Some Thoughts On Money
As my mother likes to say, there are two kinds of people, one for whom making money is a perennial difficulty, and another, for which money is everywhere the eye can see.
I have an instinct that I fall into the "money-is-everywhere" camp, but this has never been justified. Here's my (private) attempt to enumerate the different ways that there are to make money, for someone who's ~roughly like me. These things tend not to take a lot of time, or at least, not a lot of counterfactual time, in that I would do them for free. In no particular order:
Venture scouting. This is the nicest job. You make two sets of people happy (both your startup founder friends looking for investment, and VCs looking for startup founders), while creating real value in the world. And you can perhaps be paid for this. It requires very little time, and you can capture some of the upside of each deal, or alternatively be paid a fraction of the assets under management. The best here are informal arrangements, where you help make a few connections for free, and then they might offer to pay you. Hang out with the VCs. There is a general lesson here: create so much value that both parties on either side of the transaction feel bad that you are not profiting. Worst comes to worst, you've made the lives of the people you care about better. Best: profit.
Writing for outlets. Established magazines or news outlets pay! Yes, of course, the archetype of the struggling freelancer writer is real. But the good ones pay ~$0.5 - $1 / per word, which, for a regular 2000 word piece (done in a reasonable amount of time, say 10-15 hours), is not a bad salary. At least for a thing I currently do for free.
Donor advising. Sometimes rich people want to donate money. You can help them be more effective! You can also be paid for this.
Tutoring. Not a thing I've done personally, but many friends have. Particularly good if you can get group lessons going, and oftentimes rewarding too. Convert your credentials and time into cash. Also interview preparation. Particularly if you work in big tech.
Research Consulting. Do you have a particular skill? Economic modelling, writing well, web design. You can be contracted to help do those things for established organizations (or just latently keep an eye out for such opportunities when they arise)
Building apps or side-projects that generate revenue. Turns out there are things that are useful that you can build that people may want to spend money on. They need to be really useful, though, and people must really want to spend money on them. Pretty hard, all things considered — never done myself.
Other money-shaped advice:
Negotiate hard, as a principle. Normally you aren't burning that much goodwill. And you can always donate any additional money that feels frivolous to have.
Buy things early. If you have wanted a thing for 3 days in a row (and are convinced you will continue to do so for a few months), buy it immediately, rather than deliberate for 6 months and then decide afterwards. You can enjoy it for longer.
For things under $X, just decide that you'll buy it if you need it. Have a low bar for "need." Like you do actually need health insurance or new socks or a password manager, probably much before the time that thought has consciously crossed your mind. Same with things you want. Though if this will bankrupt you, consider that you may want too many things, and close that thing-shaped-hole in your heart instead. For small enough purchases (eg. under $5), just assume they round down to 0.
Save on big things. Negotiate, hard, on big purchases and try to find the best deal. Be scope sensitive — waste very little time on small decisions. If you are going to a conference, or buying lawyers, or anything that can be "business-expensed" (under traditional rules), you probably can get them business-expensed.
Value your time highly. You probably aren't earning as much money as you could, because you care about other things than maximizing money. That means that your counterfactual time should be used most on those things you care about — and that you can trade hard currency for additional time. Online delivery is very cheap. Amazon and instacart everything. You should probably Uber more (if you're in the US). This is only true insofar that you earn a reasonable / livable amount of money, and so ensure you are able to do that.
Become very quick at estimating the EV of certain things. Is the marginal hour you spend on your decision actually going to change the quality of your decision very much?
Most things that are worth doing will pay you if you ask. That's not to say you should always ask. But if your work is truly valuable, usually the organizations that you are doing the work for will proactively offer to contract you (in which case you should negotiate).