When it comes to passing down wealth, the biggest question isn’t just how—but when. Should you give while you’re alive to see the impact firsthand or structure your estate to provide for loved ones only after you’re gone? How do you navigate fairness, avoid creating dependency, and ensure your legacy aligns with your values?
Julia Tierney, CFP®, Director of Legacy Planning at Vista Capital Partners, and Emily Karr, Partner at Stoel Rives LLP and Chair of Benefits, Tax and Private Client Group, recently led a panel discussion titled “A Gift in Life or Death? The Tough Choices of Family Wealth.” Moderated by Rob Greenman, CFP®, Chief Growth Officer of Vista Capital Partners, the conversation unpacked the emotional, financial, and practical factors that shape decisions around giving now versus later.
What emerged was a broad spectrum of perspectives shaped by values, life stage, and family dynamics. While there’s no one right answer, it’s clear today’s families are looking for ways to make giving more intentional, aligned, and meaningful across generations.
Values and changing perspectives
Julia Tierney shared that her team is seeing clients come in with new perspectives about money. “More and more clients are thinking beyond the numbers—reflecting on how their values are expressed through their wealth and what message that sends to future generations.”
Tierney emphasized that not everyone thinks about money the same way. “Each generation has different values and experiences that shape their views on money.” For many, that includes a desire to do things differently than their parents, especially when it comes to openness. “We often hear from clients who grew up in households where money wasn’t talked about or it was a source of stress. Now, they want to shift that narrative by creating transparency, sharing values, and making intentional choices that reflect who they are.”
There is truly no right or wrong way to approach these conversations. Each person has to decide what works for themselves and their families.
Questions to consider:
- Are your family members aligned in their financial priorities and values?
- How might generational perspectives influence family discussions about wealth transfer?
- How can you ensure that each generation understands your intentions and values?
The impact of rising costs and lifespan
Emily Karr addressed the practical concerns many clients face today, particularly regarding rising living costs and increasing lifespans. “People are living longer and want to ensure they have enough to take care of themselves, but they also want to support their children or grandchildren,” Karr said. “The challenge is finding a balance between providing support now and preserving assets for later.”
Karr also noted how living longer creates a timing dilemma where adult children could potentially be into their own retirements before receiving any money, which doesn’t always sit well with her clients.
Questions to consider:
- How is flexibility built into my plan, given the uncertainty around life expectancy and future expense?
- If I wait until death to pass on assets, will it still be useful—or meaningful—for my grown children?
Minimizing taxes through gifting
Karr offered practical insights on how clients can use lifetime gifting to reduce estate taxes and support their loved ones particularly in states like Oregon and Washington where estate tax exemptions are relatively low. “You can give $19,000 per person per year—or $38,000 as a couple—without having to file a federal gift tax return,” Karr explained. She also reminded attendees that certain payments, such as tuition or medical expenses made directly to the provider, don’t count as taxable gifts at all.
In addition to these annual gifts, Karr encouraged clients to think about the trade-offs: while lifetime gifts can reduce your taxable estate, they may also pass along a low-cost basis, potentially triggering capital gains for your heirs later. That’s why she emphasized the importance of working with a team of professionals to weigh both the tax implications and your long-term goals. “It’s not just about saving on estate taxes. It’s about making thoughtful decisions that reflect your values and your family’s needs.”
Questions to consider:
- Am I using annual gifts or direct payments to support family members in tax-efficient ways?
- Have I considered how capital gains could affect my heirs based on the assets I give?
- What professional guidance do I need to ensure my gifting strategy supports both my tax goals and family relationships?
Fairness, communication and family dynamics
Fairness in wealth transfer is a deeply personal and nuanced decision—one that doesn’t always align with strict equality. While many families divide assets evenly, others choose to account for individual circumstances, such as giving more to a child with greater financial need. There’s no single “right” approach. As Tierney shared, “We really encourage clients to gain clarity on what fairness means to them and to their children.”
What matters most is that these decisions are made thoughtfully and, when possible, communicated clearly. Open dialogue can help ensure that loved ones understand the intent behind the choices, reducing the risk of hurt feelings or lasting resentment.
Questions to consider:
- What does fairness mean to me? How might that differ from equality?
- Are there meaningful differences in my children’s circumstances that I want to account for in my plan?
- Have I clearly communicated my intentions to avoid confusion or unintended hurt feelings?
Avoiding dependency while providing support
One concern that came up throughout the panel was the risk of creating dependency through lifetime gifts. While many clients want to help their children or grandchildren, especially with rising living costs, they’re also mindful of preserving a sense of independence and purpose. Karr noted that many of her clients are worried about “not wanting to ruin my kids or grandkids through substantial annual gifting. They don’t want them to miss that opportunity for self-achievement.”
For that reason, Karr mentioned it’s rare to see families initiate significant gifts before their kids reach age 30, unless it’s tied to a specific event like tuition, medical expenses, or a first home purchase. Even financially responsible adult children often benefit from structure and guidance when receiving larger gifts. Some families are getting creative, making modest gifts of investments and then meeting quarterly to review and learn together, fostering both stewardship and connection.
Others involve trusted advisors early on to help coach or mentor the next generation, ensuring that any wealth passed down supports, not sidelines, their personal growth.
Questions to consider:
- How can I support my children or grandchildren without undermining their independence or ambition?
- Are my loved ones ready, emotionally and financially, to receive a gift?
- Should I consider strategies or structures, such as trusts, to help steward the gift?
Communicating legacy wishes
Legacy letters emerged as a valuable tool during the panel discussion. Unlike a legal will, a legacy letter conveys personal values, life lessons, and hopes for future generations. “A simple legacy letter can be a powerful tool,” said Tierney. “It doesn’t have to be perfect—it just needs to start a conversation.”
Karr agreed, highlighting that such letters can help avoid misunderstandings and emotional turmoil, particularly when dealing with assets like family vacation homes or closely held businesses.
If you’re ready to write your own, Vista created a Legacy Letter Kit to help you get started.
Conclusion: The power of planning
As the panel wrapped up, Greenman reminded attendees that planning is not just about financial strategies—it’s about aligning actions with values and creating a roadmap for family harmony.
If you’re looking for guidance on wealth transfer and estate planning, Vista Capital Partners is here to help. We encourage open conversations to help families make the most of their resources while strengthening their relationships.
