Every October, National Estate Planning Awareness Week can prompt us to ask a question many of us put off: What happens to what we’ve built — and who benefits — after we’re gone? For Bob Goldman, Managing Partner at the Salem and Boston firm Goldman Drake LLP, that question has shaped an entire career.

An estate planning attorney and Fellow of the American College of Trust and Estate Counsel, Bob has spent more than 30 years helping families think thoughtfully about philanthropy and the legacy they hope to leave—work he first discovered not at a law firm, but through his own passion for giving back.

We sat down with Bob to talk about how families think through charitable gift planning, the misconceptions that hold people back, and what a partner like CJP offers donors who want their generosity to last.

What is it about helping clients think through charitable giving that you find most rewarding? 

For many estate planning lawyers and their clients, charity is an afterthought — a clause that kicks in only if every child and grandchild happens to die out. I actually watched a well-regarded trust and estate lawyer brag on a conference stage once that he always suggests that his clients be charitable when they get to that clause, and it floored me. The reality is, that's a gift that's never going to happen.

Instead, at a subsidiary my old firm set up for strategic philanthropic advising, I got to take grandparents, parents and teenagers through real conversations about their own values and vision, then connect that directly to their giving. That's the part I love: it's not really about the tax benefits. It's the chance for a family to say out loud, across generations, this is what mattered to us, and we hope it matters to you too. Discussing values, exposing kids to your giving, matching a gift if they volunteer or join a nonprofit board—these are conversations I never had growing up, but I speak about them constantly now.

What are the most common ways people build charitable giving into an estate plan?

Donor-advised funds come up a lot. They’re flexible, and they let you take a deduction today for money you’ll give away tomorrow. At your death, your children can take over as the charitable advisors, and these funds can be a great place to leave your IRA and retirement benefits that otherwise are going to be exposed to both income tax and estate tax. For clients who are concerned that their children might need those funds, we designate a trust as the beneficiary that provides that a child can keep these benefits and pay the taxes, or waive the benefits in favor of a donor advised fund with the child as the charitable advisor—free from those taxes.

For wealthier families, I’m a big fan of charitable lead trusts at death. The idea is simple: tell me the base amount you want your children to have, and I write that into the plan. Some specific amount above that base amount (maybe everything above it) goes into a trust that pays all of its assets plus a required interest rate to a charity (including potentially a donor advised fund) over a set number of years.

There is no estate tax due on the amount passing to this trust because all of its assets plus all of its growth (as predicted by the interest rate, which is the only growth that the tax law assumes) is passing to charity. If the trust’s investments outperform the interest rate, that extra growth is “frosting on the cake” that flows back to your kids free from estate tax. Whether there is frosting or not, your children get what you wanted them to have, and the charity gets a meaningful gift.

What themes or motivations do you hear most from clients who include charitable gifts in their estate plan?

A lot of it is about replacing a gift, not just making one. If you’re a major donor during your lifetime, that annual gift ends when you die, unless you plan for its continuation. I tell clients: the charity will struggle to replace your annual gift, but you can ensure they don’t have to. Sometimes that means endowing it outright, even using a life insurance policy. Other clients care more about a cause than one specific charity, so we set up a fund that supports the cause through a community foundation, or an organization like CJP, that can manage it well after they’re gone.

What are the biggest misconceptions about charitable estate gifts?

Here’s one that surprises people: a gift made at death isn’t income tax deductible. If you want that benefit, give during your lifetime. There's a teaching we recall every Yom Kippur, the Jewish Day of Atonement: repent one day before you die. Since none of us knows when that will be, the answer is to repent today, and every day. I tell clients the same logic applies to giving — don't wait.

Another misconception is that once you leave money to a charity, you have no say in how it’s used. That’s not true. You can put restrictions in a gift agreement, and you can authorize someone, or an institution like CJP, to enforce the restrictions. People are relieved to learn that.

A third misconception is that this kind of giving is only for the ultra-wealthy. Some of the most meaningful endowment gifts I've seen come from donors giving at moderate levels over a lifetime — it's not the size of the estate that matters.

What tends to stop people from moving forward, even when philanthropy matters to them?

The number one concern is, “Will my kids need the money?” My answer always is: give your children a base amount first, enough that they’re taken care of. Or, let each child decide what to keep (subject to tax) and what to waive to a charity or to a donor advised fund with the child as the advisor.

Some clients are pleased to make a binding pledge that will make a charitable gift at their death, and they often are happy to receive public recognition for the pledge (as they should be). Other clients are more comfortable with a nonbinding pledge and no public credit until after their deaths when the pledge is paid. My own parents made a gift like that. Their name went on a wall—and then their circumstances changed. My mother was mortified at the idea of taking the gift out of her will, even though she wanted to. Ultimately, circumstances shifted again, and all was fine. Just be careful of pre-death credit for a post-death gift.

My advice: start smaller, start now, during your lifetime. And add to it later at your death, if you can. It’s a lot more rewarding to see your gift at work during your lifetime than to leave it all for later.

What if a client makes a gift but then decides they actually need the money — say, their cost of living or care expenses grow more than expected?

You don't have to give the money away today. If you're worried you might need it later, keep it, and let it pass to charity through your will instead — nothing changes for you now, and the gift only takes effect once you're gone.

If cost of living is a concern, I'd caution against locking yourself into something like a charitable remainder trust, which pays you a fixed amount for life but doesn't let you access more if your needs change. If you're genuinely worried about running short, a revocable deferred gift could be the better tool.

When a client brings up CJP or the Jewish community, what do you tell them about giving through a partner like that?

I want them to know an institution like CJP has the staff to actually follow the restrictions you set and to invest the funds until they spent. These organizations get audited, and auditors check whether restrictions are being honored. That gives people real peace of mind. And, it’s just very Jewish to make your final charitable mark with a Jewish organization.

Bob’s advice comes down to something simple: start the conversation before you think you’re ready, and build a plan that takes care of your family first.

If you’re thinking about your own legacy, CJP’s gift planning team can help. Visit cjp.org/legacy to learn more, or contact Shira Kraft to start the conversation.

Disclaimer: Bob Goldman’s ideas are of a general nature and should not be considered legal advice. CJP does not provide tax, financial, or investment advice. If you have any tax, investment, or financial questions, please consult your own qualified advisor or counsel.