Investment strategy meets real life: closing the planning gap

Uncertainty is not a reason to wait. Across the 4,800+ families we advise, the households that felt most secure this year were not the ones with the boldest forecasts — they were the ones that made a small number of deliberate decisions and stuck with them.

Below are the five planning moves we are discussing with clients before 2027. None of them require a windfall. All of them require a clear plan, good timing and the discipline to leave the rest alone. If you want the full data behind our view, our 2026 Retirement Confidence Report covers the methodology in detail.

1. Turn savings into a retirement paycheck

Many retirees leave money on the table because withdrawal decisions are made by habit, not by evidence. Accounts are drawn down in whatever order feels easiest, required distributions arrive as a surprise, and nobody owns the full picture. That is exactly the kind of gap a focused review can close in a single season.

• Map every source of income — Social Security, pensions, savings — against your spending.
• Split your spending into three buckets, not one total:
  • essentials you must cover whatever markets do;
  • lifestyle spending you can flex in a bad year;
  • legacy and giving goals with the longest time horizon.
• Decide in advance which account you will draw from first.

Where to start

Start with the accounts you already have. The years between retirement and required distributions are often a low-tax window, because income has dropped but savings have not. For one client couple, a series of partial Roth conversions is projected to lower their lifetime tax bill. Individual results vary.

A quick check for your household

1. Do we know what we spend each month, and what is essential?
2. Which account will we draw from first, and why?
3. When did we last check our tax bracket for the years ahead?
   1. If it was more than 18 months ago, start there.
   2. If you have never modelled it, look at the years before required distributions begin.

2. Harvest tax losses all year, not just in December

Every dip in a taxable account is a chance to bank a loss that can offset gains elsewhere. Yet in many of the portfolios we review, losses are only looked for in the last week of December, after markets may already have recovered.

The families we work with treat tax losses like any other asset: they know where they sit, which lots they belong to and how long they can be carried forward. They agree on a single, written set of harvesting rules before markets test their nerve.

That sounds unglamorous. It is also the foundation for several other moves on this list — you cannot plan withdrawals, gifts or a sale around tax numbers you do not track.

“We stopped dreading every red day in the market and started asking what we could do with it. That shift alone changed how we invest.”

— Client since 2018, New York

A practical first step is to write your rules down. For example, we define a harvest_threshold as the loss on a position, measured against its cost basis, that is large enough to act on — and we write that rule down where everyone can see it:

# plan/tax-rules.yml — single source of truth
harvest_threshold:
  owner: advisor
  formula: "unrealized_loss / cost_basis"
  refresh: monthly
wash_sale_window:
  owner: tax_team
  formula: "days_before_sale + days_after_sale + 1"
  target: 61

3. Build a cash reserve before markets wobble

The swings of the last five years taught many investors that being fully invested is not the same as being prepared. A cash reserve is not exciting — but it is far easier to build before you need it than in the middle of a downturn.

Here is how the five moves compare on time, review cycle and complexity, based on our work with 4,800+ client families:

Planning move	Time to set up	Review cycle	Complexity
Retirement paycheck	4–6 weeks	Every year	Medium
Tax-loss harvesting	1–2 weeks	Every quarter	Low
Cash reserve	1–3 months	Every year	Low
Estate documents	2–3 months	Every 3–5 years	Medium
Liquidity planning	12–36 months	Before any sale	High

A plan is not a list of things you might do. It is a short list of things you will do instead of everything else.

Daniel Whitmore

4. Treat your estate plan as a living document

The most common estate planning problem we see is not a missing will. It is an old one — written before a marriage, a move, a new grandchild or a business sale, with beneficiary forms that no longer match the plan.

1. List every account and the beneficiary named on each one.
2. Reread your documents for guardians, trustees and executors who may have changed.
3. Meet with your attorney with the right people in the room:
   • your estate attorney, who drafts the documents;
   • your CPA, who checks the tax consequences;
   • your Corwell advisor, who checks the plan against your accounts.
4. Sign and store — and tell your executor where everything is.

For a deeper look, read Sofia Delgado’s notes on planning for families across borders.

5. Plan a liquidity event before it happens

For founders and executives, the largest financial decision of a lifetime often arrives on someone else’s timetable. In our experience, the best outcomes come from planning the taxes, the giving and the diversification years before the term sheet arrives.

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Model the sale before you negotiate it, consider funding trusts while values are lower and agree a diversification schedule. It is the slowest move on the list, and the one with the longest tail of consequences.

The bottom line

You do not need to make all five moves at once. You do need to choose — deliberately — which two or three matter most for your family in 2027, and give them proper attention. If you would like a second opinion on your shortlist, talk to one of our advisors.