Climb the Ladder. Just Not That One. — by Dan Lynn
By Dan Lynn
We spend our whole lives climbing the ladder. That's the deal we're handed early: work hard, reach the next rung, then the next — more responsibility, more income, more security. And for most of your working life, climbing is exactly the right move.
But I met a man who taught me there's one ladder you shouldn't climb.
I was at a diner one morning, sitting at the counter, and got to talking with the guy next to me. He'd just retired — decades of climbing behind him, the finish line finally crossed. Then he told me what happened. One afternoon he leaned a ladder against a tree and climbed up with a chainsaw to cut down a branch. The saw hit the branch, kicked back, and he went off the ladder. When he came to, he was flat on the ground with the chainsaw still running next to his ear. He wrecked his shoulder, badly. He looked at me and said the saddest thing: "I ruined my retirement." Then he gave me the only advice he had: "Don't climb ladders when you retire."
Think about the trade he made. The upside: a trimmed branch, a couple hundred bucks saved. The downside: everything he'd spent his whole life climbing toward.
So climb the ladder. Climb it hard, your whole life. But once you've reached the top, hire the kid with the truck and watch from the porch. Some ladders just aren't worth climbing anymore.
Questions this Key Learning answers
Should I still do risky home projects after I retire?
The author’s lesson is that some physical risks are no longer worth taking after retirement. A retired man climbed a ladder with a chainsaw to save money, fell, and badly injured his shoulder. His advice was simple: “Don’t climb ladders when you retire.” Dan Lynn suggests hiring someone else and watching from the porch.
How do I decide whether saving money is worth the risk?
The author frames the decision by comparing the limited upside with the potentially enormous downside. In the story, trimming the branch saved a couple hundred dollars, but the fall threatened everything the man had spent his working life building toward. Some savings are not worth risking the security and freedom earned over decades.
What does it mean to stop climbing once I reach retirement?
Dan Lynn is not arguing against ambition. He says climbing the professional ladder is the right move for most of a working life. His warning is more literal: after reaching retirement, avoid unnecessary physical risks that could ruin it. Keep what decades of work created rather than gambling it on a task someone else can handle.