First of all, let's face the facts. Working 9 to 6, you won't have any time during the day. If you choose to have a second job during the evening hours, you'd get burnt out very easily. Chances are that you might under-perform in both the jobs. I recommend having a side business rather than a second job. Some investment of money and time would be required at first. I have come up with a few options that would require less work from you but would be a decent second source of income.
Good ranking FS, I’d have to agree with the rankings. And it looks like your portfolio covers five of the six! Some people consider real estate passive will others classify it as active. But every scenario is different, whether you are doing all the maintenance and managing yourself, or you are contracting out a lot of the work. Obviously it takes a lot more time and effort than purchasing a 36 month CD and “setting it and forgetting it.”
If you are good at some subject, especially maths, science subjects, accounts or economics, you will have an upper hand in this business. There are plenty of such coaching centers so you will have to face some stiff competition in the beginning. But if you can get good results from your students, congratulations! You have made yourself a name and now parents will send their children in big groups to your center.
I guess I just don’t understand why the specific importance of focusing on “dividends” instead of focusing on the total return of your investment, including stock appreciation. I don’t really care if a company decides to issue a dividend or not; presumably, if they don’t issue a dividend, then they’re doing other things to increase the value of the company, which will be reflected in the stock price of the company. As an investor, I can make money by selling a percentage of my holdings or collecting dividends, and I don’t really care how that’s divided up – it’s an artificial distinction.
I’m a 45 year old business owner who also has focussed on diversifying my income streams. I have a short term vacation rental in Florida that I bought for $390k in 2012 and net rental income for the last three years has been growing steadily. 2015 I am at $70k gross right now but should end up at $80-85k with net around $45k plus we use the place about 35 nights a year.

Index funds provide you with a way to invest in the stock market that is completely passive. For example, if you invest money in an index fund that is based on the S&P 500 Index, you will be invested in the general market, without having to concern yourself with choosing investments, rebalancing your portfolio, or knowing when to sell or buy individual companies. All that will be handled by the fund which will base the fund portfolio on the makeup of the underlying index.
"That's certainly true for entrepreneurs, but even for people who work inside a company, cultivating a side income stream of some sort — whether it's having an Etsy store on the side, or doing a little bit of coaching or having a workshop now and then, whatever it is, doing a little bit of paid speaking — having that sideline gives you additional protection against uncertainty and also has a lot of other benefits.
One of the easiest ways to get exposure to dividend stocks is to buy ETFs like DVY, VYM, and NOBL or index funds. You can also pay an algorithmic advisor like Wealthfront to automatically invest your money for you at a low fee. In the long run, it is very hard to outperform any index, therefore, the key is to pay the lowest fees possible while being invested in the market. Wealthfront charges $0 in fees for the first $15,000 and only 0.25% for any money over $10,000. Invest your idle money cheaply, instead of letting it lose purchasing power due to inflation. The key is to invest regularly.

In focusing on your wealth management goals, investment income is obviously critical but you might fund your goals from wider sources of income.  A typical long-term portfolio might produce about half its return as income and the other half as capital growth, though in times of duress the capital growth component wanes.  In this low-interest rate climate, some sources of income have become quite expensive and may prove disappointing against your spending needs.  But by tax efficiently and sustainably drawing income from wider sources, you might meet your goals while more prudently balancing risk against reward.

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