One minute you’re a Nobel Prize-winning doctor pulling in six figures. The next you’re holed up in an aluminum-sided mobile home and your car’s been stolen. LIFE is funny that way.

Not real life, so much. But we can all have a good chuckle when such twists of fate befall our limb-less little game pieces in Milton Bradley’s classic family board game, The Game of LIFE.

Now and again, my son and I take a spin around the old gameboard, taking equal glee in its little plastic churches and universities, its molded green mountains and the omnipotent spinner that (click! click! click!) launches players into outrageous fortune or calamitous destitution depending solely on the torque of one’s thumb and forefinger.

Game nights let my kid and me bond over something besides American Idol (“Yes, his song choice was dope, son, but his performance was all a bit cabaret”). And they’re educational, too. During a recent game, I learned that fantasy play is a pleasure one never really outgrows.

It’s just that the fantasies change. And change dramatically.

Created in 1860 by Mr. Milton Bradley himself, the game was originally called The Checkered Game of Life. It promised players a “happy old age” if they made virtuous choices along the temptation-fraught path from infancy to infirmity.

Its modern incarnation, The Game of LIFE, was created in 1960 for the company’s 100th anniversary. It’s been updated a few times; today it rewards players for biking to work and helping the homeless, and docks their pay for having cosmetic surgery and buying high-def TVs.

But as time inches forward, like a game piece creeping across the board, social ideals aren’t the only things about LIFE that change. I’ve noticed that as we players plod from childhood to adulthood, the game’s entire appeal shifts.

For my fourth-grader, it’s all about ownership: Holding, counting, and fanning out his rainbow of play money. Buying stocks and real estate, and fingering the deeds. In our latest game, he obsessively studied the fine print on his insurance policy and meticulously paid back his student loans when they came due. Along the path of LIFE, he collected all the symbols of adulthood he could wrap his nine-year-old fists around: a spouse, two kids, a boxy car. Basically, he had my life.

And I, quite deliberately, did not.

Because for me, the fantasy that LIFE affords is not in managing assets, changing careers, and hoping you can hold out till pay day. That’s not entertainment; that’s called “your thirties.”

For me, the game’s allure is freedom. The liberty to do it all over again — but less cautiously. To wit, I skipped college entirely and married a woman (less hair in the sink). A fateful spin of the wheel sent us skidding right past the treacherous “Baby boy!” and “Baby girl!” spaces on the board, protecting us from costly daycare costs down the road. The wife and I shacked up in a modest log cabin without a shred of home insurance, or prudence, or even guilt. And we were deliriously happy, at least till that tornado hit.

All told, my delight in the game isn’t so different from my son’s. We both relish the chance to do things we can’t do in real life, and to do them in a fail-safe environment.

Despite my lackadaisical approach to finances, I think I won that game. It’s hard to know for sure because determining a victor is a complicated process requiring more math than anyone should have to do at 8:30 at night. If I have any criticism of this otherwise superbly escapist pastime, it’s that after a long and colorful road full of unexpected twists and surprising developments, the end is an anti-climactic hassle.

But hey, isn’t that LIFE?