Everyone Wants the Fruit, But No One Wants to Plant the Tree

Man planting trees at sunset with quote about legacy and future generations.
Reading Time: 5 minutes

Why planned giving is the most powerful fundraising tool your nonprofit isn’t using.

Introduction: The Invisible Power We Keep Ignoring

We say we care about the future—but our actions rarely align with our words. It’s like admiring an orchard while refusing to pick up a shovel. In fundraising, as in life, we chase what’s immediate, visible, and easy to measure. And while that might work in the short term, it starves the long-term systems that sustain us. That’s why planned giving—which represents billions in annual charitable donations—continues to be neglected by most organizations despite its transformative potential.

Everyone wants the fruit. But no one wants to plant the tree.

This article explores why planned giving is so often overlooked, how institutional culture contributes to its marginalization, and what must change if nonprofits truly want to build for the future.

A Culture Addicted to Immediate Returns

Fundraising teams focus almost exclusively on quick wins—year-end appeals, gala events, direct mail returns, and major gift asks. These are necessary. But they are also reactive, driven by short-term metrics and institutional pressure.

Meanwhile, planned giving is viewed as optional. It’s misunderstood as technical, slow-moving, or reserved for “someone else’s desk.” It lacks the visible, short-term thrill of a six-figure check.

But major gifts are rare. According to national data:

    • Only 1.5% of Americans earn over $500,000 annually.

    • Most planned gifts come from modest, middle-class donors who value loyalty, meaning, and legacy.

Typical Case Study: When Margaret Wilson, a retired schoolteacher, passed away in 2023, she left $1.2 million to her local literacy foundation. The organization’s leadership was shocked—they had no idea Margaret had such wealth. In truth, she didn’t. She had simply set aside a small percentage of her teacher’s salary each month for forty years. Her unremarkable annual gifts of $100-200 gave no indication of the transformative legacy she was quietly building.

Donors Think in Legacy. Institutions Think in Quarters.

This is the great mismatch—and a systemic problem. Donors—especially those considering legacy gifts—are thinking decades ahead. They want to be remembered. They want their values to outlive them.

But when they see:

    • Buildings renamed

    • Statues removed

    • Founders quietly forgotten

…they wonder: Will I be remembered with gratitude, or erased with convenience?

Planned giving requires trust. And trust requires memory.

If institutions won’t honor the past, how can they ask donors to invest in the future?

The Flight Risk Fallacy

Air travel is the safest form of transportation.

  • Odds of dying in a plane crash: 1 in 11 million
  • Odds of dying in a car accident: 1 in 5,000
  • You're more likely to be struck by lightning

But when a plane crashes, it dominates the headlines for weeks.

That's how fundraising works, too. Major gifts grab attention. Planned gifts happen quietly, reliably, beneath the surface.

The real risk? Ignoring the strategy that sustains your future.

The High Turnover Crisis: No One Left to Steward the Seed

The average fundraiser changes jobs every 1.6 years. This revolving door damages long-term donor relationships—especially in planned giving.

Why is the turnover so high? Because nonprofit fundraising roles often lack real incentive. These jobs come with enormous emotional and strategic pressure—but little of the compensation, recognition, or long-term career structure that exists in the for-profit world. Burnout is common. Growth is limited. And people leave.

Maybe it’s not the people. Maybe it’s the model for nonprofits.

Legacy gifts take time. They require follow-up, familiarity, and a stable point of contact. When the fundraiser is gone in a year and a half, who continues the conversation?

This isn’t just poor staffing. It’s institutional memory loss. It’s a signal to the donor that no one will be there to remember them either.

High turnover equals institutional memory loss.

When the Winds Shift: Navigating Regulatory Change

Every sector faces unexpected regulatory challenges. For nonprofits, these shifts can dramatically impact fundraising operations, creating new compliance burdens that disproportionately affect smaller organizations.

Recent years have seen increased filing requirements, cross-state registration mandates, and changing tax incentives for charitable giving. These changes aren’t targeted at any specific organization—they’re systemic responses to isolated incidents that end up affecting the entire sector.

This isn’t about targeting. It’s about timing. And sometimes, we’re in the path of the wave.

Organizations with diversified funding streams—including robust planned giving programs—weather these storms more effectively than those dependent on a single funding source.

Incentives and Human Nature: The Double Bind

Only the top 1% of society are consistently proactive—whether it’s with their health, finances, or estate planning. Planned giving falls squarely into that category. It asks for foresight, discipline, and commitment, which means that most people—fundraisers and donors alike—are naturally inclined to put it off.

Planned giving is a proactive discipline. But most people—fundraisers and donors alike—are reactive by nature.

Only the most disciplined routinely take long-term action:

    • They save.

    • They plan.

    • They give with intent.

Everyone else? We put things off. We’re human.

Ever tell yourself you’d work out tonight instead of this morning—then push it to tomorrow instead? Then told yourself, “Tomorrow morning, I’ll get to it.”

Even I did this. For years I put off checkups, scans, and appointments. It wasn’t until cancer and open-heart surgery that I realized: I have to schedule these things. I have to prioritize them. X-rays, CAT scans—you never know what’s going on inside.

And yes—it’s late in life to learn that. But it’s also never too late. That’s the lesson.

That’s how you get the fruit. That’s called planting the tree. Now.

