Boats and cars depreciate in value pretty hard, so those are most likely sunk costs. Now mark has a cool boat and car, but that doesn't guarantee you a social network, much less a social network of professionals.

A doctor wanting to start a practice in the slip over would be quite a stroke of luck. An even bigger stroke that he would be any good, and yet even bigger stroke that he would want to start his practice with some random dude on a boat. All that for a shot at putting in the hard work so you can maybe have a successful practice.

In your scenario, it seems likely that Mark is actually pretty charming, and that's what would lead another boat doctor to want to start a practice with Mark. If so, then Mark probably doesn't need the boat or car to charm a peer from his existing network. Which would almost certainly be better ROI.

Additionally, even if everything went wrong for Sam, as you describe, he would have learned a ton for future cash flowing assets, and can probably sell them for what he purchased them for, possibly more if he improved the numbers. Between the knowledge, and the intermittent cash, Sam almost certainly has a much better ROI.

I would like to point out though, that I don't fully agree with the goal of the article. Sam seems like he is going to wake up one day and wonder where his life went. Doesn't sound like he is making any great new memories. Mark, on the other hand, probably won't be retiring in the Hamptons, but he will probably look back on his life and have made some awesome memories.

The sort of meta-comment that I think the article kind of doesn’t address at all is that there’s a lot of personal growth and development books that are all about “core competency”. Figure out what your core competency is and double down on that, make sure that is tended and watered and growing every single day, because that’s the thing you do better than other people.

Sam’s core competency is presumably being a doctor, but he has all these distractions. The author can say “passive income”, but it’s a drag even when things don’t go as wrong as my overwrought scenario. My father had a ton of “side hustles”, and some worked better than others, but they were all some amount of psychic drag on his attention and focus.

Mark isn’t necessarily doing the right thing from that perspective either, but we could imagine a third person, Alice. Alice is making the same money, but instead of either of the two previous paths, she devoted her free time to working in a clinic, did research, wrote papers, went to conferences. She studied on her own time, and worked to improve her craft and reputation. She hires an accountant to deal with her taxes, a money manager (or roboadvisor) for investments, outsources everything so she can focus on being the best at what she does.

That seems pretty likely to yield dividends too, imho.

To be fair, the original author makes some very improbable assumptions. Several people have posted research they've done or experience in things like vending businesses. At one point the author says that even with Covid affecting the short term rental market Sam could still get a 20% return in year 1. To make that math work he needs to make $100 profit a month from the rental property during a pandemic when he would actually have a hard time just minimizing his losses.

I wonder if these stories are appealing because it seems like an “easy” path to wealth, whereas “work hard at a demanding job” seems hard.

That makes me wonder though: how would I even determine if an opportunity or side hustle is worth pursuing? If every SWE followed our logic, Silicon Valley would be a very different place.

I guess, there’s a big difference between starting an AirBnB and starting AirBnB: the latter has much higher potential reward. So if you’re going to start a side hustle, it better have the potential for fast growth.

In programming terms, choose a side hustle where O(Side Hustle) >= O(Career)

Granted, you likely have the privilege of working in an in-demand field so you won't be out of a job for long, but not everyone is like that.

I’m a super biased reader though. I get very anxious when it comes to money so when the going was good for me, I used all the extra earnings to secure a moderate income outside my job.

How? You make it sound straightforward, but I wouldn't know where to begin.

Let’s say I have $1M liquid (I don’t) and I want to “build passive income”. What do I do? Specifically, what are the actual steps? As in, I pick up the phone and do what? Should I buy a laundromat? Great! HOW do I do this? Where is eBay For Laundromats? Once you but it you’ll need to hire someone to run it. How?

Buy a bunch of duplexes and be a landlord? OK... where is the step-by-step guide?

The answer of course is that it is not straightforward. It is complex and requires experience and not-widely-known niche know-how, and that’s why not everyone just does it.

I would say the scenario with the lowest amount of luck is not really outlined here, which is: get a good job with a high probability of stability. Work hard at it, spend less than you earn and put it in a diversified portfolio of investments and then don’t think about it once it’s in there.

As my grandfather used to say, "If you sold $20 bills on the corner for $19 all you'd do is get arrested."

Since it's so common knowledge, can you point me to where I can buy a website that makes $200/month for $3000?

Immensely powerful quote.