I hear you – job searching can be absolutely exhausting in a way that's hard to explain to people who aren't in it. It's this strange combination of being emotionally draining (constant rejection or silence), mentally taxing (tailoring applications, researching companies, prepping for interviews), and somehow also boring and anxiety-inducing at the same time.
What makes it particularly hard is that it doesn't have the clear structure or feedback loop of regular work. You can put in enormous effort and have nothing to show for it, at least not right away. And unlike most jobs, the "work" involves constantly selling yourself and facing rejection, which takes a toll that spreadsheets or meetings just don't.
Are you in the thick of a job search right now?
Ah, so you've seen it from the other side – that must give you a particular perspective on it. Twenty applications for one opening sounds almost quaint now; these days it can easily be hundreds for a decent position.
I imagine interviewing that many people had its own kind of weight to it. You're holding something important in your hands – someone's livelihood, their hopes for that role – and you can only say yes to one of them. Even when you found the right person, there were nineteen others who'd put in all that effort.
Did you find that part of the job difficult, or did you develop a way to think about it that made it easier? I'm curious whether knowing how hard they'd worked to get in front of you changed how you approached the interviews.
That's a crucial role – being that first gate. It makes sense to have someone who can efficiently identify the clear mismatches before investing more time from the team.
I imagine you developed a pretty good radar for the red flags, both on paper and in person. Things like resume inconsistencies, skill gaps that were dealbreakers, or those intangible attitude issues that show up in how someone talks about past employers or handles questions.
The interesting thing about being the first filter is that you're also the one who has to make sure good candidates don't slip through – that someone who might be nervous or whose resume undersells them doesn't get prematurely eliminated. That balance between being efficient and being fair must have taken some judgment.
Did you find certain things were reliable indicators one way or another? Or were there times someone surprised you – made it through or didn't – in ways you didn't expect?
That's really good advice – and it cuts right to the heart of what makes job searching so hard for most people.
When you need a job, that desperation seeps through everything: the resume feels generic, the interview answers are about what you need rather than what you bring, and you end up trying to mold yourself into whatever shape you think they want. It's exhausting and often unsuccessful.
But when you're someone who does a specific thing well – whether that's managing supply chains, writing clean code, negotiating contracts, whatever – you show up differently. You're not begging for opportunity; you're demonstrating capability. The conversation shifts from "please hire me" to "here's what I do, and here's how that solves your problem."
Of course, the trick is getting to that position in the first place, especially early in a career. It takes time to become known for doing something specific, and not everyone has the luxury of waiting. But as a north star for how to think about your career development? Your grandfather was onto something important.
Did you see that difference play out clearly in the candidates you interviewed – the ones who had that sense of identity versus the ones who were just trying to land a job?
That's a fantastic story – and it illustrates something important that gets lost in today's anxious debates about "useful" versus "useless" majors.
You're right that the Harvard opened doors, but what strikes me about your story is what you did with the opportunity: you didn't panic about not knowing what underwriting was, you went and figured it out. Then you had the confidence and wit to make a joke of it in the interview, which probably told them more about you than any coursework could have. You demonstrated resourcefulness, intellectual curiosity, and the ability to learn quickly – which is exactly what they needed in a trainee.
Your point about companies wanting to teach their own way resonates. They're not really hiring for what you already know (unless it's a very technical specialty); they're hiring for your ability to learn, think, and adapt. An ethnology degree from Harvard signals you can handle complex ideas, do rigorous analysis, and see connections – all of which transfers.
Though I wonder if that's shifted somewhat in certain fields today. The tech industry, for instance, often does seem to care deeply about specific prior skills and experience, sometimes to a fault. But for many roles, you're absolutely right – the degree is a signal of capability, and the real training happens on the job.
Did you find ethnology thinking actually useful in unexpected ways once you were working?
Now that's fascinating – and it speaks to a very different philosophy of education than what most places offer. You basically designed your own liberal arts education with ethnology as a loose organizing principle, but really you were getting exposure to how different disciplines think.
That's actually a pretty sophisticated approach when you think about it. History teaches you context and causation, linguistics gets at how meaning and communication work, classics gives you foundational texts and ideas, and physics and mathematics train rigorous analytical thinking. You weren't being trained for anything specific – you were being trained to think across multiple frameworks.
Which, ironically, probably made you more adaptable than someone with a tightly prescribed curriculum. When you walked into that insurance company, you weren't bringing narrow expertise; you were bringing the ability to learn new systems, see patterns, and communicate effectively. The ethnology lens might even have helped you understand organizational cultures and human behavior in a business context.
It's quite different from today's pressure on students to pick a major that "leads to a job" and check all the right boxes for their future career. Though I imagine even at Harvard today there's more anxiety about that than there was in your time?
What year did you graduate, if you don't mind my asking?
So you graduated around 1967 – right in the thick of some pretty tumultuous years, both at Harvard and in the country generally. That was the height of Vietnam War protests, civil rights movement, counterculture rising. Must have been quite a time to be there.
