The Red Wellington Boots


During our training to become an Ollie Coach we ask our trainees to write a metaphor of their Ollie Journey.  

The Red Wellington Boots

The red Wellington boots arrived before the rain did.
They stood alone by the door of a lonely seaside shop in Jersey, glossy as cherries, startling against the pale, cobbled streets and the grey skies of the English Channel. The traveller bought them because her old shoes were too small and pinched her toes. She had grown and needed shoes to fit her purpose. There were plenty of options in the shop: beach shoes, boating shoes, wetsuit shoes - but the red Wellington boots spoke to her. They were bright, they were bold, they were unique. They made her smile.
The shopkeeper wrapped them up in brown paper and winked.
“Those’ll take you wherever you need to go,” he said.
At the time, she thought he meant the potato fields of her ancestors. Black Wellington boots had always sat at the back door of her home waiting for her but she knew that the time had come for her to try something different, something that made a difference.
The traveller wore the boots along cliff paths salted by sea wind, through narrow lanes lined with wildflowers and chestnut trees, across beaches where the tide erased footprints before she could turn around to study them. Each day, the boots brought her joy and strengthened her smile. She walked fearlessly and confidently with a song in her heart.
Until she entered the town.
Everywhere she went, people noticed the boots and they frowned at her. Her boots were too bright, too alive, too different for the careful colours most people wore. She was embarrassed, so her joy faded.
But she refused to take off her red boots. They were sturdy and had proved their worth over any terrain. Their philosophy was simple: feel the wind, trust the path, step onwards.
The traveller left the island eventually. Ferries carried her toward larger places and larger uncertainties. She arrived in Lincoln beneath cathedral shadows and wide inland stormy skies far from the sea breeze that had given her the air she needed to breathe. The city felt older than memory itself, full of steep streets and echoes trapped in stone.
Here, life became heavier. Here, no one noticed her at all.
She learned loneliness can exist even in crowded places: especially there. Some evenings, she watched others put on high-heeled shoes and dance in the rain. The traveller watched them - the dancers - their shoes clicking like laughter on the wet pavements. She felt the rain on her face but not the rhythm in her bones. Her song was gone and so was her smile. Her red boots, once so full of promise, felt suddenly out of place. They were made for walking, not for whirling under streetlamps. They were made for journeys, not for belonging.
Still, she trusted in the words of the shopkeeper, so she wiped her boots clean each day, buffed their shine and continued travelling.
Months and months went by. Some mornings, she climbed the steep hill toward the cathedral, the boots thudding against ancient stone as though trying to wake something that had been sleeping inside her. Other days, she wandered the meadows and flatlands beyond the city, where the wind moved across the fields like a memory trying to return. The boots carried her through all of it — the quiet, the ache, the stubborn hope.
One stormy afternoon, as heavy rain bounced on the paths of the city college park and goslings sheltered under the trees, she caught her reflection in the glass of a café window. The boots glowed like embers against the grey pavement. For the first time in forever, she paused long enough to really look.
They were still bright.
Still bold.
Still uniquely hers.
And something inside her — something small but determined — stirred.
Perhaps the boots weren’t too bright for the world.
Perhaps the world had simply forgotten how to notice colour.
She stepped inside the café, leaving a trail of rain behind her. A young boy in a red shirt at a nearby table pointed at her feet and grinned, wide and unfiltered.
“Mum, look! Her boots are like cherries!”
The traveller felt warmth rise in her chest. Not embarrassment this time — recognition. A reminder that joy doesn’t disappear; it only waits for the right eyes to see it again.
She ordered tea. She stayed awhile. She let herself be seen.
The mother of the child noticed that the traveller looked tired and alone so she invited ‘the lady with the cherry red boots’ to sit with her, her son and their friends. They shared stories, laughed, cried, listened and learned from each other.
Outside, the rain softened.
Inside, the traveller's smile returned — not the carefree, fleeting smile of cliff paths and sea winds, but a resolute, unwavering smile that made her feel complete.
She gazed out to the park which began to fill with people as the sun broke through the clouds and poured its warmth on her face. She wriggled her toes in her red boots while they rested beneath her chair, still glossy, still bright, still bold and unique.
The shopkeeper had been right. Her red boots had taken her wherever she had needed to go - along the coast, over the sea, through the countryside and in the city, through song and silence, through forgetting and remembering. And they would take her further still.
After all, their philosophy would never change: feel the wind, trust the path, step onwards.
KH OS21