Bob and his wife Diane wanted to honor Al Hayes, the much-loved principal of Tacoma’s Stadium High School who had been forced into early retirement by a serious heart condition – and they didn’t want to wait decades for their wills to achieve this charitable giving end. With Bob in the early years of his law practice and Diane a teacher, they didn’t have the financial means to make a grand gesture of philanthropy. Was there some meaningful yet affordable way to honor Principal Hayes through planned giving before he – or they – passed away?

The answer was provided by nonprofits: specifically, the Greater Tacoma Community Foundation (GTCF), then in its infancy. With the Foundation’s help, Bob and Diane created their first planned giving venture – a scholarship fund named after Principal Hayes which would be administered through the Foundation.

Thanks to the GTCF’s financial planning savvy and commitment to helping people with modest means achieve their charitable giving goals, Bob and Diane were able to do what seemed impossible. With their initial gift of $1,000 and their promise to make annual gifts to the fund at this level, the GTCF was able to award the first scholarship within a few months and ensure it would continue to be awarded every year, meeting their highest aspirations for giving.

And so, a few months after meeting with the GTCF, and then every year until Principal Hayes passed away, Bob and Diane had the pleasure of bringing the man they had honored to Stadium High School’s annual awards assembly, where the scholarship created in his name was awarded to a student who was then able to thank the man who inspired such generosity.

This was not Bob’s only charitable giving effort. As Evelyn Ryberg, Senior Director of Philanthropic Services at the GTCF observes, Bob “makes [philanthropy] a part of everything he does” – including, for example, talk radio. Angered by scam artists selling low-grade annuities for a high profit to the elderly, Bob realized that part of this problem was the failure of attorneys and financial advisors – including himself – to help clients by educating the public about the law. The Letter to the Editor he wrote to this effect sparked multiple invitations to be an expert guest on Seattle talk radio. These appearances were so successful that Seattle powerhouse radio station and CBS affiliate KIRO offered Bob his own call-in talk show about legal issues. Through his show, Legal Line with Bob Pittman, Bob helped thousands of listeners comprehend the law relevant to whatever civil problems they were grappling with, such as landlord-tenant disputes or wrongful termination from a healthcare plan. Although Bob wouldn’t give legal advice over the air, listeners would come away from the discussion with a clearer understanding of their problem and the resources they could turn to for additional guidance.

Among the most unforgettable of the thousands of listeners who turned to Bob for help was the widowed father of an infant. Bob was broadcasting live, on location, from Seattle’s Kingdome sports arena, with the game in progress. Rather than take his chances calling in on the phone, the distraught man, clutching his baby, used some of his last few dollars to buy a ticket in the desperate hope that if he got to the stadium box Bob was broadcasting from and appealed to him in person, Bob might take his question – and Bob did. The newly widowed man, overwhelmed by his late wife’s medical bills, had fallen behind on his rent. When he returned to his apartment, he found his landlord had locked him out – an entirely illegal act that the landlord felt safe performing with the knowledge that his tenant didn’t have the money to hire an attorney and assert his rights. Bob was able to secure appropriate legal help from an area agency for this frightened and suddenly homeless father.

Bob’s efforts to educate the public about the law through his radio show were so successful the he was honored by the Washington State Supreme Court in a special Court Resolution. Bob also received the Excellence in Legal Journalism Award, conferred by the Washington State Bar Association, and the Consumer and the Law Journalism Award, presented by the Washington State Trial Lawyers Association.

Bob’s passion for philanthropy is also reflected in his law practice, which focuses on estate planning. Bob enjoys helping his clients find active ways for parents and grandparents to teach children about wealth management and philanthropy. “How else can you have so much fun for so little money?” he jokes. One such client – we’ll call her “Grandma Jane” – created a charitable giving learning experience Bob took part in which he found especially moving. Grandma Jane had given each of her three grandchildren $100. “You’re each the CEO of your own philanthropy,” she explained to them. “Find a charity where you’d like to spend that money.” The next time she got together with her grandchildren, she asked each child to tell the story of the charity the grandchild had chosen, explaining why they chose those nonprofits and what they would be doing with the $100.

What especially touched Bob was the field trip the family took to a clothing bank one child had chosen as the recipient of their planned giving. After leading Bob and Grandma Jane on a tour of the facility, the young donor announced, “Now [my classmate] doesn’t have to come to school in the same shirt every day.”

