I’ll tell you a story now. The story of a generation that gets easily overlooked and technically isn’t even a generation at all. Why does it get snubbed? Because it’s a fortunate generation, a generation of great promise, ambitions and privilege. There’s a tendency not to think about people like that. Instinctively, we prefer to devote our attention to the disadvantaged and unlucky. The seemingly well-endowed don’t deserve consideration and pity because they possess the attributes commonly associated with well-being. If they dare complain, it provokes outrage and accusations of hypocrisy. Well, my story is exactly about those people. It’s not about the victims of globalization, the 58% unemployed Spanish youths, the homeless or other losers of society. They’re getting plenty of coverage already. This story is about those handed the very best opportunities for a successful career and a rich life. I call them “Generation HEDO” – a generation growing up with High Expectations but struggling with the Disappointing Outcomes of their biographies thus far.

The story is worth telling mainly for one reason: it hasn’t been told before. This may be due to the fact that people don’t identify with it and therefore don’t care. More importantly, though, the representatives of Generation HEDO aren’t very forthcoming regarding their predicament: the creeping realization that things didn’t turn out as planned; that expectations and hopes have been shattered along the way; that things are different now than they were just a few years ago and may never be the same again. The real predicament, however, is that these things can easily be rationalized yet it’s exceedingly difficult to act upon them. To a large extent, that’s the HEDOs’ fault. Partly because they’re caught up in a line of thinking that dies hard and, frankly, is hard to let go. And partly because of mundane practical considerations. But they’re not entirely responsible.

That all changed, of course, on one day in September of 2008. Despite the diverse backgrounds of the HEDOs, it was the watershed moment for their generation – enter DO (Disappointing Outcome) with a bang. At first, the onset of the financial crisis was just a shock, a surreal experience with an uncertain outcome. But after a while, as the slump wore on, it started to dawn on the HEDOs that this was no mere shock but a secular shift affecting the financial industry as a whole and, more importantly, their very own life prospects. It’s always easy to speak about a crisis in abstract terms. But for most HEDOs, being in the eye of the storm proved challenging. Many lost their jobs – but you can recover from that if you’re young, energetic and smart. What really pulled the rug from under their feet was the collapse of the worldview upon which their future plans were built. That worldview is a complex animal. It is a messy blend of naïve hopes and projections, institutional memory, entrenched behavioral patterns and classical conditioning. All in all, it is very hard to escape. In fact, escaping gets harder the longer you’re exposed to that worldview. So, just by virtue of their age, the HEDOs’ bosses inadvertently passed on this institutional memory (firmly footed in war stories of successes past) to them, reinforcing a sense of disconnect with reality.

The timing aspect is of the essence here. To illustrate its relevance, it’s worth turning to Howard Marks’ extremely intelligent observations on the topic in a recent memo to clients aptly titled “Getting Lucky”. In it, he analyzes the old commonplace of “being born at the right time and the right place”. Well, that commonplace isn’t so trivial after all. The pioneers of IT and personal comptuing – Bill Gates, Bill Joy, Steve Jobs – were all born in the mid-1950s. Had they been born ten years earlier, they couldn’t have honed their computer skills in school. Had they been born ten years later, they would have been way too late, period. The same goes for the pioneers of corporate law and the pop music business. As Marks points out: “The bottom line is simple: it’s great to be in the vanguard of a new development. Talent and hard work are essential, but there’s nothing like getting there early and being pushed ahead by the powerful trends in demographics and taste that follow.” In other words: success is determined to a large extent by luck and circumstances. And that sheds an interesting light on the concept of meritocracy. The inventor of the term himself, Michael Young, says this: “If meritocrats believe, as more and more of them are encouraged to, that their advancement comes from their own merits…they can be insufferably smug”.

Of course, the HEDOs were raised as perfect meritocrats. They were convinced that they could at least replicate the heydays of the booming 1990s and 2000s if not exceed them. And yes, that resulted in a certain smugness, at least in the eyes of lookers-on. Especially because money was the driver and the prize in most cases. But that’s irrelevant. Judging their motivations from some pseudo-ethical high horse is unhelpful when trying to explain what happened to the HEDOs. The answer is short: they simply missed the boat. They got the timing wrong, not by their own mistake but because they happened to be born in the wrong years and bet on the wrong horse. Sure, that assessment is easy to make in hindsight. But it doesn’t make it less true or change the facts.

The facts are these: the HEDOs have to come to terms with the widest gap between aspirations and reality of any generation. The ones before them continuously beat the odds of success and came out on top, way above what they could have hoped for. The HEDOs are the first generation having to admit defeat in that respect. They are experiencing the inevitable flipside of luck – the mentally discounted but statistically high probability that things turn out worse than expected despite their best efforts to the contrary. As one HEDO admits, “there’s been a cultural humility that’s come out of the financial crisis”. The disappointment is compounded by the fact that HEDOs are surrounded by and look up to people who did get lucky: in financial markets as in business, having five years more or less under your belt can make a huge difference. It all depends on the point at which you enter the cycle.

To be clear, I’m not suggesting that the HEDOs are doing so bad. Relative to their peers, they’re actually in a very comfortable situation. But that’s not who they benchmark themselves against. The bar set by their role models, their bosses and possibly their parents, all commingled into a tangled bunch of expectations, is much higher in fact. It’s not surprising that the inability to fully live up to these expectations is a sobering feeling. You can’t blame the HEDOs for clinging to pre-conceived notions of what could have been. Circumstances can undergo drastic change and obliterate carefully laid out plans and projects in a heartbeat. Adjusting your worldview to this changed reality takes much longer. It’s like the ballet dancer losing a leg or the tennis player breaking his wrists: a hugely disorienting experience. The HEDOs are exceptionally smart people with huge potential seeking to adjust to a new roadmap. That takes time. In order for them to succeed, two things need to be happen. Obviously, they have to learn to let go, even if they’re still clinging to some residual hope that things might turn around. On the other hand, the world must avoid schadenfreude. Just because HEDOs have a reputation of being cocky, it doesn’t mean they don’t deserve to reinvent themselves. Finger-pointing combined with malicious glee is an unproductive reflex. It is mostly motivated by envy rather than telling arguments. And trying to pigeonhole the HEDOs into some ideologically deluded categories of human nature does not do them justice. It’s immature and it’s stupid.

This is not where the story ends, however. It’s merely where it begins and will continue to be written in the years to come. It will be interesting to see what the HEDOs do with the cards they’ve been dealt. And if they’ll turn into a lost generation that can’t stop chasing pipe dreams, unable to adjust to the new normal, whatever that is. Maybe we go full circle back to the status quo ante. Probably not, but who knows. In any case, the jury’s still out on how the HEDOs will cope over time. Some will manage to make a successful transition, others will realize that they’ve dug themselves a hole they can’t get out of. Either because they’re bogged down by commitments and overstretch, financial and otherwise, or because their conception of personal accomplishment is too firmly anchored in prior experience or hearsay. A 30-year-old HEDO, Tim Kleinman, recently made a statement to Bloomberg that perfectly sums up this ambiguity in all its glory: “That world that I’m imagining [sic!], where I’m a partner  [at a hedge fund] and I’ve made all my money, who knows what that world’s going to look like? So why not try something now?” It seems like the penny is on the brink of falling but hasn’t quite dropped yet. The HEDOs are still figuring out how merge the promise of material success and a traditional career with the exigencies of the post-2008 characterized by concepts like “meaning” and “personal fulfillment” into a functioning whole. Give them more time. It is the biggest challenge of their lives.