This week I am pleased to feature a guest post by Richard Sheffield, the author of Spend Your Damn Retirement Money: Beat the Spending Fear to Find Your Dream Retirement. Richard also contributes regular retirement advice on Medium.
Retirement advice has a weird habit of sounding like the last ten minutes of a Mission Impossible movie.
Cut the red wire, not the blue.
Take Social Security at exactly the right age.
Withdraw the correct percentage.
Downsize, but not too much.
Spend, but not recklessly.
Stay invested, but not emotionally.
Don’t run out of Money.
Also don’t die with too much.
By the time you finish reading posts from the gurus, you’re convinced that if you make one “Sub-Optimal Allocation,” your entire financial existence will detonate, leveling three city blocks and causing every smart-fridge in the zip code to spontaneously order a case of rainbow kale.
This is, to use a technical financial term, baloney (or bologna depending on your Adjusted Gross Income — Line 11).
Not every retirement decision has to be perfect. In fact, you are socially obligated to get some of them spectacularly wrong. What else do we have to laugh at these days?
You’ll wait too long to spend. Or you’ll spend too soon and realize you’ve bought a $90,000 Italian sports car that you literally cannot get in or out of without starting and ending up on your hands and knees (just Google the Lambo crawl). You’ll stay too conservative, or you’ll discover that your “Dream Retirement Town” is charming for exactly 36 hours, about the time it takes for the local “Historical Society” to tell you that your mailbox is the wrong shade of “Colonial Eggshell.” After which the town reverts to its true form: a desolate museum of closed shops, aggressive brunch, and people who have very strong opinions about leaf-blowing (and those doing the blowing).
The real problem isn’t making a mistake.
The real problem is what happens after.
A lot of retirees make one imperfect decision and immediately turn it into a personal mythology.
I took Social Security too early.
We bought the wrong house.
I should’ve stayed more invested.
We should’ve traveled sooner.
It’s too late now.
That’s the second most dangerous phrase in financial planning, the first being, “this time it’s different.”
But, “It’s too late now,” is right up there in the top flight of wrong ideas.
Because in most cases, it’s not too late. It’s just no longer ideal.
And “ideal” left the building a long time ago anyway.
You are allowed to adjust in retirement.
This should not be a radical statement. It should be the sort of thing everyone nods at politely, the way we nod when someone says, “Water is wet,” or “You probably shouldn’t store gasoline next to the toaster.”
You are allowed to admit the dream house isn’t dreamy and sell it.
You are allowed to spend more if fear has had both hands around your wallet for ten years.
You are allowed to work part-time if you want income, structure, or a reason to wear big-boy pants twice a week.
You are allowed to stop if your “fun little retirement project” has quietly promoted itself to Director of the Department of Things That Were Supposed to Be Relaxing.
None of that is failure.
Pilots adjust. Good investors adjust. People driving through LA traffic definitely adjust. Why would retirement be the one part of life where changing course is treated like some kind of moral collapse?
Part of the problem is that the retirement world loves precision. It loves charts, withdrawal models, optimized claiming strategies, and neat little projections that imply if you just plan carefully enough, you can avoid uncertainty forever.
But the fundamental problem with the “Experts” is that they believe Retirement is a Math Problem, like calculating the trajectory of a deep-space probe or figuring out how many “Reward Points” you need to fly to Cleveland the morning before a periodontist’s convention.
Your Health changes. Your energy changes. Your Marriage changes. Your interests change. Your tolerance for airports, stairs, winter, and golf communities change. The plan you made at 61 may look pretty questionable at 71.
That doesn’t mean the plan failed.
It means the plan was a draft.
A lot of retirement “mistakes” are less catastrophic than people make them out to be.
Took Social Security earlier than the mathematically perfect age? Fine. Maybe it gave you freedom sooner. There’s value in that.
Stayed too conservative? Then rebalance.
Waited too long to spend and now regret it? Then stop making today worse by fucking repeating yesterday.
Bought the wrong house? Sell the damn house.
Retired and discovered you hate unstructured time? Also normal. Some people don’t need endless freedom. They need rhythm, purpose, and something on the calendar besides “wander around Costco.”
A lot of what retirees call disaster is really just revision.
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That’s an important distinction.
Disaster is running out of money with no options.
Disaster is major illness with no plan.
Disaster is fraud, denial, or total paralysis.
But “we chose the wrong location,” “we’re too cautious,” “this house doesn’t fit,” or “we should have started enjoying this money sooner” … those are not disasters.
Those are course corrections.
In a world run by greed-heads and lizard-brained actuaries, the idea of ‘getting it right’ is a cruel joke played on us. You will fail. You will buy into a fraudulent ‘Luxury Retirement Compound’ in the high desert that turns out to be a sun-bleached concrete slab guarded by a man with a sawed-off shotgun and a profound hatred of outsiders. At that point, ‘Accuracy’ is irrelevant. What matters is Surgical Recovery. It’s about Recovering Intelligently, which is a technical term for “Let’s try not to cry in front of the Realtor.”
Can you notice when the plan and reality are no longer aligned?
Can you admit it without turning it into a courtroom drama?
Can you Claw Your Way Out before pride wastes another five years of your dwindling biological clock?
That’s the skill.
Not perfection.
Not prediction.
The only skill that counts when the engine starts smoking and the sky turns the color of a bruised kidney is Adaptation. You don’t need to review the old map; you need the animal instinct to move before the concrete sets around your feet. Adapt or die, those are the only two options left on the menu. In a world of shifting markets and predatory heirs, ‘Perfection’ is a sucker’s bet, a cheap parlor trick for the rubes.
Some retirees put all their confidence in the size of the pile. This is a dangerous hallucination. In a world governed by the laws of Savage Entropy, the size of your pile is irrelevant when the sky starts raining bricks. You can have a pile the size of the Matterhorn, but if you’re too paralyzed by the The Fear to move when the ground starts shaking, you’re just the richest corpse in the rubble.
True confidence… the kind of cold, jagged nerve you need to survive the Final Stretch doesn’t come from the ledger. It comes from your innate Ability to Respond when the script goes into the shredder. It’s the instinct to kick out the windshield when the car hits the swamp.
Life doesn’t care about your ‘Original Script.’ Life is a drunken editor with a grudge and a fat red crayon, and he’s going to cut your favorite scenes without warning. Your only hope is to be faster than the blade. You have to be able to look at the smoking crater where your ‘Safe Harbor’ used to be, shrug your shoulders, and find a new way to get to the coast before the tide comes in. It’s not the size of the hoard that saves you; it’s the speed, and willingness, of the pivot.
That doesn’t mean your retirement is broken. It means you’re still in it.
And unless you are somehow reading this from the afterlife, which would be a hell of a subscriber perk, the story is still being written.
The ‘Perfect retirement Plan’ is a simpleton’s fantasy, a shimmering mirage for the terminally naive. You will blow the engine. You will smell the failing transmission of your own bad decisions. But a good retirement is simply one where the smoking wreckage doesn’t get the Final Word. After the car flips, you don’t sit in the seat and wait for the explosion… you grab the bag, reload your nerves, and keep moving toward the coast.
