Post-Lottery Life

If you won the lottery today, let’s say for $1 billion, how would that change the way you spend your days?

For most people, a few things might come to mind. You might quit your job, travel more, read more, or finally make time for the gym. But for most people, it is hard to say all of the ways in which they would spend their days differently if they won the lottery today. I think the honest answer for a lot of people is that, in addition to whatever else comes to mind, they would spend a lot more time figuring out how they want to spend their time. Figuring out is different than thinking about. It involves active experimentation — in other words, trying things. There are lots of things that can take weeks, months, or even years to effectively experiment with.

I’m not a millionaire (yet), let alone a billionaire (yet), but already, in my 20s, I have been able to give myself 2-3 years of cumulative time and space to follow my interests, try things, and figure out how I’d want to spend my days, independent of financial considerations. I have learned that I like writing, podcasting, investing, coaching basketball, spending time with friends and family, traveling and seasonal living, doing life advice calls, reading, running and lifting, golfing, walking while talking, and a bunch of other things. All of these are elements of how I would spend my days if I won the lottery, and I’ve been fortunate to spend a lot of time doing all of these things in my times of free time so far.

During these times, in which I have given myself tremendous freedom of time, it has been hard to completely ignore any considerations around money given that I do not have nearly enough to sustain myself and my eventual family for the rest of my life. That said, I worked hard over multiple multi-year periods and saved and invested well enough to feel good giving myself permission not to worry about money for months at a time. I still end up worrying about it from time to time during those times, and it may influence my decisions around how to spend my time to some degree, but I largely try not to let it do so.

I want to know what I would do if I could do anything I wanted to, because I believe that, for the most part, I can. Perhaps ignorantly, I believe that if I keep doing whatever I want to do, if I keep trying things and seeing what I’m best at doing and what I like doing best, the money problem will eventually and sustainably solve itself. Until then, I’m happy to “sell my time” from time to time, whether that means working a job or running my own business or something else, so long as it seems like a worthwhile experience.

In the long run, I’d like to continue trying different things and figuring out more and more how I would like to spend my time if I won the lottery. I don’t think the difference between how I spend my time and how I would spend it if I won the lottery needs to be nearly as large as most people assume. I hope to continue experimenting for months or years at a time, and to spend my time more or less however I want during those times, increasingly figuring out how I would spend my time if I won the lottery. And then I want to spend most of my time that way anyway, without having to win the lottery first.

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