However, this isn’t always possible. For instance, you may have a $150 digital music player and want a small refrigerator worth $100. In this case, if both parties are certain of what they want and understand the difference in value, there should be no barterer’s remorse. Alternatively, you can ask for the mini-fridge plus $50 to make the trade – the worst anyone can say is “no.”
Although, as a general case, a ship unlucky in falling in with whales continues to cruise after them until she has barely sufficient provisions remaining to take her home, turning round then quietly and making the best of her way to her friends, yet there are instances when even this natural obstacle to the further prosecution of the voyage is overcome by headstrong captains, who, bartering the fruits of their hard-earned toils for a new supply of provisions in some of the ports of Chili or Peru, begin the voyage afresh with unabated zeal and perseverance.

When barter has appeared, it wasn’t as part of a purely barter economy, and money didn’t emerge from it—rather, it emerged from money. After Rome fell, for instance, Europeans used barter as a substitute for the Roman currency people had gotten used to. “In most of the cases we know about, [barter] takes place between people who are familiar with the use of money, but for one reason or another, don’t have a lot of it around,” explains David Graeber, an anthropology professor at the London School of Economics.

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Economic historian Karl Polanyi has argued that where barter is widespread, and cash supplies limited, barter is aided by the use of credit, brokerage, and money as a unit of account (i.e. used to price items). All of these strategies are found in ancient economies including Ptolemaic Egypt. They are also the basis for more recent barter exchange systems.[15]
Whitmer of Florida Barter says that limited and strategic bartering is best. “We’re not going to help anybody pay their electric bill or their mortgage,” he says. “But we can help them maintain their business and get sales they never would’ve had otherwise.” The best barters, he says, are for things you might normally have spent cash on anyway, “like printing, advertising, marketing, or promotional T-shirts with your logo on it.”
Bartering is based on a simple concept: Two individuals negotiate to determine the relative value of their goods and services and offer them to one another in an even exchange. It is the oldest form of commerce, dating back to at time before hard currency even existed. (Learn more about how bartering evolved, read The History of Money: From Barter To Banknotes.)

In the United States, Karl Hess used bartering to make it harder for the IRS to seize his wages and as a form of tax resistance. Hess explained how he turned to barter in an op-ed for The New York Times in 1975.[31] However the IRS now requires barter exchanges to be reported as per the Tax Equity and Fiscal Responsibility Act of 1982. Barter exchanges are considered taxable revenue by the IRS and must be reported on a 1099-B form. According to the IRS, "The fair market value of goods and services exchanged must be included in the income of both parties."[32]
As Orlove noted, barter may occur in commercial economies, usually during periods of monetary crisis. During such a crisis, currency may be in short supply, or highly devalued through hyperinflation. In such cases, money ceases to be the universal medium of exchange or standard of value. Money may be in such short supply that it becomes an item of barter itself rather than the means of exchange. Barter may also occur when people cannot afford to keep money (as when hyperinflation quickly devalues it).[14] 

It’s no scam, but it can be complicated to the uninitiated. As Lombardi explains, “We run like a little bank.” Members are paid in “barter dollars,” which they can exchange with other members for goods and services. Within the bartering community, it’s the only acceptable currency. “It’s like going to a barter mall,” Lombardi says. “They can do all their holiday shopping. They can get the carpets cleaned. They can pay for their child’s orthodontic work. It’s almost limitless.”
Anthropologists have argued, in contrast, "that when something resembling barter does occur in stateless societies it is almost always between strangers."[6] Barter occurred between strangers, not fellow villagers, and hence cannot be used to naturalistically explain the origin of money without the state. Since most people engaged in trade knew each other, exchange was fostered through the extension of credit.[7][8] Marcel Mauss, author of 'The Gift', argued that the first economic contracts were to not act in one's economic self-interest, and that before money, exchange was fostered through the processes of reciprocity and redistribution, not barter.[9] Everyday exchange relations in such societies are characterized by generalized reciprocity, or a non-calculative familial "communism" where each takes according to their needs, and gives as they have.[10]
Throughout the 18th century, retailers began to abandon the prevailing system of bartering. Retailers operating out of the Palais complex in Paris, France were among the first in Europe to abandon the bartering, and adopt fixed-prices thereby sparing their clientele the hassle of bartering. The Palais retailers stocked luxury goods that appealed to the wealthy elite and upper middle classes. Stores were fitted with long glass exterior windows which allowed the emerging middle-classes to window shop and indulge in fantasies, even when they may not have been able to afford the high retail prices. Thus, the Palais-Royal became one of the first examples of a new style of shopping arcade, which adopted the trappings of a sophisticated, modern shopping complex and also changed pricing structures, for both the aristocracy and the middle classes.[18]