What is Oversimply, and how can you help me?

Oversimply is the name of the services provided by me, Jill Mastroianni. Oversimply helps individuals and families navigate the complexities of end-of-life preparation with clarity and compassion. Whether you’re organizing essential documents, ensuring your wishes are clearly communicated, or preserving your legacy, I simplify the process to make it clear, approachable, and manageable. I specialize in demystifying legal documents and processes, providing practical guidance, and helping you feel confident and prepared for the future.

Are you a lawyer? Can you draft legal documents for me?

Yes, I have a law degree from Vanderbilt University and a masters in tax law from New York University. I am licensed to practice law in the state of Tennessee, but I am not currently practicing law. Instead, I use my legal education and 12 years of experience in trusts, estates, probate, and tax to help clients navigate complex documents and processes with clarity and confidence. Rather than drafting legal documents, I act as a legal interpreter and advocate, connecting you with the appropriate professionals in your area and ensuring your goals are clearly understood and implemented.

What makes Oversimply different from traditional estate organizing services?

I offer a unique blend of legal knowledge, empathy, and hands-on support that goes far beyond conventional checklists. My commitment is to be present, patient, and deeply responsive to your specific needs, preserving your legacy with care and attention to detail—never rushed, never robotic. With my guidance, end-of-life planning becomes a meaningful, manageable experience centered on peace, legacy, and family harmony.

What does “Legacy Preservation” include?

Legacy Preservation helps you capture and share your values, stories, and guidance for future generations. This might include personal letters, family histories, or instructions for loved ones. We work together to ensure your legacy reflects who you are and what matters most to you.

How does “Decluttering and Memory Curation” work?

I’ll guide you through sorting and organizing your belongings, helping you decide what to keep, donate, or discard. We’ll focus on preserving the memories tied to your items, ensuring your stories live on while creating a simpler, more meaningful space. Artifcts is a popular tool that I use in this type of work.

What is included in “Family Communication Support”?

This service helps families navigate sensitive discussions about end-of-life wishes and estate planning. I can prepare you for these conversations, facilitate discussions, or be present to ensure clarity and reduce conflict. My goal is to create a space where your wishes are clearly communicated and understood, helping your loved ones accept that the decisions are yours to make, even if they don’t fully agree.

How do I get started?

The first step is to schedule a consultation, where we’ll discuss your needs, goals, and concerns. This conversation allows us to determine if my services are the right fit for you and how I can best support your unique situation. From there, I’ll create a personalized plan tailored to your priorities, ensuring you feel confident and comfortable moving forward.

Do you only work with people preparing for end-of-life?

No, while much of my work focuses on end-of-life preparation, I also help families organize documents, declutter, and preserve memories for other transitions, such as downsizing or simplifying their lives.

Can you work with my family members or other professionals?

Absolutely! Whether it’s facilitating conversations with your family or coordinating with legal, financial, or caregiving professionals, I’m here to ensure you have the support you need. My goal is to help bring clarity and alignment to your situation by connecting you with the right people and resources, making sure your wishes are clearly understood and effectively addressed.

How long does the process take?

The timeline varies depending on your goals and the complexity of your needs. Some projects can be completed in a few sessions, while others may require ongoing support.

Is this a local or virtual service?

I provide both in-person and virtual support, depending on your location and preferences. I’ll find the approach that works best for you.

How much do your services cost?

My pricing is based on the scope and type of service you need. During our initial consultation, I’ll provide a clear estimate so there are no surprises.