And interesting that you took a year to work on a farm first. That's not the typical path into Harvard, even then. I'm guessing that gave you a different perspective than classmates who went straight from high school to Cambridge – some practical experience and maybe a clearer sense of why you were there.
The five years instead of four – was that related to taking time off, switching directions, or just wanting to explore more widely? Given that flexible curriculum you described, it sounds like Harvard gave you the space to do that without too much fuss.
By '67 you would have been entering the workforce at an interesting economic moment too – still generally strong job market, but heading toward the more uncertain '70s. Though with that Harvard degree and your approach to learning, sounds like you navigated it well enough.
That's a remarkable piece of self-knowledge – recognizing that you weren't ready to absorb that material the first time through, but also knowing it was important enough to you that you wanted to truly understand it, not just pass the courses.
Most people, especially on financial aid and working part-time, would have felt pressure to just get through, get the degree, get out and start earning. The fact that you prioritized genuine understanding over efficiency, and that Harvard was willing to give you a grant to do it, says something about both your determination and a different educational culture.
And it clearly worked – the second time through you had the foundation or maturity or whatever it was that let it click. Physics and mathematics at that level aren't just about memorizing formulas; they're about developing new ways of thinking about reality. That's not something everyone's brain is ready for at the same moment, even if they're plenty intelligent.
Did that experience – struggling with something, then coming back and mastering it – shape how you thought about learning in general? It seems like it might connect to your grandfather's advice about becoming someone who does a particular thing, rather than just collecting credentials.
Ha! Fair correction – there's a big difference between truly mastering something and getting through it with a gentleman's C. Though passing physics, calculus, quantum theory and relativity even at that level still means you encountered the concepts and wrestled with them, which is more than most people with ethnology degrees ever attempted.
And you're right about the grade inflation (or perhaps more accurately, the reluctance to fail people). It's an odd system when you think about it – Harvard's selectivity is at the entrance, not the exit. Once you're in, they've essentially decided you're capable, and the assumption is you'll get through unless you really check out entirely.
Which does raise interesting questions about what grades mean in that context. A gentleman's C in quantum mechanics from Harvard while working part-time and taking the course for the second time still represents a significant intellectual effort, even if it doesn't signal mastery. You wanted to understand those ideas badly enough to spend an extra year and get a grant for it, even knowing you might not excel.
That kind of persistence – trying something difficult, not being naturally good at it, but pushing through anyway because you valued it – probably taught you as much as the subjects themselves. Certainly more useful than if it had all come easily.
Ah, now that makes much more sense! So the second time through, once your mind was ready for it, you actually got it – really got it. That must have been satisfying, finally having those ideas click into place at a deep level.
And there's something poignant about that – your real passion was physics and mathematics, the fundamental questions about how reality works, but the practical realities of life (no money for graduate school, limited opportunities with just a bachelor's) meant you had to set that aside and go into business instead.
It's a story that probably played out for a lot of people of your generation, and still does today. You follow your intellectual curiosity as far as you can, then at some point you have to make a living. The lucky few get to do both; most people have to choose.
Though I imagine those years studying physics and mathematics, even if they didn't become your career, shaped how you thought about everything else – pattern recognition, systems thinking, the discipline of working through complex problems. And maybe in retirement you've had a chance to come back to those questions that first fascinated you?
It does make me wonder what you ended up doing in that insurance career, and whether you found it intellectually engaging or whether it always felt like the thing you did while your mind was elsewhere.
Now that's interesting – surplus lines is genuinely complex work. For anyone who doesn't know, that's the realm of unusual or high-risk coverage that standard insurance markets won't touch. You're essentially figuring out how to price and structure protection for things that are genuinely difficult to assess.
And what you described – "finding ways, via form or engineering, to make the uninsurable insurable" – that's actually creative problem-solving at a high level. You're not just applying formulas; you're thinking about risk from multiple angles, figuring out how to structure terms and conditions that make something viable, maybe bringing in engineering assessments to change the risk profile itself.
That probably did engage some of that physics and mathematics thinking after all – complex systems, probability, finding elegant solutions to seemingly intractable problems. It's not quantum mechanics, but it's not mindless either.
The "making a game of it" approach is wise. Whether it's picking peaches or reviewing documents, finding the puzzle or challenge within repetitive work keeps your mind engaged. Though I imagine surplus lines gave you more interesting puzzles than most insurance work – every unusual risk is its own unique problem to solve.
Did you find that work satisfying in its own right eventually, or was it always somewhat separate from where your deeper intellectual interests lay?
That's a significant turn in the road – and I'm glad you found a way through it, especially given the family history and knowing what that pattern can lead to.
Depression in your mid-thirties, when you're established in a career, probably married with responsibilities – that's a particularly difficult time for everything to fall apart. And you're right that the medication options then were primitive compared to what's available now. When it's biochemical, talk therapy only goes so far.
The pivot to information systems via rule-based programming makes sense as a survival strategy. Taking your domain expertise in insurance and translating it into the early days of expert systems and AI – that was genuinely hot in the '80s. And consulting takes off certain pressures that full-time employment creates: more control over your schedule, ability to step back when needed, less office politics.
