Well written piece, but I question the core premise. Why the fascination with maximizing “income” (passive or otherwise). Shouldn’t the goal simply be to maximize long-term after tax growth of your entire portfolio? If this takes the form of dividend paying stocks, so be it. But what if small caps are poised to outperform? What if you want to take Buffet’s or Bogle’s advice and just buy a broad market index like the S&P 500, (no matter what the dividend because you’ll just have it automatically reinvested to avoid the transaction fees).


Pardon for being a bit of a newbie to true investing outside of a 401k. What about those of us who have 1) Just been laid off, and unable to find work due to lack of a degree (apparently 17 years in the industry with 5 certifications is just simply not enough – which is okay. It gave me the kick in the arse to get back to school finally) 2)Have three children to support (age 11 and under), and 3) Oh yeah – cannot find work. What do you recommend when the only source of positive revenue has ceased to come in and you now have less time than ever – due to responsibilities (i.e. doing well in university = academic scholarships means investment in time, plus spending 20 min breaks with kiddos) – to create positive sources of income ? I truly am wondering from an investor’s point of view how you would handle the pivot point of life if ever you had been faced with it. I realize this may be only imaginary, but at this point, I welcome your “what ifs” scenario on this one. You’ve truly done amazing work and I thank you for being so transparent.
It is hard to do both but you’re not supposed to. You’re supposed to get your safety net down THEN try to do high wire acrobatics above it – not set up the two at the same time. So get retirement and your emergency fund squared away, then consider the stock market (taxable) and real estate. There’s no rush! Don’t let others dictate your future because they don’t have the same priorities as you. 🙂
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.
Domain names cannot be replicated. If one is taken, the only recourse would be to approach the owner to discuss a sale. While there are other variations you could choose, sometimes owning a certain domain (especially if it is attached to your business) can be worth the premium. Often, people will scout out domain names that are still available, buy them, and then sit on them in order to sell them down the road. Depending on who may want the domain down the road, you could sell it for a large markup.
I read about early withdrawal penalties on IRAs/401Ks very often. Almost always with a statement of “locked up” or “can’t touch” until 59.5. I’m sure you and well informed readers as well know about SEPPs in regard to IRAs/401Ks. For those that don’t SEPPs aren’t perfect but they are a way to tap retirement funds penalty free and I will be using in the future as I have over half of my equity investments within retirement accounts. South of a mil, North of a half. Let me add that I think your blog is outstanding.
Doesn’t it sound awe-inspiring to have more than one income source? You already have one source of work with a steady flow of income and then you are creating more and more work for you with more income for you. Who does not want to have lots of money in their bank accounts floating all around? For the person who values financial security and their ultimate dream is financial freedom, creating more than one source of income becomes a necessity not just desire.
E-Commerce is taking off in India. One of my friend runs ebay shop for second income and easily earn Rs 1 Lac per month. You don’t need huge investments to start your store. Besides ebay you can create your own e-commerce website without any hassles. Recently Shopify set shop in India. Shopify is leading E-commerce platform & provide ready solutions to launch e-commerce store i.e. no need of website designing.
I am an English major and a herbalist with so many ideas and no extra income to fulfill them. I recently started renting my extra apartment in the attic with Airbnb. It’s amazing how fast I accumulated some money for few hours of work between guests. Now I want to persue all my dreams of opening an online herbal store, publishing my ebook of treating Ulcerative Colitis with herbs, blogs, and videos, and pretty much all of the ideas mentioned here. I will save this article as its really helpful for whomever needs some ideas…
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These days, low-risk bond yields aren’t enough to meet most income needs. When investing in bonds, the income typically comes as coupon payments – contractually guaranteed interest payments at predictable intervals.  There are many kinds of bond income available, so you must strike a balance between reaching for higher income (yield) and limiting risk.
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