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.
What I’m doing: I view passive income as funny money to keep myself sane during this long journey. I estimate 2-10 years to get to my goal depending on how active I am. The dollars created are just points one can accumulate. I’ve made passive income goals for each passive income type and check in at least once a year like I am now to make sure I’m on track. Passive income is also carefully managed to minimize tax liability. When you can build a buffer for a buffer, you are then free to take more risks.
Crowdfunded real estate companies like Fundrise are similar to today’s peer-to-peer lending companies. Like Lending Club and Prosper, they offer a platform that matches real estate investors with investment choices. They help people looking to invest money in real estate in a passive manner. Also, investors can avoid bargaining with sellers. No need to get involved in the transfer of ownership and management of those properties either.
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.
Within six months of selling, however, I had reinvested the proceeds from the home sale and brought total passive income for 2018 back up to an estimated $203,724. I'm not sure I would have sold the house without a clear plan for reinvesting the proceeds, since I'm bullish on the SF housing market long term. However, because I did have a plan, and the challenges of raising a newborn and dealing with rowdy tenants left me feeling a bit stretched, I decided to simplify and sell.

One aspect you might want to add to your scoring is “inflation protection”. At one end, bonds and CDs generally pay a fixed nominal coupon that doesn’t rise with inflation. Stock dividends and Real estate rents (and underlying property value) tend to. Not reallly sure how P2P lending ranks- though I suppose the timeframes are fairly short (1 year or less?) and therefore the interest you receive takes into account the current risk free rate + a premium for your risk. Now that I think about it, P2P lending probably deserves a lower score in the activity column than bonds too (since you probably need to make new loans more often).
If someone stole my hard work and passed it off as their own, I’d be livid and would pursue them to the ends of the Earth for full restitution. A man I hired to work with me registered my preferred domain name of my business and has re-registered it in subsequent years. That’s bad enough; I’m mad as hell. The worst aspect of his behaviour is that I don’t know WHY he has done that; I paid him the fee we had agreed on and thanked him for his input. We also got along perfectly well during the project so far as I know, so I don’t see what his problem is.

Skillshare is more of a social learning platform where you can teach real-world skills. The range of skills that you can teach is only limited by your imagination - from board game strategies, garment construction, cooking tutorials, travel hacking, and relationship tips. I even saw a course on how to build a grown man's wardrobe. Creating a class on Skillshare is free. For each student who enrolls, Skillshare takes a 30% fee (Similar to Udemy). You are also provided a unique teacher referral link that lowers the fee to 15% for students who enroll via your referral. Note that all online courses on Skillshare go through an approval process based on specific criteria.

I just found your site & so far I like what I see. I am 50 years old & will be retiring at the end of Jan 2019. I turn 51 the following month. I will have a pension income of $60,000 per year & an additional $5,400 from a survivors benefit. I was able to save $200,000 in a deferred comp program through my employer & wish to know what to do to generate a passive income? I can leave it in the plan which will generate about 3.5% or invest it. My concern is the tax liability of taking out a large sum from that fund & leaving me less to invest. I do have an opportunity to invest in a bar/restaurant with family (my main concern) that currently generates $120,000 annually for an absentee owner. It would be a 3 way partnership if I did that. I do like your idea of creating my own product such a blog with a goal of $12,000 to $18,000 passive income I feel that may be my best option. Any thoughts or advice would be greatly appreciated.