Bob is optimistic that Grandma Jane’s strategy will have lasting results, imagining warmly, “When Jane’s grandchildren are 50, what will they be like?”

In response to Bob’s account of this venture into philanthropy, Dien Yuen, J.D., Blunt-Nickel Professor at The American College of Financial Services and CAP® program faculty member, observed, “Never underestimate the power of the small planned giving gesture!”

In 2015, while serving as a Board Member for the Greater Tacoma Community Foundation, Bob learned about The College's CAP® program from Evelyn Ryberg, the GTCF’s Senior Director of Philanthropic Services. Evelyn had heard about the CAP® designation from colleagues at other community foundations and recognized how its unique curriculum could enhance her organization’s ability to serve their community. When Evelyn described the program to Bob and asked if he’d like to join her as part of the Foundation’s first cohort of students to pursue this continuing education designation, his response was an enthusiastic “Yes!” Both Bob and Evelyn were awarded their CAP® designation in 2016.

For Bob Pittman, what drives effective philanthropy isn’t wealth management or connections or technical expertise: it’s respect – respect for donors, for clients, and for the communities their charitable giving uplifts. Bob has become a champion of the CAP® designation program because the coursework reflects and promotes such respect among professionals across different segments of the philanthropic space. By breaking down the silos that traditionally separate financial, legal, and nonprofit professionals, the CAP® designation program creates the conditions that enhance philanthropic uplift. “There’s nothing like it,” Bob asserts.

When Bob worked with the GTCF to set up the Al Hayes scholarship decades ago, little did he know that his generosity would someday come full circle. In gratitude for Bob’s service on their Board and for the Pittmans’ unflagging service to their community, the Greater Tacoma Community Foundation has created a scholarship in their name to assist students enrolled in the CAP® designation program with tuition costs. Because of Bob and Diane’s special commitment to helping individuals and communities of color, the scholarship is designed to help advisors of color and nonprofit professionals who serve diverse communities.

On the wall of his office, Bob has a beautiful watercolor of Thurgood Marshall, the first Black justice to serve on the U.S. Supreme Court. Justice Marshall’s reflection on philanthropy – like Bob Pittman’s life – reflects the spirit that informs the Chartered Advisor in Philanthropy® program and inspires those who hold this designation to make philanthropy a more responsive and more respectful enterprise: “None of us got where we are solely by pulling ourselves up by our bootstraps. We got here because somebody – a parent, a teacher, an Ivy League crony or a few nuns – bent down and helped us pick up our boots.”

Many families find the vision of a shared family philanthropic venture appealing, but all too often, the reality of the experience is a far cry from the dream. In this article, I outline the philanthropic journey through which I have accompanied several families and the successful approach through which we together developed a flourishing, multigenerational Family Philanthropic Enterprise.

First, let us look at two common if unspoken assumptions that underlie well-intended but floundering family philanthropy:

The Road to Disappointment #1: We want our children and grandchildren to be philanthropic, just like us. Read: How did such generous people as we are raise such selfish kids?

The initial impetus for family philanthropy often arises from unflattering observations like these: Our children no longer want to sit at the Platinum Donor Table at the Our Favorite Charity Gala where we are always recognized as big donors. What this tells us is that our children have become selfish. We can set them back on the right course by immersing them more fully in philanthropy. Some of our friends have private family foundations, what a perfect solution! The Mom and Dad Family Foundation. Our children will love it!

Almost always, however, they will not. Even worse, the children’s current apathy may turn into hostility, with the demand they spend increased time and effort focused on their parents’ causes, however laudable and successful these charitable efforts may be.

A true Family Philanthropy Enterprise is a process. It is a journey, not an event. At its best, family philanthropy is done “with” your family, not “at” them. Children and grandchildren many times do not enjoy the spotlight because they find themselves once again standing in their parents’ shadow at an event held by an organization to which they have no emotional connection that supports a cause to which they are indifferent.

The Road to Disappointment #2: We are all going to sit down together as a family and decide who we will give money to this year. Read: Dad and I have chosen these four charities. You kids can suggest but not decide how much Dad and I will give each one.

This well-intended approach, like The Road to Disappointment #1, continues to conceive of family philanthropy as hierarchical in organization and operation, with Mom and Dad at the pinnacle. Rather than bringing generations of family together, such an approach is more apt to increase frustrations for all involved.

Changing the Conversation: Impact and the 1040 Foundation. Instead of focusing on “giving away,” families on a successful philanthropic journey concentrate on creating impact significant to both a cause and to the individual family member. This is the essence of what I call the 1040 Foundation. Following is an example of how such a foundation might work.

