How to let go of “shoulds”

Letting go

This is a written excerpt of Rest & Recreation, a companion to Routines & Ruts conversations podcast. Each week, host Madeleine Dore shares reflections from previous interviews and interesting reads to offer you a moment of R&R. Listen on Apple iTunes, Spotify and others.

Words by Madeleine Dore


This year, many of us have been forced to let go. Let go of various plans, projects, ideas, jobs, daily habits, expectations.

It’s disorientating and trying for many and the hardship that comes with such loss is not something to take lightly. Yet many people have described this time of forced letting go as a catalyst to let go of other things in their daily lives.

Perhaps those very things can be found on our own to do lists. 

There’s a line in Pandora Sykes new book, How Do We Know if We’re Doing it Right? that really spoke to this: “When I moan about how busy I am, what I actually mean is that I have a lot that I should be doing."

For as long as I can remember, I’ve prided myself on being someone who juggles various projects—I have enjoyed the rush of several to do lists, the calendar that’s always filled, wearing different hats.

But after a while, having all these scattershot projects like an events series, different newsletters, various Instagram accounts, started to feel like a long list of things I was telling myself I should be doing. I’d say no to spontaneous dinners with friend’s because “I’ve got to do this thing”—forgetting that it’ a personal project, and I determine the to do list. 

Sometimes, our doing, our complicated schedules, are of our own making. And so it’s up to us to let go in order to leave space for what we want, rather than what we think we should be doing. 

What's empowering about personal projects—or the things we do for recreation—is that we can keep experimenting and tweaking to get unstuck, but we can also let go. 

Of course we can’t simply drop everything we don’t want to do at any given moment. The lines might blur between a should and a responsibility, but there is a distinct difference between the two.

A should is an expectation from ourselves or others – and when inspected it might seem flat, expired, empty, or heavy. 

A responsibility, however, might not be something we wish to do – it might be uncomfortable, or boring, or difficult, but it feels rightful to see it through.

But it’s not always easy to let go of a “should”. As Pandora Sykes said in our conversation for Routines & Ruts, every gain comes with a loss.  

A gain can come with a loss because we have to question who we are if we don’t do that thing. Be it a project, a job, a hobby, a habit, a relationship. We become attached to our identities as morning people, vigilant news readers, multi-hyphenates, or a certain profession, without asking ourselves if our circumstances or interests still require that routine, or that paycheque, or that type of love. 

So maybe there’s something within your control that you want to let go of too, but either don’t quite know how or can’t quite put your finger on it, or feel you have to work really hard to fill the space.

I’ve been there again and again myself, and in those times I’ve found it helpful to survey my “shoulds” to be a guide for letting go. Here are the surveys that help me inspect my shoulds and let go.

1. A retrospective survey

Look back. If you keep a planner or calendar, look back on the previous week, month, even season or year to identify what you did because you felt you should and experienced a feeling of resentment. How many of those shoulds are you holding onto? Is it within your control to let go? If so, why are you holding on?

2. A real-time survey

Here, take note. Over the next day, week, or month or year, check in with your various moments and interactions. What are you doing that is clearly a should? How do you feel while doing it – or avoiding it?

I’ll pay particular attention to what I’m putting off and ask if you can let go or whether it’s time to stop adding it to my to do list.

3. A to do list survey

Take a moment to write out your entire to do list – every single task, commitment, job, project, idea, correspondence, and chore that comes to mind. The list might be very long. Survey the list: what is an expired idea, what is an old want, what is impossible, what is unnecessary, what is unsatisfying?

Then, I’ll start culling and crossing off anything that feels expired, impossible, unsatisfying.

4. A ‘who says’ survey

Looking at your retrospective, real-time or your to do list survey, what or who is driving each task? Is it yourself? Is it someone else? Who is saying you should be doing something, and why might that be?

Some final notes on letting go

What has helped me in that sometimes uncomfortable, uncertain space between a loss and a gain is  recognising that you don’t have to do anything to let go–you don’t need to fill the empty space. You can simply be in it, unsure for a while. 

We need empty, undesignated space so we can keep figuring it out, over and over. As dancer and choreographer Agnes de Mille once said:

“Living is a form of not being sure, not knowing what next or how. The moment you know how, you begin to die a little. The artist never entirely knows. We guess. We may be wrong, but we take leap after leap in the dark.”

To take this survey of shoulds to the next level, inspect what you might be filling your time with to avoid having empty time. Experiment with declaring: I don’t know what I want, but I don’t want this.

Can you remove these shoulds, bit by bit, and sit with the moments of not being sure?

Madeleine Dore