The only way to get money is to try to get money. But the act of trying to get money can lead me to doing things that I don't enjoy, am not good at, and so can't make money doing because I'm not good at them... even though that's the primary reason I'm doing them.

How can I make money without trying too hard to make money?

This thought is prompted by a quote I recently read in a transcript of a podcast by Naval. He's just been asked the best way to build specialized, valuable domain knowledge you can leverage to make money:

...if you go around trying to build it a little too deliberately, if you become too goal-oriented on the money, then you won’t pick the right thing. You won’t actually pick the thing that you love to do, so you won’t go deep enough into it. – Naval Ravikant

This quote is very scary, because in this paradigm, the only way to be successful seems to be to get lucky, and you can't get lucky through careful planning (though it is possible to increase your luck surface area, which is helpful).

How do I resolve this seeming paradox?

On one hand, I might adopt a mercenary mindset: I'll do anything to make money. This leads to people taking jobs that make them miserable, but pay well: personal injury lawyers, Wall Street quants, SEO specialists.

On the other hand, I could adopt the starving artist approach, and derive great personal fulfillment from my work, yet be unable to support my family. For me, that would be doing things like writing fantasy, composing music, studying philosophy and writing, and hacking with lower-level programming languages (maybe building videogames for hoots?).

Surely there must be some middle ground that might be arrived at not merely by chance but through an intentional, planned course of action in an area which is both of interest to me, yet also financially profitable.

In a paragraph previous to the one quoted above, Naval says this:

I actually think the best way is just to follow your own obsession. And somewhere in the back of your mind, you can realize that, actually, this obsession I like and I’ll keep an eye out for the commercial aspects of it. – Naval Ravikant

Right. Okay. Follow my obsession.

...

Naval has a very valid point. But the solution he offers is frustratingly vague. Kind of reminds me of this meme – "How to draw an owl":

Step one: identify the problem – I am pursuing money too closely.[1]

Step two: don't do that, but make a bunch of money anyway.

Alternative step two: just give up on making money and supporting myself? Nah, ain't gonna happen.

So, follow my obsession, and keep an eye out for things that I can monetize? It sounds like a lot of fun, and I'd appreciate nothing more than a permission slip from the Source of Indie Hacker Money to go off gallivanting down the halls of my obsessions, but I can't in good faith do that without some kind of plan, some kind of timeline, right?

Look, I think part of the problem here, and the reason that Naval is being so vague is that he is aware of the dangers of survivorship bias.

https://xkcd.com/1827/

Perhaps this is why he refuses to give more specific anecdotal advice about his or somebody else's experience, correctly realizing that just because it worked for him doesn't mean it'll work for me, or Joe down the street.

But that doesn't help me in this situation.

And at the end of this post, I'm afraid I don't have a good answer, really, just another question for the Question Bank:

How can I make money without trying too hard to make money?

I will continue to edit this post, though, as I think and learn more about this problem.

[1] I'm making an assumption that this is the reason I have not succeeded yet. But is the problem really that I'm pursuing money too closely? I don't have any proof that it is. This is one hypothesis among many about why I'm not doing as well as I'd like to be doing.