US Supreme Court chief justice John Roberts is the highest judge in the land. His job is to be a wise man, and it’s apparently a quality that extends beyond the bench.

Recently, Roberts handed out some surprising advice at a commencement ceremony at Cardigan Mountain School in New Hampshire. The chief justice was charming but contrary, freely admitting that his advice would sound strange. Then he went on to wish graduates just enough angst to make them the sorts of decent humans who understand other people and their troubles.

The message was aimed at children, including his own young son who was graduating from the private boys boarding institution for sixth to ninth graders. Yet the wisdom is worth considering at any age, providing a poignant reminder for adults of the upsides of inevitable suffering. Specifically, Roberts said:

I hope you will be treated unfairly, so that you will come to know the value of justice. I hope that you will suffer betrayal because that will teach you the importance of loyalty. Sorry to say, but I hope you will be lonely from time to time so that you don’t take friends for granted.

Roberts also appeared to reveal something about his view of himself in the speech, perhaps accidentally. He came off as humble, seeming to attribute his undeniable professional success in part to luck and privilege:

I wish you bad luck, again, from time to time, so that you will be conscious of the role of chance in life and understand that your success is not completely deserved and that the failure of others is not completely deserved either.

Among other mixed blessings, Roberts hoped the kids would be ignored so they’d learn to listen and suffer some pain so that they become compassionate. The justice, who has spent much time considering difficulty in his professional career, told them, “Whether I wish these things or not, they’re going to happen. And whether you benefit from them or not will depend upon your ability to see the message in your misfortunes.”

The justice also urged the students to be a little dissatisfied with who they are, and not just settle for being themselves. “In a certain sense, you should not be yourself. You should try to become something better,” he suggested.

If Roberts didn’t already have such a great gig, the chief justice could land a job hosting a talk show that keeps it real. He spoke gently yet reminded the boys that life is sometimes harsh for all, even privileged private school students.

But suffering can make us better humans, he said, if we’re conscious. Becoming conscious, Roberts said, takes a thoughtful approach to existence that goes beyond a “just do it” attitude. On that note, he relied on a citation for his final piece of “deep advice,” reminding the students that the unexamined life is not worth living, per Socrates.

There were some tricky topics Roberts wouldn’t touch. “You’ve been at a school with just boys. Most of you will be going to a school with girls,” he said, pausing thoughtfully and smiling slightly before concluding, “I have no advice for you.”