From Task Management to Relationship Building

Too many fundraisers are buried in logistics. They’re maintaining databases, managing events, editing newsletters. All valuable. None of it fundraising.

Real fundraising is:

You don’t close a planned gift with a spreadsheet. You earn it by showing up, again and again, with presence and purpose.

Three Ways to Shift Today:

    1. Block sacred time – Set aside 2–3 hours weekly exclusively for donor calls and visits

    1. Share the administrative load – Train volunteers to handle data entry and event logistics

    1. Create relationship metrics – Measure meaningful interactions, not just dollars raised

Even in our digital age, planned giving remains fundamentally personal. Technology should enhance, not replace, human connection. Use digital tools to track touchpoints and preferences, but never substitute emails for conversations when discussing someone’s legacy.

Legacy Requires Memory

A legacy gift is not just a financial decision. It is the donor’s final act of belief. That belief is built on one thing: trust.

And trust depends on institutional memory.

When donors see institutions revise or erase their past, they wonder whether their own legacy will be respected. Planned giving collapses when memory is treated as optional.

The Tree Requires Time, Water, and Care

Everyone wants the fruit: big gifts, capital campaigns, financial stability.

But the fruit comes from something deeper—roots.
Those roots are planted in:

    • Relationships

    • Continuity

    • Culture

The best time to plant a tree was 20 years ago. The second-best time is now.

Planned giving is that tree. It won’t grow overnight. But it will sustain the mission—if you plant it, tend it, and remember who it’s for.

Is Your Organization Ready? A Self-Assessment

Ask yourself these five questions:

    1. Do we have a designated point person for planned giving conversations?

    1. Have we identified our loyal donors of 5+ years, regardless of gift size?

    1. Does our strategic plan extend beyond the next 1–3 years?

    1. Can we articulate how we honor donor intent across generations?

    1. Do we celebrate legacy donors as visibly as we celebrate major donors?

If you answered “no” to three or more questions, your organization has significant room to grow in planned giving readiness.

Act Now:
Begin Planting the Tree

Planned giving is not about money. It’s about meaning. It’s not about legal structures. It’s about legacy.

To honor the donors who built the past—and welcome those who will build the future—we must:

    • Respect memory

    • Create space for long-term thinking

    • Incentivize stewardship

Philanthropy.org logo icon

Homework: Ask Yourself these Five Questions

  1. Do we have a designated point person for planned giving conversations?
  2. Have we identified our loyal donors of 5+ years, regardless of gift size?
  3. Does our strategic plan extend beyond the next 1–3 years?
  4. Can we articulate how we honor donor intent across generations?
  5. Do we celebrate legacy donors as visibly as we celebrate major donors?

If you answered “no” to three or more, your organization has significant room to grow in planned giving readiness.

We value your insights! What stood out to you in this article? Join or start a conversation below.

Leave a Reply

Your email address will not be published. Required fields are marked *

Colored open hand illustration

Seeking Visionary Voices!

Do you have:

  • A unique insight or bold idea?
  • A story of success—or valuable lessons from failure?
  • Expert advice that could guide your peers?

Join other forward-thinkers in shaping the future of philanthropy. Contribute today and let your voice be heard.

Related Posts

Smiling financial advisor discussing philanthropic planning with a client in a bright, modern office setting.

Advisors, Philanthropy, and Donor Perceptions: Why Advisors Must Embrace the Shift

As donor expectations evolve, today’s philanthropists are seeking more from their financial advisors—beyond tax advice. They want strategic, values-aligned giving plans that include family, legacy, and impact. With over $84 trillion expected to transfer across generations by 2045, advisors who understand charitable tools like planned giving and donor-advised funds are well-positioned for growth. Learn how integrating philanthropy into your financial planning services isn’t just good ethics—it’s smart business.

Read More »
Woman planning her will on a tablet standing up

Rethinking Will Planners: How Estate Planning Tools Can (and Should) Support Philanthropy

Most will tools are built for transactions, not legacies. LegacyPlanner™ redefines estate planning by integrating it into the donor journey—educating, inspiring, and deepening engagement along the way. It’s not just about creating documents; it’s about creating impact. As philanthropy evolves, so must our tools. LegacyPlanner™ offers a glimpse into how estate planning can become a central part of donor-centric fundraising strategies.

Read More »
A diverse group of people standing together outdoors with arms around each other, facing the sunrise in a display of unity and support.

The Power of Community in Primal Fundraising: I’m Not Just Giving, I’m Sharing!

Giving feels noble. Sharing feels human. This blog explores the primal power of community in fundraising—not as a transaction, but as a mutual act of belonging. True generosity thrives when people feel they are part of something, not giving to something. Drawing from game theory, biology, and real-world experiments, it reveals why communal sharing inspires deeper, more sustainable gifts—and why the smartest fundraisers aren’t just building donors. They’re building tribes.

Read More »
How blockchain and crypto can make philanthropy more efficient

The Future of Multiplicative Giving: How AI, Data, and Collective Philanthropy Will Reshape Impact

Philanthropy is shifting from isolated donations to multiplicative giving, where every dollar generates exponential impact. AI-driven philanthropy enhances decision-making, big data enables real-time impact tracking, and blockchain ensures radical transparency. Donor collaboratives further amplify change by pooling resources for systemic solutions. As technology transforms giving, the future belongs to those who embrace data-driven, strategic philanthropy. Are you ready to maximize your impact?

Read More »