I've read that they managed to convert a significant chunk of Ukraine into a mostly-anarchic society for a couple years, but I can't seem to find much information about whether or not it actually worked very well there, compared to the systems it replaced and then was in turn replaced by.
After the October Revolution Nestor Makhno and his Black Army organized around 400 square miles in Ukraine with an approximate population of seven million into an autonomous “anarchist” region. Makhno served mostly as a military leader, and the governance of the peasant communes and the free-work soviets that formed during this period was left in the hands of local elected leaders. This collective of communes and soviets existed from 1918 to 1921 before Makhno was defeated and the area was taken over by the Bolsheviks.
By “effective” I’m going to assume you are asking about the quality of life and the standard of living in the region. I can’t necessarily give an exact answer for the entirety of the region, as by the nature of anarchism each commune or soviet was allowed to make its own policy decisions. But, for the most part life improved under the protection of Makhno. Freedoms of assembly, speech, and press were declared and each commune was allowed to work as much land as it could manage, sharing the fruits of their labor amongst themselves without any obligations to pay tax or to give money or goods to any landowner or government authority. Courts were abolished and prisoners were set free, with all matters of law and order delegated to local communities instead of an organized police force. Makhno was able to broker a trade agreement between his communes and factories occupied by anarchist workers in Moscow, allowing for an influx of textiles and other materials.
The communes were not created on the basis of example or caprice, but exclusively on the basis of the vital needs of peasants who had possessed nothing before the revolution and who, after their victory, set about organizing their economic life on a communal basis. These were not at all the artificial communes of the Communist Party, in which people assembled by chance worked together -- people who only wasted the grain and damaged the soil, who enjoyed the support of the State and thus lived from the labor of those whom they pretended to teach how to work. These were real working communes of peasants who, themselves accustomed to work, valued work in themselves and in others. The peasants worked in these communes first of all to provide their daily bread. In addition, each found there whatever moral and material support he needed. The principles of brotherhood and equality permeated the communes. Everyone -- men, women and children -- worked according to his or her abilities. Organizational work was assigned to one or two comrades who, after finishing it, took up the remaining tasks together with the other members of the commune.
This is a quote from Peter Arshinov's History of the Makhnovist Movement and it shows a basic description of what life was like on the communes and how they were organized. This also shows a quick comparison to life before the revolution and to the kind of communes organized by the Bolsheviks.
Three regional congresses were held in the territory wherein delegates from the towns and communes made decisions about the military and economic concerns of the region. A fourth was scheduled but had been banned by Bolshevik authorities in Russia. These congresses allowed the people to have a voice in the government, which wasn’t allowed under the tsarists and wouldn’t be allowed to such a degree under the communists. Schools were created in many areas that promoted not only education of children but also education of adults. Classes on history, sociology, and politics were held, as well as classes that taught illiterate adults how to read and write. Makhno also was a proponent of religious freedoms, working hard to curb anti-semitism among the peasants and recruiting Jews and other minorities into his army.
An important thing to note is that during the entirety of this period Ukraine was at war. Makhno and his partisan army fought against the Germans, Austrians, Monarchist Russians, Communist Russians, and groups of Ukrainian Nationalists. Life was improving for many of the working class Ukrainians, but they did have to face wartime conditions and by the end of the period Makhno resorted to conscription to bolster the size of his army. It fell to the people of the region to support the Black Army with both supplies and bodies, which would have placed a strain on both supplies and the workforce. Makhno is said to have relied only on voluntary support for most of the conflict, choosing not to take food or other supplies by force as would have been the norm in other armies.
The Makhnovshchina originated in the stormy era of contemporary Ukrainian life in the summer of 1918, when the entire peasantry thundered in revolt. From the first days of its existence until its very last moments, it did not have a single day of peace.
This is another quote from Arshinov's History of the Makhnovist Movement.
‘We were treated like cattle before,’ said a flaxen-haired peasant with blue eyes, ‘and it was in the name of the Little Father. Now they speak to us in the name of the Party and the proletariat, but we are treated like cattle, the same as before.'
‘Lenin is a good man,’ one of the peasants put in.
‘We say nothing against him,’ another remarked, ‘but his Commisars, they are hard and cruel’…
‘But the Bolsheveki gave you the land,’ I remonstrated.
He slowly scratched his head and a sly smile came into his eyes. ‘No, golubtchik,’ he replied ‘the land we took ourselves.’
This is a quote from Alexander Berkman’s Life of an Anarchist, and it shows a discussion between Berkman and some peasants on the Latvian border. This is obviously a different region and different people, but it shows what the peasant class thought of life under the Bolsheviks and highlights how these people may have already had some anarchist inclinations even without the guidance of men like Nestor Makhno.
Further Reading:
Peter Marshall, Demanding the Impossible, 2010
Peter Arshinov, History of the Makhnovist Movement, 1923
Andrew Berkman, Life of an Anarchist, 1992