I will attempt to answer what advice should I have given myself before I tried to be a founder.

Firstly, I wished I had spent more time understanding my motivation. What should we do once we win - isn't it the same question as before we try to found a business? I now have money and free time which are useful but not very satisfying. Know who you are, before wasting your irreplaceable years.

I suspect that the desire to start a business is really just a desire for social status. We see Gates/Bezos/Musk and we want to copy that. Engineers evade explicitly social status jobs (politicians or corporate). The anti-management talk of engineers is incompatible with running a business. Strangely it is socially acceptable and internally justified for engineers to do a startup. Hard to grok the contradictions. And geeks have their own status ladders (which outgroup laughs at).

I suspect my internal social status competition is actually against my close group of buddies from school (even though we have very different careers). People want what their peers want. https://thementalmodels.substack.com/p/mimetic-desire-why-pe... Following our own desires is hard because going against our norms is hard. Even knowing ourselves is difficult.

#1: if you want status then admit it to yourself and optimise for that. Choose your status ladders carefully and then commit to playing for them. Some status games are for losers. Playing some status games has high personal costs. Most status games are lose/lose if winning requires luck or you lack resources/network. Understand what you want from status. I see guys that actually just want to screw and even the "winners" seem very unsatisfied.

#2: Money is a poor goal to aim for. If you really want money then make decisions that will gain money - and avoid diversions that don't. FAANG employee is sensible. Don't be a wantrepreneur - startups is foolish game because the modal result for is $0 (independent of how smart one is).

#3: we don't live in a capitalist society. People choose jobs that give them status and satisfaction and usually the pay is less important. In our society money is visible but the important payments are invisible.

I don't know how we learn what gives us satisfaction. Money is not actually satisfying (much beyond the low necessary amount). The only way I can think of discovering the unknown payoffs is to work in as wide a variety of jobs that you can possibly trial. The more random the choice the better. For example try working in education: maybe as a volunteer or IT helper or teacher aide. Maybe try some temp work. Offer to help acquaintances at work: and provide value to them. In theory we could ask people what drives them - in practice I notice that people's stated drives are not what I believe they actually are. We are monkeys and we don't know ourselves well. Experimentation seems the best way to sound our desires. I pay a lot of attention to my friends and acquittances that seem satisfied (from all walks of life). I'm not sure I can learn from them but I make a lot of effort to.

Background: I've received a minor prize in the founder's game (I now have passive income). My trick was to do software work with someone who is much more money focused within a self-funded business (VC in New Zealand is toxic).

Good luck and good skills.