As WordPress continues to recycle old prompts, I pulled another prompt from The Coffee Monsterz Co to respond to today
Can you buy happiness?
Can money buy happiness? No. But it can certainly take out an extended lease on it.
Growing up as the son of a relentless, “keep-your-head-down” middle-class family and then spending my career on a school teacher’s salary, I’ve spent a lot of time dreaming of being rich. Most people do. I’d like to think that money would solve the immediate friction in my life. I’ve joked elsewhere on this blog that my retirement plan is “death,” which is really just a blunt way of saying I’m not expecting a windfall in my golden years. I’m just plugging along.

The view from the road: A constant reminder of the ‘different game’ I’m not sure I’m ready to play.
The “Lottery Math” and the Different Game
Just like everyone else, I see those billboards for the Michigan Mega Millions or Powerball and I start to do the “lottery math.” I think about what I would do with even a fraction of that money. It would be a game-changer, for sure. But I’ve realized it would also put me into a completely different game—one I’m not sure I’m equipped to play.
I’ve seen enough episodes of the old VH1 series Behind the Music to realize the trajectory: the moment you become the “cash cow,” every single person you’ve ever met reaches out—usually with hat-in-hand. I specifically remember the stories of MC Hammer and Vanilla Ice. As soon as they became wealthy, friends seemed to come out of the proverbial woodwork. They stuck around as long as the cash cow was still producing, but the moment the money ran dry, those so-called friends were gone.
In my writing, I often talk about the importance of being seen for who we are, but total wealth creates a screen that makes true validation almost impossible. People stop seeing you; they see the prize.
Protecting the Prize (and the Peace)
Then there is the terrifying loss of privacy. In many states, including here in Michigan, you can’t always just take the check and disappear; you’re often required to go public. I’ve heard of people setting up LLCs or legal trusts just to claim their winnings through a corporate mask, trying to buy back the anonymity they’re about to lose.
I’ve taken the daydream even further than a legal trust. I’ve sat in my car and played out a scenario where I don’t claim the ticket at all. I’d have a trusted shield—a friend or family member—step into the spotlight and take the “credit” for the win. They’d get the public attention, the cameras, and the relentless phone calls, and I’d reward them handsomely for the protection.
Of course, I know enough attorneys to know that before I made a move like that, I’d be sitting in their office for a very long consultation to make sure every “i” was dotted and every legal hurdle was cleared. It’s a high-stakes chess match just to keep the peace.
Looking Toward the Horizon
I’m not naive. I understand that money is essential for survival in the 21st-century Western world. But here in the United States, I think we take our obsession with material goods way too far. For many, the Almighty Dollar is worth even more than a human life.
I’ve realized I don’t actually want the “Mega” life. That’s just a different kind of stress. What I’m really looking for is the freedom to exist without looking over my shoulder—the ability to slow down and actually see the world around me without a bill collector standing in the way. I don’t want to be a jackpot; I just want to be enough.
What about you?
If you hit the jackpot tomorrow, would your first call be to a travel agent or an attorney? Does the idea of “going public” change the way you look at that giant billboard on the highway?
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The article “Why I’d Pay Someone to Win the Lottery for Me” first appeared on Rebuilding Rob.
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