I have two major dilemmas: (1) Should I wait to start investing (at least until the end of the year where I’ll hopefully have $5k+ in savings) in things like CDs? I ask because a little over $2k doesn’t seem significant enough yet to start putting my money to work (or maybe it is? that’s why I’m coming to you for your advice haha) and (2) I want to invest in things like P2P and stocks but I’m honestly a bit ignorant of how it trully works. I know the basics (high risk, returns can be volatile, returns are taxable). Do you have any advice on how I can best educate myself to start putting my savings to work?

Two months into my work hiatus and I’m doing well. I’ve made a little bit more than I’ve spent and I’ve worked about four hours a day on average. Ultimately, I’ll know I’m ready to make the permanent jump to a 4 day work hour when my passive income plus side incomes equal my day job income. Until then, I’m going to go back to my day job and keep grinding it out.
In order to build an audience, you need to have a platform. You need to have something worth following and sharing; something that’s valuable to others. And that, of course, takes time. That’s not to say you can’t build a huge audience in a short amount of time. But as much as we hear about the people who’ve succeeding at doing this, we don’t hear about the millions of others who are struggling every day to get just a few more fans and followers.
I enjoy how you lay out real numbers. A lot of people wouldn’t do that. While you admit that you are somewhat conservative, I think the $1M in CD’s is just too conservative. Assuming you don’t need the cash flow now (which you say you just save anyways) then all that could be invested for potentially higher returns. For example, what if you bought San Francisco real estate along the way instead of CD’s. Or, an SP500 Index fund. I bet your average return would have been higher than 3.75%. Sure you could lose it, but the point is if you don’t need the cash flow now, you should try to increase that nut as high as possible until the day you actually need it. Your nut could be $5M right now if you had invested in asset classes other than CD’s for the last 14 years. Don’t get me wrong, you have done far better than me, but I guess I would take a little more risk if you don’t rely on that cash flow.
That strategy seems waaaayyyy less risky than actively picking stocks of supposedly “reliable” stocks that issue dividends, which could be cut at any time due to shifting industry trends and company performance. Dividend investing feels like an overly complex old-school way of investing that doesn’t have a very strong intellectual basis compared to index investing.
"But for our jobs, for how we make money, I think many of us — most of us — have one way we make money. It can be very risky. I've really come to believe, and have done a lot of research over the years, that one of the best ways that we can create real, legitimate professional stability for ourselves is by choosing to cultivate multiple income streams.
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These days, low-risk bond yields aren’t enough to meet most income needs. When investing in bonds, the income typically comes as coupon payments – contractually guaranteed interest payments at predictable intervals.  There are many kinds of bond income available, so you must strike a balance between reaching for higher income (yield) and limiting risk.

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