Why Wealthy Kids Don't Just Have It All Made in the Shade
To set your children up for success, money isn't the only factor. Parents have some major money lessons to teach, or they risk a rocky wealth transfer.
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.
You are now subscribed
Your newsletter sign-up was successful
Want to add more newsletters?
Delivered daily
Kiplinger Today
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more delivered daily. Smart money moves start here.
Sent five days a week
Kiplinger A Step Ahead
Get practical help to make better financial decisions in your everyday life, from spending to savings on top deals.
Delivered daily
Kiplinger Closing Bell
Get today's biggest financial and investing headlines delivered to your inbox every day the U.S. stock market is open.
Sent twice a week
Kiplinger Adviser Intel
Financial pros across the country share best practices and fresh tactics to preserve and grow your wealth.
Delivered weekly
Kiplinger Tax Tips
Trim your federal and state tax bills with practical tax-planning and tax-cutting strategies.
Sent twice a week
Kiplinger Retirement Tips
Your twice-a-week guide to planning and enjoying a financially secure and richly rewarding retirement
Sent bimonthly.
Kiplinger Adviser Angle
Insights for advisers, wealth managers and other financial professionals.
Sent twice a week
Kiplinger Investing Weekly
Your twice-a-week roundup of promising stocks, funds, companies and industries you should consider, ones you should avoid, and why.
Sent weekly for six weeks
Kiplinger Invest for Retirement
Your step-by-step six-part series on how to invest for retirement, from devising a successful strategy to exactly which investments to choose.
A central goal for most, if not all, of our clients with children, is to make sure that their kids are in a position to succeed when they enter adulthood. As parents, they worked their entire lives to make life easier for their children than they had it, and to provide a great education and the freedom to follow their dreams.
For affluent families, one might assume that their children will start their adult life at the finish line. With proper estate planning and tax planning, their children will be the beneficiaries of a considerable estate, so, game over, right? Not so fast.
There are many variables that need to be addressed first. From financial education to stewardship, parents and their children have some work to do together to ensure a smooth transfer of family wealth.
From just $107.88 $24.99 for Kiplinger Personal Finance
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
Financial Education
When children grow up in an affluent household, they may not understand the impact that one financial decision can have on other areas of the family’s finances. For instance, when they passed their driver’s test, they got a car. When they were accepted to college, they went to school. What they might not be aware of is how that car was paid for or how much it actually cost. They may not understand how a loan can be structured, how assets can be owned and used for payment, or even how a large down payment may save or cost money in the long run. To set children up for success, parents should sit down with them and explain how large purchases are evaluated, planned for and made.
In my experience, the most impactful lessons are ones that directly affect the next generation. These opportunities will naturally occur as children grow into adulthood — don’t let them pass you by. When your son or daughter needs a car, apartment or prepares to begin college, take advantage of the fact that they now have some skin in the game and use it as an opportunity to talk through the decisions. Too often, affluent parents simply handle the bills and perpetually delay these discussions, missing the opportunity to talk though real-world examples.
Long-Term Goals
Another key component to bridging this gap is explaining and discussing long-term goals and planning. Like everyone else who’s consumed media on virtually any platform, your children have surely heard of investing and retirement, and may even have a grasp of their significance with respect to their family. However, it is far less likely that they have a good understanding of what planning is.
A prerequisite for discussing planning with your child is honesty — about the extent of your family’s wealth, long-term goals and the challenges you faced to keep your goals intact. In many families of wealth, the children know they live in a nice house, and take great vacations, but may have no real knowledge of the assets their family owns, what the liabilities are, or how much they actually stand to inherit. This can lead to a host of problems, including an overestimation of the family’s wealth or damage to the parent-child relationship inflicted by a perceived lack of trust.
Also important is listening. To have a meaningful conversation with your kids about planning, it’s imperative to be able to listen to what they hope to accomplish, without passing judgment or trying to “correct” their perspective. For example, if your child wants to start a high-end sneaker-trading platform, you should take the opportunity to talk through how one might get such an operation off the ground.
The value of the conversation is that by discussing these ideas in real terms, as peers, not only will you learn more about your child’s aspirations, but you drastically increase the likelihood that they will listen to you.
Family Vision and Personal Responsibility
One thing I’ve learned as a financial adviser for affluent families, is that while many business owners and executives are great at making money, far fewer have a clear understanding of why it’s so important to them. Aside from paying for their children’s education, the purpose of wealth is often hard for people to define.
In my experience, setting a meeting dedicated to the topic, and talking through my client’s concerns and goals, is a best practice I employ to help them define their family vision. Communicating this vision, and engaging their children to clarify the role they will play in the stewardship of the family’s wealth can be powerful tools to help fill that generational gap. And the lessons of stewardship — which typically include budgeting discipline, coordinated planning and asset protection — are incredibly valuable, and will likely prove to be far more important than the actual inheritance they receive.
The question parents need to answer as they build the foundation of their children’s success isn’t how much money to provide, but rather, how prepared will they be to manage and protect it. In our society, money is a taboo subject — parents are trained to refrain from talking about it. I encourage you to break the norm, tell your children your goals and ask them about theirs. It will only increase transparency and trust with the next generation.
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Casey Robinson is the Managing Director of Wealth Planning at Waldron Private Wealth, a boutique wealth management firm located just outside Pittsburgh. He focuses on simplifying the complexities of wealth for a select group of individuals, families and family offices. Robinson has extensive experience assisting multi-generational families with estate planning strategies, integrating trusts, tax planning and risk management.
-
The New Reality for EntertainmentThe Kiplinger Letter The entertainment industry is shifting as movie and TV companies face fierce competition, fight for attention and cope with artificial intelligence.
-
Stocks Sink With Alphabet, Bitcoin: Stock Market TodayA dismal round of jobs data did little to lift sentiment on Thursday.
-
Betting on Super Bowl 2026? New IRS Tax Changes Could Cost YouTaxable Income When Super Bowl LX hype fades, some fans may be surprised to learn that sports betting tax rules have shifted.
-
The 4 Estate Planning Documents Every High-Net-Worth Family Needs (Not Just a Will)The key to successful estate planning for HNW families isn't just drafting these four documents, but ensuring they're current and immediately accessible.
-
Love and Legacy: What Couples Rarely Talk About (But Should)Couples who talk openly about finances, including estate planning, are more likely to head into retirement joyfully. How can you get the conversation going?
-
How to Get the Fair Value for Your Shares When You Are in the Minority Vote on a Sale of Substantially All Corporate AssetsWhen a sale of substantially all corporate assets is approved by majority vote, shareholders on the losing side of the vote should understand their rights.
-
How to Add a Pet Trust to Your Estate Plan: Don't Leave Your Best Friend to ChanceAdding a pet trust to your estate plan can ensure your pets are properly looked after when you're no longer able to care for them. This is how to go about it.
-
Want to Avoid Leaving Chaos in Your Wake? Don't Leave Behind an Outdated Estate PlanAn outdated or incomplete estate plan could cause confusion for those handling your affairs at a difficult time. This guide highlights what to update and when.
-
I'm a Financial Adviser: This Is Why I Became an Advocate for Fee-Only Financial AdviceCan financial advisers who earn commissions on product sales give clients the best advice? For one professional, changing track was the clear choice.
-
I Met With 100-Plus Advisers to Develop This Road Map for Adopting AIFor financial advisers eager to embrace AI but unsure where to start, this road map will help you integrate the right tools and safeguards into your work.
-
The Referral Revolution: How to Grow Your Business With TrustYou can attract ideal clients by focusing on value and leveraging your current relationships to create a referral-based practice.