We are entitled to absolutely nothing. There are no privileges that come with birth and none that accompany us as we grow older. As adults, it’s unreasonable for us to expect that life will yield certain rights or powers to us.

Nevertheless, most of us, especially those of us who grew up in relatively financially well-off countries, and especially those of us who received the good fortune of a secular education, feel like we ought to be reaping some sort of goodies. We’ve been taught, innocently, or not, that with geography, or with effort, and certainly with both, comes payoff. 
The truth is somewhat different. Nothing is guaranteed. Not health. Not wealth. Not relationships. Not winsomeness. Nothing.
Most of us fail to grasp reality and whine, or worse, when we don’t get what we allege is our due. Sometimes great loss, as made manifest in the death of dear ones, as made manifest in our own dire illness or injury, as made manifest in financial distress, etc., wakes us up to a higher level of living, alerts us that we need to dwell in gratitude, not in expectation. Other times, no matter the nature and kind of the challenges we experience, we continue to be adamant about our deservedness.
Such insistence on dispensation leads to hurt, to anger, to resentment and to much poorer behaviors. Families and businesses get destroyed, neighborhoods come to odds, entire nations engage in conflict. All of this animosity occurs because someone, somewhere, is upset that his or her lot is not what he or she projected. These actions are absolutely antithetical to what The Boss wants from us, namely to live together in peace.
Said differently, a “good life” is not a benefit that necessarily follows from making good choices. Whereas, we might rationalize away our supposed dearths, and claim, accordingly, that “it’s better to receive reward in the infinite world to come, than in this finite, present world,” deep down, if we are honest with ourselves, many of us fume when our “needs” and wants go unmet. What’s more we “bargain” to try to “win back” some of our estimated “prizes.” In the least, such attempts are pathetic. More terrible, they are damaging to us and to the folks with whom we interact.
For example, I’ve “negotiated’ rather than accepted. I didn’t expect to continue on as a full-time rhetoric professor after making aliyah because such a role requires a command of highly abstract language and I was only at the aleph level of ulpan when we moved up. Nonetheless, I had looked forward to a part-time post or to some other socially recognized remuneration for all of my years of studies and for all of my years of scholarship and pedagogy.
Similarly, after I injured multiple discs in my back and ripped the meniscus in one of my knees, I imagined I would “made due” with swimming even after having to discontinue my routine of biking and of weight lifting. I supposed exercise would remain central to my life.
What’s more, and most horrible of all, when things went amiss in certain of my most special relationships, I blamed the other persons involved. It never occurred to me that I might be partially, let alone entirely, culpable for the ills in those connections.
To say I missed the mark is an understatement. A better choice, in each of those instances, would have been to focus on gratitude. I was able to: move to Israel, remain alive, and stay in my relationships. Sadly, at the time, I groused instead of glorified.
There’s more. I’m a Baalat Teshuva who has long bemoaned not having been born into a frum family. That thought, if nothing else, makes me an ingrate. I have no right to presuppose that I know how to run the universe better than does Hashem. The Boss wanted me to walk the particular path of my life on which I found myself.
A corollary to the aforementioned misplaced principle of mine is the wrong notion I had that my kids, having grown up frum, would grasp Torah life more readily than did I. In that case, too I anticipated my misinformed idea that I could control the lives of even a few people. My sons and daughters grew up, b’ayin tova, to be morally focused people. Some of them grew to the same level of observance as did I, some grew to a greater level, and some grew to a lesser level. I’d be a misguided to claim that their value to me, to The Almighty, or to themselves, is measured by how many humrahs, personal stringencies, any of them keeps. 
Additionally, in another, more universally identifiable domain, I had been wearing “self-appointed prerogative’s” opaque glasses. One doesn’t have to have narcissistic personality disorder to make such mistakes. More exactingly, I had expected that existent residents of the State of Israel would be delighted that my family came to help fill the ranks. 
In reality, every person dwelling here is of equal value. All of us are tested and many of us become vehicles for each others’ tests. To wit, my kin encountered much anti-Anglo hostility, in general, and many attempts to use us as fryers/suckers, specifically. Beyond the airport welcome hosted by Nefesh b’Nefesh, there were no bands, carpets, or collective fests (friends extending warmth excepted) of any sort to greet us, and, in hindsight, there ought not to have been. 
I think one reason people fail to get beyond assumptions about “warranted” advantages is because we use empirical evidence to build our hopes. Consider that the yetza hara has many agents, the least of which is contemporary science (e.g. often families have allowed themselves to become discouraged because some medical expert sited statistics or because some school administrator pointed to test scores). Yet, much quantifiable data is faulty and most “proven” facts are subject to an array of interpretation.
Even if science was omniscient, and even if “everybody else” enjoyed a certain facet of life, those verities would not ensure any of us getting similar opportunities for anything. The weevil in the flour is the conviction that because something makes causal sense, something else necessarily follows. Empirical evidence is as naught in the face of our Creator’s plans.
Let’s flip it around. EVERYTHING is a gift. The sooner we embrace that concept, the sooner our lives become joyful.
Again, in borrowing from my life, b’ayin tova, I adore my children. It’s also true that I had gestation problems after the birth of my youngest. The multiple hemorrhages I suffered, following the multiple pregnancies I lost, caused both my rabbanim and my doctors to forbid me from further increasing my family. No matter my pain, it was never mine to say that I was more worthy of my kids than was the lady down the street who struggled to have two, or than was the lady on the next block who made great efforts and had none.  
As well, b’ayin tova, I’m the author of multiple books. Each text was a process of development and of “birth.” Yet, honesty espouses that my writings are no more needed that are the writings of other individuals with similar ideas and that my writings are no better than are the writings of authors with similar skills.
Then there is the fact of living in Eretz Yisrael. In my family’s set of circumstances, it was revealed that some unnatural tweaking took place. Both the relationship among the events that brought us to The Holy Land and the transparency of those relationships were gifts not to be taken for granted. We are Blessed twice over to be here.
My list of gratitudes could and should go on. The point is not what I feel I ought to have received or to have been spared from in life nor is the point my underdeveloped appreciation. 
The point is that all of our lives are not ours to determine and that any anger or resentment we feel for “regrets” is a waste of resources. It never did and never will matter if it’s “reasonable” to harbor expectations. Life is about Avodah Hashem and about doing our histadlut. No matter how much we protest to the contrary, life is NOT about entitlement.