Beneficiary designations, account titling, trust funding, and the other items that need to be reviewed as your income and assets grow.
Why Estate Planning Gets Deferred
Estate planning sits in an uncomfortable category for most people — important enough to know it needs to happen, unpleasant enough to keep putting off. For tech executives and entrepreneurs specifically, there’s an additional layer: the financial picture is complex enough that doing it right feels like a significant project, and doing it wrong feels worse than not doing it at all.
The result is a pattern that shows up consistently. A will gets drafted at some point — usually triggered by a major life event like a marriage, a child, or a business milestone. The documents get signed. The attorney gets paid. And then nothing happens for years while the income grows, the assets accumulate, the business becomes more valuable, and the estate plan sits unchanged in a drawer.
The documents aren’t wrong. They’re just not current. And the gap between what the documents say and what the financial picture actually looks like is where estate planning fails the people it was supposed to protect.
This checklist is designed to close that gap — item by item, across every component of an estate plan that needs to be current to actually work.
Section 1: Core Documents
These are the foundational legal documents that every estate plan requires. If any of these don’t exist or haven’t been reviewed in the last three to five years, they need attention.
Will
- A current will exists and has been reviewed within the last three to five years
- The will reflects the current family structure — marriage, divorce, children, stepchildren, other dependents
- Guardianship designations for minor children are current and reflect the right people
- The executor named in the will is still the right person and is willing to serve
- The will accounts for the current asset picture, including the business
Revocable Living Trust
- A revocable living trust exists if appropriate for the estate size and complexity
- The trust has been reviewed and reflects current intentions for distribution
- The successor trustee named is still the right person and is willing to serve
- The trust terms account for the business interests and how they should be handled
Powers of Attorney
- A durable financial power of attorney exists and names the right person to manage finances if incapacitated
- A healthcare power of attorney exists and names the right person to make medical decisions
- Both documents have been reviewed recently and reflect current relationships and intentions
Advance Healthcare Directive
- A living will or advance directive exists that documents healthcare preferences
- The document reflects current wishes and has been reviewed after any significant health changes
- Copies are accessible to the right people — not just filed away where nobody can find them
Section 2: Beneficiary Designations
Beneficiary designations are among the most important and most frequently neglected components of an estate plan. They override the will — meaning the account passes directly to whoever is named, regardless of what the will says. Getting them wrong is one of the most common and most costly estate planning mistakes.
Retirement Accounts
- Primary and contingent beneficiaries are named on all retirement accounts — 401k, IRA, Roth IRA, SEP-IRA, Solo 401k
- Designations reflect the current family structure — updated after marriage, divorce, death of a named beneficiary, or birth of a child
- The contingent beneficiary is named — not just the primary — so there’s a clear line of succession if the primary beneficiary predeceases
- Designations have been reviewed in the last three to five years or after any major life change
- The named beneficiary is a person, not the estate — naming the estate as beneficiary eliminates stretch IRA options and can create unnecessary probate exposure
Life Insurance
- Primary and contingent beneficiaries are named on all life insurance policies
- Beneficiary designations reflect current intentions — not the person who was the right choice when the policy was purchased years ago
- Trust is named as beneficiary where appropriate — particularly for policies with large death benefits intended to fund a trust for minor children or estate planning purposes
Annuities and Other Accounts
- Beneficiary designations on annuities are current
- Any transfer-on-death or payable-on-death designations on bank and brokerage accounts are reviewed and reflect current intentions
Section 3: Account Titling
Account titling determines how assets pass at death and who has access during life. Errors in titling can create probate exposure, unintended transfers, and gaps between what the trust says and what the accounts actually do.
Personal Accounts
- Taxable investment accounts are titled correctly — individual, joint, or in the name of the trust depending on the estate plan structure
- Bank accounts are titled to reflect the estate plan — payable-on-death designations or trust ownership where appropriate
- Real estate is titled correctly — individual ownership, joint tenancy, tenancy in common, or trust ownership depending on the goals
Trust Funding
- Assets intended to pass through the trust have actually been retitled into the trust — a trust that isn’t funded doesn’t control anything
- Real estate has been transferred into the trust via a new deed where appropriate
- The trust is named as beneficiary on accounts where that’s the intended structure
- Any assets acquired since the trust was established have been reviewed for whether they should be titled in the trust
Business Interests
- Business ownership interests are titled correctly — operating agreement, shareholder agreement, or partnership agreement reflects the current ownership structure
- The estate plan addresses what happens to the business interest at death — does it pass to the trust, to a co-owner via buy-sell, or to specific heirs?
