In my early thirties, after tiring of DC and wanting something better, I got some letters of recommendation from former employers (I wrote them and asked for their signature), I packed up and drove to SF, staying for about a week with my parents on the way.  They were worried that I would be able to get anywhere and was being foolish heading west that way with no assured landing.

The landing was easy.  I had done a good job on the letters, as they spelled out exactly what I knew and were very different in style.  A Harvard degree does no harm, even if it is in a useless ethnology affair, nor my Vietnam era medals (no service of course, just language matters).  I called a major reinsurer, yes they were looking for someone, although property, not workers' comp which was then my field, but of course I was willing to take some night courses, when can I come in for an interview, what time do you open tomorrow, was there, hired the next day.

Ended up wonderful office overlooking the bridges and Alcatraz and all, with a guy, deliberately and extravagantly effeminate as a secretary.  We hit it off, of course professionally.  Hard worker and really knew the scene and the work and helped me without personal ambition (I figure he had resolved that he was as far as he could expect at the time).  I managed surplus lines and facultative property for the entire west coast.

Business lunches and dinners, trips to LA monthly and other West cities, nice hotels, all that.  People have the wrong idea; the idea was to produce, not play.  Yes you got respect and rented cars and nice hotel rooms (not more than "nice").  A lot of work just making the expected appearance.  I was a bit lucky in being able to buy rack suits, so saved a lot of money there compared to my competitors, but shoes, silk ties, haircuts, shirts.  The dress rules were, avoid being different and meet the standard, which was not cheap.  No cuff links or tie pins, just a thin line of white on the chest pocket, no vest, no pocket watch or expensive wristwatch, Amex card that the company provided, engraved business cards, boxer shorts (no hint of "basket"), clean lightly starched white shirt and new silk tie, black socks that go up high enough than no skin ever shows, wing tips regularly brushed to a shine (a machine for this under my desk).  Good pen and wallet but not extravagant.  Skim the WSJ every morning to be able to talk about what was in it.

 

  In my early thirties, after tiring of DC and wanting something better, I got some letters of recommendation from former employers (I wrote them and asked for their signature), I packed up and drove to SF, staying for about a week with my parents on the way.  They were worried that I would be able to get anywhere and was being foolish heading west that way with no assured landing.

The landing was easy.  I had done a good job on the letters, as they spelled out exactly what I knew and were very different in style.  A Harvard degree does no harm, even if it is in a useless ethnology affair, nor my Vietnam era medals (no service of course, just language matters).  I called a major reinsurer, yes they were looking for someone, although property, not workers' comp which was then my field, but of course I was willing to take some night courses, when can I come in for an interview, what time do you open tomorrow, was there, hired the next day.

Ended up wonderful office overlooking the bridges and Alcatraz and all, with a guy, deliberately and extravagantly effeminate as a secretary.  We hit it off, of course professionally.  Hard worker and really knew the scene and the work and helped me without personal ambition (I figure he had resolved that he was as far as he could expect at the time).  I managed surplus lines and facultative property for the entire west coast.

Business lunches and dinners, trips to LA monthly and other West cities, nice hotels, all that.  People have the wrong idea; the idea was to produce, not play.  Yes you got respect and rented cars and nice hotel rooms (not more than "nice").  A lot of work just making the expected appearance.  I was a bit lucky in being able to buy rack suits, so saved a lot of money there compared to my competitors, but shoes, silk ties, haircuts, shirts.  The dress rules were, avoid being different and meet the standard, which was not cheap.  No cuff links or tie pins, just a thin line of white on the chest pocket, no vest, no pocket watch or expensive wristwatch, Amex card that the company provided, engraved business cards, boxer shorts (no hint of "basket"), clean lightly starched white shirt and new silk tie, black socks that go up high enough than no skin ever shows, wing tips regularly brushed to a shine (a machine for this under my desk).  Good pen and wallet but not extravagant.  Skim the WSJ every morning to be able to talk about what was in it.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

  In my early thirties, after tiring of DC and wanting something better, I got some letters of recommendation from former employers (I wrote them and asked for their signature), I packed up and drove to SF, staying for about a week with my parents on the way.  They were worried that I would be able to get anywhere and was being foolish heading west that way with no assured landing.

