How to Stop “Shoulding” on Yourself

Image Credit: https://www.lummi.ai/creator/mikiwa

TL/DR:

• A "shouldless day" = no obligations, all spontaneity.

• Pick a day, clear your schedule, and plan to have no plans

• Instead, let the question "What do I feel like doing?" guide you.

• Reflect and repeat as needed!

The whole shebang:

When was the last time you had a “shouldless day”?

What the heck is a “shouldless day” you ask?

It’s a day free of “shoulds”.

It’s a day where you do whatever you want.

A day that is not guided by what you should do, but by what you want to do.

This phrase - “shouldless days” - has been kicking around my brain for the last several years, after I listened to an interview with Ellen Burstyn on the Anna Sale’s “Death Sex and Money” podcast.

I don’t remember much else about the interview, save for the fact that Ellen, at the wise old age of 85, talked about the fact that she regularly plans “shouldless days”.

And ever since then, I’ve been trying to incorporate a lot more “shouldless days” into my own life.

Now, if you’ve been around here awhile, you know that I find a lot of value in planning (even when plans don’t exactly pan out.)

But, I think critically, at least for me, a “shouldless day” is a day that isn’t planned out.  

It’s a day where spontaneity guides.

Planned for? Yes.

Planned out? No.

Now, is a possible to plan a shouldless day?

I suppose.  

But you do run the risk of “shoulding” on your fun.

Let’s say, for instance, that you plan out a fantastic day, full of plans with friends.  You’re going to see a movie, and go out for brunch, etc.

But then, you wake up, and you don’t really feel like going out. 

And you remember that you’ve made all these very fun plans for your “shouldless day”, but now, you want to cancel, you just want to take a nap, and you find yourself saying “well I SHOULD be going out and having this super fun day. 

And suddenly, you’ve defeated the point.

So, how can you plan for a shouldless day?

It’s easier than you might think.

(And yes, you can do it even if you have small kids, or other caregiving responsibilities.

If you do care for others, you may want to first start with securing care for them, whether it’s for the whole day, or just a few hours, whatever you can swing.)

Then, just clear your schedule.  

Don’t make any plans for that day.

Don’t set an alarm.

Instead, wake up when your body feels like it naturally.

And then, ask yourself one question:

“What do I feel like doing?”

And then do it.

And when you feel done with that activity, ask yourself again:

“What do I feel like doing?”

If what you feel like doing is leisurely staying in bed, resist the urge to call yourself “lazy”.

If the word “should” crosses your mind, remind yourself that that word is banished for the day.

Tap into the present moment.

And when that “shouldless day” is over, reflect for a moment. 

How did it feel to spend a day, or even a few hours, focusing on yourself, your own wants and needs, without guilt or burden?

And if, upon reflection, you liked it, that’s your sign to plan another “shouldless day”.