To me, there is no greater leader than Abraham Lincoln.

I have written about him extensively before, but I keep returning to his life because it resists the tidy stories we tell about purpose. Lincoln did not spend his early years steadily advancing towards the presidency, each setback secretly preparing him for greatness. For much of his life, greatness was far from assured.

If his story had ended before the age of 50, we might remember him as a gifted lawyer and an intermittently successful politician. He had served one term in Congress. He had lost more elections than he had won. Almost everything for which he became immortal still lay ahead.

It is tempting to say that Lincoln spent those years waiting for his purpose. But he was not waiting. He was reading, arguing, practising law and testing himself against the questions that troubled him. He studied history, political theory, Shakespeare and mathematics. He was following an intellectual hunger that seemed excessive, perhaps even peculiar, to those around him. He could not have known where it would lead, only that it was his to follow.

Viktor Frankl once used the image of an architect strengthening a weakened arch. The architect does not remove weight from the structure. He adds weight, forcing the stones to press more firmly into one another. Frankl believed human beings also require tension: the gap between who we are and what our lives might still require of us. Our instinct is often to escape it. We distract ourselves, begin something new, abandon something difficult or reach for an answer simply because uncertainty has become uncomfortable.

Lincoln did something harder. He stayed under the weight.

In December 1817, John Keats wrote a letter to his brothers in which he tried to describe the quality that made Shakespeare so extraordinary.

He called it Negative Capability: the ability to remain “in uncertainties, mysteries, doubts, without any irritable reaching after fact and reason.”

Keats was not praising confusion. Nor was he arguing that truth does not matter. He was describing the ability to resist imposing an answer before experience has yielded one. Shakespeare could inhabit Lear’s madness, Macbeth’s corruption, Hamlet’s hesitation and Falstaff’s appetite without reducing any of them to a lesson. His characters were not mouthpieces for a system. He allowed contradictory truths to remain alive at the same time. That was what Keats admired. Shakespeare did not tidy up the human condition.

Most of us would prefer a conclusion. We want to know what the difficult period meant, whether we should stay or leave, whether the project will work, whether the relationship is right, whether we have found our calling or merely another diversion.

Sometimes an answer is necessary. Sometimes the demand for one is simply anxiety.

Negative Capability is the ability to tell the difference.

I used to think life evolved more neatly than it does. I thought Negative Capability described the period before action. You wander, wrestle with the questions and wait. Eventually the fog clears, purpose reveals itself and you step forward with conviction.

I no longer think it works like that. Lincoln did not leave uncertainty behind when he entered the presidency. He had a moral conviction about slavery, but conviction did not free him from contradiction. He had to preserve the Union while deciding what preservation meant. He had to act against slavery within constitutional and political limits he could not ignore. He had to lead people whose motives differed from his own, including people who supported the right action for the wrong reasons.

His task was not to become certain about everything. It was to act with courage while much remained unresolved.

Negative Capability is not what we practise until action becomes possible. It is what allows us to act without pretending that every contradiction has been solved.

But we should be careful not to let uncertainty become an alibi. There is a point at which staying with the question becomes hiding inside it. We can spend years “exploring” because choosing one path would close another. We can call ourselves patient when we are frightened, curious when we are avoiding commitment, open when we simply do not want to be judged by an outcome.

I know this because I have done it. The opposite mistake is to force clarity because ambiguity feels unbearable. We announce a new identity, launch the business, leave the job or construct a five-year plan. The decision may create relief, but relief is not always truth.

The real challenge is neither endless waiting nor reckless certainty. It is participation without guarantees.

Participation without guarantees does not mean proceeding without focus. If anything, Negative Capability requires a deeper kind of focus: not attachment to a particular outcome, but fidelity to a question that feels peculiarly our own.

Lincoln’s study was not preparation for a destiny he could already see. But it was not random either. He possessed an unusual need to understand things, to reason clearly and to make himself worthy of the esteem he desired. Law, Euclid, Shakespeare and politics gave that need somewhere to go.

To his peers, studying geometry late into the night may have looked like a curiosity. It offered no obvious advancement. Yet Lincoln was following something in himself before he could know what use it would eventually have.

