On January 27, 2022, I sat in a small plane at Raleigh Exec Jetport, about to take my first solo flight.
Before I taxied to the runway, my flight instructor told me something that changed how I think about retirement planning.
“If anything feels wrong, you don’t have to take off today. Remember: takeoff is optional. But landing is mandatory.”
Four years later, I think about that line every time I sit down with someone five years from retirement.
Because you have three landings coming in retirement. And you may not realize you’re already in the air.
What My Instructor Really Meant
Before takeoff, you have all the choices. You can turn back. You can go home. You can wait until tomorrow. The decision to take off is yours.
But once the wheels leave the ground, one thing is certain. The plane will come back down. Sooner or later, safely or not, the landing will happen.
My instructor wasn’t trying to scare me. She wanted me to remember that the choices I made on the ground mattered most. The pre-flight check. The fuel. The weather. The plan if something went wrong at 3,000 feet.
Once I was in the air, my options got a lot smaller.
Here’s the difference between you and me
On that January morning, I still had a choice. I could taxi back. I could go home. My takeoff was optional.
But if you’ve been saving for retirement for years, you’ve already taken off. Your accounts are already built. Your tax situation is already in place. Your beneficiaries are already on the forms, even if you don’t remember exactly what you wrote.
The plane is already in the air.
What you get to choose now is how you land. Intentionally, at a runway of your choosing, or wherever the aircraft ends up when the fuel runs out.
The Three Mandatory Landings
You face three landings in retirement, whether you plan for them or not. I call them the Mandatory Landings.
Landing 1: The Tax Bill
Every dollar in your traditional IRA or 401(k) will be taxed as ordinary income on the way out.
Your only choices are when it comes out and at what rate.
If you don’t decide, the IRS decides for you at age 75, through required minimum distributions.
Landing 2: The Health Decline
Every year in your sixties brings a real chance that something changes. A knee gives out. A back doesn’t recover. An unexpected diagnosis.
Your most active retirement years, what I call the Go-Go years, are the ones with the shortest supply.
Every year you postpone using them is a year you don’t get back.
Landing 3: The Estate Transfer
Someone will inherit what you’ve built. Non-spouse beneficiaries must empty an inherited IRA within ten years.
Which means your children pay the tax on your savings, at their tax rates, often during their highest-earning years.
You can plan the transfer. Or the tax code will plan it for you.
Tax bill. Health decline. Estate transfer. These three landings are coming. The only question is whether you flew the plane, or the plane flew you.
What ‘Just Wait’ Actually Costs
Delay has a cost that doesn’t show up until years later. Let me name it specifically.
If you delay tax planning by five years
You lose five years of the Roth conversion window. That window opens the day you retire and closes when required minimum distributions start. Every year that passes is a year of low-bracket space you can’t get back.
If you delay retirement by three years to feel safer
You could give up about 150 Go-Go weeks from the front of retirement. These are your healthiest, most active weeks. They come off the beginning, not the end.
If you delay estate planning
Your heirs could pay the tax bill at their peak-earning rates. On a large IRA, that can easily be tens or hundreds of thousands of dollars in extra tax per child.
Each delay is a landing you didn’t plan. The landing still happens, just on someone else’s terms.
Why Smart People Delay Anyway
The people I meet who have delayed these decisions aren’t lazy. They aren’t uninformed. They’ve read the articles. They’ve done their homework.
They delay because delay feels safe.
Nothing bad happens today when you skip a Roth conversion. Nothing bad happens today when you don’t update your beneficiary form. Nothing bad happens today when you push retirement back one more year.
The cost of delay isn’t visible until years later. And by then, some of the choices you had are already gone.
This isn’t a moral failing. This is how brains work. We respond to what’s in front of us. Retirement decisions almost never put anything painful in front of you today. So you wait.
Recognizing that pattern is the first step to changing it.
What Planning the Landing Looks Like
Planning the landing isn’t about being perfect. It’s about making small decisions before they become forced decisions.
Instead of waiting for RMDs at 75 to trigger a large tax bill
You look at Roth conversions in the lower-income years right after retirement.
Instead of drifting into ‘one more year’ because you can’t picture retirement
You pick a date on purpose, and you plan what comes after.
Instead of leaving your beneficiary form at whatever it said 15 years ago
You update it. You think through whether direct-to-children or a trust fits your situation. You choose with intention.
Each one of these is a small decision that removes a bigger, uglier landing later.
The pilot analogy still holds. You do the pre-flight check. You plan the fuel. You look at the weather. And then the landing is something you flew toward, not something that happened to you.
Where This Doesn’t Apply
To be fair, the Mandatory Landings idea doesn’t apply the same way to everyone.
If you’ve already done the work, updated the beneficiaries, run the Roth conversion analysis, and picked your retirement date, this is just confirmation. That’s the goal.
If you don’t have significant pre-tax retirement accounts, the first landing is smaller for you.
If you plan to leave most of your estate to charity, the third landing changes. Charities don’t pay income tax on inherited IRAs.
So this isn’t universal. But if you’re in your fifties or sixties, have meaningful savings, and a few decisions you’ve been putting off, this is for you.
What You Can Do This Week
If you want to see how you’re doing with your own three landings, the free Retirement Confidence Assessment is a good starting point. It takes about 5 minutes and gives you a snapshot of where you stand.
If you’d rather sit down and plan the landings together, you can schedule a complimentary planning conversation with my team. On that first call, we’ll review your numbers, talk about the landings that matter most to you, and figure out what fits your situation.
Or call my office directly: (919) 290-7800
Takeoff is optional. Landing is mandatory. And you don’t always get to choose where you land.
That’s how you build real confidence for your retirement.
ABOUT THE AUTHOR
Sunwook Jin is a Certified Financial Planner and the author of There Are No Do-Overs at Retirement. He leads a team at Redwood Financial Network that helps people approaching retirement turn their savings into income, reduce tax surprises, coordinate their savings, pension, Social Security, and estate strategies, and see their entire plan in one place.