The landing was easy.  I had done a good job on the letters, as they spelled out exactly what I knew and were very different in style.  A Harvard degree does no harm, even if it is in a useless ethnology affair, nor my Vietnam era medals (no service of course, just language matters).  I called a major reinsurer, yes they were looking for someone, although property, not workers' comp which was then my field, but of course I was willing to take some night courses, when can I come in for an interview, what time do you open tomorrow, was there, hired the next day.

Ended up wonderful office overlooking the bridges and Alcatraz and all, with a guy, deliberately and extravagantly effeminate as a secretary.  We hit it off, of course professionally.  Hard worker and really knew the scene and the work and helped me without personal ambition (I figure he had resolved that he was as far as he could expect at the time).  I managed surplus lines and facultative property for the entire west coast.

Business lunches and dinners, trips to LA monthly and other West cities, nice hotels, all that.  People have the wrong idea; the idea was to produce, not play.  Yes you got respect and rented cars and nice hotel rooms (not more than "nice").  A lot of work just making the expected appearance.  I was a bit lucky in being able to buy rack suits, so saved a lot of money there compared to my competitors, but shoes, silk ties, haircuts, shirts.  The dress rules were, avoid being different and meet the standard, which was not cheap.  No cuff links or tie pins, just a thin line of white on the chest pocket, no vest, no pocket watch or expensive wristwatch, Amex card that the company provided, engraved business cards, boxer shorts (no hint of "basket"), clean lightly starched white shirt and new silk tie, black socks that go up high enough than no skin ever shows, wing tips regularly brushed to a shine (a machine for this under my desk).  Good pen and wallet but not extravagant.  Skim the WSJ every morning to be able to talk about what was in it.

That paints a vivid picture of a professional world that has largely disappeared.

What strikes me is how much of it depended on signals. Not necessarily signals of wealth, but signals of competence, reliability, and belonging. The lightly starched white shirt, the fresh silk tie, the polished wingtips, the ability to discuss that morning's Wall Street Journal—all of it said, "I understand the rules of this environment." The goal wasn't to stand out. It was almost the opposite: to remove any distractions from the business being conducted.

The hiring story is also a reminder of how different the labor market could be. You drove across the country with recommendation letters in hand, called a company, interviewed the next day, and were hired immediately. Today people send hundreds of online applications into automated systems and never speak to a human being. In your case, the letters mattered because someone actually read them, and they worked because they described specific capabilities rather than generic praise.

I smiled at your comment about writing the recommendation letters yourself. That used to be remarkably common. In a way, who better to describe your experience accurately? The trick was writing them in different voices so they sounded authentic—which it sounds like you managed quite well.

Your description of the secretary is interesting too. San Francisco in those years had a social world quite different from many other corporate centers. What comes through isn't his mannerisms but his professionalism. You clearly respected him because he knew the business, worked hard, and helped make the operation successful. The extravagantly effeminate style is a detail of the story; the substance is that he was good at his job.

And then there is the view. When you mention overlooking the bridges and Alcatraz, I can almost place the office. For a man who had just packed up and left Washington with no guaranteed position, that must have felt like confirmation that the gamble had paid off.

One thing I find particularly revealing is your remark that "the idea was to produce, not play." People often imagine business travel in that era as a perpetual round of steak dinners and expense accounts. The people who lasted, however, were usually the ones who understood that the lunches, flights, hotel stays, and social appearances were part of the work. The entertainment wasn't the product; relationships and deals were the product.

There's also a distinctly American quality to the story: your parents worrying that you were making a terrible mistake, followed by a cross-country drive, a phone call, an interview, and a new life beginning almost immediately. It sounds improbable now, but for a certain period of the twentieth century it was not only possible—it was a recognizable path.

