While stocks are terrific income producers, they can be volatile. Every few years, the stock market tends to stagnate or drop for a while before recovering, and that can be problematic if you were counting on your stocks having a certain value at a certain time. One way to lock in an income stream is by buying a fixed annuity (as opposed to variable or indexed annuities, which can have steep fees and overly restrictive terms). Annuity contracts will be more generous when interest rates are higher, but here's how much income they might deliver at recent rates:
My suggestion is to move and rent out your old home. It’s a good way to start if you’re ready to move anyway. If you don’t want to move, then I don’t know. 🙂 Maybe just keep an eye out for a good deal. It’s great that you have income from other sources. They are small now, but I’m sure you can grow them if you put more time into them. It’s a good experience.
After these tenants move out, I'm thinking of just keeping the rental empty with furniture. It sounds stupid to give up $4,200 a month, but I really hate dealing with the homeowner association, move-in/move-out rules, and maintenance issues. Given that the condo doesn't have a mortgage and I have to pay taxes on some of the rental income, I'm not giving up that much. The condo can be a place for my sister, parents, or in-laws to crash when they want to stay in SF for longer than a week or two.
Let’s say a company earns $1 a share and pays out 75 cents in the form of a dividend. That’s a 75% dividend payout ratio. Let’s say the next year the company earns $2 a share and pays out $1 in the form of dividends. Although the dividend payout ratio declines to 50%, due the company wanting to spend more CAPEX on expansion, at least the absolute dividend amount increases.
I actually spent a year and a half working as an affiliate marketer (mostly selling drumming related products – lessons, kits ect). 5 years on and one of my one page sites (which I’ve not touched) still nets me about $150 a month. I won’t be retiring off that but only really now appreciate the reverse pyramid approach to entrepreneurship (working for nothing initially but later being paid without effort!)
Finally, make sure you can service multiple types of clients. This is the best egg to have. Even for something as simple as a dog walking business, you can service multiple types of clients. For example, you can offer a puppy walking service and an adult walking service. You can have weekends at the park services. You can offer to take the dog to the groomers. Try to meet client’s individual needs.
Income-generating assets are another of many passive-income opportunities. A classic example is making money in real estate via owning rental properties. It can seem perfect: You buy an apartment building or house, rent it out, and then sit back and collect checks every month from your tenants. The reality isn't always so rosy, though. For one thing, you'll need to maintain and repair the property, as well as paying taxes on it and insuring it. It may not always be occupied, either. You may have trouble finding tenants, or finding tenants who pay their rent reliably. Some tenants may damage the property, and others may be hard to get rid of. You'll be the one they call in the middle of the night if the roof is leaking, and you'll have to clean and perhaps freshen up the property between tenants. You can outsource much of this to a property management company, but it will take a cut of your income, often about 10%.
I’m looking at accepting a professor job. It’ll be more than a 50% pay cut. But I’ll have the same life you describe – endless summers and an entire month every winter to ski. I’m thinking in the end, eventually, I might even end up wealthier in more ways than one. Happy people tend to be the most successful. I have no desire to diversify. Dividend stocks allude me. CDs seem like a good choice for older people, but I have time on my hands and real estate knowledge, so I’m sticking with what I know, despite the fact that most people will tell me it is foolish and I should diversify.

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