A manual to leaving well?

There’s a fine line between endings and new beginnings

Louise Armstrong
Leaving well


by Louise Armstrong and Nour Sidawi

If you’ve ever struggled with having a thoughtful ending — of transitioning from one thing to another — this blog post is for you.

This blog post isn’t written to give advice so much as it is to comfort and console and to lift our gaze up to the concept of organisational separation through a process of ‘leaving well.’

It is a long post that might need more than one sitting to get through but the topic is worthy of the time invested. One doesn’t approach such a topic, so central to our experience of being human in this world, lightly or casually.

Caption: image of swirling bark with ‘leaving well’ sketched, by hand, on top.

Tracing the path of loss

Leaving organisations can be messy and complex. It shapes us. And the realisation often doesn’t come from some climatic third act. Instead, it is the acknowledgement of a simple truth: that sometimes, it’s ok to walk away. There is a difference, albeit subtle, between what’s hard and what’s Sisyphean and continually unfolding.

We aren’t less than for changing course and finding new paths. Yet we can find ourselves confused and misaligned in the separation process. Yes, it’s hard to let things, people, places, and habits go — but it’s also illuminating to see what needs to be released for us to do that.

So what happens when we cannot push any longer? What happens when we reach the end of our journey such that we have no choice but to let go and try to grow?

At life’s busy pace, there is often no time for examining this loss. In planning our departures from organisations, we rarely think about how to “leave well.” We might have a general idea of how we want to leave, but the actual path to leaving is unclear. We may hit a few dead ends and have to trace back a few steps. But every departure is a loss, because every one of us leaves a distinctive mark on what an organisation is, has done, and continues to do every day of its existence.

Often the picture is more clear after we have left. But the thing about unresolved shadows is that, the more you suppress it, the more it comes out sideways. Hence the need for leaving well, most importantly for the individual themselves.

Because the reasons for leaving aren’t always clear-cut. They can’t be encapsulated in a single word. It requires a story, to sit down with a coffee held tight in our hands and tell the stories of how we chose something different. We try to communicate a feeling that has to be experienced to be understood, and we try to make sense of something that sometimes doesn’t make sense to anyone else.

Whilst the experience of leaving is never easy, the explanation is even less so. That tension makes it hard to find nuanced conversations about how to leave organisations well. Often, it feels easier not to try. And so we’re left with the paradox of ‘leaving well’: we have to talk about it, but we can’t.

What does it mean to “leave well”?

We (Louise and Nour) have been wrestling with these questions for the past year. What we noticed again and again is that there is grief and confusion around that very question. How do we release what no longer feels right?

It started where many good things do: with a tweet, followed by a comment on a blog post. A connection between two people — unknown to each other — with a shared interest and willingness to experiment.

Caption: Message by Louise Armstrong — “I loved this, thanks for taking the time to do it. I experienced the power of writing my own organisational ending story last year too — reading yours, now seeing it as a valuable practice and part of the healing and grief work needed with that. Wondering about there being a collection of ‘ending stories’ that we could curate?” Reply by Nour Sidawi — “Ah, a pleasure. When I think back to my own organisational ending, I’m flooded with emotions (after all this time)…I was left with unresolved feelings. It’s easy to lose sight of the human element in endings that includes the need for time and space to grieve. I’d love to curate a collection of ‘ending stories’ — I think there are many of them out in the world :)”

We have both had radically different experiences of leaving organisations in recent years. We openly turned to writing and crafting our stories as part of that process, having a conversation with ourselves on paper. Everything spilling out in a bizarre stream of consciousness.

We have had to come to terms with having to walk away from things, relationships, and identities that no longer fit. We have learned to accept and find gratitude in learning to put things down — especially things not meant for us. That deconstruction was a necessary part of the opening to what comes next. It’s messy and sometimes dishearteningly slow. Sometimes only years later do you realise what you did or what it meant. But it’s also the condition-creating for a new way.

We know that others have found our goodbye blog posts interesting because they know that, someday, they will be faced with the calculus of whether or not to leave. When is it the right time? How do you figure out what’s next?

Whilst there is no end of HR process and procedures that comes with leaving roles — resignation letters, exit interviews — there is rarely space for the more human and emotional processing that is needed when making these significant life transitions. When not tended to, or held well, these moments can too quickly turn into traumatic experiences for people.

So how can we help others on their own journeys? Well, this is our attempt to do that.

How did we do this?

We decided to go with the energy, learn by doing, and test out some of our hunches. We were delighted at the ease and flow that followed through that process.

Inspired by the Manual of Me and seemingly everyone talking about ‘user manuals’, we played around with the ideas of the Manual for Leaving.

A simple and lightly-structured process which creates a space for people to come together and share their thoughts and feelings around leaving. Something that can be done individually through writing or in a group discussion.

  • Round 1: Where are you in your journey of leaving? What’s your experience been?
  • Round 2: What would have better enabled your journey/process of leaving? What did / might enable the process for you?
  • Round 3 What did it take of you? What did it give you?

We decided we needed to test our process out with people. So, we hosted a “leaving well” listening circle. It was inspired by the disarmingly simple “Spaces For Listening” format that Brigid Russell and Charlie Jones have developed (you can read more about it here). We invited seven people who were in the process of leaving a role, having recently left one, and were also considering making a move. They each knew one of us, but not each other.

In the three rounds of questions, we asked ourselves what deconstruction was needed. We asked what new possibilities were unveiled in us. And we asked what we might find if we dug into places long hidden and opened them up. We wondered what we would like to lay down, what we would like to pick up.

The long arc of leaving — choices and costs

So, what did we learn?

