Why Every Retirement Plan Needs a Pre-Flight Checklist
Before every flight, no matter how experienced the pilot, there is a checklist.
Not because pilots don’t know what to do.
Because memory is unreliable.
Stress changes behavior.
And small oversights compound quickly at altitude.
Retirement is no different.
Before income begins, before assets are relied upon instead of earned, there should be a deliberate pre-flight checklist.
Not a projection.
Not a generic allocation.
A checklist.
In Aviation, Routine Prevents Regret
As a flight instructor, I logged over a thousand hours teaching students how to fly safely.
One of the first habits we build is procedural discipline.
Before engine start:
Fuel levels verified.
Oil pressure confirmed.
Flight controls checked.
Before takeoff:
Instruments set.
Trim adjusted.
Emergency procedures reviewed.
The point isn’t perfection.
It’s preparation.
Because once you’re airborne, your margin for error narrows.
Retirement is similar.
Once paychecks stop, the financial engine changes.
You don’t want to discover structural weaknesses after you’ve taken off.
What a Retirement Pre-Flight Checklist Should Include
Most retirement advice focuses on:
“How much do you have?”
The better question is:
“How prepared is the structure?”
A real pre-flight checklist for retirement should examine:
Income durability
Tax sequencing
Withdrawal order
Survivor planning
Concentration risk
Liquidity reserves
Spending flexibility
These are not theoretical concerns.
They determine whether retirement can withstand turbulence.
Sequence Risk Is the Crosswind
In flying, crosswinds require preparation.
If you ignore them, landing becomes unstable.
In retirement, sequence risk plays a similar role.
A downturn in the first few years of retirement can materially change outcomes.
If a portfolio has no income segmentation, no guardrails, and no margin, withdrawals amplify damage.
The checklist forces you to ask:
What happens if markets fall 30 percent in year one?
Not “Will they?”
But “If they do, are we prepared?”
Fuel Reserves Matter
Pilots do not fly with exact fuel requirements.
They build reserves.
In retirement planning, reserves may look like:
Multiple years of staged income
Cash or short-duration assets
Guardrails that allow spending adjustments
Reserves reduce fragility.
Without them, minor disruptions escalate quickly.
Survivor Planning Is Often Ignored
Many retirement plans focus on joint projections.
Fewer stress-test what happens when one spouse passes.
Tax brackets compress.
Social Security changes.
Fixed costs often remain.
A pre-flight checklist asks:
Is the surviving spouse structurally protected?
That question should be answered before departure, not mid-flight.
Overconfidence Is Dangerous
Experienced pilots are not exempt from checklists.
In fact, the more experience you have, the more discipline matters.
Affluent households in Grosse Pointe often feel financially secure.
Significant assets.
Strong careers.
Good savings habits.
That confidence can create blind spots.
Retirement is not just about having enough.
It’s about having the right structure.
The Goal Isn’t Elimination
In aviation, risk never goes to zero.
In markets, uncertainty never disappears.
The purpose of a checklist is not to eliminate risk.
It’s to reduce preventable mistakes.
It’s to ensure:
Assumptions are tested
Weaknesses are addressed
Everyone understands the plan
Because once you are airborne in retirement, corrections become harder.
The Real Question
Before you retire, ask yourself:
Have we run the checklist?
Not just:
“Do we have enough?”
But:
“Is the structure resilient?”
Markets will move.
Tax laws will change.
Unexpected events will occur.
Preparation does not remove uncertainty.
It improves response.
And response determines durability.
