Re-Imagining “I Should…”

Reimagining our Future
3 min readDec 2, 2020

As a social worker, therapist and healer, I often run into challenges and roadblocks with the stories I tell myself — the sense-making apparatus that I have developed up until now.

After experiencing a recent loss, I had the thought that I should really find a therapist now that I’ve settled in my new city

That should… created the question for me. Is that really what I need? Or is that what I have been socialised to think I need? How often do I really ask myself what I need? Could my soul actually be seeking a visit with an old friend, a beautiful meal, or a dip in the cold ocean, a day/week/month off?

That should is important to reflect on. To feel.

Ram Dass jokingly, but with all seriousness, says “I’m tired of being ‘should’ upon” (instead of I’m tired of being ‘shit’ upon). When is the last time you have been ‘should upon’ or you ‘should upon’ someone else?

Think of the well-intentioned mother that tells their adolescent child they should go to university. Or the teacher that tells the student you should do your algebra homework, even though, deep down, they know it is not completely practical or needed. Or your inner-voice that tells you that you should wear a certain style of clothes, get a certain haircut, lose weight.

The words we choose are powerful. A simple shift in words can make a huge shift in meaning (i.e. I have to pick up my children from daycare. → I get to pick up my children from daycare.) What if we flipped more of our ‘shoulds’ to ‘coulds’, what difference might that make?

Photo by Hamid Tajik on Unsplash

Lead Author: Rosie O’Connor (first 3 paragraphs)

For some people, COVID times have been an opportunity to reconnect to time, space, nature, animals and humans. Personally, it has given me the freedom to let go of many of my previous expectations, and to recenter my values of community, intuition and presence. This is not to say that there still isn’t pain. Instead it is the acceptance and honoring of the pain, Adrienne Maree Brown’s Emergent Strategy has reminded me of the waves, the fungi, the states of this world and the fact that in life there is death, just like in joy there is sorrow — and to accept, explore, and work with it all, with community, is the gift. Rosie O’Connor is a healer and social worker in unceded Duwamish territory often referred to as Seattle. Feel free to reach out for coaching, conversation or questions at

Anchor Author: Daniel Rudolph

Daniel Rudolph is interested in exploring alternative, experiential learning opportunities for people of all ages. He is passionate about forming community, and building public spaces for meaningful, transformational gathering. Currently he is spending a lot of his time learning juggling and facilitating gatherings. He also enjoys writing and sharing poetry. Daniel is a very curious and playful person and is always open for creative collaborations.