Laurence McCahill
The Happy Startup School
3 min readDec 8, 2023


Navigating Endings: A Reflection on Transitions and New Beginnings

Next Friday we’re having an exciting conversation with Dougald Hine, a social thinker, author, and founder of A School Called Home.

His book At Work In The Ruins delves into how we navigate crises, particularly the climate crisis, and the concept of endings.

I’d like to explore these insights shared by Dougald and how they resonate with our journeys here at The Happy Startup School.

Rethinking endings in business

In preparation for next week’s conversation I’ve been immersing myself in Dougald’s work and I came across a conversation he had with Bayo Akomolafe, where a fascinating perspective emerged regarding the traditional view of endings, especially in business.

There’s a common notion of abruptly ending one venture and swiftly starting another; the path of the serial entrepreneur. As entrepreneurs, we often experience transitions as abrupt shifts — ending one project to initiate another.

However, I believe that there’s an alternative perspective that emphasises a more gradual, intentional approach.

Reflecting on personal experiences, such as ending Spook Studio to start The Happy Startup School, this perspective prompts us to reconsider how we approach transitions.

Rather than a sudden stop followed by a void, the idea of hospicing suggests gently bringing things to a close, harvesting what worked, and ritually letting go of what no longer serves.

This process fosters clarity about what lies ahead, even in the absence of a clear plan.

The fragility of new beginnings

Starting something new is a delicate time, especially when it involves a significant shift in career or lifestyle.

The sudden cut-off of familiar structures, such as income streams or established routines, can be challenging. Within our community, the challenge is met by tapering off the addiction to old ways gradually.

Instead of abruptly stopping what you’ve done before, how can you continue the work and bring that journey to an end in a way that allows space and safety to explore new paths?

This approach acknowledges the fragility of birthing something new, and the importance of a supportive environment in navigating this uncertainty.

Communities as incubators for change

Considering communities as experiments and prototypes of the worlds we wish to live in, you can think of The Happy Startup School as an incubator for new ways of working.

It acts as a supportive space where individuals can explore and experiment without immediately severing ties with their past.

These micro-worlds become essential in trying out innovative approaches within a broader societal context that may still operate in older paradigms.

The ripple effect of personal transitions

As we embrace gradual endings and new beginnings on a personal level, the impact ripples out to our broader communities and society.

The ability to put things to rest, create a different relationship with endings and death, and accept uncertainty becomes a powerful force for positive change on a larger scale.

The upcoming conversation with Dougald Hine promises to be a thought-provoking exploration of different ways to navigate personal and professional transitions.

By embracing the concept of hospicing and gradual change, we can cultivate a mindset that fosters creativity, reduces anxiety, and encourages bravery.

Our hope is that the insights shared in this conversation may well become a guiding light for those seeking a new way of working — one that encompasses happiness, purpose, and financial sustainability.

So, if you’re on the journey to find an exciting new way of working, mark your calendars for this conversation — next Friday 15th December at 12pm GMT.

It may just provide the inspiration and practical insights you need to embark on your unique path toward a fulfilling and purposeful future.

Carlos Saba
Co-founder The Happy Startup School



Laurence McCahill
The Happy Startup School

Designer, coach, entrepreneur. Co-founder The Happy Startup School.