A Sample Decision Register

The Harris Family — Decision Register

A record of key decisions — their rationale, and their consequences.

The record that makes the Wealth Operating Manual and the Annual Wealth Operating Review possible, not the other way around. Every structural decision, on the day it was made: why, under what assumptions, what was rejected, and — the field most advisors skip — what would change our mind. This is an illustrative sample for a fictional family.

Currententries DR-001 – DR-005 · opened February 2026append-only · nothing deleted, only superseded
I

What separates a record from a note

A dashboard reports what happened. A note says what was decided. Neither answers the question that actually matters five years on: why did we think this, and what would have told us we were wrong? Four fields make that answer retrievable instead of remembered.

Rationale

Why, in the family's own goals — not just what was chosen, but what it was for.

Assumptions

The rates, law, and facts on the day of the decision — exactly what quietly goes stale.

Alternatives

What was considered and rejected, so the ground doesn't get re-litigated from zero.

Trigger

The condition that reopens this decision. This is the field that makes review an act, not a re-read.

II

The record

Reverse-chronological. Nothing is deleted — only superseded.
DR‑001

Route the life insurance through an ILIT, not personal ownership

Confirmed
Estate Decided Q1 · Owner: Estate attorney + Driftwood

Held personally, the $2.0M death benefit would have landed inside an already-$8M estate — pushing it further past the point where the family's liquid assets could cover a federal estate-tax bill inside the nine-month window. Routing it through an irrevocable trust removes it from the estate and creates a liquidity pool that arrives exactly when the return is due, instead of forcing a sale of the business or the concentrated stock under time pressure.

Assumptions at the time
  • Current federal estate-tax exemption and portability rules hold
  • The policy's insurability and premium structure don't change
  • Tom remains the insured
Alternatives considered
  • Leave it personally owned; fund the estate-tax bill from a future business sale — rejected, a forced sale under a nine-month clock destroys value
  • A grantor trust instead of a standard ILIT — rejected as unnecessary complexity for a single-purpose liquidity vehicle
Reopens if

The federal estate exemption is cut materially, the death benefit no longer covers the projected estate-tax liability as the estate grows, or Tom's insurability changes.

Checked: held at the most recent Operating Session — no trigger fired. Risk register: liquidityAWOR: Q1
DR‑002

Establish Texas residency before sequencing the business sale — not after

In progress
Multi-state · Business Decided Q3 · Owner: Tom & Dana, Driftwood, business counsel

The order, not the components, is what the outcome hinges on. Selling first and moving after leaves the full gain exposed to Illinois sourcing rules; establishing and substantiating Texas domicile well ahead of a closing shifts a material share of that gain out of Illinois' reach. The same sale, the same buyer, the same price — sequenced differently, it is a different tax outcome.

Assumptions at the time
  • Current Illinois/Texas nexus and sourcing rules hold
  • The sale doesn't close faster than residency can be defensibly established
  • Days-in-state, intent, and documentation are actually executed — not just claimed
Alternatives considered
  • Sell first, move opportunistically after close — rejected; this is the exact ordering error the sequencing exists to avoid
  • Split the sale across two tax years instead of resequencing residency — rejected, addresses the bracket exposure but not the sourcing exposure
Reopens if

A buyer's timeline forces a close before residency can be defensibly established, Illinois changes its sourcing rules for a sold business, or the family's residency facts drift in a way that would fail a challenge.

Status: residency clock running; sale sequencing pending. Risk register: domicileThe $600,000 conversation
DR‑003

Sell down the concentrated RSU position on a schedule, not a signal

In progress
Investments · Concentration Decided Q1 · Owner: Driftwood

A single employer now represents a large, involuntarily growing share of net worth every vesting cycle. Waiting for a "better price" turns a diversification decision into a market-timing bet nobody asked to make — and concentration risk compounds the way debt does: it doesn't announce itself until it matters. A programmatic, bracket-aware sell-down converts an emotional decision into a mechanical one.

