Giving While Living: Joy in Lifetime Gifting

When it comes to passing on wealth, many people instinctively think of estate planning after death. Yet, gifting assets during your lifetime can be an incredibly rewarding strategy — both financially and emotionally.

So why don’t more people do it? The answer lies not just in tax codes, but in human psychology.

Why We Hesitate to Give While Alive

Even when the numbers make sense, many people struggle with the idea of gifting assets during their lifetime. Some common reasons include:

• Fear of Running Out: Even with a strong financial plan, the “what ifs” — like medical expenses or market downturns — can make us hold back.
• Loss of Control: Assets represent security and freedom. Giving them away can feel like losing control of your own future.
• Deep Emotional Ties: Wealth is often tied to years of hard work, sacrifice, and identity. Letting go can feel like letting go of part of ourselves.
• Family Dynamics: Concerns about fairness, misuse of money, or strained relationships can make people hesitant to gift too early.

These feelings are completely natural. But understanding them can help us make more intentional choices about when and how to share our wealth.

The Psychological Benefits of Gifting Now

Overcoming those barriers unlocks meaningful rewards:

• Witnessing Joy Firsthand: Unlike estate transfers, lifetime gifts let you see your loved ones build, grow, and thrive with your support.
• Strengthening Relationships: Acts of generosity often deepen family bonds and create shared memories.
• Peace of Mind: Knowing that you’ve helped set your heirs on a stable path can reduce anxiety about their future.
• Leaving a Living Legacy: You’re not just remembered for what you leave behind — you’re celebrated for what you contributed during your life.

I recently worked with a client in her early 70s who, based on her financial plan, would never outlive her money. Despite this, she hesitated to gift any of her assets — always worried about the “what ifs.” She brought it up in almost every meeting, but never seemed able to gain the comfort she needed to actually move forward.

That changed when her adult daughter went through a sudden divorce and had to rebuild her life from the ground up. Her daughter — who had always worked hard and been financially secure — was now facing both the emotional toll of the breakdown of her family and new financial pressures she had never experienced before. Watching her daughter struggle brought my client to tears in several meetings.

Together, we revisited her plan. We determined an amount she would feel comfortable gifting, structured it in a tax-efficient way, and re-ran her numbers. Even under worst-case scenarios — where she might need to draw more heavily from her plan — the gift had little impact on her ability to fund her own lifestyle. In fact, she had been living well below her means, which is something we often see with retirees who find it difficult to spend what they’ve worked so hard to accumulate.

With that clarity, she decided to gift her daughter a significant sum to help secure housing and provide stability during this difficult transition. The outcome was powerful: her daughter regained her footing more quickly, and my client experienced profound joy and pride in watching her child find strength and independence again.

She later told me, “I thought giving would feel like a loss — but instead, it was the best decision I could have made.”