That time I told my wife I wanted to quit my job
Beyond earning a salary, the 2 biggest issues i face if i were to "go it alone":1. My lack of skills as a lead salesperson. I'm really effective at many roles - both for enterprise and start up (e.g. - CTO, dev, BA, product mgr, project mgr, etc.)...but when it comes to selling/sales...wow, do i suck...at least as the lead. I'm really good as a wingman/second banana...but to get leads, or close that deal as the lead salesperson...well, that has been my greatest weakness...and honestly one that i've never desired to be good at...but then if i were to go into business for myself, i would either need to improve, or get a partner who is good at that.2. Secondly, the cost of health care - at least in the U.S. (where i live/work). I'm able to bring lots of other costs down (home mortgage or apartment rent, etc.), but not health care...at least not for my family's needs (*NEEDS*, not wants!). So, if/when i were to go into business full-time for myself, i would need to ensure i can cover such costs...and that makes things quite difficult...especially as per my point #1 above....Which is all to state that i'm highly respectful and in awe for folks who *can* make it on their own.  Kudos to the post author, and to anyone else who can make it happen!