We were *pleasantly* surprised at the depth of honesty and reflection we got from a group that didn’t know each other. We felt moved by the tiny taste of all the leaving stories we heard, for what people shared of themselves. Hosting the space showed us there is a need and interest in this, with people offering so much more of themselves than we anticipated.

From the conversation, a set of insights and shared messages were revealed:

Leaving is a bereavement…and a liberation

“The old structures that held and constrained [me] are now gone — I now come up with my own divisions about what I choose to do or not do.”

Sometimes it can be good to get things off your chest. To have the space to share, to be listened to, and to hear others. For topics that we don’t often make space for, it can create a surprising sense of relief to give voice to the lesser spoken things.

In the group, people spoke about needing the confidence and courage to leave, and the preparation that took longer than it should have. And how liberating it was to realise that you can create your own stories — and that made the act of leaving a transformative experience.

Some felt they could reflect in real time or near the moment of leaving, others only when years had passed and there was space and distance to be able make sense of it. Some realised that they were in a place of leaving when they joined the organisation.

It was highlighted how frightening it is to let go of identity, status, salary — everything that is wrapped up within roles and organisations. It was strange to feel that loss and bewilderment so keenly and wonder, “Who am I now?” Looking back, it was only with time, space, reflection, and support that the ending really be processed. To enable us to decide what was ourselves to keep and what was the organisation’s.

How much of ourselves we give to our roles distracts from the choices we have

“The experiences continued to take their toll on me in unexpected ways, long after I left…[the organisation and its wider community] took a bit of my heart, soul, and spirit.”

There was also reflection that we can find ourselves being consumed by a role, filling all our focus, taking all our energy. If we even recognise it, we tell ourselves that it will only be a temporary situation — but it rarely is. And we find ourselves consumed by the organisations we are part of, which want us to feel indispensable but to actually be disposable, and thus to distract attention from the choice we have in staying or leaving.

Our roles can become so intertwined with our lives, identities — our pasts, present and future — and it’s no wonder more support is needed to make sense of this. When you’ve been somewhere for a long time, the organisation’s boundaries are your boundaries.

All had thought deeply about their place in the system, how much emotional commitment it required to stay…and also to leave. To even question it was ground shifting. There was a sense of feeling adrift in the transition. Of not realising your mind was on fire until the smoke gets in your eyes.

Beginnings are hard — but regretting never starting is even harder

“Who am I without the work…?”

Leaving had, over that time, come to loom so large in the minds of each person that it could not be ignored. It caused them to examine choices that previously they did not know they had. To stay or to go, there was always a choice.

Why does it take us so long to realise? Well, the act of self-discovery felt difficult to prepare for. It was terrifying to take that first step. The realisation that each person was not going where they thought they were — and things look like barriers weren’t really when pushed at them. Nothing was coming back from that point on.

The conscious uncoupling of organisation and self meant exercising the ability to be more conscious about where to put time and energy. That where someone stood to do the work was a choice. But it also often resulted in losing a whole community along the way.

What each person learned of themselves in the process of leaving was revealing. But progress often felt slow in the moment, coming and going in waves. It was only when looking back from the shoreline, every now and again, did we see how far we had come.

To start where we are

“I’m really hoping that leaving will give me a new sense of who I am and what I can do in the world — but we’ll see”

Many of us spoke about how we might have left a physical place, role and organisation — but the relationships and the things we wanted to keep remained. Leaving the place, not the people, though that slow process of disentangling was tricky to navigate. But for some, in a sense, that left us still in relationship with the organisation, unclear on what they should be.

There is no one-size-fits-all leaving journey. Along with loss and grieving, we explored the sense of still being relevant and useful, of belonging to something, somewhere that mattered. And how to find ways to keep that wholeness grounded whilst also feeling completely ourselves.

Ultimately these reflections are stories about the long-term arcs of life. Deeply pondering what leads to what and how our choices made at one point in time shape our happiness for years to come. Leaving has given us all the space, energy, confidence, and time to do so many of the things we’d designed out of our lives. And our stories were a celebration of the things we’ve done, the people we are, and those we were in service of.

We’re still collectively working out what we want to do when we grow up though!

Where to from here?

Leaving well reminded us to release what needs to be released. It allows the room and opportunity to discover what nourishes and what drains, what heals us and what harms us. We can be grateful for a season — and also be glad that it’s over.

We have learned that we do not have to struggle through things just because of the time invested. We can forge bonds out of emotions and the unknown. We can wonder what the world is like outside the lines drawn for us. We can part ways and trust the re-route instead.

With this in mind, we’ve created a number of resources (links below) to support those wanting to host a listening circle or reflect on their own ending journey to do so more easily. We’d love to hear of the tweaks and adaptations you make, and how they work out for you.

Resources and inspiration

Manual for Leaving Well

We’ve created a short guide and set of questions, which is good for:

  • Individuals — wanting to reflect on your transition / leaving
  • For people who want to host a leaving well listening circle and explore this topic with others

This is our adapted version of the Spaces for Listening format is a prototype — and we’re still learning about how to use this so we’re keen to hear what you think and how you’ve used it.

Stories of Leaving Well

Looking for inspiration? Want to hear how others have navigated leaving well? We’ve started a Medium publication — if you have a story that you’d like to be part of the publication, get in touch with us (we will add it on for you) or use the prompts in the Manual for Leaving Well to help craft a story for yourself.


While this is something many of us do, it;s suprising how little it’s spoke about. We’re sharing some of the people and things we’ve been inspired by through this process that might be of interest for those wanting to explore this topic more:



Louise Armstrong
Leaving well

#livingchange / navigating / designing / facilitating / doula of change