Shirtsleeves to Shirtsleeves in Three Generations


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Money Matters

October 10, 2025 by Scott Crosby

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Shirtsleeves to Shirtsleeves in Three Generations

Back in the early 1900s there was a saying:  “Shirtsleeves to shirtsleeves in three generations.”

The saying arose because people noticed that a man might rise from being a day-laborer, and by dint of hard work and great effort, create a successful business that earned him a lot of money.

That businessman’s children inherited the business, but they were not so hard-working; they made much less effort, or even made no effort at all – just living off the fortune made by their father.

S1151-1.jpgThe business, of course, dwindled away as a consequence of that laziness, and with it, the fortune.  Their children – the third generation –were reduced once again to being day-laborers.  

Hence, “Shirtsleeves to shirtsleeves in three generations.”  The sequence occurred often enough to give rise to a piece of American folklore.

But as common as it is, this series of events need not occur.  If you are the parents that are successful and well off, how do you break the stereotypical mold?

The choices made by parents regarding how they raise their children, of course, are the crux of the matter.

The family may live in an expensive house, or even a mansion.  The parents may drive expensive cars.

But letting the children just float along in this environment while growing up does not teach them anything about what is required for them to live as adults.  The parents, of course, are at fault.  

Several years ago, a successful, well-to-do acquaintance told me about his 25-year-old son.  That young man had not been taught how to be an adult.  At 25 years old, he was still living at home, with no job, and being given an allowance.  For all intents and purposes, he was still a boy.  Without any incentive, that will never change.

Like anything else, a child must learn that money must be earned.  It is the responsibility of parents to teach each of their children that there is no free lunch.  That training must be an intrinsic part of the child’s growing up.  Waiting until his teens, or having a “sit-down talk” a year or two before he is expected to leave home, is far too late.  

From the very first allowance a child receives, that allowance must be earned through assigned chores. Particularly as a child begins wanting to buy their own clothes rather than accepting whatever their parents buy, it is the parents’ responsibility to introduce each child to the value of money, how to earn money, and mandate that earning it is required, like it or not.

People do not instinctively know what is required to live; each person must be taught what he needs to know.  Parents are the ones responsible for that teaching.  Schools are no substitute; they teach only knowledge.  What a person ought to do is something the child will learn from his parents – or not at all

Parents, for better or worse, set the example their children will follow.  That is not only true financially, but also in the time and attention parents spend with their children, and the effort parents put into making sure the children have the self-discipline and know-how they will require to be able to pass along that crucially-important knowledge to their own children.  

Doing that ends the fate of “shirt sleeves to shirt sleeves in three generations”.

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