Learning accounting with Ledger

I'm currently living off of savings. I'm looking into generating an income online, in a location-independent manner, but I'm not making any money at the moment. I hope to fix this initially by freelancing, eventually by building some kind of Internet business.

Being in this situation makes me slightly anxious. Part of the anxiety is irrational unfounded fear of not being able to make it. Another part is just a consequence of the bad job I'm doing of (not) tracking my expenses, not having a budget and not really knowing how long I have left until my money runs out. I'm also not sure how much I'm spending on different things and I don't have a sense of where I'd be able to cut down on expenses to make my money last longer. I'd also like to figure out how much money I save by living in cheaper countries, now that I'm doing the nomad thing. I currently have the impression that my savings are offset by the money I spend on flights and other travel related expenses, but I'm not sure how true that is.

Some products and services that seem popular are Mint, Quicken, Quickbooks and YNAB. I like Ledger. I like that is geeky, simple, robust, hackable, future-proof. I have some hesitation around the fact that it has no bells and whistles (although that seems intended as a feature, not a bug) and the fact that the learning curve seems steep. But I guess that has to do with my lack of knowledge of accounting more than the difficulty of learning ledger. I'm going to start with Ledger, but I'm not sure if I should choose hledger instead. They're both quite similar, the second being a Haskell port of the first one.

Another concern is having to spend a lot of time inputting or managing the system. Ideally, I should do nothing. Every bit of information would be pulled and aggregated for me automatically and I'd just have to interact with a beautiful interface that tutors me in accounting concepts when needed. There seems to be no product or service doing that. The ones that come close are commercial solutions that cost a decent amount of money or aren't very transparent about their goals or business model. I might be wrong, though, I haven't done a very comprehensive search.

So, I'm going to try to get into using Ledger. I'll be using ledger-mode since I already have Emacs open at all times. My current approach is going to be to use Ledger for one month or two. Figure out if I enjoy the process of keeping the system up to date and using the exercise to get a better understanding of accounting concepts and process.

A bonus might be that Ledger is also apparently designed as a time tracker. I'm currently using the free tier of Toggl and I'm not totally happy with it. I might try to satisfy my time keeping needs with Ledger (although, now that I think of it, org-mode might be an even better solution and I never got around to figuring out how to use it for that).

Lets see how it goes. I'll report back with my findings.