Assumptions at the time
  • Continued employment and normal vesting cadence
  • No change to employer trading-window restrictions
  • Capital-gains rates and the family's bracket stay in a similar range through the sell-down
Alternatives considered
  • Hold and hedge with options instead of selling — rejected; cost and complexity outweigh the benefit at this concentration and liquidity level
  • Sell the full position in one tax year — rejected; unnecessarily front-loads the tax bill into a single bracket year
Reopens if

The position's share of net worth moves materially in either direction, the company's risk profile changes, or a life event (the move, the sale) creates a lower-bracket year worth accelerating into.

Status: sell-down running on schedule. Opportunity register
DR‑004

Run a Roth conversion ladder, timed to the family's low-bracket years

In progress
Tax · Retirement Decided Q4 · Owner: Driftwood + CPA

The family will pass through at least one genuinely low-bracket window — around the Texas move and before the sale closes — and converting inside that window locks in today's tax cost on dollars that would otherwise be taxed at a higher marginal rate on withdrawal, decades from now, on a schedule the family doesn't control.

Assumptions at the time
  • Current tax brackets and conversion rules hold
  • No conversion year crosses an IRMAA surcharge cliff
  • The low-bracket window materializes as sequenced — depends on DR‑002 executing on schedule
Alternatives considered
  • Convert the full balance in one year — rejected; pushes the family through several brackets and possibly into IRMAA territory at once
  • Wait until after the sale to reassess — rejected; guarantees converting in a permanently higher-bracket world instead of using the window that exists now
Reopens if

DR‑002's timeline shifts and the low-bracket window closes or moves, conversion rules or bracket structure change, or an unplanned high-income year collides with a planned conversion.

Status: first conversion of the ladder complete. AWOR: decision timeline
DR‑005

Hold the gifting strategy pending the sale outcome

Open
Estate · Family Decided Q2 · Owner: Estate attorney + Driftwood

Gifting appreciated business interests ahead of a sale locks in today's — lower, pre-sale — valuation for gift-tax purposes, and the valuation refresh just completed makes this a genuinely live window. But the sale's terms aren't set. Deferring is a decision, not an absence of one: a gift made ahead of a firm price risks being unwound or second-guessed once the number is real.

Reopens if

The business sale's terms (price, structure, timing) are set — at which point this entry is superseded, not edited.

Status: deferred by design, revisited once the sale is decided.
Illustrative — how this entry evolves

When the sale terms are set, DR‑005 is not overwritten. A new entry is opened, and DR‑005 is marked superseded — the original reasoning for waiting stays on the record, next to what changed.

DR‑005 supersedes into DR‑005b
DR‑005b

Gift a fixed share of the business ahead of closing, at the appraised pre-sale value

Illustrative — not yet decided
Estate · Family Supersedes DR‑005

Shown here only to make the mechanic concrete: once a firm sale price exists, DR‑005's original condition for waiting has been satisfied, and the deferred question becomes an answerable one. The family's actual record will read this way when — and only if — that happens.

Lineage: DR‑005 remains on the record, marked superseded, not deleted.

This is not the Decision Dashboard. The Manual's Decision Dashboard looks forward — what's coming, and what to review before it happens. The Decision Register looks backward — what was already decided, and why. Read together, a household can answer the only question that actually protects it over time: does what we're about to do agree with what we already decided, or does something need to be reopened first?

See it in context: the Wealth Operating Manual · the Annual Wealth Operating Review · how the review runs.

Related

The Operating Manual (rev. 06) — where each confirmed decision lands in the ledger.

The Opportunity Register — where matters live before they become decisions.

The Annual Review — where every open trigger is re-checked, yearly.

Supersedes

Nothing yet. Entries are never deleted; a reversed decision stays in the record, marked superseded by the entry that replaced it.

Illustrative sample — not investment, tax, or legal advice. The Harris family is fictional; this document is shortened and simplified for illustration. A real Driftwood Decision Register is private to the client, begins at onboarding, and is never edited — only extended. Privacy Policy · Terms of Use