I wonder if the winning game becomes your own boss and tiny companies.
I want to do the jump, but lack of courage, good ideas, sales skills and a very good salary still holding me back (open for suggestions). But if the very good salary would go away, the scales tip instantly.
That was always the "winning game". Only problem is that's a lot of work. The more things change, the more they stay the same; if you want more money, work harder. People who don't want to work harder complain that other people make more money because they either don't understand or are in denial about the amount of work the people they envy put in.
Yes there are exceptions. No pointing out exceptions won't help you, though it might make you temporarily feel better about yourself.
What you describe is the reason the web site you posted it on exists.
I've considered it myself; I don't want to make a business doing contract work again, because I did not enjoy that.
If I were to start my own business it would have to be a product. I have plenty of interesting projects that I work on in my free time, but I'm not sure any of them are monetizable, or at least not monetizable enough for a venture capitalist to throw money at me (especially since most of them do not involve AI). I could probably think of something that could be monetizable if I really tried but if I don't actually enjoy the work I'm doing on the side for fun then I'm probably not going to do a particularly good job on it.
Though even if I did have some brilliant project that I could sell, I have no idea how to go about finding VC investors. And even if I knew how to find these investors, I think I would ultimately be too afraid to actually commit to it.
Increasingly it's seeming that I will probably not be worth billions of dollars in my lifetime, for no other reasons than I'm too much of a coward and I'm too discriminating with what I actually work on. Sometimes it depresses me to think about it, but hard to feel too sad for myself when I still have a high salary job that involves me staring at a computer screen all day.
Wait til you find out what customers do to figure out the lowest. There’s a little more accountability.
Probably not the answer you want to here but I'll share my perspective. Three years ago my wife and I sat down and optimized our finances so I could soft-retire and focus on a few of my life goals while simultaneously working on ways to generate income without the stress of being in the employ of others. It was tough work which mainly involved paying down a lot of debt so we can live more lean. We did a lot of optimization and of course some compromise and lifestyle changes. Fortunately, my wife earns enough for us to still live comfortably on a single income.
Now I am her part-time personal assistant which has taken a big load off her plate and reduced her stress significantly. A lot of this work is clerical: writing emails, grants, curriculum/lessons (she's a teacher), ordering supplies, working with spreadsheets, doing misc. graphic design and other office work. I also take care of the household, finances (mostly) and pets. In my spare time I pursue my lifelong passions (writing, game design, and programming), but with each of these my focus has been channeling those passions into generating income. This is not a requirement of my soft-retirement, but rather a choice I made to create balance between us.
Overall, we are much happier and fulfilled and have managed to carve out a life where we work meaner and leaner without huge sacrifices. In reality, it feels like we are financially better off than we were before.