What would you do if you won the lottery?
The honest answer is that my life wouldn’t change as much as people might expect.
I wouldn’t quit teaching. I wouldn’t buy a mansion or a fleet of exotic cars. I wouldn’t disappear into some sun-drenched version of early retirement. What I would do is remove pressure—the kind that hums quietly in the background of adult life and never quite turns off.
The first thing I’d do is make sure the people I love are secure. My grandson’s—and my yet-to-be-named granddaughter’s—college futures are already handled, which is a gift I don’t take lightly. Beyond that, I’d help Lizzi with a down payment on a house. My mom and dad did that for me, and it changed the trajectory of my adult life. I’d want to pass that along to her. I’d offer the same help to my stepchildren as well—because fairness and family both matter.
I’d also look hard at our own living situation. I’d probably sell our current home and buy something a little larger, a little more stable—something that better fits the life we’re building now rather than the one we backed into years ago.
Next, I’d invest in time.
Time to write without watching the clock.
Time to read books I’ve been meaning to get to “someday.”
Time to do things slowly instead of squeezing meaning into long weekends.
That includes travel. Daryl and I haven’t traveled the way we’ve talked about and dreamed about—not because we don’t want to, but because life always puts limits on the calendar and the budget. Lottery money would open doors to places we’ve imagined for years: Paris. Great Britain. Australia. Cities closer to home, too—New York, Washington, D.C.—not as whirlwind trips, but as memory-making ones. Not luxury for luxury’s sake, but experiences that deepen a shared life.
I’d also give more intentionally. Quietly. Thoughtfully. The kind of giving that strengthens rather than spotlights. Schools, ministries, people doing good work who don’t have time to chase funding. My church has some major projects that need funding, so I’d definitely help them accomplish those as much as possible.I wouldn’t want my name on a building. I’d want my resources to be invisible but effective.
Some of the money would go toward creative projects that live at the intersection of passion and storytelling. Scott and I have talked for years about expanding our bourbon club into something bigger—a Southern Sports Stillhouse that blends bourbon, Southern sports culture, and storytelling. Blogs. Videos. On-site broadcasts from big SEC matchups, postseason championships, and bowl games. A lottery windfall would make it possible to travel, record, publish, and build something meaningful without worrying whether it pays for itself on day one. Along the way, sure—we’d do some incredible barrel picks and finally grab a few true bucket-list bottles. But the heart of it would still be the stories.
And yes, I’d still enjoy small pleasures. A great meal. A special bottle shared with the right people. Front-row seats to moments, not just events.
Winning the lottery wouldn’t be about acquiring more.
It would be about removing obstacles—so I could live more fully into the life I already value.
Copyright © 2026 Doug DeBolt.
Great choice!