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Taylor’s Story

Taylor’s Story

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Taylor Jessee Headshot

Taylor's Story

Published on March 2, 2026

In the United States, nearly half of cancer patients and survivors report carrying medical debt as a direct result of their treatment, and many make major lifestyle sacrifices just to afford care. The most recent comprehensive estimates, from 2019, show that cancer care imposed more than $21 billion in patient economic burden nationwide, including over $16 billion in out-of-pocket costs and nearly $5 billion in time costs such as travel and waiting for care.

Financial planner Taylor Jessee, CPA, CFP®, has met these realities head-on, offering clarity, compassion, and stability to people facing serious illness and financial disruption. Taylor discovered pro bono financial planning in 2021, when he connected with Foundation for Financial Planning (FFP) grantee CancerLINC, a Richmond-based nonprofit that connects cancer patients with free legal and financial assistance.

Taylor’s found that every engagement starts with listening. He begins by learning what is weighing on each client, then works with them to identify manageable steps that reduce stress and restore a sense of control during treatment.

In one case, Taylor discovered that a client was having taxes withheld from her Social Security benefits even though she was not required to file tax returns. By helping her submit amended returns, he secured several years of refunds—funds that made a meaningful difference at a critical moment.

Another client, reliant on Medicaid, had inherited a $150,000 IRA and felt overwhelmed by the implications. Taylor helped her navigate required distributions and understand how the inheritance could affect her disability status and health coverage. The case was technically complex, but it received the same care and diligence he brings to every client relationship.

Across his work with CancerLINC—having supported 10 clients to date—Taylor emphasizes that technical expertise alone is never enough. Many clients need someone who will listen without judgment, offer steady guidance, and remind them they are not facing their challenges alone.

One experience in particular affirmed the impact of that approach. A cancer survivor Taylor had supported invited him to speak at her Veterans Affairs survivors group. Hearing her describe how financial guidance helped her regain confidence during an uncertain time reinforced the profound difference compassionate advice can make.

Taylor’s commitment to service extends beyond cancer care. Through FFP’s platform, ProBonoPlannerMatch.Org, Taylor connected with another opportunity with the nonprofit After Innocence, an organization that supports individuals who were wrongfully convicted and later exonerated. The mission—and the resilience of the people served—deeply moved him. “These are some of the most joyful, hopeful people I’ve ever met,” Taylor reflects. “Reading their stories is heartbreaking. That reality makes you want to work even harder for them.”

Through After Innocence, Taylor helps exonerees build financial foundations—managing compensation settlements if applicable or rebuilding from the ground up when no financial award exists. He has worked with seven individuals through the program.

For Taylor, pro bono service reflects both his faith and his professional values. He feels a responsibility to provide objective, fiduciary financial advice to people who might not otherwise have access to it. As a self-employed advisor, he values the flexibility—and accountability—to devote time to work aligned with those principles.

The work has also shaped him professionally. Supporting clients through cancer diagnoses, Medicaid eligibility questions, wrongful conviction settlements, and overwhelming medical debt has exposed Taylor to challenges many advisors never encounter. Each case expands his technical knowledge, sharpens his judgment, and deepens his empathy.

Thirteen years into his career, those experiences continue to reframe his perspective.

“The stock market isn’t the center of the world,” Taylor says. “Real people are facing real problems—medical debt, lost income, trauma—and they need someone in their corner.”

Helping them doesn’t feel transactional.

“Helping feels like a responsibility,” he says. “A calling to do the work I’m meant to do.”

“Real people are facing real problems—medical debt, lost income, trauma—and they need someone in their corner.”
–Taylor