Perhaps this is what gives Negative Capability its direction. We do not need to know where the work will lead, but we need some reason to remain with this work rather than the thousand other things we might do.

The reason is rarely a complete vision. It may begin as a question that refuses to leave us alone, a subject to which we keep returning, or a kind of difficulty we are strangely willing to endure. It may appear in different jobs and projects before we recognise the thread connecting them.

The focus is personal, but it is not exempt from reality. We still need to ask whether the work is deepening our capacities, becoming more particular and creating some response beyond ourselves. Otherwise, what we call fidelity may simply be repetition.

Negative Capability asks us to hold two things together: commitment to the question and openness about the answer. Too little commitment and we drift. Too little openness and we force the question into the first available form.

You cannot live on mystery alone. There are bills to pay, groceries to buy and people who depend on us. Uncertainty sounds romantic when you have enough money to absorb it. When you are living on precarious income, caring for someone or waiting on a diagnosis, uncertainty can be paralysing.

A meaningful life needs a stable floor: work that keeps the lights on, routines that hold us together, promises we intend to keep.

But it also needs an open ceiling: some part of life that has not yet been reduced to a title, target or business model. A question we are still living. A project whose value cannot yet be demonstrated. Work that may become important, or may simply change the person doing it.

For me, DBN has existed somewhere between the two. I have written essays, hosted conversations, recorded a podcast and begun running workshops. I believe there is something here. I also cannot honestly say what it will become or whether it will ever provide the autonomy I want from it.

Perhaps I have been asking DBN to answer two different questions.

Is this work worth doing?

And can it become the source of income and independence I want it to be?

The first question has begun to answer me. The writing has changed me. Readers have responded. Conversations, workshops and unexpected relationships have grown from it. There is enough reality there to keep going.

The second question remains unanswered. Meaning is a tough business model to crack, and personal transformation does not pay the rent. DBN may deserve a place in my life without yet having earned the right to carry the whole of it.

There are days when continuing feels like Negative Capability: remaining faithful to work whose final shape I cannot see. There are other days when I wonder whether uncertainty has become too flattering a description. Perhaps I am not patiently allowing the work to emerge. Perhaps I am postponing the harder act of choosing what it must become and accepting what that choice might cost.

I do not yet know.

That is not the conclusion I would prefer, but it is the honest one. Negative Capability does not promise that an answer will arrive. It does not mean that every period of confusion contains a hidden destiny. Some experiments fail. Some questions remain unanswered. Some paths only become clear after we have chosen another and lost the chance to take them.

It asks something more difficult than optimism. It asks us to remain open to reality while still participating in it. To notice what answers back. To resist both premature certainty and indefinite delay. To make the next honest move without demanding that the whole path be revealed.

Lincoln did not know what history would make of him. He prepared, chose and acted inside conditions he could never fully control.

Perhaps that is as close to clarity as most of us get.

A quick note before you go.

I’m running the next Finding Meaning in Work workshop on Saturday 29 August.

I’ve run this workshop a few times this year, and each time I’ve been struck by how useful it has been for the people in the room to have a few hours, thoughtful prompts, and the space to think honestly about work, identity, direction, and what their life is in service of.

This session is for people who are doing fine on paper, but know something in their work needs proper attention. Maybe the work is going well enough, but no longer feels fully yours. Maybe you’ve become good at something without stopping to ask whether you still want it. Maybe Sunday night keeps telling you something your calendar keeps drowning out.

That’s what the workshop is for.

You’ll leave with a workbook, a personal manifesto, and clearer language for what has been sitting in the background.

When: Saturday 29th August, 11am–3pm

Where: Sanders Place, Richmond

Lunch: included

If this feels timely, reply with “workshop” and a line or two about where you’re at with work right now.

And if someone came to mind while reading this, feel free to send it their way. The simplest way to describe it is: a reflective workshop for people who are doing fine on paper, but feel something in their working life needs closer attention.

If you’re unsure whether it’s a fit, reply with a line about where you’re at with work right now and I’ll tell you honestly.

If you’d like to join, you can book below. Use DBN2026 at checkout..