Helping Families Build Financial Confidence
By Jill Dolan
October 2026
There are many things I value about my job at TCV, but at the very top of that list are the long-term relationships we build with our wonderful clients. It is especially rewarding when those relationships become multigenerational, and we get to know and work with the children and grandchildren of many valued clients. This gives us the opportunity to see the benefits of financial education and support over generations.
We typically advise most of our clients to involve their adult children in conversations about their estate planning over time. We find this communication and transparency makes future estate and trust administration less stressful, and it can be a nice segue to making sure children and other beneficiaries put their own estate plans in place. Many of our clients do take this advice, and we assist in talking to their kids about estate planning.
Another suggestion we often make is that clients talk with their families about their own savings and financial planning, but I find that most people are less likely to have these conversations. Financial topics can feel uncomfortable or even taboo to discuss with friends and relatives, and access to other financial education such as personal finance classes in high school or college can be limited. The result is that by the time most people reach adulthood, they have not had adequate opportunities to build the financial literacy needed to make good choices regarding debt, savings, and long-term planning.
The Questions:
- How much should I have in an emergency fund and where should I keep it?
- My workplace has a 401(k) and it has a ton of options. How should I set that up?
- How much of my paycheck should I save in my retirement accounts? When should I increase my savings?
- What investment option is best for me in my retirement account? Should I use a target date fund or something else? Should I invest in stocks or bonds?
- How should I approach a larger financial goal, such as buying a house? Is it okay to decrease retirement savings for a period to prioritize saving for a down payment?
- My employer is giving me stock options. I don’t know what this means or how to manage this asset.
- I own my own business, and do not have a 401(k). What is the best way for me to maximize my savings?
- Should I save more in my retirement accounts, or should I make extra payments on my mortgage instead?
- I want to save money for my new child—what vehicle should I use for this?
- Should I maximize my own retirement savings before saving for my child’s college education?
- Should I take a HELOC to finance a home renovation?
- I’m thinking of buying a second property—what is a budget that would appropriate for this?
- Am I targeting savings goals that would let me retire early? At my current savings rate, when can I expect to retire?
- How much will I be able to spend in retirement?
- If I need long-term skilled nursing care, will my savings support it?
- Is my current asset allocation still prudent given my upcoming retirement?
- What is the most efficient way to manage my various retirement accounts and required minimum distributions?
- I want to make gifts to charities and family members. How should I structure them?
We are always happy to sit down with you and your family members—whether that be a teenager with a first job and wanting to talk about savings (let’s open a Roth IRA!), a young adult with questions about a workplace plan, or parents navigating high daycare costs and the daunting task of saving for college. As Chris Cassidy mentioned in his article, the earlier you begin preparing for financial success, the better.