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.
With personal finance software you can schedule automatic payments and transfers between all of your imported accounts. Automatic transfers will help to make sure you have the necessary funds in the right account to ensure all bills are paid on the appropriate date. Late fees are annoying and do nothing but cost you money. It’s time that you said goodbye to them once and for all.
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Another way to generate passive income is to invest and be a silent partner in a business. This is very risky, but with risk comes the potential for high returns. For example, several years ago both Lyft and Uber were looking for private investors to invest in their companies. Today, they are worth billions - but you as an investor would only reap that benefit if they go public via an IPO, or get acquired. So, it's risky.
What I did:The first two years of work in NYC was brutal. I told myself there was no way I could work on Wall St for my entire career because I’d probably die from heart failure by age 40. Having an early death in my mind willed me to save 50%+ from the first year onward and devise a CD, real estate, and stock investment distribution system for my savings every year. I thought about starting this site for at least a year before I hired someone from Craigslist to give set me up and push me forward. Hiring someone to get started is totally worth it if you are a master procrastinator. You can now learn how to start your own site with my step-by-step guide to save yourself time and money. 
Money from dividends, for example, are taxed at a lower rate than money from a job. A business owner who works in the company she or he founded would have to pay more self-employment payroll taxes compared to someone who merely had a passive interest in the same limited liability company who would pay only income taxes. In other words, the same income earned actively would be taxed at a higher rate than if it were earned passively.
There was a time when CDs would produce a respectable 4%+ yield. Nowadays, you’ll be lucky to find a 5-7 year CD that provides anything above 2.5% The great thing about CDs is that there are no income or net worth minimums to invest, unlike many alternative investments, which require investors to be accredited. Anybody can go to their local bank and open up a CD of their desired duration. Furthermore, a CD is FDIC insured for up to $250,000 per individual, and $500,000 per joint account.
One word of advice, and something I intend to do once I have the money saved up, is to build or buy out property that can support apartments or townhomes. One tough mistake some people make is buying a pair of homes to rent out and they get a nice $2,000-$3,000 a month but that’s it. Buying a house is expensive and the rental prices keep lower income families from potentially coming to you with their money to rent. If you have an acre to work with (more or less is OK too) you should be talking to a contractor to build apartments or townhomes. You will make a little less per unit BUT your audience grows significantly because now you can have college students, single parents, older folks, etc. all able to afford your rental units AND instead of capturing one $1,000-$1,500 a month payments, you can probably charge $700 a month per unit (or more, depending on the market) and build maybe 3, 4, 5, 10 units for the price of a home or two and now you’re making something like $2,100-$10,000 a month. It all depends on what you have to invest but if you’ve got $250,000+ I’d highly suggest you talk to a bank/investor that can get you in touch with a good contractor to build on a property and get permits and take out a matching $250,000 loan (I’ve read that $500,000 is plenty to build a good amount of apartments to start) and you can fill up your apartments and make a killing every month. You’ll have more tenants to deal with but if you’re competitive with your pricing you won’t have a hard time keeping tenants or replacing them.
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