For a long stretch of my life, I measured myself by the rung — what title sat next to my name, and how that lined up against the people I started out with. I would not have admitted it out loud, but that was the scoreboard I checked, not what it took to get anywhere but the position reached, frozen at a moment like a photograph.

I have come to think that is the wrong measure. And the cleanest argument I have read against it comes from a man who had every reason to know better than most.

What Washington actually wrote

The line everyone quotes is the back half of a fuller sentence. Washington wrote, “I have learned that success is to be measured not so much by the position that one has reached in life as by the obstacles which he has overcome while trying to succeed.” Those first three words matter. He is telling you what experience taught him, not handing down a law.

And the experience behind it is worth knowing. Washington was born into slavery in 1856. After the Civil War freed his family, he worked from before dawn in a local salt works, and later in a coal mine, as a child. He went on to found the Tuskegee Institute in 1881 and to advise two presidents. The success quote first ran in a New York periodical called The Outlook on November 10, 1900, before his autobiography arrived the following year. 

Why the scoreboard measure is the easy one

Position is easy to measure because it is visible. You can see a title, a salary band, a house, a LinkedIn page. The obstacle someone climbed to get there is invisible. So the lazy default is to rank everyone by where they landed and ignore the gradient they had to walk up to land there.

The trouble is that this measure quietly punishes anyone who started further back. Two people reach the same rung. Perhaps one coasted down a gentle slope. The other clawed up a cliff. The scoreboard scores them identically. 

A study in the Journal of Happiness Studies found that comparing yourself to people who are better off drags your well-being down, and that this upward comparison is the stronger force. I know this well. For me the pressure was never one dramatic moment. It was the diffuse by-thirty script, the sense that there were milestones you were meant to have hit by a certain age, and that falling behind on them was a kind of quiet failing. No single scene crystallized it. A slow drip, and the career milestone was the one that bit hardest.

The obstacle measure in my own life

Around thirty, I left a job running an adult language school, where I was the manager responsible for a sizeable team, to become an intern at a venture capital firm. Then an analyst. On the scoreboard, that is a clean status drop. Manager to intern, at an age when several of my peers were already qualified accountants, settled on a track, moving up and not back.

The move turned out well. I mostly have no regrets. But I will be honest that the what-if-I-had-stayed voice still bites in waves, and I admire the friends who walked the straight line. By the position-reached measure, taking that step backward was indefensible. By the obstacle measure, it was the most useful thing I did, because the hard part was choosing to look like I was losing in order to get somewhere real. The obstacle measure is the better one. Not because struggle is noble, but because the scoreboard measure is a lie about how people actually arrive anywhere.

What the obstacle measure does not mean

The obstacle measure is one short step away from a romance of struggle, and that is a place I do not want to go. It does not mean suffering is good, or that you should go looking for obstacles to rack up a score.

My coffee business failed. I feared it failing, then it failed, and the strange part was that the fear had been worse than the reality. Only afterward could I see what I had learned from it. That is the honest version. The dishonest version would dress the failure up as a noble trial, which it was not.

Washington himself flirted with the stronger version of this claim, suggesting in the same passage that a hard and unusual struggle could be an advantage in real life. That goes further than I will. The obstacle is not the prize. It is the unit you should be measuring with, because the position alone tells you almost nothing about what a person did to reach it. Keep the scoreboard if you want, but know it is the wrong instrument. Washington had it right: the climb is the data, the rung is just the label.