Meet Harold

It’s 1973. Harold—just a regular Harold from Wisconsin, not the famous planner Harold Evensky—is sitting at his kitchen table with the morning paper and a steaming cup of coffee. Outside, the leaves are turning. The house smells like fall. He’s newly retired after forty years in management accounting. Showed up every day. Raised three kids. Saved diligently.

He expected the golden years.

Instead, he got the Arab oil embargo, gas rationing, inflation roaring like a bear rooting through the dump behind town, and a stock market that fell by nearly half.

And the worst part?

Nobody ever warned him that when bad returns arrive matters just as much as how bad they are.

Across America, thousands of Harolds were learning the terrible math of retirement:

You can do everything right… and if the storm hits your village in the first five years of retirement, the rest of your plan might never recover.

This is why I build portfolios the way I do today.

Before Retirement: The Village Is Busy and Resilient

When you’re working, market swings are like loud rumors drifting through the village square—annoying, but not life-threatening. You’ve got steady income coming in. You’re gathering resources. And every market dip means you’re buying future harvests at a discount.

You might roll your eyes at the noise, but the village keeps humming.

In Retirement: The Storms Start to Matter

But retirement changes all that. Now your village isn’t expanding—it’s living off what it has stored, grown, and invested. And if the weather turns against you early, you’re drawing down your reserves while the fields are producing less.

That’s the danger of Sequence of Returns Risk.

Retirees who left the workforce in 1973, 2000, or 2008 still talk about it the way villagers talk about the Great Storm that knocked out half the valley.

So the question becomes:

How do you build a village resilient enough to survive whatever storm arrives—early, late, or unexpectedly?

That’s where time segmentation comes in.

Not as a spreadsheet trick.
Not as some academic formula.
But as a way of organizing your financial village so every citizen—every dollar—has a job and a season.

The Fable of the Three Workers

Every retirement portfolio is, in a sense, a small village. And in that village, three core workers keep things running: The Guardian, the Worker, and the Dreamer.

Each one has a distinct job.
Each one works on a different timescale.
The village only thrives when their roles are respected.

Let me introduce them.

1. The Guardian (Years 1–7)

The Guardian is the villager everyone trusts.

Cautious, skeptical, and wary.
Standing watch at the front gate.

The Guardian doesn’t care about stock prices or market forecasts.
His job is simple:

Keep the village alive today. And tomorrow. And the next day.

The Guardian stores firewood, grain, and warm blankets—your cash, your short-term bonds, and your multi-year ladder of reliable fixed income. These stores mature exactly when needed, year after year, like scheduled deliveries to the village square.

Accumulation-oriented advice insists you need only 6 months, maybe a year of stores.

But history—1973, 2000, the long stagnation of 1966–1982—has shown that storms can last much longer.

A 6 month supply is like filling the pantry for a long weekend and hoping winter plays nice.

A seven-year Guardian’s reserve—not stuffed entirely with cash under the floorboards, but built from a thoughtfully structured bond ladder—is the sweet spot. Long enough to endure a hard stretch. Productive enough not to rot or be eaten by inflation mice.

The Guardian protects you from panic, bad timing, and your own very understandable human fears.

2. The Worker (Years 8–15)

If the Guardian is the protector, the Worker is the backbone of the village.

Up before dawn. Hands calloused. Steady and productive.
He tends the fields, mills the grain, repairs the tools, and refills the Guardian’s stores each season.

The Worker handles the mid-term tasks—those that don’t pay off immediately but don’t require decades, either.

That might look like:

Private credit producing steady yield
Interval funds that hold real estate and business loans
Semi-liquid private markets designed for patient capital
Or a straightforward global 60/40 asset allocation

The important thing is this:

You don’t need every dollar in your village to be instantly accessible.

Villages that insist on perfect liquidity at all times get lower harvests.
Convenience comes at a cost.

Some crops take longer to grow.
Some fields produce more if you don’t harvest them early.

That’s the illiquidity premium: the extra bounty you earn for letting things mature in peace.

And because the Guardian shields your first seven years, the Worker can keep harvesting—even through short-term disruptions like liquidity crises and redemption freezes.

The Guardian buys the Worker time.
The Worker gives the Guardian resources.
It’s a beautiful feedback loop.

3. The Dreamer (Years 15+)

Finally, we come to the Dreamer—the villager with the long view.

He’s the orchard planter, the inventor, the one who sketches maps to distant lands. He’s not thinking about next month’s bread—he’s planning for your 70s, your 90s, your grandkids, and the projects that will leave the world a better place.

The Dreamer invests in the long-term projects—the orchards that take decades to bear fruit but feed generations.

And the data here borders on magical:

1-year returns can be volatile
5-year returns get calmer
15-year rolling returns?
We have yet to see a negative nominal return.

That’s why the Dreamer embraces equity.

This is where Roth IRAs become orchards that grow tax-free fruit.
This is where compounding—the true “eighth wonder of the world”—does its quiet, patient work.

Time is fertile soil, and the Dreamer plants deep.

The Choreography: How the Village Survives

Most people think the village works like this:

“When the Guardian runs low, you sell some of the Dreamer’s orchard to refill him.”

But that’s like chopping down your young apple trees during a storm.
You lose what you need most.

The real strength of a time-segmented village is in the choreography:

The Guardian buys you time
The Worker produces the ongoing harvest to replenish the Guardian
The Dreamer grows in peace until his orchards are ready—often far later than expected

It’s intentional design.

Because you’re not just allocating assets.
You’re allocating purpose.

And when every villager does the job suited to their season, the entire village becomes resilient.

Why This Matters Today

Somewhere out there is another Harold. He may be you.

He’s hearing panicked rumors in the village square—bear markets, political upheaval, inflation scares.
He’s seeing the storm clouds gather, even if he doesn’t have the language for it.

What he needs isn’t a spreadsheet or a chart.
What he needs is a story he can step into. A village he understands.

A village where:

Storms aren’t fatal
Illiquidity isn’t frightening
Growth isn’t reckless
Cash isn’t dead weight
And time isn’t an enemy. It’s the backbone of the plan.

This isn’t just investment management.
This is the architecture of a life.

A village built intentionally across decades.
Sheltered from the things we can’t predict.
Powered by the things we can control.
Designed to give people something most portfolios cannot promise:

Confidence.

That’s what you build at Encore Retirement Planning.