One of the hardest truths in financial planning is this: most people don’t live a linear life. Sure, the software makes it look like we do. It plugs in neat little projections—future inflation, market returns, big purchases, home sales. A tidy arc from now to retirement.
But real life? Real life has curveballs.
What we really need isn’t better software. We need something more like *The Game of Life*.
Yes, *that* Game of Life. The one with the tiny cars, plastic pegs, and a spinny wheel of fate. I keep the board game in my office, not just for nostalgia, but as a reminder: chance plays a much bigger role in our financial lives than most plans account for.
What *Life* gets right is that something always happens. You spin the wheel, and boom—twins! Or a surprise bill. Or a new job. Looking at the board, I’ve thought of a few modern updates that reflect how unpredictable adulting can be.
We’d need new gameboard stops like:
- Complications after a knee replacement require unpaid time off;
- The company you work for folds, and at 55, job hunting is brutal;
- Your adult child moves back home, struggling with personal challenges;
- The world economy tanks—everyone suffers;
- A natural disaster strikes—everyone suffers;
- Health, home, and auto insurance premiums all spike at once;
- Middle-age FOMO hits, and after two glasses of Chardonnay, you book a non-refundable trip to Paris, blowing your emergency fund and waking up with a hangover and financial anxiety;
- You walk away from a high-paying job for ethical reasons, only to find out ethics don’t cover the mortgage;
- You live responsibly for decades… and still get scammed out of $100,000;
- Divorce. Suddenly solo. Out of work.
But it’s not all doom and gloom. The game also needs more cards in the “pleasant surprise” pile:
- A distant, elegant aunt leaves you an inheritance—mortgage paid off;
- Your dusty company stock turns out to be worth a fortune;
- Your doctor calls you “medically exceptional”;
- The roof never leaks, the kids find dream jobs, and your family is healthy;
- The economy booms, and everyone benefits;
- You land a job with no commute and finally start exercising again;
- Night classes pay off—you get the job you actually wanted;
- Your friends are awesome, and you love spending time with them;
- Your family grows closer after years of drift;
- You rediscover joy in hobbies and contentment in work;
- Your emergency fund is fully funded;
- You’re debt-free;
- You own your home outright;
- Leprechauns leave pots of gold on your porch.
Life, in these moments, is really good. And maybe—just maybe—you get to retire with a little extra cushion and a big, satisfied smile.
Because real financial planning isn’t just about numbers on a spreadsheet. It’s about resilience, readiness, and a healthy sense of humor for when the wheel spins. So let’s plan—wisely, intentionally—but let’s not forget to make room for life.