- The buy-sell agreement, if one exists, is current and funded appropriately
Section 4: Business-Specific Considerations
For business owners, the estate plan has an additional layer that purely personal planning doesn’t address. The business interest is often the largest single asset in the estate — and it’s also the most complex to transfer.
Buy-Sell Agreement
- A buy-sell agreement exists between co-owners if the business has multiple owners
- The agreement is funded — typically through life insurance on each owner — so a buyout can actually be executed
- The valuation method in the agreement is current and reflects how the business would actually be valued in a transaction
- The agreement has been reviewed after any significant change in business value, ownership structure, or owner circumstances
- The agreement addresses disability, not just death — what happens if an owner can’t work but hasn’t died?
Key Person Coverage
- Key person life insurance exists on the owner and any other individuals whose absence would materially affect the business
- Coverage amounts reflect the actual financial impact of losing a key person — not a number set years ago when the business was smaller
- The business is the owner and beneficiary of key person policies — not the individual
Business Valuation
- The business has been formally valued recently — not just estimated
- The estate plan reflects the current business value for estate tax planning purposes
- Gift and estate tax implications of the business interest have been reviewed with the estate attorney
Section 5: Tax Considerations
At higher net worth levels, estate planning and tax planning converge. The decisions made about how assets are held, transferred, and structured have long-term tax consequences that compound over time.
Federal Estate Tax
- Current net worth has been evaluated relative to the federal estate tax exemption — which is scheduled to sunset and decrease significantly after 2025
- Strategies for reducing the taxable estate — gifting, irrevocable trusts, charitable giving — have been discussed with the estate attorney
- Any prior taxable gifts have been tracked and the lifetime exemption usage is documented
Annual Gifting
- Annual gift exclusion amounts are being used if gifting is part of the estate plan — currently $18,000 per recipient per year
- 529 plan contributions and superfunding strategies have been evaluated for education planning
- Gifts to irrevocable trusts are being made with proper documentation and Crummey notices where required
Charitable Giving
- Charitable intentions are reflected in the estate plan — outright bequests, charitable remainder trusts, donor-advised funds, or other structures
- Appreciated assets — stock, real estate, business interests — are being used for charitable giving where appropriate to maximize the tax benefit
- A donor-advised fund exists if charitable giving is a regular part of the financial picture
Roth Conversion Strategy
- Roth conversion opportunities have been evaluated given the current income level and estate planning goals
- The impact of large tax-deferred retirement accounts on the estate — and the tax burden on heirs — has been discussed
- A multi-year Roth conversion strategy is in place if the retirement account balances are significant
Section 6: Protection
Estate planning isn’t only about what happens at death. It’s also about protecting what’s been built during life — from liability, from creditors, and from the gaps in coverage that most people don’t find until something goes wrong.
Insurance Review
- Life insurance coverage reflects the current financial picture — income, debts, business obligations, and the financial needs of dependents
- Disability insurance coverage is adequate for the actual income — including variable compensation, not just base salary
- Umbrella liability coverage is in place and the limit reflects the current net worth
- Long-term care insurance has been evaluated given the potential cost and its impact on the estate
Asset Protection
- Personal assets are held in a way that maximizes creditor protection under applicable state law
- Retirement accounts — which are generally creditor-protected — are being maximized as part of the overall strategy
- Any trusts intended for asset protection purposes have been properly structured and funded
- The line between business and personal assets is clearly maintained — no commingling that could expose personal assets to business liabilities
Section 7: Keeping It Current
An estate plan that was built correctly but never updated is an estate plan that will eventually fail. Life changes. The financial picture changes. The law changes. The plan needs to keep up.
Trigger Events That Require an Immediate Review
- Marriage or divorce
- Birth or adoption of a child
- Death of a named beneficiary, executor, trustee, or guardian
- Significant increase in income or net worth
- Business sale, acquisition, or major change in value
- Relocation to a different state
- Major change in tax law
Routine Review Schedule
- Estate plan documents reviewed every three to five years even without a trigger event
- Beneficiary designations reviewed annually as part of the year-end financial review
- Account titling confirmed after any new account is opened or asset is acquired
- Estate attorney and financial advisor connected at least annually to confirm the financial and legal sides are aligned
The Coordination Point
The most common reason estate plans fail isn’t bad documents. It’s disconnection — between the documents and the accounts, between the estate attorney and the financial advisor, between the plan that was built and the life that has happened since.
Working through this checklist is a starting point. The follow-through — updating the documents, retitling the accounts, funding the trust, connecting the advisors — is where the plan actually becomes functional.
If the last time this picture was looked at comprehensively was more than three years ago, or if a major life or financial event has happened since, the review is overdue.
