There is an element of truth in what you say, and yet it is not completely true.
It used to be that, if you wanted to make it as a writer, you got a job at a factory or a restaurant or something to pay the bills while you tried to make it as a writer. (It was called a "day job".) You wrote before or after work, or on the subway to or from work - all the time you could find, in fact. You didn't have much of a social life, because all your spare time went into writing.
And, reading the article, the author shows a lot of evidence of "not doing something". She expects to be able to make a living as a writer right out of the gate. (In fairness, she did have an actual magazine job at one time.) She's buying wine at bars and $8 coffees, and then she doesn't have enough money for renting an apartment. It's like she's paying no attention at all to what she's doing financially, and then she's surprised that she doesn't hit that well-moneyed point when she expects financial stability to appear.
So that's the element of truth in what you say. The not-completely-true part is this: An awful lot of good-paying, long-term-stable jobs have disappeared, and they aren't coming back. This makes it considerably harder for large chunks of the population to make it to that relatively-well-moneyed point of stability.
You're both ignoring an important contextual clue.
We’d have $8 drip coffee in the mornings with a rosemary or lavender scone, or something else ridiculously fancy, rubbing shoulders with the people our age and older who actually made money.
Pick up any guide on how to get ahead in business or sales, and it will include advice to project an air of success and engage heavily in networking activities. Now I'm personally pretty frugal, but that in itself can be a limitation. You're not likely to meet your next hot netowrking prospect standing in line at Dunkin' Donuts, even less so making coffee in your kitchen and hunching over your computer at the library.
I'm not saying the way to success is to go out and spend yourself down on fancy coffee. but look at how so many startups operate; they set up very very nice work environments and then burn through their runway cash hoping they can innovate enough to attract another funding round while also attracting talent by creating a great team with a great place to work. This writer is just trying to leverage the same approach that is promoted all over the place. I don't think she's doing a very good job of it, but if you want to meet people who can advance your career then you need to put yourself out there and putting yourself out there costs money.
I can concede that most startups operate as you describe. However, most startups also fail. If you fail in a startup, you can dust yourself off and try again. If you fail in your life, you're going to have a harder time of it.
Maybe it's not best to follow the all-or-nothing strategy that works for startups (or, should I say, that works for the VCs that fund them because they can spread their risk over many investments).
I think part of the thesis of the article is that the concept of a "day job" is also unachievable, meaning a full time job that pays you enough to live on, that is stable and has some benefits.
If all the jobs that you have available are part-time and no benefits, where you have to have a minimum of two to make ends meet, that does not leave you much time to do anything else but hustle for your next gig; not to mention the vulnerability inherent in their no-benefits nature, no healthcare, likely very little sick time or time off etc.
Not having a social life for people in the "gig economy" also seems like a very bad decision, because if your network is not large it will be very difficult for you to find your next part-time gig when one of your current ones ends. As much as a $8 something is a lot of money, if that $8 enables you to meet somebody that knows somebody that can get you a gig it might be a necessary investment unfortunately.
The margin for error nowadays is extremely thin: some years back let's say you made a bad decision and went for an "unmarketable" degree, if you finished it you were still very likely to get a better-than-minimum-wage job, and it would be extremely unlikely that you'd be in any significant debt. This job would also likely have been full-time, and paid enough for you to have a modest lifestyle without having to depend on handouts, couch surfing, subletting etc. etc.
Until not that long ago a lot of people were able to put themselves through college by working summer jobs, that does not seem as realistic nowadays with the costs involved.
Also nowadays once you get out of college what next? entry-level jobs that lead to a full time career are few and far between, factory jobs are a shadow of what they once were, there are a plethora of "gig jobs" but they don't really allow one to consider things like settling down and having kids due to their temporary nature.
As much as the author of the article might have made some mistakes (who doesn't) it still doesn't disprove their thesis of the "gig economy" not fostering a stable and predictable life path, or at least not as stable and as predictable as it used to be one or two generations back.
It used to be that, if you wanted to make it as a writer, you got a job at a factory or a restaurant or something to pay the bills while you tried to make it as a writer. (It was called a "day job".) You wrote before or after work, or on the subway to or from work - all the time you could find, in fact. You didn't have much of a social life, because all your spare time went into writing.
And, reading the article, the author shows a lot of evidence of "not doing something". She expects to be able to make a living as a writer right out of the gate. (In fairness, she did have an actual magazine job at one time.) She's buying wine at bars and $8 coffees, and then she doesn't have enough money for renting an apartment. It's like she's paying no attention at all to what she's doing financially, and then she's surprised that she doesn't hit that well-moneyed point when she expects financial stability to appear.
So that's the element of truth in what you say. The not-completely-true part is this: An awful lot of good-paying, long-term-stable jobs have disappeared, and they aren't coming back. This makes it considerably harder for large chunks of the population to make it to that relatively-well-moneyed point of stability.