Special thanks once again to rojie for today’s prompt. if you haven’t done so already, definitely check out her blog justrojie.com. I
If you became very wealthy after living a life, from paycheque to paycheque, in what ways would you help your family and friends financially?
I’ve heard a lot of stories from musicians and I used to watch quite a few episodes of Behind the Music back in the day. One thing that both athletes and musicians will tell you about is that when you become very wealthy overnight, it seems like every person you’ve ever known suddenly comes out of the woodwork, and quite a few of them are looking for a handout of some sort.
If I were to suddenly become very wealthy, I would try to keep it on the down low as much as humanly possible. I know that in several states if you win the lottery, you actually have to come forward, and they usually appear in a formal press conference where they receive an oversized check for the jackpot. I would not want to take part in such an event. In fact, I would probably retain a lawyer immediately after I won the lottery—and likewise, if I just came into some money out of the blue.
First and foremost, I would be sure that both my boys, Kid 1 and Kid 2, are taken care of for life. Even if I had to set up some kind of trust fund where they didn’t have access to all the money immediately, but were able to get a living stipend and then keep enough in the bank for them to just accrue interest, they would basically be set for the rest of their lives. Beyond basic financial security, I’d want to make sure the boys got all the education they ever needed or wanted.
Then, of course, I would certainly set something aside for my mom, my sister, and my brother too. Certainly not as much as I will leave for my boys, but they would be my core priority.
When it comes to drawing the line, I know it’s easy to say in the abstract, but I think I would really just draw a hard boundary around the people I talk to on a pretty much daily basis: my mom, my sister, my brother, Sierra, the boys (and not necessarily in that order). They are the people I concern myself with first. Once you step outside that inner circle, it’s a slippery slope.
Of course, it would be tough. In the aforementioned example of athletes and musicians, I’m sure I’d have people either asking for handouts or asking me to invest in some business venture they want to take on. Bad investment decisions have been the downfall of a lot of professional athletes. So many so, in fact, that I’ve heard stories about how during NFL training camps, they actually have financial advisors come in to talk to rookie players in order to prepare them for the substantial pay raise they’re about to see.
Money is such a weird thing. I think it could bring out the very best in some people, like seeing people donate massive amounts of money to charity, but I think other people on your periphery bring out their very worst.
Beyond just living comfortably and securing the future, the big thing I would want to do with sudden wealth would be to travel. Seeing the world without constantly checking the balance would be the ultimate game-changer. But naturally, my first priority would always be my kids, my immediate family, and the core people who matter most.
Rebuilding a life takes grit, consistency, and a lot of ‘Option C’ thinking. Having crossed the 1,000-day milestone, I’m now charting the territory beyond. The mission remains the same: No glitz. Just the work. New to the blog? Start your journey here to see the blueprint and the ‘Tricorder’ perspective behind the rebuild.
Today’s post is inspired by the WordPress Daily Prompt. While I’ve taken the topic in my own direction for the Road beyond 1,000 Days, you can find more responses to today’s prompt HERE.
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The article “Out of the Woodwork” first appeared on Rebuilding Rob.


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