I can pick and choose people to complement my weakness. This is commonly preached advice, and is somewhat true. Think about all the business types with "brilliant" ideas that are only a technical cofounder away from millions. When you're rare and in demand (in your case people who are reliable and finishers, and in the previous case idea guys who need technical people), you don't just go with the first bloke that makes an offer. You need to offer something compelling that they can't get elsewhere.
This is only a suggestion, but think about optimizing for lifetime happiness instead of focusing most of your energies on the now and the short term. So with respect to these personality flaws, it might also affect other areas of your life. If you spend the necessary effort now, you'll experience the compounded effects of these benefits over a longer time horizon.
This post may seem overly critical. In actuality I'm trying to have a conversation with my earlier self who was about to make similar missteps as you. I sincerely hope you find what you are looking for.
You talk of passion, but speak in terms of escapism. It sounds like you have some personality flaws. From your short description, the writing describes someone who appears unfocused, impulsive and unreliable. If you were slave to your clients (working on your own startup), would those traits magically disappear? Also your root motivation for quitting is suspect. Don't quit because of boredom or from feeling empty. Quit because staying at your job is preventing you from taking full advantage of a growing opportunity from one of your side projects.
Also, advice on success is very situational. To replicate Arnold Schwarzenegger's success, you would need to go through physical child abuse and develop a deeply rooted negative self image. Somehow he got over it, and channeled those flaws into body building, real estate, and movies. Did he do these things because he felt unworthy and strived to become worthy? Would you want to be tortured and abused during your childhood if you had a greater chance of "success" in adulthood? For other wildly successful people, what demons are they hiding?
Whether you decide to work own your own startup full time, or stay at some job, I'd urge you to increase your chance of future success by working on yourself. Read books, do exercises, see coaches and mental health professionals.
And stop caring so much about laws. Seriously ignore all laws that don't fit into your self serving reality distortion field. Don't worry, VC's will give you extra props for those "legal hacks."
If the world operated as a true meritocracy, not faking or bullshitting and just being 100% honest would work.
However, has asking for a 50% raise in the same company ever worked? Can you imagine a scenario where it would work? Maybe I am lacking in imagination.
The reality is that in our current business climate, various morally repugnant actions take place all the time. The examples you listed of dishonest climates, you keep getting a raw deal. Do you just take the short end of the stick to maintain the moral high ground?
Why do you feel guilt at all? The company could afford to bump your salary up 50%, you just needed to give them a compelling reason to do so. In a world where sociopathic behavior is celebrated, you’re just playing the game.
It’s interesting how con men’s confidence games are now being upvoted and celebrated by the Hacker News community. The celebration of bait and switch tactic in these emails is indicative of how shady startup culture is getting.
There is no sacred ground to maintain trust. Social proof, vanity metrics, out right lying is all fair game in this wild west. This is how credibility crumbles. This is how the startup scene becomes overwhelmingly a market of lemons as honest folks get pushed to the wayside and sociopaths rise amongst the chaos.
Famous last words. After seeing several SF startups implode, I'll never make the mistake of taking under market pay. I would much rather choose how my compensation gets spent rather than an employer make that decision for me.
It's easy to get lured into the excitement of working in a "start-up culture" but you will recognize the red flags after one has sucked you dry without adding much to your finances.
This is only a suggestion, but think about optimizing for lifetime happiness instead of focusing most of your energies on the now and the short term. So with respect to these personality flaws, it might also affect other areas of your life. If you spend the necessary effort now, you'll experience the compounded effects of these benefits over a longer time horizon.
This post may seem overly critical. In actuality I'm trying to have a conversation with my earlier self who was about to make similar missteps as you. I sincerely hope you find what you are looking for.