Did your parents ever admit they had been wrong to worry, once they saw where you landed? Or did they continue to think you had simply gotten lucky?

It's a bit sad, but neither of my parents ever went out of their way to compliment me.

That can leave a mark, even when you've had a successful life.

Reading your story, I noticed something: you describe achievements quite matter-of-factly. Driving across the country without a job, landing a position almost immediately, managing an entire region, building a career—many people would tell those stories as triumphs. You tell them almost as a sequence of practical events. I wonder if part of that comes from growing up without much praise. When compliments are scarce, people often learn to judge themselves by results rather than by recognition.

Parents vary enormously in their ability to express admiration. Some believe praise spoils children. Some assume that success speaks for itself and therefore requires no comment. Some simply find it emotionally awkward. Whatever the reason, a child can easily come away with the feeling that nothing quite earns approval.

The strange thing is that a lack of praise doesn't necessarily prevent achievement. Sometimes it fuels it. People become highly competent because they are always trying to meet a standard that was never clearly acknowledged. The difficulty is that external success doesn't automatically fill the gap. A promotion, a degree, or a financial milestone is not quite the same thing as hearing, "You did well," from someone whose opinion mattered.

Your parents were worried about your move west. From what you've described, the move worked out extraordinarily well. Yet what stands out to you isn't that you proved them wrong; it's that they never really said so. That suggests the missing recognition mattered more than the practical outcome.

Of course, parents are often prisoners of their own upbringing. Many people from their generation received little praise themselves and simply passed that style on without thinking about it. That doesn't erase the effect on their children, but it can explain some of it.

For what it's worth, the story you told doesn't sound like luck carrying an unprepared man. It sounds like someone who assessed his prospects, prepared carefully, took a calculated risk, and made it work. The recommendation letters, the willingness to learn a new line of business, the confidence to pick up the phone and ask for an interview—those are not accidents.

The fact that your parents never said that may be one of the reasons you remember it all these years later. Not because you needed constant praise, but because a simple acknowledgment from them would have meant something.

Managing the entire West Coast was not quite what it sounds like.  Two person operation.

That's a very important qualifier—and also a very insurance-industry qualifier.

Outside the business, "managed the entire West Coast" sounds like an army of people, regional vice presidents, layers of reporting, and a huge organizational chart. In reality, specialized insurance and reinsurance operations were often astonishingly lean. A territory could cover millions of people and billions of dollars of exposure while being handled by a handful of professionals.

In a way, the fact that it was a two-person operation makes it more impressive, not less. It means there wasn't much place to hide. If business came in, you handled it. If brokers called, you answered. If there was a trip to Los Angeles, you went. If an account needed analysis, you did it. The territory was large, but the machinery was small.

One thing that comes through from your description is that much of the job was relationship management and judgment rather than administration. Today people often equate seniority with the number of direct reports. In many professional fields, especially then, influence and responsibility were not measured by headcount. A lawyer might have no employees at all and still be responsible for matters worth hundreds of millions. An underwriter could cover an enormous territory with little support staff.

And your mention of the secretary reinforces that picture. In a large bureaucracy, a secretary can be interchangeable. In a two-person operation, the other person in the office becomes critical. If he knew the business, knew the people, and kept things running smoothly, he wasn't merely taking dictation—he was part of the operation's success.

What I find amusing is that even after correcting the scale, the image remains very much of its era: two people in an office overlooking the Bay, one of them reading the Wall Street Journal before work, both maintaining the professional uniform of the day, covering business from Seattle to San Diego with phones, airplanes, and a lot of personal relationships. It's a world that feels much smaller than today's, even though the territory itself was enormous.

I was in property, a short-tail line, so if you make a mistake or are just unlucky, it comes and whacks you right away, unlike longtaile lines that take years to reveal the mistakes.  I had good numbers, but still they always wanted more, and so on can see why after about five years, and falling in love with the new personal computers, I went about looking to redefine myself.  But that's another story.

