George Washington was keenly aware of the psychological pressures of being in debt. He once advised a nephew on the subject:
There is no practice more dangerous than that of borrowing money…for when money can be had in this way, repayment is seldom thought of in time…Exertions to raise it by dint of industry ceases. It comes easy and is spent freely and many things indulged in that would never be thought of, if to be purchased by the sweat of the brow. In the mean time, the debt is accumulating like a snowball in rolling. 
These are prudent words; but as so often happens, they are easier to state than to practice. After his military service in the French and Indian War ended in the late 1750s, Washington married and took on the burdens of family and plantation life. But Virginia country squires in his era were often “land rich and cash poor,” as the saying goes; and the future president fretted continually about money despite owning a huge estate. His biographer, Ron Chernow, documents in fascinating detail Washington’s finances. He was no skinflint; he understood the importance of bearing, presentation, and charisma, and spared no expense in outfitting himself as he felt his circumstances required. He was ambitious, and knew that to advance he had to cultivate a certain level of appearance and poise.
As manufactured goods in the American colonies were not plentiful, Washington was obliged place orders with the firm of Robert Cary and Company in London. He and Martha Washington had an extensive account with this vendor, and bought all kinds of households goods from them, both routine and luxury. Washington even relied on them to manufacture clothing to his specifications; he had an oddly shaped body, with wide hips, thick legs, and a robust torso, and would provide London with detailed measurements of his limbs. In matters of his clothing, he never hesitated to make himself clear. As Chernow records, one letter to his vendor registers a very prickly tone:
I desire you to make me a pair of breeches of the same cloth as my former pair, but more accurately fitting. These breeches must be roomy in the seat, the buttons firmly sewn on…These breeches must be made exactly to these measurements, not to those which you imagine that they may stretch after a period of use. 
Yet Washington, like many of his fellows in the Virginia landed aristocracy, felt constantly put upon by his British creditors. He suspected them of shipping him substandard goods, of inflating their invoices, and of a general tone of condescension to him as a “colonial.” If to this we add the stresses of life as a planter—the constant variability of tobacco prices, the difficulty of managing an immense estate—we begin to understand the origin of Washington’s simmering grievances against London. The idea of cutting back his own expenses, of course, was not something he seems to have considered.
These resentments against the British were added to those that he already harbored from service as an army officer in the French and Indian War. Washington was an aggressive, capable commander who led by example and, although not exactly loved by his men, was deeply respected by them. As he saw it, however, the officers of the regular British army who were sent to America refused to adapt themselves to local conditions: they looked down on colonial officers, asked them to bear the brunt of the fighting, and wrongly believed that European military tactics could be effective in the forested American wilds where French and Indians flourished as guerrilla fighters. While he had once sought a career in the British army, by the war’s end a disillusioned Washington had had enough; he realized that there was no place for him as a colonial in the regular army. So did life experiences plant the seeds of future rebellion in the breast of this headstrong Virginia aristocrat.
But what strikes one about Washington was his incredible sense of composure, his bearing, and his mastery over his volcanic emotions. Contrary to what some believe, this was not a trait that came naturally to him; it was the result of iron discipline earned though many years of effort. Washington was, in fact, a man capable of both intense anger and tender solicitude; but he had learned from experience that it was better to keep these extremes of emotion in check. After some youthful indiscretions in his twenties, he learned how to say the right things in different social situations, and when to keep his mouth shut: these are not insignificant achievements.
I recently read an amusing anecdote that reminded me of Washington’s astute personality, his adroit way of extricating himself from difficult situations. I wonder, in fact, if he ever heard it himself, and whether he would have nodded in approval at hearing it. It appears in the Roman writer Macrobius (I.6.18). We should note first that in ancient Rome, there was a type of toga called the toga praetexta. This was a white toga with a purple stripe on its edges, and was worn by freeborn youths before they came of age, after which they would don the toga virilis. There was once a youth named Papirius, whose senator father would often bring him to the senate-chamber to hear the political debates. One of the rules of the senate was that if an issue was being discussed, and the members adjourned for the day, the senators were obliged to keep the subject matter of the debates confidential until the session resumed.
After one such senatorial session, Papirius was approached by his mother at home and was asked what the senate had been discussing that day. The boy tactfully but firmly replied that he could not reveal that information. As often happens with secrets, the more Papirius tried to deflect the matter, the more curious his mother became. Finally, he hit up on a clever way of extricating himself from the questioning: he told her the senate had been debating the question whether it would be in public interest to allow a man to take two wives, or to allow a wife to take two husbands. When Papirius’s mother heard this “news,” she became agitated, and spread the word to her friends; soon the grapevine of Roman matrons had broadcast the information all over the city.
The next day, a large group of woman congregated outside the Curia, demanding that they be allowed to marry two man, rather than the opposite. Of course, the senators were taken aback by this strange request, and could not understand how such a bizarre issue had arisen. The boy Papirius, who was present, then stood up and told the assembled senators how the rumor had started, and why he had done it. The senators roared with laughter, impressed both by the boy’s fidelity and by his agility in crafting the ruse. It was a custom in old Rome to grant a surname as a way of memorializing an important event or achievement; and as a token of their appreciation, they decided to confer on him the honorific surname Praetextatus. Whether the story is apocryphal does not concern me. What matters to me is that the anecdote reveals the kind of trustworthiness and, at times, the restrained sense of humor that Washington learned to develop as a young man; these are things that can only be learned through stumbling experience and painful errors. And for me, this is good enough.
 Id., p. 105.
Read more in Digest, the complete essays from 2016 to early 2020: