That strategy seems waaaayyyy less risky than actively picking stocks of supposedly “reliable” stocks that issue dividends, which could be cut at any time due to shifting industry trends and company performance. Dividend investing feels like an overly complex old-school way of investing that doesn’t have a very strong intellectual basis compared to index investing.
Have you always wanted to own your own business? You could start a side business while you work a full-time or part-time job. For example, if you're a graphic or web designer, you could start your own graphic or web design business on the side. If you like to make jewelry, you could sell at craft fairs and online. Starting a business may be daunting, but if you believe in you and your work, you could earn a decent living, maybe even quit your day job. Search out those who are doing what you want to do and interview them. Find out the mistakes they made and ask for guidance.
You can try and start another travel blog, but every twenty-something who’s visited South East Asia has one; the market is so saturated that it will be very difficult for you to stand out and start making money. Instead, if you find something you’re interested in that is underserved, you’re far more likely to be able to carve out a space. You’ve a far greater chance of making money with a blog for vintage BMW owners than another generic Thailand travel guide.
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Stocks, bonds, 401(k)s, annuities, etc. are great ways to earn passive income. If you're not financially savvy, you'll want to hire a financial advisor who'll help you choose the right investments for you. You may want to take a couple of finance classes to understand what your advisor is speaking about when he/she recommends an investment strategy. Done right, investments can pay off for years.
Bravo! Dr. Kim on your courage and innovation and honesty! Medicine has changed from what we knew or thought as kids and continues to change. It requires a constant reassessment to align with our values and dreams. I have seen Robert Kiyosaki speak and tell me I am in the worst tax quadrant which motivated me to join a mastermind group and stretch my mindset on who I am and what is possible. Your blog keeps me heading toward a direction that excites me and balances the intensity of medicine and improves my life. Thank you.
I do remember you mentioning that & how it was your ticket to exit softly and give you time to build the passive income side. Most likely when I do exit it will either be through a sale of the business which would come along with a employment contract or if a worthy successor(s) can take it over, then the business is just another annuity throwing off income. Anyway, I’d enjoy writing a guest article after I survive the next few weeks of work and weddings.
Awesome article…if this does not give somebody a clear roadmap, they probably were never going to get there in the first place! I’m kind of like you trying to figure out where to place “new” money and maturing CD’s in this low interest environment. Rates have to go up eventually…I dream of the days again where you can build a laddered bond portfolio paying 8%. I plan for a 5.5% blended rate of return, with big downside protection.
I wanted to specifically call out one particular strategy within equity investing that bears mentioning – dividend growth investing is when you focus on stocks that not only pay a dividend but have a history of strong dividend growth. When I was first building my portfolio of individual stocks, I focused on buying companies with a history of dividends, a history of strong growth, and financials that supported a continuation of both.
I make a little bit of money off of referring people to services I truly believe in. I never recommend things I don’t personally use, but if I’m going to refer friends to Shopify, products on Amazon, or Udemy courses besides my own, I have no shame making a couple bucks off it. In most cases, these referral sales come from older links within my podcasts or courses, and therefore, are completely passive.

I decided to develop some passive income streams late in 2009 and started with writing an ebook… It took me 10 days to setup, writing the book, creating the pdf, wrote the sales page, created the website, registration on Clickbank, etc. It sold so well, on complete autopilot, that I used the ebook content to create a membership site and over 1,100 people have been through the membership site.
Basically, people looking to borrow money will make a listing on the site. Those borrowers are then placed into a category and given a “rating” based on their credit history and rate. You, as an investor, will contribute money to these loans and then be paid back at the predetermined rate of interest. Invest and see those monthly interest payments deposited into your account.
If you need cash flow, and the dividend doesn’t meet your needs, sell a little appreciated stock. (or keep a CD ladder rolling and leave your stock alone). At the risk of repeating myself, whether you take cash out of your portfolio in the form of “rent”, dividend, interest, cap gain, laddered CD…., etc. The arithmetic doesn’t change. You are still taking cash out of your portfolio. I’m just pointing out that we shouldn’t let the tail wag the dog. IOW, the primary goal is to grow the long term value of your portfolio, after tax. Period. All other goals are secondary.

Everything passive first takes active energy. The time to put in the effort is when we are young and not ravaged by disease or burdened by family obligations. I remember being able to snowboard from 9am until 4pm every day for a year. Now, I’m lucky to last from 11am until 2pm without wanting to go to the hot tub and drink a bucket full of beer! If we can appreciate how lucky we are when we are young, we’ll be able to maximize our vitality and live financially freer when we are older.


There are a couple of problems with direct investment in real estate though. It’s expensive to buy even a single property, a minimum of tens of thousands of dollars, and there’s no way most investors can build a portfolio of different property types and in different regions to protect from those risks when you have all your money in just one or two investments.
I own several rental properties in the mid west and I live in CA. I have never even seen them in person. With good property management in place (not easy to find but possible) it is definitely possible to own cash flowing properties across the country. Not for everyone and not without it’s drawbacks, but it seems to be working for me so far. I’m happy to answer any questions about my experience with this type of investing.
One of the most important assets you have is your credit score. By taking care of it and pursuing the steps to improve your credit score, a world of opportunity can open up for you. If you need a loan to buy that rental property or some quick funding through a business credit card, a good credit score will help you get approved so you can build passive income.
However, this comes back to the old discussion of pain versus pleasure. We will always do more to avoid pain than we will to gain pleasure. When our backs are against the wall, we act. When they're not, we relax. The truth is that the pain-versus-pleasure paradigm only operates in the short term. We'll only avoid pain in the here and now. Often not in the long term.
Secondly – and this is just quibbling – I’d change that risk score. The risk of private equity is incredibly high and should be considerably riskier than bonds! You are providing a typically very large amount of capital to one business that you agree to have no control over, and the success or failure of that business over a locked, predefined term determines your return. And in the few deals I’ve negotiated for clients, my experience has been that there are often management fees, performance fees, etc. that may cut into your potential gains, anyway. You’re putting a lot of eggs in one basket, and promising an omelet or two to the management no matter what. You really need to be confident that you found the next Uber before you take this giant risk!
What I Do: I’ve set up multiple investment accounts outside my main operations bank that deals with working capital e.g checking, paying bills. By transferring my money to a couple brokerage accounts and two other banks as soon as it hits my main bank I no longer have temptation to spend on frivolous things. As a result, I can wake up 10 years later and reap the rewards of compounding. My 401(k) is the best example where constant contributions over 18 years has grown to over $500,000 without any savings pain given it just became a part of life. Real estate is also a fantastic asset class for the long term. It’s fantastic to enjoy your home, pay down your mortgage each month, and end up with a paid off asset that has likely appreciated during your time of ownership. 
John has a daily (yes, daily) podcast where he features an interview with a successful entrepreneur. Now, John enjoys many hundreds of thousands of downloads per month, he’s written a book, has products and has opened up a ton of opportunities for sponsorships and partnerships that wouldn’t have come otherwise. He’s not the first person to have a show dedicated to interviewing rock star entrepreneurs—not even close—but he’s definitely the fastest to see these kinds of results.
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