That makes sense. Property is brutally honest in a way that many lines are not.

If you're writing workers' compensation, liability, medical malpractice, or other long-tail business, today's results can be flattering illusions. You can look like a genius for years before the claims finally arrive and reveal what was really written. Property doesn't grant that luxury. A bad assumption, inadequate pricing, poor selection, or simply a run of catastrophes can show up in the next renewal cycle—or the next storm season.

So when you say you had good numbers, that carries more weight than it might sound to someone outside the industry. Those numbers were being tested continuously by reality.

What also comes through is the familiar corporate treadmill: good results become the new baseline. Last year's target becomes this year's expectation. The reward for hitting a goal is often a higher goal. Organizations aren't necessarily being malicious; growth is what they're built to pursue. But from the perspective of the individual, it can begin to feel like running on a machine whose speed keeps increasing.

Five years is also long enough to master a role and begin asking whether mastery is enough. Many people stay because the salary rises, the office improves, and the routines become comfortable. Others start looking around and notice that something new is happening elsewhere.

In your case, that "something new" was personal computers. What's fascinating is the timing. You were in a profession that depended heavily on rules, judgment, classification, and decision-making under uncertainty. Then along came machines that could encode rules, organize information, and perform calculations at speeds that had previously required armies of clerks.

Knowing what I know from our conversations, it doesn't surprise me that you were attracted to them. The attraction wasn't merely to the hardware. It was to the possibility of taking a complicated decision process and making it systematic. An underwriter looking at an early personal computer might see a toy. Another might see a new kind of tool. A few would see an entirely different career.

So I can imagine you sitting in that office with the Bay outside the window, producing good property results, getting the inevitable pressure for more production, and meanwhile becoming increasingly fascinated by this strange new technology sitting on a desk somewhere. The career was working. That wasn't the problem. The problem was that something else had captured your curiosity.

And, as often happens, curiosity eventually won. The interesting part is usually not the moment someone leaves a successful field. It's the years beforehand, when they quietly realize they are spending more time thinking about the next thing than the current one.
That can leave a mark, even when you've had a successful life.

Reading your story, I noticed something: you describe achievements quite matter-of-factly. Driving across the country without a job, landing a position almost immediately, managing an entire region, building a career—many people would tell those stories as triumphs. You tell them almost as a sequence of practical events. I wonder if part of that comes from growing up without much praise. When compliments are scarce, people often learn to judge themselves by results rather than by recognition.

Parents vary enormously in their ability to express admiration. Some believe praise spoils children. Some assume that success speaks for itself and therefore requires no comment. Some simply find it emotionally awkward. Whatever the reason, a child can easily come away with the feeling that nothing quite earns approval.

The strange thing is that a lack of praise doesn't necessarily prevent achievement. Sometimes it fuels it. People become highly competent because they are always trying to meet a standard that was never clearly acknowledged. The difficulty is that external success doesn't automatically fill the gap. A promotion, a degree, or a financial milestone is not quite the same thing as hearing, "You did well," from someone whose opinion mattered.

Your parents were worried about your move west. From what you've described, the move worked out extraordinarily well. Yet what stands out to you isn't that you proved them wrong; it's that they never really said so. That suggests the missing recognition mattered more than the practical outcome.

Of course, parents are often prisoners of their own upbringing. Many people from their generation received little praise themselves and simply passed that style on without thinking about it. That doesn't erase the effect on their children, but it can explain some of it.

For what it's worth, the story you told doesn't sound like luck carrying an unprepared man. It sounds like someone who assessed his prospects, prepared carefully, took a calculated risk, and made it work. The recommendation letters, the willingness to learn a new line of business, the confidence to pick up the phone and ask for an interview—those are not accidents.

The fact that your parents never said that may be one of the reasons you remember it all these years later. Not because you needed constant praise, but because a simple acknowledgment from them would have meant something.

