Hypothetical scenarios

What the work looks like, before you hire anyone.

Four situations we see often, written out in full. Not case studies and not clients — illustrations, so you can see the shape of the work rather than read another paragraph about being comprehensive.

Please read this first

Every scenario on this page is hypothetical and entirely illustrative. These are not actual clients, not composites of actual clients, and not descriptions of anything that happened. They contain no investment results, no performance figures and no dollar outcomes, because presenting either would be a claim we cannot make. They exist to show what gets examined and in what order. Your own situation will differ, and so will the answer.

Where people start

Most of these begin with nothing being wrong.

The event-driven cases are the memorable ones. The common one is the professional who has simply earned well for a long time, has no hours left to organise it, and has never been shown what the pieces do to each other.

Hypothetical · No triggering event

The specialist earning well, with no plan behind it.

A surgeon in her early forties. High income for over a decade, two young children, and nothing has gone wrong — which is exactly the problem. There has been no sale, no inheritance, no event that forced anyone to sit down. Money accumulates in whatever account was open at the time.

What was already true

  • A workplace retirement plan, contributed to but never reviewed
  • A taxable brokerage account holding whatever was bought first
  • Cash well beyond any stated purpose, because nobody decided otherwise
  • A will drafted before the second child, never revisited
  • A tax return prepared each spring by someone who has never seen the portfolio

What the planning work looks at

  • Whether the cash has a job, and what it is costing to hold it without one
  • Which of these accounts should hold which kind of asset, and what the current arrangement costs each year
  • Whether the retirement plan is being used to its full extent given her income
  • What the estate documents actually say now that the family has changed
  • Getting the tax return and the portfolio built at the same table
Hypothetical · Liquidity event

The founder with a letter of intent on the desk.

A business owner in his late fifties with a signed LOI and roughly ninety days to close. Most of his net worth has been inside the company for twenty years. The question he arrives with is what to do with the proceeds. The more expensive questions are the ones that close before the deal does.

What was already true

  • A purchase price agreed, but the structure of it still open
  • An accountant focused on this year's return rather than on the transaction
  • No estate work done in advance of a change in net worth of this size
  • Charitable intentions discussed for years and never formalised
  • A plan for after the sale that consists of the word 'retire'

What the planning work looks at

  • How the deal is structured, and what each structure means for after-tax proceeds
  • Which planning steps must happen before signing, because they cannot be undone afterwards
  • Whether charitable intent should be executed pre-sale, and in what form
  • What income needs to look like when a business stops being the source of it
  • Coordination between the attorney, the CPA and the advisor before the closing date, not after
Hypothetical · Concentrated position

The executive whose company did very well.

An executive at a public company whose equity compensation has vested over several years and now represents an uncomfortable share of the family's wealth. Selling feels disloyal and expensive. Holding feels reckless. Nobody has put numbers to either feeling.

What was already true

  • A single position larger than the rest of the portfolio combined
  • A vesting schedule that keeps adding to it
  • A large embedded gain that makes any sale a tax event
  • Trading windows and company policy constraining when anything can happen
  • A spouse who is worried about it and a holder who is not

What the planning work looks at

  • What the position actually is as a percentage, stated plainly
  • What a reduction costs in tax, in which years, and whether it can be spread
  • Whether charitable gifting of appreciated shares does part of the work
  • What the plan requires the money to do, and how much concentration that can tolerate
  • A written schedule made in advance, so the decision is not made in a volatile week
Hypothetical · Practice owner

The dentist with two practices and one exit.

A practice owner in his mid-fifties with two locations, strong income, and a retirement plan that was set up years ago and has not been revisited since the second location opened. He wants to be out by sixty-two and has not tested whether that is a number or a wish.

What was already true

  • A retirement plan design chosen when the practice was half its current size
  • Personal and business finances that overlap in ways nobody has mapped
  • Real estate held in a structure chosen for reasons long since forgotten
  • Associates who might buy in, and no agreement describing how
  • A target retirement age that has never been tested against the numbers

What the planning work looks at

  • Whether the plan design still fits the practice, and what a better one allows him to contribute
  • What the practice is likely to be worth, and how much of the retirement it has to fund
  • The order of operations for an internal sale versus an external one
  • What the real estate should do at exit, which is often a separate decision from the practice
  • Whether sixty-two works — and if not, what specifically has to change
The pattern underneath

Four different lives. The same missing piece.

In every one of these, the individual parts were being handled by someone competent. What was missing was anyone making sure a decision in one part did not create a problem in another — which is the only thing that is genuinely hard to buy piecemeal.

01

The accountant sees the return, not the portfolio

So the tax consequence of an investment decision arrives after the decision, in April, when nothing can be changed about it.

02

The attorney sees the documents, not the balances

So an estate plan is drafted against a picture of the family's wealth that was accurate when it was drafted.

03

The advisor sees the accounts they hold

Which is rarely all of them — and a plan built on part of the picture is a plan with a hole in it that nobody can see.

04

Nobody owns the seams

Every one of these professionals is doing their job properly. The gap is between them, and it is where the expensive mistakes live.

This is why our tax practice sits inside the firm rather than down the street, and why the plan, the portfolio and the estate structure get built by one team at one table.

Start here

See your own version of this, with your actual numbers.

A complimentary strategy session: what you own, what it costs you in tax, and where the seams are. You leave with the analysis whether or not you hire us.

→Schedule your strategy What to bring to a first meeting

All scenarios shown are hypothetical illustrations. They do not represent actual clients or actual results, are not testimonials, and are not a guarantee or projection of any outcome. Nothing on this page is investment, tax or legal advice. Investing involves risk, including the possible loss of principal. Advisory services offered through Cannon Capital Management, Inc., a Registered Investment Adviser.