I've always had things I work on, and I've always been an iconoclast. I call myself an "internet plumber and data sous chef" ("internet plumber" is on my business cards).

I struggle with the notion of this activity being "working on side projects" because I was a consultant for 20 years.

I come from an age where PDPs roamed the Berkely campus and LSD came from the drinking fountains. There was no commercial internet. Software development and uptake was not driven by advertising air wars. There was no GitHub; there was no GPL. Since even then my poorly formed notion was to work horizontally across industries, it was important that I be able to retain and reuse a collection of tools and libraries and I wrote that into contracts as "software tools of the trade"; and one of the key differentiators was that I did work on them for multiple clients, or for my own account.

That was then, this is now.

I went to work for a cybersecurity company and ended up playing a lot with DNS. The first few years were complete chaos, but hella fun! But that changed, and my suggestions weren't listened to. In my opinion, Sand Hill Road has ruined the threat indicator space (omitting the journey for brevity).

I suppose what I'm doing now is 1) illustrating cool or quirky things about the technology and 2) making winners and losers in the DNS / DDI space.

I don't know that someone without the discipline to run their own business (and the wisdom not to if you don't have to, IOW move fast or go far) is going to be able to make money on side projects consistently. I'm not really trying to. So let's talk about the non-monetary rewards.

I meet the other fanatics in this space. When I make winners, they're allies. When I make losers, they provide me with free publicity. I have an awesome rollidex (look it up). <--- these are the true reasons I do it

Does this ever make me money? Indirectly yes I suppose it does. I know what I can do, and other people at the top of their game know what I can do; and I know who's at the top of their game (and oftentimes who's not). People reach out to me about quirky opportunities: I spent last winter hunting medical devices on a network (because DDI).

Would you do anything for money? Would you do anything your heart called you to do? Think about what truly motivates you and why. How does your project align with your motivation?

Make a pitch deck for your project, or for the problem area it addresses (a plea for help). In my case, I always produce working code; so that's what I do. Then publicize it, see what feedback (any kind) you get; be gracious (ok, at least try).

How'd it go? Check back with your motivation compass: is the path from here to the North clear? If not, can you plot a course? Yes? Pivot. Repeat. Just like a business, really. No? Move on to something else.

Meta: You're using words like "managing", "discipline", "slacking", "guilt"... and also "relaxing" and "working". But you don't use them in the same paragraph as "money".

1) Above, I made a comment about "move fast or go far": in my experience things oftentimes start out as "move fast" and transition to "go far". Are you a go-it-alone person, or do you find safety in numbers?

2) Baseball. Do baseball players make better baseballs because they know how to hit home runs? Is winning the game the result of discipline and training, or is it just something that tends to happen more often when you're part of (or are) a cold-blooded, well-oiled and single-minded machine?