Questions, questions, questions. Labour meets on the Mersey riviera under a cloud of questions. Shadow cabinet member Liam Byrne is on the billing for an event entitled: "How does Labour win back the middle?" His frontbench colleague Peter Hain will be chairing a session asking: "Are progressive alliances the key to Labour's future?" Another really good question will be discussed by two more shadow cabinet members, Douglas Alexander and Sadiq Khan. Their event is called: "Can Labour win in 2015?"

That they are debating this in the form of a question indicates that members of Labour's senior team are not terribly confident that the answer is a resounding yes. I remark on this not to mock them. It shows that there are some Labour people who do appreciate the scale of the challenge.

Many of their party still can't bear to face the facts. It is simply too painful for them to contemplate just what a disaster they suffered at the last election. Gordon Brown took Labour to its second-worst defeat since 1918, only just failing to beat the record set by Michael Foot in the "suicide note" election of 1983. It was especially bad in the south of England where, outside of London, Labour has just 10 MPs out of 212. That low base for recovery will be further depressed if the boundary changes, which hurt Labour most, go through. There is the additional threat that the rampant Nationalists in Scotland will translate their success at hammering Labour in Holyrood elections to beating them in Westminster seats as well.

Mr Alexander has made a contribution to The Purple Book, a collection of essays by Labour thinkers and politicians. The shadow foreign secretary notes: "Few parties ever manage to come away from a bad defeat, look hard at their record, and come up with something new and inspiring in a matter of four or five years. That is the scale of the task before the Labour party today."

And it is a challenge that has repeatedly crushed the party in the past. After the 1931 defeat, it was nine years before Labour ministers were back in the cabinet room and it took Hitler and the formation of a wartime coalition to get them there. They had to wait 14 years, to 1945, before there was another Labour prime minister. After the party's defeat in 1951, it was 13 long years before Labour returned to office. After being booted out in 1979, Labour didn't see office again for 18 even longer years. It has been an almost iron rule that Labour spends more than one term in opposition. The exception is Harold Wilson's return to power in 1974 after just three-and-a-half years of Ted Heath. Labour won, but without a Commons majority and having polled fewer votes than the Conservatives. That is not a terribly encouraging precedent either.

Whether Ed Miliband's Labour can break this historical pattern depends on finding the right answers to some other questions that the party ought to be asking itself in Liverpool. A very big one is: how do we regain credibility on the economy? Markets are convulsing, unemployment is rising and the International Monetary Fund has downgraded its forecast for British growth and advised flexibility on the coalition's austerity programme.

Labour is bound to claim vindication for its view that the government is cutting too far, too fast. It is easy to think that, if Britain slides into another recession, the next election ought to be Labour's to lose. Easy and also highly risky. Labour would be rash to work on the basis that economic woe is in itself enough to guarantee that the pendulum of power will swing back. "We would make a profound error if we assumed that," says one member of the shadow cabinet.

The coalition's economic judgment is being daily tested by events, but voters continue to place more of the blame for the pain on the last government than they do on the current one. There are some disturbing warnings for Labour in a pamphlet published by Policy Network and written by Patrick Diamond, a former adviser to Gordon Brown, and the Labour peer, Giles Radice. Drawing on polling and qualitative research, they conclude that Labour is failing to connect with disillusioned voters. "This mood of disengagement is especially bad for Labour, since parties of the centre-left depend on creating a climate of hope and optimism about the future. If voters come to believe that little can be done by governments, then the main beneficiary is likely to be the Conservative party, whatever their record in office."

In the interview with Ed Miliband which we publish elsewhere in today's Observer, the Labour leader concedes that "we've got further to go" on the "big job" of persuading people that Labour can be trusted again with the nation's finances.

That is enmeshed with another question which goes to Labour's very soul: what is the social democratic offer when there is no money? Protracted austerity will require even more rigorous thinking from Labour about how it reimagines the party's purpose in straitened times. Voters are going to be deeply sceptical of anyone who promises to create a New Jerusalem, especially if there is any suggestion that the building work is going to be paid for on a credit card. In his interview with us, Mr Miliband makes a spending pledge by announcing that a Labour government would cut the top level of tuition fees from £9,000 to £6,000. That would be paid for, he says, from a mixture of increased contributions from higher earning graduates and taxes on the financial sector.

That sounds good, it generates a nice headline for the opening of his conference, and it places him on the side of students against greedy bankers. But however tough you are on bankers – I'm all for some of that – you can't spend taxes on the City more than once. The question remains: what is the purpose of Labour government when there's no cash?

Mr Miliband's answer to all these questions is that we are now on "fresh terrain" in which historical precedents do not apply and "old debates" about how Labour should position itself have become irrelevant. Why he thinks that is explained by an essay in the latest issue of the New Statesman by Stewart Wood, one of the Labour leader's most senior advisers. He writes: "Britain in 2011 is witnessing the death throes of the neoliberal ideology that has dominated Britain for more than 30 years." When I quoted this to Mr Miliband, he replied that he was going to say something very similar in his conference speech, "but in slightly more comprehensible language maybe. The neoliberal death throes is not going to be in my speech, I promise you".

He believes that the latest crisis of capitalism has shattered the economic settlement established by Margaret Thatcher and largely continued under Tony Blair and Gordon Brown. The idea is that the reckless irresponsibility of some at the top of society has opened space for Labour to pull the country leftwards. Of course, he doesn't put it quite like that. He insists it is not a shift to the left, preferring to say he is establishing "a radical, new centre-ground". But it is clear that this is to the left of where Mr Blair and Mr Brown believed the centre-ground to be.

The Labour leader is not wrong to think that voters are scared by economic insecurity and resentful of those who brought it about. The big, big problem for Labour is that fear and loathing of what unrestrained markets can do hasn't made voters any more enamoured of the state. It is quite possible to hold both thoughts in your head at the same time: over-mighty markets can't be trusted and neither can over-weening governments. Polling commissioned by the thinktank Demos in the immediate aftermath of the last election found that more than one in four of voters who abandoned Labour saw government as "part of the problem, not the solution".

Many on the left initially assumed that the financial meltdown of 2008 had to work to their political benefit; it just had to be good for the left, its ideas and values because of the monumental scale of the market failure. Yet that crisis has since mutated into another crisis about national debts and the incapacity of governments. Political deadlock in both the United States and Europe is not doing anything to restore public faith in the state. In most democracies, the economic emergency has not created a "leftwing moment". The recent return to power of social democrats in Denmark is a rare exception. The more common experience of centre-left parties – from Germany and Holland to Sweden, Finland and Portugal – is defeat.

So those of his critics who describe Ed Miliband as timid, unimaginative or directionless are not correct. The Labour leader does have a strategy and it is really rather breathtaking in the boldness with which it challenges both conventional wisdom and historical experience. Successfully moving Britain to the left, doing so from opposition at a time of austerity and pulling it off in just one term would be in defiance of both Labour's past record and the contemporary experience in other European democracies. Whatever you think of Ed Miliband's strategy, absolutely the wrong word for it is cautious.