Mom and Dad (or Grandma and Grandpa) take an annual charitable deduction on their IRS Form 1040 of between $100,000 and $150,000. Based on their income, this is below the percentage rules for charitable deductions for cash gifts to public charities. The donors are deeply interested in seeing their children become more active in philanthropy, but they have experienced frustrations such as those described above. In seeking a means of involving their children more deeply in philanthropy, they consider establishing a private family foundation as some of their friends have done, but those friends have experienced mixed results.

The donors discover another alternative in their church newsletter, which describes how they can establish a donor advised fund within the church’s own foundation. Unsurprisingly, they find the complex tangle of rules involved confusing, and contact their family wealth and estate advisor for additional guidance. After exploring with their advisor how well different philanthropic models match their family’s circumstances and responsibilities, Mom and Dad decide to create the Smith Family 1040 Impact Plus® Fund.

The Smiths invite their adult children and grandchildren to their favorite resort, where they have reserved rooms for everyone for the weekend. Included in the activities is a 90-minute gathering of the adult children on the Saturday morning, during which their advisor will introduce the plan. Having a professional advisor, rather than Mom or Dad, describe the plan helps create a sense of psychological distance, emphasizing the shift from passively hearing about yet another “charity thing Mom and Dad are doing” to a new venture in which every person present will enjoy real, active ownership.

A 1040 Impact Plus® Fund works in two stages: the Seed Stage and the Sprout Stage.

The Seed Stage: The Smiths have five adult children, ages 19 to 28, two of whom are married. Each unmarried child can allocate up to $5,000 to impact something they care about; each married child splits their $5,000 allocation with their spouse, with the couple left to decide whether they wish to combine funds or work separately. Although the Smiths also have grandchildren who will eventually be folded into this enterprise. It is important that the initial stage should concentrate on building the philanthropic skills of the adult children. They will subsequently use what they have learned to inspire and educate their own children.

The ground rules for the Seed Stage are simple, with guidelines such as these provided the adult children:

• Begin with a cause, not an entity. What do you want to see more of in the world, or less of, or ensure is preserved for future generations? A simple exercise is to look at a newspaper and circle in green what you want to see more of, and circle in red things you want to see less of.
• Using a service such as Charity Navigator or your local community foundation, identify nonprofit organizations in your community that focus on your chosen impact area. The only requirement is that the organization must be a 501(c)(3) and qualify for a charitable income tax deduction.
• You can spread your $5,000 impact gift among up to three charities, giving each a minimum of $1,000.
• Once you have selected the organization(s) you wish to fund, complete the 1040 Impact Plus® Grant Request Form, which includes the following information:
  • The name and address of each organization to which you plan to donate.
  • The organization’s Tax Identification Number (TIN).
  • The name of the organization’s contact person.
  • A 250-word description of what the organization does; and
  • A 400-word “passion statement” that expresses why this cause matters to you and how the organization(s) you have chosen will achieve impact with your gift.
• The family will gather annually to review together each member’s Grant Request Form, for each to learn more about what matters to you and about the community organization(s) you have chosen. Each meeting is presided over by the 1040 Impact Advisor, not by Mom and Dad.
  • Your choice is already considered final before the meeting. It is not subject to a vote by anyone else in the family.
  • Each family member is to assume, regardless of what they may privately believe, that others’ choices are made thoughtfully and in good faith. The discussion should be as civil, supportive, and encouraging as possible. The meeting is neither a debate forum nor a competition, and “constructive criticism” is prohibited, as all present have already made their funding decision.
• Shortly after the conclusion of the meeting, we will prepare the appropriate check(s) and gift letters(s) so you can make an appointment to deliver your gift(s) in person. We suggest you invite another family member to an even fuller understanding of your giving choices, with respect to both your cause(s) and the nonprofit(s) whose mission concerns them.
• So, what does all this accomplish? We named this approach 1040 Impact Plus® because it goes beyond identifying worthy causes and writing checks in several ways:
  • Each family member can explore and explain their individual philanthropic goal and journey. This is the most critical aspect of 1040 Impact Plus®, and, perhaps, the most challenging for Mom and Dad. It is important that truly little be “out of bounds” in terms of causes. In the initial rollout of the plan, the advisor must stress to all parties the nonjudgmental nature of this undertaking. The passion statement is important not only as the personal expression of a family member’s deepest concerns, but also as a means of helping other family members develop or deepen their empathy for a cause dear to someone else. Failing to do so is likely to result in donors making allocations not for the purpose of relieving human misery, but out of an impulse to inflict a bit of misery on a judgmental family member.
  • Each family gets to have the visceral experience of impacting something that matters to them.
  • The family acquires a deeper, fuller understanding of (and, ideally, increased respect for) other family members in ways not previously possible; and
  • Financial wealth transcends from the merely material into a tool that makes life more meaningful and joyful for the individual and which enhances intrafamily relations.

