Choose Number Five
On 30 May 1965, in Naperville, Illinois, a judge stood in front of a graduating class and told them she had one last exam for them. Multiple choice. One question. Five possible answers, and they had to pick exactly one.
The question was what they intended to do with the rest of their lives.
Edith Sampson had earned the right to ask it. She had opened a law practice on the South Side of Chicago in 1924, become the first Black delegate the United States sent to the United Nations, the first Black American to represent the country at NATO, and the first Black woman elected to the bench in Illinois. She was not handing out platitudes. She was handing out a test she had taken herself.
I came across the speech late, sixty years after it was given. What struck me is not that it aged well. It is that all five answers are still on the sheet, and that four of them have become considerably easier to choose.
Choice one: close the drawer
Sampson’s first option is to put the diploma in a convenient drawer, close the drawer, and close your mind along with it. Avoid stimulating people. Avoid complicated realities. Read nothing that argues back.
In 1965 that took effort. You had to actively avoid things. The 2026 version requires no effort at all, because it does not look like avoidance. It looks like consumption. The scroller is not starved of input. The scroller is drowning in it, four hours a day, and takes in nothing that survives contact with the next morning.
This is the choice I find hardest to name out loud, because it is the one that wears the costume of engagement. A closed mind used to look empty. Now it looks busy.
Choice two: no strain, no pain
The second option, in her words, is to go out into the world, carefully assess the prevailing opinions, and then conform. Read only the newspaper that agrees with you. Say the sayable thing. You, too, can be a pillar-of-society conformist. No strain, no pain. Well, almost no pain.
That “almost” is the whole speech in one word. She grants that it works. She just does not pretend it is free.
I spent years on the platforms filing down my own edges into a headline. The professional conformist of 2026 does not merely hold the prevailing opinion, they publish it, in a carousel, with a hook and a call to action, and they call the result thought leadership. The opinions are not wrong. They are simply the ones already in circulation, returned to circulation with a photo attached.
I deleted those accounts last year. Not out of purity. Because I noticed I had become quite good at the exercise, and being good at it was the problem.
Choice three: amused contempt
The third option is subtler and, for people like me, more dangerous. Join a small elite. Acquire a genuine specialism. Cultivate an advanced-guard taste. Then regard everything popular with amused contempt.
This one flatters. It looks exactly like discernment, and part of it genuinely is: real expertise is real, and I make a living from having some. The tell is the contempt. The moment the specialism stops being a way of seeing more and starts being a way of belonging to fewer, choice three has closed around you.
Our industry runs on it. The language you write in, the editor you use, the cloud you refuse, the framework you have outgrown. I have written a manifesto or two about small, sovereign, hand-built software. I stand by every line. I also know that the same convictions, held for the pleasure of not being the others, would cost me nothing to keep and teach me nothing at all.
Choice three is choice one with a better vocabulary.
Choice four: your enemies are already identified
The fourth is to join a movement at one extreme or the other. Sampson’s promise here is almost gentle: once you commit, your enemies are immediately identified, and thinking becomes unnecessary.
In 1965 you had to go and find that movement. Attend a meeting. Take a position at some personal cost.
In 2026 the movement finds you. Ten minutes of hesitation on a piece of content is enough for a recommendation system to work out which side you can be sorted into, and to start delivering the sorted version of the world. Nobody sets out to become an extremist. They set out to watch one video. The radicalisation is not a decision, which is precisely what makes it Sampson’s fourth choice rather than a fifth one she failed to anticipate: the point was never how you arrived. The point is that on arrival, thinking stops being required.
Choice five, and what it costs
Then there is the fifth. Wide-ranging reading and deep-probing thought. Refuse the stereotype. Stay compassionate toward people you find hard. And, as she puts it, live constantly with the acceptance that there are no simple answers in this world because there are no simple questions.
Sampson is honest about the price. She says this choice asks so much. She does not promise it will make you happy. She promises it will keep you awake.
I recognise the bill because I get it monthly. A dirigeant calls with a question that has a simple answer available, and the simple answer is wrong, and my job is to say so and then stay in the room while it gets complicated. Should we move everything to the cloud. Is this vendor a risk. Will AI replace this team. Every one of those has a confident one-line answer circulating somewhere, and every one of those one-line answers has cost somebody real money.
The refusal of the simple answer is not intellectual vanity. It is the actual service. Choice five, billed by the day.
Sixty years, one sheet of paper
What unsettles me about the speech is not its diagnosis of 1965. It is how much cheaper the first four choices have become. Each of them used to demand something: incuriosity took discipline, conformity took a village, snobbery took a scene, extremism took a meeting. Now all four are frictionless, ambient, and free.
Only the fifth still costs what it always cost.
Sampson ended by asking the graduates who chose five to write and tell her. Not to post it. Not to signal it. To write to her, personally, so she would know.
I like that she asked. It suggests she was not confident about the count.
Hang loose, but stay vibrantly alive. — Edith Sampson, commencement address, Naperville, Illinois, 30 May 1965