I think the holy grail of financial freedom is having so many passive income. This way you will never worry about your financial needs because everything is taken care of your assets. You will have all the your time in the world and visit all places you dream about. You have your time and money. This is the dream of most people which only few ever achieved.
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.

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?
Dividend stocks tend to be more mature companies that are past their high growth stage. Utilities, telecoms, and financial sectors tend to make up the majority of dividend paying companies. Tech, Internet, and biotech, on the other hand, tend not to pay any dividends because they are reinvesting most of their retained earnings back into their company for growth.
Wow! What an awesome list! My favorite is the stock photography because I love photography. I have had some success there, particularly with one photo I make some decent income from. I think the key with stock photography is finding a shot that is high demand. Then, find a new unique way to frame that shot. This is the reason my St. Louis Arch photo is a top 10 on both ShutterStock and iStockPhoto. Thanks for the awesome ideas above!

When a taxpayer records a loss on a passive activity, only passive activity profits can have their deductions offset instead of the income as a whole. It would be considered prudent for a person to ensure all the passive activities were classified that way so they can make the most of the tax deduction. These deductions are allocated for the next tax year and are applied in a reasonable manner that takes into account the next year's earnings or losses.


Real Estate Crowdsourcing – After selling my SF rental house in mid-2017 for 30X annual gross rent, I  reinvested $550,000 of the proceeds ($810,000 total) in real estate crowdfunding, based in San Francisco. My goal is to take advantage of cheaper heartland real estate with much higher net rental yields (8% – 12% vs. 2% – 3.5% in SF) and diversify away from expensive coastal city real estate which is now under pressure due to new tax policy which limits SALT deduction to $10,000 and new mortgage interest deduction on mortgages of $750,000 from $1,000,000 for 2018 and beyond.

Of course, there’s nothing to say you can’t do both. You can manage your own commercial real estate rentals and flip houses while you have someone else help manage residential rentals. You can invest in REITs and real estate crowdfunding. You’ll get the higher returns of active management while benefiting from the diversification and ease of passive income through other sources.
When a taxpayer records a loss on a passive activity, only passive activity profits can have their deductions offset instead of the income as a whole. It would be considered prudent for a person to ensure all the passive activities were classified that way so they can make the most of the tax deduction. These deductions are allocated for the next tax year and are applied in a reasonable manner that takes into account the next year's earnings or losses.
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