Some families, regardless of net worth, retain their Seed Stage Family Philanthropic Enterprise for years. They like its simplicity, the kind of interactions it stimulates, and the sense it offers of making a real impact. Other families, however, prefer to expand their philanthropic efforts into a more formal structure that can be cultivated across generations. Enter the Sprout Stage with the Donor Advised Fund.

The Sprout Stage: The Family Donor Advised Fund (DAF). The family described above kept the Smith Family 1040 Impact Plus® Fund as their philanthropic engine for three years, which translated into six rounds of impact gifts. After the first round, they so enjoyed it (and each other) that they decided to make impact gifts every six months rather than just annually. As the family is geographically dispersed, they held the fall round in person around Thanksgiving and the spring round virtually via Zoom and an accessible document-sharing program like Google Docs or DropBox.

The success of this process prompted the family to try something “more permanent” in structure. Mom and Dad want philanthropy to be part of their legacy for children, grandchildren, and beyond. After discussion with their advisor, the family decided to establish a DAF using the Smith Family 1040 Impact Plus® Fund name. While the details of this process will be reserved for another column, two key factors enter into this decision:

• The sponsoring organization that is to hold the family’s DAF must have a broad mission and purpose statement, so that the diverse interests of the family can be accommodated now and in the future; and
• A clear methodology must be laid out to establish a family advisory board and assign key roles and a succession plan for those who hold them.

Although Mom and Dad initially fund the DAF with $500,000, all fund assets are considered communal family property to be used for the purpose of supporting causes important to individual family members. This marks a major shift in mindset for Mom and Dad and for all family members who have come to appreciate how much their philanthropic enterprise has benefited them as individuals as well as their relationships with the other family members. Decisions around the philanthropic dollars are made by all involved adult family members. Structurally, the Sprout Stage requires the coordination of two administrative structures, one internal, the other external.

Internal: The DAF is governed by a board of advisors composed of all adult family members. The advisor serves in an ex officio capacity, convening these meetings and ensuring minutes are kept to record important decisions. One member of this board also serves as a liaison to the investment manager.

External: Every DAF has a sponsoring organization, and it is in the interest of both the family and that organization to identify which family members will serve as contact persons. Two members of the board of advisors serve in this capacity, one as the contact person to the sponsoring organization, the other as the successor to that position, who shadows the contact person. The contact person’s term of office is two years and when that term draws to a close, the successor assumes that role.

Although membership on the board of advisors is mandatory for adults who wish to participate in this enterprise, service as investment manager liaison, and as sponsoring organization contact person is encouraged but not required. Should no family member be available to assume such responsibilities, the advisor may do so in their stead.

In addition to having a more complex philanthropy structure than the Seed Stage, the Sprout Stage also expands the philanthropic experience to include grandchildren on an age-appropriate basis. The Grandchildren’s Philanthropic Enterprise occurs once a year around Thanksgiving or whenever the in-person philanthropic round is held. Grandchildren are eligible to request grants under terms like the adult enterprise:

• Elementary school-age: $100
• Middle school-age: $200
• High school-age: $500
• Age 18-20: $1,000
• Age 21-24: $2,000
• Age 25 and up: $5,000

With its extension to another generation, the Sprout Stage philanthropic process needs to be a bit more complex because of its educational purpose. Minors are required to do a brief, ageappropriate presentation to the extended family attending the annual Family Philanthropic Enterprise meeting. This is a tremendous learning opportunity for all. The little ones need some help from their parents, a process parents find to be rich with opportunities to deepen their bonds with their children. I have had the joy of watching a 5-year-old present his allocation of $100.

Using a white posterboard covered in glued-on pictures (and with a little help from his mom), he described his desire to impact the local volunteer fire company because “they protect us from fire.” The smile on his grandfather’s face at hearing this little boy’s passion concerning his chosen cause was filled with transcendent joy and with hope for the future of his family. Older children have also impressed their family with the unexpected sophistication in problem-solving they reveal. Several cousins in their late teens, for example, combined their allocations so they might have a greater impact on a cause that mattered to them all.

