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Estate Planning Checklist

Outdated Wills, Missing Beneficiaries, and No Plan: The Estate Planning Mistakes We’re Seeing Every Week

September 03, 20253 min read

In just the past month, we’ve had eight families come to us with urgent estate planning needs:

  • A son discovered his parents’ only will was drafted over 40 years ago

  • A daughter struggled to make medical decisions for her mother with dementia — no health care directive was in place

  • A young family scrambled to set up a will and guardianship for their kids

  • A recent divorcee needed to update documents so assets would pass to children, not an ex-spouse

Different stories, same problem: outdated or missing estate plans. When that happens, families end up in court, assets get tied up, and wealth is lost to taxes, fees, or the wrong hands.


The Core Documents Everyone Needs

At a minimum, every adult should have:

  • Will: Directs how assets are distributed and names guardians for children

  • Durable Power of Attorney (POA): Appoints someone to manage financial and legal matters if you can’t

  • Health Care Proxy / Advance Directive: Ensures your medical wishes are respected and prevents family conflict

  • Beneficiary & Contingent Beneficiary Designations: Must be kept current on retirement accounts, life insurance, and bank accounts. These override your will.


Trusts: When You Need More Than a Will

Trusts can take estate planning further:

  • Revocable Living Trust: Flexible, can be changed anytime, avoids probate, keeps transfers private

  • Irrevocable Trust: Harder to change, but offers tax advantages and creditor protection. Often used for large estates, business transfers, or advanced tax planning

If you own significant assets — especially a business — a trust can be the difference between a smooth transition and a financial nightmare.


Why Updating Matters

Having documents is step one. Keeping them up to date is step two. Review your plan whenever life changes, like:

  • Marriage or divorce

  • Birth of children or grandchildren

  • Business growth or ownership changes

  • Health issues or major life transitions

An outdated will or retirement account with an ex-spouse listed as beneficiary is a ticking time bomb.


Business Owners: Special Considerations

If you own a business, estate planning must cover more than personal assets:

  • Succession planning: Who runs the business if you’re gone tomorrow?

  • Buy-sell agreements: Funded by insurance or assets so co-owners and family aren’t left fighting

  • Trust planning: Holding company shares in trust to avoid probate and minimize taxes

  • Liquidity planning: Ensuring cash is available for taxes and expenses so the business isn’t forced into a fire sale

Without these, your life’s work could be dismantled in months.


Solutions: Working With the Right Advisor

It’s not just about creating documents — it’s about keeping them aligned with your financial life. At Compound Advisory, we:

  • Review wills, POAs, health directives, and beneficiaries regularly

  • Coordinate with estate attorneys so everything works together

  • Ensure accounts, trusts, and estate documents are consistent and up to date

  • For clients who qualify, include fundamental estate planning as part of our service


Don’t Leave It to Chance

Estate planning isn’t just paperwork. It’s about peace of mind for you and clarity for your family. Waiting until a crisis happens is the worst time to fix your plan. By then, it’s too late.

Take 15 minutes now to protect what you’ve built. Schedule your free call today and let’s make sure your estate plan and financial plan are working together to secure your family’s future.

Heath Harris is the founder of Compound Advisory, where the spreadsheets are sharp and the advice is sharper. After nearly 20 years helping business owners, professionals, and retirees make smart money moves, he launched Compound to deliver real planning — not sales pitches. Heath brings a mix of market smarts, tax strategy, and no-BS guidance to every client conversation.

When he’s not building plans that actually work, he’s probably lifting heavy things, avoiding seed oils, or explaining why cash flow beats guesswork — every time.

Keep compounding.

Heath Harris

Heath Harris is the founder of Compound Advisory, where the spreadsheets are sharp and the advice is sharper. After nearly 20 years helping business owners, professionals, and retirees make smart money moves, he launched Compound to deliver real planning — not sales pitches. Heath brings a mix of market smarts, tax strategy, and no-BS guidance to every client conversation. When he’s not building plans that actually work, he’s probably lifting heavy things, avoiding seed oils, or explaining why cash flow beats guesswork — every time. Keep compounding.

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