If you need cash flow, and the dividend doesn’t meet your needs, sell a little appreciated stock. (or keep a CD ladder rolling and leave your stock alone). At the risk of repeating myself, whether you take cash out of your portfolio in the form of “rent”, dividend, interest, cap gain, laddered CD…., etc. The arithmetic doesn’t change. You are still taking cash out of your portfolio. I’m just pointing out that we shouldn’t let the tail wag the dog. IOW, the primary goal is to grow the long term value of your portfolio, after tax. Period. All other goals are secondary.
Has this thought ever struck you mind as what if your boss fired you overnight, what your course of action would be? I guess the answer is NOTHING! You have no monthly pay checks coming in, how are you going to put roof above your family’s head? How are you going to manage the bills payment? What would you feed to your family? An answer to all this lies in darkness…complete darkness in that situation. But I have answer to this question, because I am my own boss managing multiple things and earning from all of them at a time, losing one would not be that big deal to me.
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Book sales ($36,000 a year): Sales of How to Engineer Your Layoff" continue to be steady. I expect book sales to rise once the economy starts to soften and people get more nervous about their jobs. It's always best to be ahead of the curve when it comes to a layoff by negotiating first. Further, if you are planning to quit your job, then there is no downside in trying to engineer your layoff so you can get WARN Act pay for several months, a severance check, deferred compensation, and healthcare.
Venture Debt – I invested $120,000 in my business school friend’s venture debt fund. He started his own after spending 8 years at one of the largest venture debt funds as a Managing Partner. I’m very focused on income generating assets in this low interest rate environment. The true returns are yet to be seen, as the fund has a 5-7 year life before it returns all its capital.

This is mostly passive once you have it all set up, but it does take a lot of work at the beginning. Real estate investing also requires occasional maintenance. Currently, we invest in a couple of rental properties and earn about $500 profit from each per month. You can read more about my rental properties at MoneySmartLife.com: How and Why I Became a Landlord.
A normal distribution (bell curve) is the limit of what one would find by adding up the value of many independent quantities such as the height of people in a large group. A power law distribution is the limit of what one would find by multiplying the value of many independent quantities such as the relative size of forest fires over a large enough area and a long enough period of time.
Wages received for services rendered inside the territorial limits of the United States, as well as wages of an alien seaman earned on a voyage along the coast of the United States, are regarded as from sources in the United States. Wages or salaries for personal services performed in a mine or on an oil or gas well located or being developed on the continental shelf of the United States are treated as from sources in the United States.
If you have specialized knowledge in a certain topic, you can put together an online course to teach others. For example, if you have experience in real estate investing, you can create an online course “Real Estate Investing 101”. The benefit of an online course is that once you create the course material, you can sell it to as many people as you want.
If you are unfortunate enough to find yourself no longer able to physically work in your chosen position, developing a skill set that will allow for a complete career change is a must. The passive income route as a second career is a great backup allowing you to hire out what you can’t physically do. Early on in my career I found I was unable to physically tolerate exposure to tobacco smoke. At that time, smoking was allowed in all offices, restaurants, etc. I was blindsided; who ever thought? It virtually removed me from most positions I had schooling for. As luck would have it, I had purchased a duplex while working and saved a small sum. When I had to leave my career, I made a down payment on another duplex doing any maintenance I could myself. If a physical setback of another sort should happen, I can hire.
The one thing I learned though from all those childhood experiences though is that you never can depend on one source of income. Eventually my mom caught on and stopped giving me all those extra bags of chips and I had to figure out a new way to make money. No matter how safe something seems there’s always the chance that you could lose that income and be stuck with nothing.
Capital growth in your portfolio can offset the eroding effect of inflation.  But any capital gains that exceed the overall inflationary effect can be drawn off to augment your portfolio income.  Of course, you must first generate those gains by making thoughtful investment selections.  While allowing strongly growing assets to keep doing that, it is prudent not to allow them to become a dangerously large part of your portfolio lest they go off the boil.  So if you selectively trim profitable positions along the way, you can boost your income.