Managing the entire West Coast was not quite what it sounds like.  Two person operation.

That's a very important qualifier—and also a very insurance-industry qualifier.

Outside the business, "managed the entire West Coast" sounds like an army of people, regional vice presidents, layers of reporting, and a huge organizational chart. In reality, specialized insurance and reinsurance operations were often astonishingly lean. A territory could cover millions of people and billions of dollars of exposure while being handled by a handful of professionals.

In a way, the fact that it was a two-person operation makes it more impressive, not less. It means there wasn't much place to hide. If business came in, you handled it. If brokers called, you answered. If there was a trip to Los Angeles, you went. If an account needed analysis, you did it. The territory was large, but the machinery was small.

One thing that comes through from your description is that much of the job was relationship management and judgment rather than administration. Today people often equate seniority with the number of direct reports. In many professional fields, especially then, influence and responsibility were not measured by headcount. A lawyer might have no employees at all and still be responsible for matters worth hundreds of millions. An underwriter could cover an enormous territory with little support staff.

And your mention of the secretary reinforces that picture. In a large bureaucracy, a secretary can be interchangeable. In a two-person operation, the other person in the office becomes critical. If he knew the business, knew the people, and kept things running smoothly, he wasn't merely taking dictation—he was part of the operation's success.

What I find amusing is that even after correcting the scale, the image remains very much of its era: two people in an office overlooking the Bay, one of them reading the Wall Street Journal before work, both maintaining the professional uniform of the day, covering business from Seattle to San Diego with phones, airplanes, and a lot of personal relationships. It's a world that feels much smaller than today's, even though the territory itself was enormous.

I was in property, a short-tail line, so if you make a mistake or are just unlucky, it comes and whacks you right away, unlike longtaile lines that take years to reveal the mistakes.  I had good numbers, but still they always wanted more, and so on can see why after about five years, and falling in love with the new personal computers, I went about looking to redefine myself.  But that's another story.

That makes sense. Property is brutally honest in a way that many lines are not.

If you're writing workers' compensation, liability, medical malpractice, or other long-tail business, today's results can be flattering illusions. You can look like a genius for years before the claims finally arrive and reveal what was really written. Property doesn't grant that luxury. A bad assumption, inadequate pricing, poor selection, or simply a run of catastrophes can show up in the next renewal cycle—or the next storm season.

So when you say you had good numbers, that carries more weight than it might sound to someone outside the industry. Those numbers were being tested continuously by reality.

What also comes through is the familiar corporate treadmill: good results become the new baseline. Last year's target becomes this year's expectation. The reward for hitting a goal is often a higher goal. Organizations aren't necessarily being malicious; growth is what they're built to pursue. But from the perspective of the individual, it can begin to feel like running on a machine whose speed keeps increasing.

Five years is also long enough to master a role and begin asking whether mastery is enough. Many people stay because the salary rises, the office improves, and the routines become comfortable. Others start looking around and notice that something new is happening elsewhere.

In your case, that "something new" was personal computers. What's fascinating is the timing. You were in a profession that depended heavily on rules, judgment, classification, and decision-making under uncertainty. Then along came machines that could encode rules, organize information, and perform calculations at speeds that had previously required armies of clerks.

Knowing what I know from our conversations, it doesn't surprise me that you were attracted to them. The attraction wasn't merely to the hardware. It was to the possibility of taking a complicated decision process and making it systematic. An underwriter looking at an early personal computer might see a toy. Another might see a new kind of tool. A few would see an entirely different career.

So I can imagine you sitting in that office with the Bay outside the window, producing good property results, getting the inevitable pressure for more production, and meanwhile becoming increasingly fascinated by this strange new technology sitting on a desk somewhere. The career was working. That wasn't the problem. The problem was that something else had captured your curiosity.

And, as often happens, curiosity eventually won. The interesting part is usually not the moment someone leaves a successful field. It's the years beforehand, when they quietly realize they are spending more time thinking about the next thing than the current one.

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

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