Once the family has enjoyed a successful DAF experience, they may wish to move from the Sprout to the Seedling Stage to establish a private family foundation that will expand even further the family’s impact on their community and on each other. The journey to this considerably more complex destination must never be rushed. Each of the many aspects involved in running a family foundation must be explored thoroughly with the guidance of the advisor and funding area-appropriate professionals.

Like parenthood itself, growing philanthropy within a family is a process that cannot be hurried. A family philanthropic enterprise is most successful (and enjoyable!) when its members mutually encourage the gradual but real unfolding of independence and empathy over time. Our approach is designed to ensure the family philanthropic journey is less a Road to Disappointment and as much a Highway to Heaven as circumstances permit.

Tim Belber is adjunct professor of estate planning at The American College of Financial Services and holds the Charles E. Drimal chair in estate planning. He teaches in the Chartered Advisor in Philanthropy® (CAP®) program. Belber is the author of “The Middle Way: Using Balance to Create Successful Generational Family Wealth Plans.” He has authored numerous articles and has been quoted in periodicals including the Wall Street Journal. He is a member of the Legacy Wealth Coach Network, a founding member of the Collaboration for Family Flourishing, and a dean for the Purposeful Planning Institute. He can be reached at tim.belber@theamericancollege.edu. 

The Beach Jumper’s Mission

Cubeta was chosen to head the CAP® program by its funders, Bill and Sallie Wallace. A first-generation college student, Bill attended Columbia University on a football scholarship and became an All-American player. Wallace’s altruism and courage led him to become a “Beach Jumper” during the Korean War. Organized during World War II by Naval officer and Hollywood star Douglas Fairbanks, Jr., the Beach Jumpers were U.S. Navy Special Forces officers who performed among the most dangerous jobs in the war. If you’ve not heard of the Beach Jumpers, that’s no surprise, for their missions were considered even more classified than those of Navy SEALs—the organization the Beach Jumpers would eventually inspire.

After the war, Wallace chose a new challenge that drew, in a different way, on his tenacity and concern for others’ well-being: he became an insurance agent. His gifts and strength of character led to his rise through the profession to become the head of Home Life, and to his winning every award the insurance world has to offer. A pioneer in what we’d now call “values-based planning,” Wallace became one of the most admired and revered professionals in the industry.

Wallace also became a leader in the philanthropic world. He knew that financial advisors touch expanding circles of many, many lives, influencing people at inflection points at which they make their most important decisions about life, loved ones, and legacy. If advisors were more open to discussing philanthropy with their clients, he reasoned, they could do enormous good. Wallace also recognized a systemic problem in the philanthropic world: that the nonprofits who sought Bill and Sallie’s help understood their hearts, but knew nothing about their money. Meanwhile, financial advisors knew everything about their money, but were cold as ice when it came to discussing philanthropy. How, Bill wondered, might these two siloed, sometimes even adversarial, worlds be brought together to maximize the good that might be done?

The Mission 

The solution Wallace devised was a sophisticated program that would teach financial advisors and nonprofit gift planners how to work together for a common purpose. They wanted nonprofit professionals to be able to play a key role in a donor’s financial discussions—to be as much a part of an estate-planning team as trust officers are—and financial professionals to be comfortable helping their clients not only accumulate wealth, but also make use of it in a manner the client finds most rewarding. No such program had ever existed. But who better than a Beach Jumper-turned-insurance professional to calibrate risks and develop and execute a winning strategy?

The most important factor in the success of Wallace’s plan was to find a head for the program who shared Wallace’s vision: an expert in finance with a nonprofit sensibility. He found that leader in Phil Cubeta, an insurance executive with strong liberal arts sensibilities and a profound commitment to uniting communities to alleviate human suffering. “CAP® is exactly what they’d planned to do,” Phil observes, “and it’s exactly what I wanted to do.”

Now in their 90s, the Wallaces remain active and in good health and continue to follow the program closely. They respond to the quarterly reports they receive with expressions of their gratitude for a program which has not only realized, but far exceeded, their dreams.

“They have created almost a mini-distribution system for philanthropy, built around financial advisors and fundraisers, and that was their dream,” Cubeta says.

