As I’ve thought more deeply about how to answer this question over the years, I’ve come to a realization that the problem is not the answer, but the question itself. For those who’ve asked it, I don’t think it’s always coming from a place of “quick money.” If we reframe the question, I think there’s room to empower and actually help those who’ve asked it—to give them a foundational understanding of what it really means to generate an income online.
Become a proofreader. All kinds of businesses hire professional proofreaders to look over their copy and content for errors before they publish. This side hustle is one that could work for nearly anyone since you can work from home provided you have a computer and an internet connection. You can find online proofreading jobs through websites like Indeed.com and FlexJobs.com
If you want to clear some space out in your house and have a big stack of books you’ve been holding onto for too long, you can make money selling your books and textbooks online. Stores like Half Priced Books and others will give you cents on the dollar for each of your current books while you can check what your book is worth by simply entering the ISBN number on Book Scouter.

The first step is to get your domain. For the loooongest time ever, my blog was known as senseofcents.blogspot.com. I finally bought www.makingsenseofcents.com and haven’t looked back since. I don’t think anyone has ever said “I regret buying my domain and looking more professional.” If you sign up using my Bluehost link, then you will receive your domain for free.
The challenge I’m facing and, I know it’s a good problem, is that the SF real estate has shot up about 35% in the last couple years. I’m sure you’re experiencing the same thing! So as the net worth is rising, the yield on the total portfolio is going down. Right now, it seems the only way to increase the passive income will be to raise the rent in December and to invest some of that cash in stocks, which I’m nervous to do in this market. Current allocation:
Watch other people’s kids along with your own. There’s a good chance your friends who work outside of their homes would be thrilled to have an experienced parent watch their children while they are at the office. It can be manageable if your friend in need has only one or two kids. Plus, the new playmates will help keep your children occupied for a few hours. Pay varies widely based on where you live and the ages and number of kids you'll be watching, but babysitters and nannies typically can make up to $10 an hour in small cities and much more – even double that hourly rate – in larger cities.
We are going to start with 1.5 years of all spending needs in cash. We will draw 1800 to 1900 per month. We will add to this from the index funds by taking a portion of the gains in good years to supplement. This is the total return portion of the equation. Obviously, if stocks decrease drastically over a 5 year period, then I would have to reload by selling some of the ETF holdings.
With drop shipping, you’re effectively partnering with a manufacturer or wholesaler to sell their products. This way, you don’t pay upfront costs to buy inventory, aren’t sitting on unsold items taking up expensive warehouse space, and don’t have to deal with shipping the products yourself. You simply create your site, fill it with drop shippable products, and drive in customers, with almost everything else done for you.
Anthony, nice setup! To your question about the rental mortgages, you haven’t said what interest rate you are paying. As a start, if you are paying more than the risk free rate (Treasury bills) which you probably are, then a true apples to apples comparison would be yes, pay off the mortgage. But, if you are comfortable taking more risk, you have other options to invest in which you *hope* will yield you more over the coming years. You also didn’t say whether the rentals generate net income and if so, how much? What is the implied rate of return on the equity you have invested in them? If you pay the mortgages off, you’ll have even more equity tied up, will the extra net income make that worthwhile? Maybe you should use the money to buy more rentals instead, if purchase opportunities still exist in your town. … this is less of an answer than a framework to analyze the decision, hope it is helpful.

As far as Poker goes (at least for Texas Hold’em), I’d recommend sitting at a low stakes table (1/2 no-limit is the lowest most places have) and merely being observant/make casual conversation at the table for a while until you feel comfortable. If you’ve never played, just tell the dealer and they’ll be happy to help you out (most players will notice if you haven’t played before anyways so you’re not really at a loss there). Just play “tight” (a small range of strong starting hands) and that’s a pretty good place to start!

Now, it’s time to start creating and uploading content. Make sure you’re using a high-enough quality camera (most smartphones will work but I’d suggest at least having a tripod so your footage isn’t shaky), but don’t worry about being perfect at first. The beauty of YouTube is that you can continue to test out different content and styles as you find what works for you. Instead, stick to a regular schedule to build up your subscriber base.

Evaluate Web sites. Another way to make extra cash in a short amount time – $10 for about 20 minutes of work – is to sign on with UserTesting and evaluate Web sites. You need a computer with a microphone and Internet connection, and you’ll have to fill out a one-page demographic profile. You’ll receive work if your profile matches that of the target audience of sites being tested. Then it’s just a matter of using UserTesting’s screen recorder, which you'll need to download to your computer, to record your verbal comments and on-screen movements as you click through a site. Site owners typically are looking for feedback about whether the Web site is confusing to navigate.

MemberPress is a feature-rich plugin that will enable you to turn your WordPress blog into a fully functional membership site. Depending on how you want to run your membership site, you could have a mixture of free and premium membership plans. Premium plans could include no adverts, free downloads, access to extra content, membership forums, and much more. However, it is important to remember that if people are going to pay to view your content then it must be high quality. Otherwise, your members won’t renew their subscriptions when the time comes.
I’m a huge fan of blogging because I love writing and connecting with people all over the world. To give you an idea of what is possible with blogging, DollarSprout.com is part of a group of blogs that routinely brings in over $100,000 a month in revenue. While it takes time to build your blog up to that income level, you can get the initial set up done in under 30 minutes (no experience needed).
Upwork: This website offers a great marketplace for selling just about any professional service. You don't need a merchant account, website of your own or anything else for that matter. All you need to do is be able to provide a high-quality service at a reasonable price. But be informed, you will have to compete with many others that are constantly bidding on open jobs. 
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