I can’t speak about the immigrant experience in general, but I do know of a specific example of this kind of situation: Major General John Stark who was an instrumental but lesser-known figure of the American Revolution. If you’re not familiar with Stark, he was involved in several battles including Bunker Hill, Trenton, and Princeton, but he is best known for his moniker as the Hero of Bennington for his victory in Vermont in 1777. Shortly after, he was involved in stopping the British retreat at Saratoga. He coined the New Hampshire state motto, “Live free or die.”

John was the first generation of his family to be born in America. His father Archibald was born in Glasgow in 1697 and later attended university there. Archibald moved to Londonderry, Ireland where he met his wife, Eleanor Nichols, and they had two or three children. Life there was difficult due to the political unrest between the native Irish and the incoming Scots. As a result, the Ulster Scots began emigrating to America in droves, trying to find a place to finally call home. Around 1720 or so, Archibald and Eleanor boarded a ship with a group of settlers who intended to settle a land grant in southern New Hampshire. It was a hard journey in late fall. An outbreak of smallpox killed all the Stark children, and then the ship was turned away from port in Boston as a quarantine measure. The passengers were forced to winter on the coast of Maine in rudimentary huts. As you can imagine, a Maine winter with no shelter is a bad time. So, in essence, you have a family that couldn’t make a life in Scotland, couldn’t make a life in Ireland, and the gamble on the New World cost them everything.

In the spring, the group finally made it to their grant and established the town of Londonderry, New Hampshire in honor of where they came from. Archibald and Eleanor built a subsistence farm, and they made turpentine as a side business. As they got settled in, they had several children. General John Stark was born in 1728 during this time of calm. Archibald started to acquire some land in the surrounding towns, had growing financial success, and things were looking up. That is until the house burned to the ground in 1736.

Instead of rebuilding, the family moved a few miles north to Amoskeag, a large waterfall in what is now Manchester, New Hampshire. The area had not yet been established as a town, so Archibald saw an opportunity to plant a flag and started a 1,000-acre farm near the falls hoping to gain some fishing rights. At the time, this area was the extreme edge of European occupation and there was constant fear of attacks by Native groups still living to the west and north. It was considered the “back woods” and the people that lived there were often looked down upon by people in the larger towns that had started to acquire “culture.” They were essentially the rednecks of the 18th century.

So young John Stark is raised in this “primitive” environment where there are only 50-100 people nearby and the nearest city of any distinction is several days journey away. The family was wealthy by local standards, but it was a middling existence compared to John’s contemporaries like Washington and Jefferson. John learned to hunt, and fish, and read the land. He learned how to work the farm and run his father’s sawmill. He befriended local Indian groups that still came to Amoskeag to fish and learned about their culture (There was that one time he got kidnapped…but that’s another story). These skills are what eventually drew him to the military, first as a scout and later as a commander himself. It was a radically different childhood than his father had being raised in Glasgow, which was a larger city than anywhere in New Hampshire. This didn’t seem to bother John’s father. In fact, he encouraged John’s strengths and supported his military career. He did lament one thing though: He resented that his children, being raised in the woods, would not have a quality education like he did. Archibald and Eleanor did everything they could to teach the children themselves. John could read, and write, and do math just fine, but his lack of formal schooling made him insecure for the rest of his life.

As John moved up the ranks, he also moved up in social status. He started to interact with people who sat far above him in both wealth and clout. He even spent a private day with George Washington himself where they simply…talked and rested. Oh, to have been a fly on the wall then! John had many abilities, but unfortunately social skills were not among them. He was often described as brusque, brash, and stone faced. He also wasn’t so great at following orders. He just couldn’t overcome his inner redneck. This, combined with his insecurities about his education, made him quite bad at the game of politics, and it’s probably the reason that he never held a major office after the war. Instead, he went back to his farm where he spent the rest of his days. He died in 1822 and is still buried on the family farm in a park that bears his name.

So, in summation, the Starks didn’t have much of a choice where they settled, but they absolutely made the most of it. There is no indication that either of John’s parents resented the hardship they endured, and they never indicated a desire to return to Europe. John, for his part as a first generation American (heck, he was a straight up founding member!), seemed to appreciate the life his parents carved out for him. It was still difficult and there were things John would change if he could. But ultimately, the insecurities he had were not related to his immigrant status so much as his social and economic status. He never showed anything but devotion to his parents, and the fact that he continued to maintain the family farm when he had the means to do pretty much whatever he wanted suggests to me that he was happy with the life they gave him.

Humans are really adaptable. It’s the thing that drives us to greatness. And I think you had it right at the beginning – It doesn’t really matter what experience you have, or where you were raised, or how extreme the circumstances. All you can do is build the best life you can with what you have and try to make it a little bit better for your kids. Seems like John Stark had it right when he said “Live free or die. Death is not the worst of evils.”