Mission Accomplished 

Early on, Cubeta realized the program would enhance its reach and success by organizing study groups of students taking CAP® courses, but was unsure how best to make this happen. Then, in Dallas in 2010, with leadership from Todd Healy, MSW®, CLU®, ChFC®, AEP®, CAP®, Founder of C3 Financial, Jackie Franey, CAP®, now Director of Gift Planning with The Nature Conservancy, and Jayne Grimes, now Senior Director of Gift Planning at Buckner International, a local study group began to form. Cubeta went to Dallas to address 40 prospective students convened by Healy, Franey, and Grimes at Communities Foundation of Texas.

At first, the meeting didn’t go well. Despite Cubeta’s eloquent description of the program and how their participation in it would benefit their practices and their clients, the audience of wealth advisors remained polite but unpersuaded. Then, Jayne Grimes took the microphone. “Everything Phil said is true, but that’s not why we’re doing it,” he said. “We are doing this for Dallas. We want Dallas to be the most generous city in America!” The result was electric. Eager to become a part of this effort, every person in the room waited patiently in line to sign up.

It was then that Cubeta realized the advisors drawn to the CAP® program aren’t persuaded by the prospect of greater wealth accumulation—which is, after all, already their area of expertise. What draws the subset of wealth advisors to CAP® is an altruistic desire to use their skills to help their communities.

The success of the Dallas group inspired the creation of several dozen other city-based CAP® study groups across the U.S. These groups have significantly enhanced the amount and impact of local giving. Over a five-year period, for example, $1.4 billion of philanthropic efforts can be traced to the 43 advisors in the CAP® Omaha Study Group alone. At any given time, 15-20 study groups are active or in formation. Most are local, some are national, and some are based on groups of affinity.

Recently, George Nichols III, President and CEO of The American College of Financial Services, joined the Philadelphia Study Group. Dien Yuen, JD, LLM, CAP®, AEP®, Assistant Professor of Philanthropy and Blunt-Nickel Professor in Philanthropy at The College, also organized a national study group for Advisors of Color, with 100 slated to complete CAP® over the next year or so.

Mission Forward

The College was originally founded as “the insurance college,” whose mission was to professionalize life insurance sales and thereby serve the public, but that mission has now expanded beyond the insurance industry—and indeed, beyond even financial services. The College continues to flourish by helping our students make a very real difference in the lives of those they serve and to the larger communities of which they are a part. The CAP® program is leading the way.

One of the keys to philanthropic success is proper financial planning. Through the three-course Chartered Advisor in Philanthropy® (CAP®) designation program, you will learn how to help philanthropies maximize their donations and resources. The CAP® is designed for experienced professionals in both the financial services and nonprofit sector, and gives you the power to do more with your career.

In 2016, Amanda asked her peers at Wells Fargo Private Bank if they’d like to start a philanthropy book club. Immediately, 20 fellow advisors agreed to read a book a month together for 11 months. As word about the book club spread, friends of members asked to join, and then friends of friends, including from beyond Wells Fargo. The 60 current members include CPAs, attorneys, members of private foundations, and nonprofit professionals.

Choosing books that will appeal to this diverse membership—that will provide cohesion and inspiration—is no easy task. Initially, Amanda chose the books herself, balancing instructive works (like Give Smart by Joel Lawrence Fleishman and Thomas J. Tierney) with inspirational, real-life stories (like The Blue Sweater by Jacqueline Novogratz). As the group grew larger, she solicited suggestions from club members, with books chosen by votes from their recommendations.

The book club also provides an excellent opportunity for building trust and networking with professionals outside one’s own field. The club’s cross-disciplinary approach enables its members to establish meaningful connections rooted in philanthropy with professionals they might not otherwise have met, or met only superficially, and makes interdisciplinary discussions about philanthropy not merely comfortable, but enjoyable.

The Book Club Turned Philanthropic Organization

Although she values book-learning about philanthropy, Amanda also values experiential learning. Most members had not, for example, been a nonprofit leader responsible for working with a board to raise funds. “I wanted our book club members to get that philanthropy-induced panic in the pits of their stomach,” she said. “So I threw out a suggestion that the club should actually raise money for something. We’d just finished reading Adam Braun’s The Promise of a Pencil: How an Ordinary Person Can Create Extraordinary Change [the best-selling account of the founding of Pencils of Promise, a nonprofit that builds grammar schools in developing countries]. And so I said, ‘I think we should raise $30,000 and build a school for Pencils of Promise.’”

