When “Doing It Yourself” Starts to Cost You More Than Money

I once sat across the table from a business owner who had built everything himself.
The company. The wealth. The independence.

He was proud of that—and he should have been.

When the conversation turned to giving, he waved his hand casually. “I’ve got that covered,” he said. “I give to a few charities I care about. My CPA handles the tax side. My broker helps when there’s a big year.”

On paper, everything looked fine.

But as we talked, a different story emerged.

He had strong beliefs about education and opportunity, yet his giving was scattered across dozens of organizations. He wanted to involve his adult children, but no one had ever helped him frame the conversation. He cared deeply about impact, yet had no real way to know whether his generosity was making a difference—or just maintaining the status quo.

Nothing was wrong.
But nothing was truly aligned, either.

This is the quiet gap many successful people find themselves in.

Business owners, founders, and independent thinkers are often excellent problem solvers. They know how to hire experts when the stakes are high—attorneys for legal matters, CPAs for taxes, advisors for investments. But philanthropy often gets treated as something simpler, more intuitive. Something you can “figure out along the way.”

And that’s where opportunity is quietly lost.

A qualified philanthropy advisor doesn’t replace your CPA or financial advisor. Instead, they focus on a different set of questions—questions that don’t show up on a tax return or brokerage statement:

• What do you want your giving to stand for?

• How concentrated should your efforts be to truly move the needle?

• How do your charitable decisions fit into your broader legacy—family, business, and values?

• How do you give in a way that brings clarity and confidence, not just deductions?

Philanthropy is not just a transaction. It’s a long-term strategy—one that deserves the same intentional thinking you applied when building your success in the first place.

The irony is this: the people most capable of doing philanthropy well on their own are often the ones who benefit most from experienced guidance. Not because they lack intelligence or generosity, but because their ambitions for impact are bigger than any single advisor’s lane.

At its best, working with a philanthropy advisor isn’t about being told what to do. It’s about having a thoughtful partner—someone who listens deeply, sees the whole picture, and helps turn generous instincts into lasting, meaningful outcomes.

Most people don’t need more advice.

They need the right advice, in the one area where money intersects most closely with meaning.

That’s where professional philanthropic guidance quietly earns its place.