reconnect with what you actually want in this season of your life.

💡 Main Points

  1. "Should" can hide expectation we've absorbed from other people

  2. Not every expectation deserves to become a rule

  3. You can question your "shoulds" and make more intentional choices

  4. Knowing what you don't want is as useful as knowing what you do want

✍️ Homework

The "Should → Want" Exercise

Choose one should that's been bothering you.

Write:

I think I should ____________.

Then ask:

Who says I should?

Then:

Do I actually want this?

Finally:

If I could choose freely, what would I choose instead?

Don't worry about acting on the answer immediately.

The first step is recognizing the difference.

💭 Reflection Question

What would I choose if I stopped asking what I should do and started asking what I want to do?

✝️ 2 Cor 10:12

For we dare not class ourselves or compare ourselves with those who commend themselves. But they, measuring themselves by themselves, and comparing themselves among themselves, are not wise.

✝️ Gal 6:4

But let each one examine his own work, and then he will have rejoicing in himself alone, and not in another.

✝️ Exo 20:17

You shall not covet your neighbor's house; you shall not covet your neighbor's wife, nor his male servant, nor his female servant, nor his ox, nor his donkey, nor anything that is your neighbor's.

Connect

Join our journey to joyful, small changes.

Email

hello@sarahtyk.com

© 2026. All rights reserved.

Newsletter

Sign up for weekly encouragement.