E64: You Need a Will with Jessica Feldman Chittley
Fri Jan 30 2026
“If you die without a will… the law has written one for you.”
In this episode of The Unlimited Podcast—the first in our Wealthhard series—Brian speaks with Jessica Feldman Chittley, partner at Bales Beall LLP, about wills and powers of attorney: what they are, why everyone needs them, and how to draft them so they reduce tax and probate, protect minor children, and avoid executor headaches. Jessica explains the real consequences of dying intestate (meaning, without a will), how guardianship and trusts for minors work, and why powers of attorney for property and personal care are urgent. She also walks through the scope of the executor’s role, probate-planning options (e.g., multiple wills, bare-trust structures), and simple but powerful drafting tools that prevent family conflict. Practical, clear and essential listening for anyone who hasn’t reviewed estate documents in the last few years. And especially for those who haven't yet organized their wills and/or powers of attorney...What are you waiting for?
Jessica Feldman Chittley is a Partner at Bales Beall LLP who focuses on estate and trust planning and estate administration. She advises individuals, families and private-business owners on tax-minimization at death, drafts wills, trusts and powers of attorney, and guides executors through the administration process. Jessica serves on the Executive Committee of the Ontario Bar Association’s Trusts & Estates Law Section, is a member of Society of Trust and Estate Practitioners and the Canadian and Ontario Bar Associations, and was recognized in The Best Lawyers in Canada (2025) for Trusts and Estate.
Timestamps:
0:00 Disclaimer & Intro
1:25 Wealthhard
4:47 Why do you need a will?
7:57 What happens if you don't have a will?
13:02 The key elements of a will
18:56 The role of the executor
24:36 How a will impacts children
29:32 Planning for maximum value
31:55 What to do once a will is written
34:28 What is a power of attorney?
42:40 If Jessica could do anything, what would it be?
43:56 Outro
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“If you die without a will… the law has written one for you.” In this episode of The Unlimited Podcast—the first in our Wealthhard series—Brian speaks with Jessica Feldman Chittley, partner at Bales Beall LLP, about wills and powers of attorney: what they are, why everyone needs them, and how to draft them so they reduce tax and probate, protect minor children, and avoid executor headaches. Jessica explains the real consequences of dying intestate (meaning, without a will), how guardianship and trusts for minors work, and why powers of attorney for property and personal care are urgent. She also walks through the scope of the executor’s role, probate-planning options (e.g., multiple wills, bare-trust structures), and simple but powerful drafting tools that prevent family conflict. Practical, clear and essential listening for anyone who hasn’t reviewed estate documents in the last few years. And especially for those who haven't yet organized their wills and/or powers of attorney...What are you waiting for? Jessica Feldman Chittley is a Partner at Bales Beall LLP who focuses on estate and trust planning and estate administration. She advises individuals, families and private-business owners on tax-minimization at death, drafts wills, trusts and powers of attorney, and guides executors through the administration process. Jessica serves on the Executive Committee of the Ontario Bar Association’s Trusts & Estates Law Section, is a member of Society of Trust and Estate Practitioners and the Canadian and Ontario Bar Associations, and was recognized in The Best Lawyers in Canada (2025) for Trusts and Estate. Timestamps: 0:00 Disclaimer & Intro 1:25 Wealthhard 4:47 Why do you need a will? 7:57 What happens if you don't have a will? 13:02 The key elements of a will 18:56 The role of the executor 24:36 How a will impacts children 29:32 Planning for maximum value 31:55 What to do once a will is written 34:28 What is a power of attorney? 42:40 If Jessica could do anything, what would it be? 43:56 Outro