The Messy Middle: What Startups and Stories Have in Common

The Startup as Story

A good startup, like a good story, often begins quickly.

There is a sense of arrival, of meaning — not certainty, but orientation. A calling. Something compelling is pulling you to it. 

A world is being named, defined (to some extent) and imagined. A problem, or need, is spoken out loud. The edges of a possibility come into focus. It's exciting - the potential is captivating, mesmerising.

People gather not because everything is clear, but because something feels engaging, exciting, undiscovered. The painted picture of a potential future becomes real in the mind. Imagined. 

In stories, this opening act is brief. Roughly a quarter of the whole.
The scene is set. The characters appear. Tension hums quietly beneath the surface.

In startups, it feels the same. Energy and enthusiasm moves faster than proof. Belief, hope and spirit does much of the heavy lifting. The future is uncertain but exciting. The product is not yet complete. The work is imperfect but alive. 

Everyone knows they are early. Everyone knows they are helping write something that did not exist before.

This is the first gift of a good beginning: velocity without negativity or resistance.
We move, not because we know how the story ends, but because it feels necessary to begin. It compels us. We feel like we must join this journey.

Then comes the middle.

The part no one can skip.
The part no pitch deck can summarise cleanly.

In storytelling, the second act typically takes up half the time. It is slower. More uneven. This is where characters are refined, not introduced. Where initial ideas are tested against reality. Where tension does not resolve — it deepens.

This is the messy middle.

In startups, this is where the romance falls away and the real relationship begins.
With the product.
With the market.
With one another.
With ourselves.

The middle is full of reversals, failures.
Small wins followed by sharp disappointments.
Moments of confidence undone by new information or new insights.

Gaps in the market close, or show themselves more cleanly. 

Pivots are needed. The original painted picture needs revising, ideally without diluting hope and spirit. 
People grow — sometimes together, sometimes apart.

And here is something storytellers understand that businesses often forget:
the middle is not a problem to solve — it is the work itself.

It is the process. It is the creative action. It is the act of taking a vision and turning it into something real. It is about taking something nebulous and making it tangible.

This is where character is forged.
Where habits harden or soften.

Where culture is formed and nudged.
Where people learn what they must do when things don’t work.

Where people confront their limitations. Where reality takes a toll on energy and enthusiasm.

In a good startup, people don’t just build a product or service.
They become more precise and expanded versions of themselves.

This is also why the middle can feel rough, hard, sketchy and energising at the same time.

We long for some kind of resolution, yet are engaged deeply. We long for clarity over the long haul, yet are busy in the moment. We hope for the relief of knowing that all of this hard work is worth it, even if the hard work is enjoyable. We hope our hope and enthusiasm wasn’t misplaced. That we are growing.

But later — years later — it is almost always this act we return to.
Not because it was easy.
But because it asked something of us. It challenged us. It forced us to confront the edges of our ability and asked us to step beyond; to learn, to grow, to cultivate, to rise to the challenge.

The final act, when it comes, is faster again.

In stories, tension resolves quickly once the truth has been faced, a plan has been hatched and it’s clear there is a way through. The climax does not linger. The change has already happened — the ending merely reveals it.

So it is in startups.

Something clicks.
Or something ends.
A sale. An acquisition. A scale-up. Sometimes a quiet closing.

From the outside, this looks like success or failure.
From the inside, it feels more like completion.

The people who emerge are not the same people who began.
They are steadier. Sharper. Sometimes tired. Often changed in ways that don’t fit neatly on a CV. Sometimes with skills and experiences that don't fit in a box. Sometimes it's hard to find the right words to describe who they've become. Sometimes, they can't find traditional job roles that articulate their true breadth of character.

And if the startup was a good story, there is growth — not just financially, but humanly — it has crafted new people.

People know more about who they are under pressure. What kind of work costs them too much. What kind of work gives something back.

There is an interesting thing that happens after this.

Second and third films are often weaker than the first. Not always — but often enough to notice. The arc has already been completed. The characters have already paid a heavy price of transformation, of personal growth in the face of immense challenge. What follows can feel like motion without necessity.

Something similar happens in businesses after acquisition or scale.
The story shifts genre.

Risk becomes optimisation.
Becoming becomes maintaining.
Exploration becomes efficiency.
Experiments become a financial win/loss conversation.

There is nothing inherently wrong with this. Many people thrive here. But for those who lived inside the earlier story, something subtle is lost.

Not the chaos.
Not the stress.
But the sense of authorship.

Because what a good startup really offers is not just work — it is participation in a living and changing narrative. You are not an extra. You are not reading the script after it is written. You are shaping the story with your decisions, your attention, your courage, your commitment, your enthusiasm, your hope.

This is why people who have been through a true startup often feel restless afterwards. They are not chasing another company. They are not necessarily chasing another exit.

They are seeking the feeling of writing a narrative again.

Every business journey is a story, whether it admits it or not.

Every day we choose whether we are awake inside that story and play a key role, or merely moving through its scenes. Whether we speak lines that matter. Whether we help deepen the plot or quietly flatten it.

And perhaps this is the quiet truth beneath all of it:

We do not long for epic endings.
We long for meaningful middles.
For stories that ask something of us — and leave us changed.

A good startup, like a good story, does not promise comfort.
It promises aliveness.

And once you have tasted that — once you have helped write something that mattered — you do not forget the feeling.

You simply listen, patiently, for the next story that asks you to begin again.