Your career is what I aspired to when I started in this industry over a decade ago. But what ended up happening was that I (a) worked full-time while dabbling on nights and weekends, (b) spent several years trying to decide which project I wanted to really pursue in earnest, and then (c) after picking the project, obsessing over it so much that I never felt it was ready to release. So it's...not going well so far lol.
Can you recall any specific thing you did that brought you success?
I think first and foremost is bringing yourself into a position that gets you enough runway (time and money) to be able to take things seriously — even if that sounds like the opposite of a side project. For me it was skipping university and having kids in favour of starting a web agency in the dotcom days. Also, I don't believe in working on something you love — you just need to hate it a little less than the other ideas and be positive that someone will find it useful. Like I mentioned below, luck and timing play an important role and these days I'd say you will also need one unfair advantage (contacts, cash, distribution, etc) to increase your chances.
I just wanted to say that I love your phrasing of working on something that "you hate a little less".
In general I believe the idea of "work on what you love" to be awful advice; I have found that I get deep satisfaction out of working on something that someone is willing to pay for, even if that means that sometimes it is a headache and I hate doing some of the things that need to be done. Once you accept that those things will continue to exist and continue to need to be done, and it's not going to be bliss, those things seem to matter less.
I prefer to try to learn to love something that you believe can bring you success. It is very difficult to do something day in and day out that you don't love some part of. You just have to figure out your angle. I don't love my current business, but I love business in general and I love building things that people like to use.
The "love requirement" makes it hard to continue once you wake up one day and find you no longer love it. The "hate it a little less" is much more useful is you dont want to give up on stuff because you have a bad day/week/month with it.
Was there a general goal for each one or any sort of decision tree you used to decide on what to build next... for example, did you only work on things that could potentially be big, or huge, etc? Did you analyze the market size of each idea before starting, etc?
I've outlined a few things in an answer below but another aspect I use more and more these days is a negative inbound filter for ideas. Ranging from macro problems like 'Will it require an app' down to even 'do I need user accounts'. Basically, try to put together a few things that you need or want to absolutely avoid due to certain constraints or knowledge and go from there.
This is my story as well, more or less. Want to compare notes? Perhaps figuring out what we have in common would help us understand what we're doing wrong.
As someone who is squarely outside the industry of "side project entrepreneurism," it sounds like the problem is obsessing over minor details about the project and never launching it.
The other person literally said they tried like 50 things and you two haven't launched any yet.
I put that in there to make it more or less obvious that perfectionism was one of the reasons I haven't accomplished much yet. The point was to probe deeper and see if there's some other insight, because everyone already knows that perfectionism kills productivity.
At the same time, if you're doing it for a hobby, taking your time until you're happy can be meditative. That's why I'm taking my side project slowly - because I enjoy coding and am using my side project as a form of relaxation.
You have no idea and irregardless of evidence that you have gathered if something will work or not. Based on this, it would be very bad to work on something for a year without knowing or getting frequent feedback (cash sent to your bank account by customers).
So the only way is to treat this like poker. You place several bets over a period of time (max 1 month). This way you launch 12 projects in a year and have a better success chance of hitting something that actually works. You have to place bets until the card is right, then you can go all-in.
I launched my one and only three years ago and it still doesn't pay its own bills. I work on it when I can, but at this point I feel rather resigned to it never being something I can really be proud of.
By actually launching, you’ve achieved what most engineers only think about. I’m not sure if it would mean anything to you, but I look up to what you’ve achieved so far and hope I can ship something in the next 3 years.
Time is easy. Find a work with 20 hours/week schedule and a lifestyle to live for earned money. Should be possible for software developer. Now you have 20 hours a week without sacrificing free time (or more with sacrifices if you feel it worth it).
Choosing good idea worthy of implementation and finding enough inspiration to finish it is another matter.
I'm probably the last person you'd want to ask about this but it sounds like you failed to take risk, possibly due to mild (or not so mild?) perfectionism.
Can you recall any specific thing you did that brought you success?