Making the Most of What You Give

Many families we talk to are already generous. They give consistently. They support causes they care about. And if anything, they wish they could do more.

But when you sell an investment before giving, wait too long to plan around a major event, or rely on cash instead of more efficient assets, something unintended happens:

Taxes become one of the largest recipients of your generosity.

Individually, these decisions don’t stand out. But together, they can cost tens, or even hundreds of thousands of dollars, money that never reaches the causes you care about.

Does this sound familiar?

In most cases, the issue isn’t how much you give. It’s a handful of common mistakes that reduce what actually reaches charity.

So, what can you do?

Here are four common giving mistakes and how to avoid them.

Four Mistakes That Reduce Your Impact

Mistake #1: Only Giving from Cash

Many families limit their giving to cash, without realizing this is often the least tax-efficient way to give.

The Johnsons felt this firsthand.

They were successful and generous, but much of their wealth was tied up in investments. Each year, they gave from income, and each year it felt like they weren’t doing as much as they could.

Their cash flow dictated their generosity.

But when they stepped back and looked at their full balance sheet, they realized they could donate appreciated stock instead.

Impact: They tripled their giving in one year, giving more to charity while reducing the tax drag on their portfolio.

Mistake #2: Selling Assets Before You Give

Selling investments before making a donation is one of the most common and costly mistakes.

Sarah and Mike experienced this directly.

They sold $500,000 of appreciated stock to support their children’s school. It felt straightforward.

Impact: The sale triggered over $50,000 in capital gains taxes, money that never reached the cause they cared about.

This mistake is avoidable.

Instead of selling first, you can donate appreciated stock directly or contribute it to a Donor Advised Fund. When you do, you redirect those tax dollars to charity instead of the IRS.

Mistake #3: Waiting Too Long to Plan Your Giving

Timing is one of the most overlooked drivers of tax efficiency.

Tom and Janet built their business over decades and eventually sold it for $30 million. They planned to give $5 million to charity.

But they waited until after the sale to think through their giving strategy. By then, it was too late.

Impact: They lost nearly $1.6 million to taxes on that $5 million gift, simply due to timing.

With proper planning, the outcome could have been very different.

For example, gifting shares before the sale to a Donor Advised Fund can eliminate capital gains taxes on that portion. And if income is needed, a Charitable Remainder Trust can provide both income and tax benefits.

In one similar case, a $5 million CRT:

• • Generated $250,000 per year in income
  • Created a $1.75 million tax deduction
  • Left the remaining assets to charity

Mistake #4: Thinking You Have to Choose Between Family and Charity

For some families, the challenge isn’t tax mechanics. It is uncertainty.

Robert and Linda wanted to support meaningful causes, but they also wanted to ensure their family was taken care of. Without a clear plan, every decision felt like a trade-off.

So, they waited. No plan took shape, and taxes remained the default outcome.

But when they stepped back and coordinated their strategy, everything changed.

Robert and Linda’s original plan wasn’t really a plan. It was the default path most families are on.

Impact (Before vs. After)

Before: The Default Path

No intentional planning

• • $10M remains at their death
  • Assets stay in their taxable estate
  • Pass to family after taxes

Results:

• • $8.7M to family
  • $0 to charity
  • $1.3M to taxes

After: A Designed Plan

Same assets, structured intentionally

• • $2M allocated to a Charitable Remainder Trust (CRT)
  • $100K per year from the CRT used to fund a Wealth Replacement Trust (WRT)
  • Remaining assets coordinated across family and charitable goals

Results:

• • $8.5M to family, including $2.5M from WRT
  • $2M to charity
  • $0 to taxes

They increased their total impact, supported both family and charity, and eliminated unnecessary taxes.

Without a plan, taxes won. With a plan, both family and charity did.

The Shift: From Good Intentions to Strategic Giving

These aren’t generosity problems. They are tax and timing problems.

Giving decisions are often disconnected from:

• • Tax strategy
  • Investment decisions
  • Estate planning

And without coordination:

• • Taxes take more than they should
  • Charities receive less than they could
  • Your legacy does not fully reflect your intent

How to Make the Most of What You Give

You don’t need to give more to create greater impact. You need to give more intentionally.

1. 1. Think Beyond Cash Flow. Your ability to give isn’t limited to income. Many opportunities come from assets, not cash.
   2. Give Assets, Not After-Tax Cash. Donating appreciated assets can eliminate capital gains taxes and increase the amount that reaches charity.
   3. Plan Before Major Events. Timing matters. Planning ahead of a sale or high-income year can dramatically change outcomes.
   4. Align Family and Charitable Goals. With the right structure, you don’t have to choose. You can support both while reducing unnecessary taxes.

What Happens When You Get This Right

Across these examples, the pattern is clear:

• • $50,000+ preserved by avoiding unnecessary taxes
  • $1.6 million saved through better timing
  • $2 million directed to charity from the same $10 million estate

Same generosity. Completely different results.

A Simple Way to Start

You don’t need to overhaul everything overnight. Here’s how to begin:

1. 1. Define your “why.” What do you want your giving to represent?
   2. Rethink what you give. Are you using your most efficient assets?
   3. Start the conversation. Even a simple coffee with your spouse can begin a multi-generational impact.

Small steps today can ensure more of your wealth goes where you intend.

Your giving tells a story. But without a plan, taxes will continue to shape part of that story, whether you intend them to or not.

Let’s Help You Make the Most of What You Give

If you’re wondering how this applies to your situation, a simple conversation can help.

A 30-minute Charity Chat is designed to give you clarity, ideas, and direction, whether you implement them on your own, with us, or alongside your existing advisors.

Because every dollar lost to taxes is a dollar that never makes an impact on the causes you care about.