All of this is covered in John’s biography written by his son, Caleb Stark, which includes lots of great reproductions of letters that let you really get into John’s mindset during the war. It is also covered in “John Stark of Roger’s Rangers” by Howard Parker Moore which is a more modern history that examines several facets of the Generals life beyond just his military career.

I think in any migration where it's difficult for the next generation to reverse-migrate (because of expense, because of possible persecution or risk at their point of origin, because of legal barriers to reverse migration) there is not a lot of highly vocal resentment from the next generation because there's no point to complaining. It also depends very much on whether the next generation is born in their new home (or arrives so young that they have no memory of their former home) or whether they are old enough to have fully formed memories of their former home.

I think it's only in the latter case that you tend to see some possibility of specific bitterness between one generation and the next about the decision to migrate, but even there it's a quite particular circumstance that depends among other things on the history of family structure and ideas about adulthood. A significant amount of premodern and early modern migration in world history (when it was ostensibly voluntary on some level) didn't even involve the whole of a family--children were often left behind, sometimes spouses, until a head of household was established, at which point it was often possible to leave the decision of whether to come or stay up to children who had reached an age close enough to adulthood or majority status that they could make that decision. Our expectations today that migrations should or usually do involve entire nuclear families travelling together as a unit still don't describe a lot of the circumstances where people are moving, with various degrees of duress, from one nation or place to another.

Migrations also do reverse more often than we might think today, even in the early modern or premodern world. Americans particularly have a hard time grasping this point because so much of the mythology of voluntary migration to the US is that it was a one-time movement from Europe to North America, but in fact many of the major flows of migration from Europe to the US in the 19th and early 20th Century were circuits, with members of families (including the original heads of household) returning to their point of origin for a while or for good after spending some time in the U.S., with some notable exceptions. (European Jews and 19th C. immigrants from Ireland tended not to return, for example.) That's a sort of 'steam valve' that bleeds off resentment from the next generation if and when things aren't working out in their new home, because they may in fact have opportunities to return if they want.

When I think about the historical context I know best--southern Africa from about 1750-present--I'm hard-pressed to think of examples of the children of migrants complaining specifically about their parents' decision to migrate even when they are unhappy about some aspect of their present circumstances. I'm thinking here both about white settlers (say, for example, English-speaking whites who started arriving from Great Britain after 1820, first in the Eastern Cape, Cape Town and Natal, then after 1890 in the colonies controlled by the British South Africa Company, e.g. Northern and Southern Rhodesia and Nyasaland) and African migrants who moved within the region, typically to pursue labor opportunities in or near cities.

Part of this may be a consequence of what makes it into archives. The migrants whose personal and family papers or records end up available to us as researchers tend to be people who had some measure of success in their new home, and therefore their children often had no strong reason to resent the decision to leave. If you end up wealthier or better off or with more possibilities as a result of the migration--especially if you end up aware that you are better off because you have returned as a visitor to your parents' original community and seen for yourself that life is no better there--then the decision to move isn't something you question. If you're an adult by the time you're even thinking about the question of whether it was a good idea, you're often attached to the place you've grown up in. Many English-speaking younger white adults in the era of apartheid or in the waning years of colonialism elsewhere in the region found themselves profoundly opposed to the maintenance of white supremacy, but even those opponents rarely cursed parents or grandparents for having come in the first place if the migration had been that recent. Whites who left were as prone to go somewhere else in the Commonwealth than where they came from, often to places that (sort of) reminded them of southern Africa, just without a small white minority trying to cling to power.

The same was true for Africans who grew up in households established after parents had relocated from one part of the region to another. Even if life was a struggle where they grew up, it was just as likely a struggle, possibly a worse one, where they came from, and they might in fact end up directly witnessing that at some point by travelling back to visit family who remained there. You might be bitter about your life and life circumstances, and bitter about the way that white-dominated governments controlled land rights and migration, but most people tended to see their parents' agency as relatively irrelevant to the circumstances producing bitter feelings.

I think the thing to remember is that migration in world history is relatively uncommon among people who are powerful, wealthy, secure and successful where they are; hence, when migrants and their children find themselves in a bad situation in their new location, they are often not looking back on a former location where everything was comparatively far better. When later generations speak of regret or anger at the decision to leave, it is often two to three generations removed from the migration itself, where these views are often about trying to create solidarity between members of a group who may feel isolated, marginalized or ill-treated where they are and who are using somewhat romanticized or idealized invocations of a former homeland to strengthen that sense of connection. (This is an even more potent sensation when the migration was completely involuntary, as it ought to be, but then the resentment is especially not directed at the ancestors who migrated but at those who were involved in forcing them to move.)

You might find it's interesting to read "Uttermost part of the world" by Lucas Bridges. https://www.vayaadventures.com/blog/uttermost-part-of-the-earth-the-classic-book-on-tierra-del-fuego/ He was born and raised in the Tierra del Fuego, by the firat western family who settled there, among the indigenous Yamani and Ona people. Life was extremely hard, but also fulfilling... Bridges wrote it as an old man, and expressed no regrets (except for the plight of the indigenous people). It is a great book.