If you are lucky enough to have children—John F. Kennedy called them “hostages to fate”-who actually tell you what they are thinking and doing, you know that after a certain point usually between middle school and high school, your opportunity for influencing them substantially decreases. How many times have parents said, “I can’t wait until you have children….”

I was on the phone last weekend with one of my children who had gotten a graduate degree a year ago, looked for a job in one of the professions with the highest unemployment rate in the country and then landed a position with a small firm whose work was just admiringly profiled in the New York Times. He called to say he had given his notice after four months and was headed east from San Francisco with no plan B. “You did what?!!,” I thought to myself as I tried not to voice exactly what I was thinking: “How could you have done something so foolish and irresponsible?”

After listening to his story, as much as I wished he had kept that job for at least a year no matter what had transpired, I recognized that his employer had no idea how to manage people-at least creative people, even though the particular enterprise is all about harnessing creative energy.

Most of us think that managing people is straightforward&mdashyou tell them what you want them to do, review the results and make suggestions for improvement. What’s so hard about that? We’ve been told all our lives by parents, teachers and others how to do things better, so we all think we know how to instruct others in becoming better at what they do. But nothing is simple about managing people, because nothing is simple about people.

I recall a board we used to play as kids called “Careers.” It was a 50s- and 60s-type game. You filled out your score sheet specifying the number of points-up to 100-you wanted to collect to be a success. You could choose any combination of dollars (money), hearts (love), or stars (fame).. Like monopoly, as you moved around the board, bad things could happen unexpectedly and you could lose money, love or fame, which hurt you to a greater or lesser degree depending on how much of that ingredient you had chosen to define as part of your success and the first player to reach 100 with the specified combination of dollars, hearts or stars was the winner. It did not take too long to figure out that the meta-narrative of the game was that you needed a balance of those three basic motivations and also good luck in moving your life around the board. Of course, life is not so simple as that.

My father ran a large-ish business for its time-with 300 people whom he managed. He told me, “management is the art of getting people to do what you want.” Hmmm, that sounds pretty straightforward. But how do any of us actually get other people—not to mention your children—to do what we want them to do? Basically, it comes down to understanding individual motivation, which means understanding individuals. And because everyone is different, has a different history, a different story, you quickly run out of “rules” and plunge deep into the thicket of individual psychology. Some people need to hear lots of praise (back in less gender-sensitive times, the shorthand was “attaboys” -like stars in Careers); others are motivated by money ($$$); others by the love of making a beautiful thing or inspiring the love of a beautiful person (hearts). Some want adventure and travel, some work effectively only up against deadlines, others because they are afraid of losing their jobs; while others are motivated by space and freedom and do great work if others stay out of their way. The list of motivations is nearly endless. Life is not exactly a game of “Careers.”

All of this went through my mind as I was listening to my son’s story of willfully plunging back into joblessness after his first brief work experience. Then I remembered something that had happened to me three decades earlier. I had gotten a graduate degree and then a job that I had dreamed of getting-a forestry job in the Allagash where I would be living in remote logging camps for four and a half days a week while laying out logging jobs. My boss had told me it would take me six months to learn the private road system in the woods beyond Moosehead and Kokadjo. Part of me would have worked for nothing-in fact I started out at $12,000 a year, which even back then was underwhelming. But I didn’t care. It sounded like a great adventure-that’s what motivated me. Only the reality was different. The work was lonely and unfulfilling. The French Canadian crews spoke no English and the only pigeon French I needed was “No cupe le-epinet”—or something like that which meant “Don’t cut the spruce.” I left just shy of a year and went to work writing a natural history guide to the 200 islands Outward Bound had permission to use for $125 per month plus room and board on Hurricane Island, and access to a small private navy to transport me through the archipelago.

So just as I was about to protest my son’s willful irresponsibility, I held my tongue recalling that our means rarely know our ends.

Philip Conkling is president of the Island Institute.