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.
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.
I run several online businesses now (all it takes to start one is a domain, hosting, and maybe incorporation). There are two notable ones. The first is meal plan membership site called $5 Meal Plan that I co-founded with Erin Chase of $5 Dinners. The second is the umbrella of blogs I run, including this one and Scotch Addict. They pay me ordinary income as well as qualified distributions since I'm a partner.
An obvious example is over exposure to bank stocks, which have been excellent investments for over a century. Though a foundation of most portfolios, bank stocks do involve more risk at certain stages of the economic cycle than many realise. Being less exposed to bank shares in the last few months could have preserved some capital. So, a more diversified approach can help mitigate some of these risks.