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The literal translation of this week’s parsha, Toldot, is “generations.” It is, therefore, not surprising that the stories in this week’s parsha can teach us valuable lessons for the generations. The highlighted anecdotes shed light on how to manage our financial affairs to inspire future generations while minimizing family infighting.

The parsha starts by mentioning how Yitzchak and Rivka endure 20 years of childlessness before they are finally blessed with twin sons, Yaakov and Esav. As is common for brothers, the twins quarrel. Though interestingly their fighting starts in utero. Once born, each son takes a drastically different life path. Esav is a skilled hunter and a man of the field, while Yaakov is a scholarly “dweller in tents.” Esav ends up trading his birthright for soup, and Yaakov deceives his father (with his mom’s help) to ensure that he receives the first-born blessing.

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The above stories conjure up the following thought-provoking financial lessons:

Equity over equality: This is an often-used phrase in today’s corporate America to promote a healthy work culture. Equity means giving resources based on individual needs to ensure everyone has a fair chance to succeed, while equality ensures that everyone is treated the same. In general, equity is more important than equality. Giving someone what they need to be able to succeed is far more sensible than making sure everyone receives equal treatment.

I believe this point is central to the Yaakov and Esav dynamic and is applicable to all families. Every child is different. Siblings with the same upbringing, with the same wonderful, loving parents, may choose completely different paths in life. Each child should be given what they need in order to thrive.

This lesson applies throughout child rearing. One example among the infinite number of permutations that can describe how siblings may differ relates to hobbies. One child may appreciate reading books and going hiking in her spare time, while the other child is actively involved in team sports. Consequently, parents need to allocate their time and resources to help support each child according to their needs.

In the realm of estate planning, if one son is in kollel and the other son is an investment banker, more money may be needed to support the former. The latter may appreciate a different type of non-financial support to help them achieve their full potential.

Yaakov and Esav didn’t need the same things to excel. They needed what would be uniquely beneficial to them and their respective lifestyles. Understanding this concept can avoid a lot of hardship and frustration.

Parents should speak with one voice: I have always found it interesting that Rivka and Yitzchak are on different pages regarding the lives of their children. Yitzchak thinks Esav should receive the bechorot. Rivka is convinced that Yaakov should get it, causing her to aide in his subterfuge to ultimately obtain this blessing. While I would never question the methods of our forefathers, it does teach parents of our generation an important financial lesson: Speak with one voice!

When mom and dad have differing opinions on the upbringing of their children, it’s important for them to speak in private, get on the same page, and present a unified front and single message to their children. Psychologically, this approach helps kids clearly understand expectations and avoid confusion, ultimately leading to better behavior and a stronger family unit. It’s essential in helping children grow into thriving adults who are active contributors to society.

Financially, when parents are on the same page, it helps their kids understand unequivocally what they would like to see and minimizes the chance of family infighting after they are gone. If you want your kids to experience a harmonious relationship when you are no longer there to referee, it’s imperative to speak in one voice.

Communication: I can’t help but wonder how things would have played out if both Esav and Yaakov had an open dialogue with their parents about what each one should expect to receive, perhaps modifying their inheritance based on their respective lifestyle choices.

Properly communicating with our children about money, and what type of financial support they can expect (or not expect) to receive, is incredibly helpful. This will help each child understand what additional resources are available to them. That’s critical information as they structure their life in a way that will allow them to achieve their goals. It can also lead to dialogue amongst the family to ensure no one is hurt or offended. The goal of wealth is to enable each family member to live their best life, not to cause division amongst loved ones.

We all know stories of (or have personally experienced) families who are torn apart by family wealth. Beginning the process of discussing money with your children while they are still young, and making modifications to your financial plan, if necessary, can help ensure that all family members are on solid financial footing and prevent family infighting. Money surprises that arise after the patriarch and matriarch of a family pass away are generally not a good thing. Proper and regular communication can mitigate that risk.

As I often tell my clients, financial planning is not only about the transition of wealth, but also about the transmission of values to the next generation. If the matriarch and patriarch of a family empower their children to lead decent lives, support them according to their unique needs, and communicate in a way that helps avoid family conflict, it will put them on a path towards financial and family success.


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Jonathan I. Shenkman, AIF® is the President and Chief Investment Officer of ParkBridge Wealth Management. In this role he acts in a fiduciary capacity to help his clients achieve their financial goals. He publishes regularly in financial periodicals such as Barron’s, CNBC, Forbes, Kiplinger, and The Wall Street Journal. He also hosts numerous webinars on various wealth management topics. Jonathan lives in West Hempstead with his family. You can follow Jonathan on Twitter/YouTube/Instagram @JonathanOnMoney.