Do I Get Rich, or Go Bust? These Tools Predicted My Financial Future

THE FORTUNETELLERS SAY I'll retire rich.

Not Buffett rich, but rich enough for my wife and me to live in premium-economy comfort well into our 90s and still leave something to our kids.

Of course, there's a 17% chance-roughly the odds of rolling a seven at the casino-that we'll outlive our money. Crap.

After plugging my income, debt, assets, hopes and fears into the newest generation of financial-planning tools, these were two of the possible financial futures predicted.

No mere retirement calculators, these tools let you play out a range of financial futures and what-ifs for income, health, market turbulence, the impact of Roth conversions and the fate of Social Security.

Laurence Kotlikoff, the Boston University economist behind MaxiFi, calls it "a videogame for older people."

As a 50-year-old passive investor with an active imagination, I relished beating up my life and money with calamities worthy of a ledger book of Job. What if Elon Musk buys The Wall Street Journal and replaces me with a self-editing bot? What if my wife then leaves me for the bot? What if tax rates double, Social Security benefits halve and my 401(k) plunges to zero? I watched my future salary and net worth rise and plummet-and plummet some more. Then I made myself a drink.

"What we show you is the range of possible outcomes," Steve Chen, founder of Boldin, formerly NewRetirement, told me. "It's not a guarantee but a way to guide your decisions and avoid catastrophic mistakes."

401 kilotons

A financial adviser once assured me that money isn't nuclear physics. He was wrong.