Shirtsleeves to Shirtsleeves in Three Generations

Shirtsleeves to Shirtsleeves in Three Generations by Family Tree Video

You may have heard the old proverb, “Shirtsleeves to shirtsleeves in three generations.” In Japan, the expression goes, “Rice paddies to rice paddies in three generations.” The Scottish say “The father buys, the son builds, the grandchild sells, and his son begs.” In China, “Wealth never survives three generations.”

Around the world there are many variations on this theme, all used to describe the tendency of third generation to squander the wealth obtained by the first and second generations.

The Shirtsleeves to Shirtsleeves Cycle
Shirtsleeves to Shirtsleeves in Three Generations by Family Tree Video

The “First Generation”, born into a life of hardship, is determined to make a better future for themselves. They are willing to work hard and make the sacrifices necessary in order to achieve their dream. In time, their efforts pay off and they are able to enjoy the “fruits” of their labor, often with assets to pass on.

Their children, the “Second Generation”, grow up a witness to their parents’ struggle and understand the importance of hard work. Although they live a more comfortable lifestyle, they may still remember a childhood filled with frugality. Because of this awareness, they make sound financial and educational choices that help them build upon the foundation their parents worked so hard to create. By their later years, the “second generation” has acquired even greater wealth.

The “Third Generation” has no memory of want or struggle. They only know a life of plenty and often lack an understanding of and appreciation for the work that went into building the lifestyle they now enjoy. It is this “third generation” that is known to squander the wealth their parents and grandparents worked so hard to build.

Avoiding the Three Generation Cycle

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By keeping family stories and history alive, younger generations are better able to understand their parents and grandparents’ experience as well as the work needed to build and maintain family wealth. For families facing the Three Generations cycle, awareness of the past will strengthen any strategy for the future.


For questions to ask your parents or grandparents to learn more about their life story and your family history, check out my post: ’25 Legacy Questions’.

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Give your parent or grandparent the gift of a lifetime by capturing their life story for your family to know!

Legacy Video Questions by Family Tree Video

Here at Family Tree Video we produce Legacy Videos, modern-day memoirs that weave a filmed interview with a parent or grandparent together with family photos, documents, maps and other memorabilia. The result is a beautiful “moving portrait” capturing your loved one as they recount their life story, family history and memories – a gift your family will treasure for generations to come.

To learn more about capturing your parent or grandparent’s life story in a Legacy Video, visit us at

Family Tree Video LLC
Legacy Video Production
(312) 402-6406

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8 thoughts on “Shirtsleeves to Shirtsleeves in Three Generations”

  1. Indeed, as I (1980) was growing up, my mother and her sisters would often inculcate me in frugality with stories of their mother (my grandmother and her brothers’ struggles during the Great Depression. That, along with my own higher educational studies in Economics has\ve made me fiercely frugal.

  2. Indubitably, fortune is forged in the fire (i.e. struggle, hardship). It is rare for family fortunes to be insinuated into the fabric of a family (e.g. Rockfellers, Waltons, Bushes, et al.).

  3. Wow, I am co-writing a “Family Banking Book” right now, and found this (wonderful) little article about the “shirtsleeves to shirtsleeves” phenomenon. I LOVE what you are doing and will mention you as a resource, as indeed, telling those family stories is so important!

  4. Strong family values of people rather than wealth. Adams said he would study war so his son could study being a merchant and his grand son being an artist. Living life simply. The Tao helps me.

  5. I lived the “shirtsleeves” story. I worked in finance/insurance to help others avoid it and am now writing a book to share with the world a unique solution. I find it ironic that most successful advisors spend all of their time, energy and creativity to support only wealthy clients. We should be finding financial solutions for the middle class which is our country’s economic engine.

    • Thomas, my head is in this space too. I’m part of a second-generation business (in today’s world it would qualify as a small or micro business). It is also right slap in Africa, a region often overlooked on the business front. However, we also do not have many enterprises that survive beyond the first or even the second generation. Once the founder dies or falls ill, the business venture collapses.

      I find that the literature & books out there are just on the ultra-wealthy families in the West.

      I’ve now started writing about “African Family Businesses” and will see how it turns out.

      And thank you, Family Line Video, for sharing this article. I hope you don’t mind if I can reference it in my book.


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