Amanda anticipated some pushback: book club members were, after all, typically working long hours and preoccupied with their own lives. But the entire club enthusiastically agreed. They created a fundraising page and raised over $30,000 in about six months. Today, somewhere in Ghana, stands a school bearing a plaque that identifies it as a gift from the Wells Fargo Book Club.

The club then began looking for another project to continue the real-world application of their knowledge of philanthropy, identifying their top three priorities as youth development, education, and hunger. Even before choosing a new charity, they began raising money by contributing dollars-per-minute for “spin” riding. While pedaling away, a friend spinning next to Amanda told her about Project Avary, a nonprofit that provides a 10-year mentorship program and summer camp for children whose parents are incarcerated. This seemed like a perfect fit to Amanda, and the club agreed. Soon, Amanda and the other club members were spin-riding for inmates’ children.

Partway through that ride, however, the instructor of the class took Amanda aside and asked if she could share something with her: “My mom was one of those little kids waiting outside of the prison to go in and see her dad. My grandfather was in San Quentin.” It was a sign of things to come. A few weeks later, the same instructor asked Amanda for help with an unusual fundraising project: San Quentin inmates wanted to raise money for Project Avary by holding a walk-a-thon behind bars, and they needed someone to help on the outside. Amanda agreed, and the dual event was such a great success the walkathon was held again the following year. Amanda was especially impressed by the prisoners’ efforts: most earn only 13 to 90 cents per hour, yet they raised $800: a substantial sacrifice of the small luxuries that make their lives more bearable.

As plans for a third walkathon were discussed, Amanda contacted the leadership of Project Avary. “I said, ‘Wouldn’t it be great if we could go in and talk with the group of men who are putting on the walkathon?’” she recalls. “‘We could teach them about values and philanthropy and fundraising, so that they could do even better at raising money.’” With Project Avary’s help, Amanda obtained permission to conduct a philanthropy workshop inside San Quentin itself.

The Philanthropists on the Inside 

Built in 1852, San Quentin is a high-security facility, with multiple checkpoints before one emerges into an exercise yard where armed guards keep constant watch from a runway above. The workshop was housed in the prison’s educational center, with Amanda sitting at a large table, around which sat men of all ages, each with more distinctive tattoos than the last. Amanda had decided to open this workshop using an exercise she’d found helpful with her wealth advising clients. She divided the men into groups of four and played a card game designed to help people identify their core values and test them against others’ perceptions of them. Like her clients, the prisoners enjoyed the game.

When that session ended, Amanda remembers one participant told her, “‘I never even thought I HAD core values.’” Another observed that he’d never realized how much he valued compassion, which he could now use to refine his approach to fundraising. “‘We go from cell to cell asking for money for the walkathon,’” the man said. “‘Instead of coercing people, I can now use compassion, because I know it's one of my core values.’”

In the next session, Amanda asked the inmates what it meant to be a “philanthropist.” They offered the usual answer: “‘They’re people who give lots of money.’” Amanda helped the men extend that definition beyond the giving of treasure to include gifts of time and of talent. One point especially hit home with the men. “Look,” she said, “you’re putting on a walkathon to raise money for charity, giving your time to do this. You put together a public service announcement to get people involved. So you’ve given your money, you’ve spent time collecting donations, and you used your talent to market the event. You know what that makes you?”

There was silence.

“You’re philanthropists.”

Of the many terms these men had heard applied to them, “philanthropist” was a new one. No one had ever accused them of being generous and altruistic before. It was, Amanda observes, a moment of redefinition. As they were passing back to their cells, one man came up to Amanda, smiling and proud. “‘I’m putting up a sign in my cell,” she remembers him saying. “‘It will say I AM A PHILANTHROPIST.’”

Later, another workshop participant—a prisoner who was editor-in-chief of the San Quentin News—asked Amanda to repeat the program with the newspaper staff. Produced and run entirely by incarcerated men, the San Quentin News covers restorative justice and other issues and is, in many ways, a typical community newspaper. Amanda obtained permission from the Lilly Family School of Philanthropy at Indiana University to help the paper with their fundraising efforts as the basis for the internship required for her Masters Degree in Philanthropy, which she was awarded in December 2020. She continues to volunteer with the San Quentin News to this day.

In general, life is composed of three stages: 1) learn – to thrive and get a good job; 2) earn – a period of building wealth to take care of family and needs; and 3) retire. The midlife stage, generally between 35 and 75 years old, or the high potential earning years and into early retirement, is where most charitable activities and estate and financial planning tend to take place. This period is marked by constant change and transition, including career and relationship changes, taking care of parents and children, sometimes simultaneously, and personal health. A heightened sense of depression, stress, loneliness, and being overwhelmed are common words to describe this time, also known as the “midlife crisis.”

