My son entered the United States Military Academy as a member of the Class of 2026. Having attended West Point myself, I did my best to prepare him for what he was to encounter. There’s an old joke about that small military school on the Hudson: “220 years of history, unimpeded by progress.” So, it was with great confidence that I shared expectations from an experience I had 25 years prior. While most of them held true, there have certainly been many good and thoughtful changes.
However, it’s been comforting to learn that the things you’d want to see stay the same when preparing future leaders have indeed remained constant.
The struggle is part of the programming, failure is a required experience, and fortitude still wins the day. Yes, there are laptops instead of PCs, tablets instead of legal pads, electronic security measures instead of a rubber doorstop, and submission websites instead of hard copies in brown bomber folders. But there’s still daily drill with rifles and sabers, every Plebe (freshman) still takes boxing (male and female), there are still customs and courtesies observed, still more homework than is possible to complete, and still a healthy disdain for that academy south of us that plays with boats. Every new generation that joins The Long Gray Line finds better tools and new perspectives while fulfilling the same mission.
But this is a blog about money because this is a financial event supported by a financial firm, and I’m a financial advisor. So what’s the parallel?
Teaching your kids about money has the same generational impact as the aforementioned historical institute of higher learning: many things may change, but the main thing stays the main. There are obvious new tools and perspectives that have impacted wealth savings and management, such as Apple Pay, Venmo, Robinhood, cryptocurrencies, Reddit, and many others. But disciplined stewardship, opportunity cost, understanding debt, and communication are still the backbone of personal finance. If the mission is still to retire with dignity and have the financial freedom to be philanthropic, then your duty is to pass on your wisdom regarding these consistent pillars to your next generation. And as luck would have it, I have a blog that will make for a handy resource in arming yourself for such a campaign.