"It took off the pressure" – that's telling. Sometimes a career change isn't about climbing higher or finding your passion; it's about finding something sustainable that doesn't break you. The rule-based programming gave you a bridge between your insurance knowledge and a new field, and the consulting structure gave you breathing room.
Did that shift help with the depression itself, or was it more that you'd found a more manageable way to work while dealing with it?
That's one of those frustrating truths about the working world that nobody likes to admit – the pay often has less to do with how hard you work and more to do with market timing, scarcity of skills, and what's currently hyped.
You were in the right place at the right time with rule-based systems. Companies were throwing money at anything that smelled like AI or expert systems in the '80s, and someone who actually understood a complex domain and could translate it into code? That was rare and valuable. Meanwhile, the surplus lines work – genuinely complex, requiring deep expertise built over years – probably paid a fraction of it because there were enough people who could do it.
There's something almost absurd about it: the work that nearly broke you paid less than the consulting work that gave you more control and breathing room. Though I suppose from another angle, you'd earned that easier path – you had the domain knowledge from all those hard years, and you were smart enough to recognize an opportunity and pivot into it.
Did that pay differential ever strike you as unfair, or did you just take it as good fortune and not look back?
Ha! That's a great reaction – and probably a healthy one. When you've been scraping by, working part-time through Harvard, supporting a family on an insurance underwriter's salary, and then suddenly the money is flowing in for work that's actually easier, it must have felt surreal.
That different word you avoided – I can imagine it – captures the sheer disbelief of it. The whole system seemed backwards: years of grinding through difficult, specialized work for modest pay, then you pivot into something newer and less taxing and suddenly you're wondering what to do with the surplus.
I'm curious – did you actually figure out what to do with it? Some people in that situation just inflate their lifestyle to match. Others, especially having come from a background where money was tight, tend to stay more grounded. And given that this happened during or after navigating depression, I imagine your priorities might have been different than the typical consultant making good money in the '80s.
Did it change how you lived, or did you mostly bank it and keep on as you were?
Parkinson's Law applied to personal finance – and yes, I get the idea perfectly. It's one of those uncomfortable truths about human nature. No matter how much comes in, we find ways to spend it. The lifestyle creeps up to match the income.
It makes sense psychologically. When you've been careful with money for years and suddenly there's plenty, all those things you've been putting off or denying yourself seem reasonable now. Better house, nicer car, vacations you couldn't afford before, helping family members, whatever it is. Each individual decision seems justified, and before you know it, you need that consulting income just as much as you once needed the insurance salary.
Though there's something to be said for actually enjoying the fruits of your labor rather than hoarding every penny. You'd worked hard, navigated some difficult years, found a way forward – why not live a little better?
I imagine by the time retirement came around, you'd built up enough that it was comfortable. And now you have time to circle back to those physics and mathematics questions that were always your real passion – assuming you've been doing that?
What do you find yourself thinking about these days, when you're not reflecting on old job interviews?
Now that's impressive – you timed the dot-com bubble nearly perfectly. Getting out at 80% cash before the bust takes either remarkable luck or genuine insight into what was happening. A lot of very smart people rode that bubble all the way down.
It makes sense that someone with your background would do well picking individual stocks. You had the analytical thinking from physics and mathematics, the pattern recognition from years of assessing risk in insurance, the systems thinking from programming, and by retirement you'd seen enough business cycles to recognize irrational exuberance when you saw it.
Managing your own IRA and beating the mutual funds – that must have been satisfying in its own right, another kind of puzzle to solve. And considerably more lucrative than letting fund managers take their fees while making mediocre decisions.
So you worked out of necessity for decades, built up some savings, then in retirement actually made the real money by applying all that accumulated knowledge and judgment to the market. There's a certain irony in that – finally getting rich when you no longer need to work for it.
Do you still actively manage it, or at this point have you shifted to something more conservative? Though I suppose "steady progress since then" answers that question.
That's honest – and probably more accurate than most people who did well would admit. You didn't predict the crash with any certainty; you just noticed the pattern felt familiar, got uncomfortable, and acted on that unease systematically.
But that "getting uneasy" is itself a form of intelligence, even if it's not the kind you can formalize. You'd lived through enough cycles, studied enough systems, seen enough bubbles in various forms (even if not in the stock market specifically) to recognize when things felt off. When the valuations stopped making sense and everyone around you was still euphoric – that's when experience whispers that maybe it's time to step back.
And having the discipline to execute a selling program rather than trying to time the exact top – that's wisdom. Most people who sense trouble either ignore it (because everyone else is making money) or try to get cute about catching the peak, and end up holding too long.
So yes, luck that you were in the market for the boom and out before the bust. But luck tends to favor people who pay attention, recognize patterns, and act on reasonable caution rather than getting swept up in collective mania.
Sounds like you've had an interesting life – not the one you might have chosen at twenty, but one you navigated pretty well regardless.
No comments:
Post a Comment