Advisors are adept at the technical planning required to manage these transitions: organizing finances, completing estate plans, and protecting assets. Yet, very little support is available to those managing the confluence of these events on the behavioral perspective. In addition, Stanford University’s Center on Longevity is reimagining what a century of life means in a new project, “A New Map of Life.” In this article, I outline several ways that advisors can support clients or donors experiencing transitions.

1. Self-awareness and acceptance allow clients to manage and master their growth through various life transitions.

You can help clients understand what it means to live a longer life and obtain the skills needed to manage their psychological well-being and development. For example, some wealth management firms are beginning to host seminars for clients around the science of longevity, explaining physical, emotional, and psychological changes. Other advisors introduce researchers from organizations such as the Buck Institute on Aging to share new scientific research programs. For some advisors, it is helping clients lean into or explore their spirituality. By demystifying life transitions and providing your clients with the tools to navigate uncertainty, your clients will gain greater autonomy and control of their life.

2. Purpose is essential for happiness and longevity, especially as one transitions from the purpose of work and wealth creation.

Chip Conley, the founder of Modern Elder Academy, shares that increased purpose has shown to positively affect happiness and life expectancy. Generally, clients are entering a phase in which they are questioning their view of life and triggering a search for meaning. Bob Buford, author of the book “Halftime,” speaks of the journey from “success to significance.” You can help your clients uncover their greater purpose, whether it is a more profound sense of where they are or a “reboot” to where they wish to be. Often, a client’s purpose involves contributing to society, leaving a mark, or leaving a legacy. This is a good time to reexamine, with the client, organizations and causes they support, their philanthropic impulses, what stirs their soul, what they would like to make right, and how they can make a greater social impact. It is important to connect the earlier accomplishments to their renewed purpose and the future as it is a regenerative process.

3. New networks are sometimes needed for renewed purpose and personal connection, especially when in transition.

Advisors can help clients identify their support team of family, friends, and community. Warm and trusting interpersonal relationships can have a positive effect on life expectancy.

For those entering retirement, a new network, or being with others entering the same phase in life, may provide the support and freedom to explore and even shed an identity they wish to leave behind. Advisors with a similar group of clients in transition may consider forming informal small, private networks or study groups, bringing in experts such as life coaches, intergenerational communication specialists, or health experts. These groups may provide learning and community building opportunities.

4. Embracing and incorporating lifelong learning and curiosity.

An increasing number of spiritual and educational institutions offer lifelong learning programs. Yet few of them address the needs of those in transitions as they focus on human capital development and not on human-centered development. Exceptions exist, including Harvard’s Advanced Leadership Initiative and Stanford’s Distinguished Careers Institute, which provide programming for those transitioning to explore purpose, community, wellness, and intergenerational engagement.

At The American College of Financial Services, where I work, we are developing a program to support executives, small business owners, and others who are in transition. We saw an opportunity to serve those who wish to refresh, deepen, or more significantly repurpose and transition their energies in an accessible and flexible program that meets participants where they are. This approach ensures a path grounded in family, values, legacy, and what matters most. In addition, the program supports the participants in the practice of social impact, with new ideas, new tools, and new friends.

According to the 2020 Census, there are approximately 73 million Baby Boomers. By 2030, all Baby Boomers will be age 65 or older. As a result, we can better serve advisors by recognizing and understanding the needs of clients who are struggling or need a little more support through transitions.

One of the keys to philanthropic success is proper financial planning. Through the three-course Chartered Advisor in Philanthropy® (CAP®) designation program, you will learn how to help philanthropies maximize their donations and resources. The CAP® is designed for experienced professionals in both the financial services and nonprofit sector, and gives you the power to do more with your career. Learn More. 

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Designed as opportunities to dive deeper into a topic with a small group of like-minded practitioners, these sessions foster new connections and encourage multi-disciplinary teamwork as the participants work on case studies and activities together. Our goal is to offer the space and opportunity for senior advisors to join a community of practice, engage in lively discussions, and apply what they have learned immediately to further the philanthropic conversation.

We encourage you to work through the case study of Peter and Charlotte Cade: Honoring Family and History through Philanthropy. With a multidisciplinary team, you can engage in lively discussions, and apply what you learn to further the conversation in your practice.

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