That young man with the waxed mustache and gallic countenance is my son Cole, age seven. We’ve been studying division, going on long walks with Sadie the dog, and thinking about walking together all the way across the USA, which would require by our calculation 138 days of walking with no days off. This has made Cole very sad because he’s done a further calculation and concluded that he is unlikely to have 138 consecutive days available until he’s well into his 20’s and by that time he figures I’ll be dead.

Kids have a thousand ways of breaking your heart.

Sentiment aside, Cole might well be correct. He’s a busy kid and I’m an older father. When he is 25 I’ll be 76. And while I don’t expect to be dead at that age, Cole quite pragmatically looks at my father — Grandpa Ray, who died at 70 — as a pretty good predictor. Cole actually thinks about this stuff.

And it has made me do some thinking, too, like what advice I can give Cole and his two brothers should I be unable to guide and protect them as long as I have been planning to?

Our society, culture, and economy have turned to quagmires all at the same time. Nothing is as it was nor is anything even like it appears to be, so how does a seven year-old prepare for the future? “What will you be when you grow up?” is a much harder question than it used to be.

There are near term and longer term implications to this question. In the near term how do we creatively respond to jobs going overseas? In the longer term what happens if Ray Kurzweil is correct and the Singularity rolls along in 2029 or so and humans suddenly become little more than parasites on a digital Earth?

The easy answer to this problem has been the same since the 1960s — become Paul McCartney. But how many Beatles can the world sustain?

My friend George Morton has a daughter (I know nothing about those — wrong datatype) facing the same quagmires as my sons, so here’s a synthesis of our thinking.

Remember the old Robin Williams joke about his son’s future: “Hello Mr. President” or “Do you want fries with that?” Career planning at this point probably requires a combination of serendipitous opportunity plus being curious. This in turn requires an educated mind that allows for serendipity to play a large role in discovering opportunities and staying just outside of your comfort zone.

We start with a Catch-22: You can’t get a job because no one will ever hire you. Now what are you going to do about it? The answer is of course everyone works for themselves, there are no employees, and everyone is just a subcontractor.

There are two times this really sucks — when you don’t have a job and when you see your current job going away. Many of us are in both situations nearly all the time. I know I am.

How do you educate yourself to deal with the changes in your business knowing that whatever you do is going to be replaced by a computer sometime in the future? First concentrate on the structural parts of any enterprise that are likely to never go away, computers or no: 1) finance; 2) marketing; 3) production or service.

The key change in any industry is the delivery method. Change the method of distribution and you change the business model. iTunes destroyed record stores, digital cameras destroyed Polaroid and Kodak; the list goes on. The key change was distribution.

Look, for example, at what’s happening to Electronic Arts (EA). It was pinball versus Pac Man, then PC’s with retail distribution, then Internet distribution, now smart phones. Every time the distribution system changed so did the price point, which is now down to 99 cents. EA still doesn’t know how to build Angry Birds. iTunes changed the distribution system for users and developers so now it doesn’t look good for EA at 99 cents.

Note on my EA crack from an EA employee — “Battlefield 3, an ‘old school game’ retailing at $60 just broke records and sold 5 million copies DAY ONE. FIFA 12 did 3.2 million end of September. There is plenty of life in the old dogs yet.” I’d note, however, that they are old dogs.

Change like this is rapidly coming to every industry. Talk to book editors, as I sometimes do, and hear the terror in their voices. What if books simply go away?

Getting, keeping or making that future job starts with understanding the distribution system and your place in that process. And to survive even mid-term the key is to position yourself as the linchpin. Your knowledge has to be critical to the success or failure of the process. That would seem to call for specialization but specialists often don’t see the ball even coming. You need a broader view.

But not an MBA. Those will go away. So will MD’s, CPA’s, and even CCIE’s, replaced with new acronyms for new certificates, so be ready to get a new label every few years.

Where you live counts as much as anything else, too, so position yourself in a city that has high serendipity. Any kid living with his parents in Palo Alto can get a job today simply because he already has a place to live. No skills required.

If you want to be in finance, going to Alabama is not going to help you develop the next big financial idea, but Boston, New York, London, Chicago will. If you want to play with new business opportunities in IT, you get the picture. So for an education; are you going to a school that helps you to develop serendipitous opportunities for your lifetime?

Go to a second or fourth grade teacher or even a high school guidance counselor with these ideas and they think you are crazy, but that’s part of the problem — the educational establishment is as reactive (and sometimes as reactionary) as any other government agency. They have no better ideas than we do what to do with our kids.

Jaron Lanier once told me that you can have enough money, enough power, but you can never have enough experience, so I plan to give my kids as much experience as they can handle, keeping in mind the fact that even post-Singularity it may still matter more who you know than what you know.

Live in the coolest place, I tell Cole and his brothers. Have the coolest friends. Do the coolest things. Learn from everything you do. Be open to new opportunities. And do something your father hasn’t yet figured how to do, which is every few years take off 138 days and just walk the Earth.