Resurrecting this thread....I was going to post one very similar to the OP here (fed up with the day job, time to get out), and this one popped up. Curious how things worked out for the OP?
I have had an LLC for about 10 years now - residential rentals, and my pro audio company (local/regional live music). Trying to get some background/info on carrying my own insurance. Healthy, non-smoker, non-drinker, no chronic issues, no regular meds besides multivitamins and a baby aspirin, active, good BMI, no diabetes...worst I have going is, I wear glasses/contacts. I go to the doc when I can't walk from the pain, and that's about it - I'm not a "omigodIneedabandaidwhere'sadoc" person. Anything not requiring stitches...I'm good on my own.
I will likely keep SOME sort of day gig for now, but I think it may be prudent to just switch to my own insurance, in case I decide to quit working for people who think "customer perception is reality" more than "you need to come to work on time, be there when you are scheduled to be there, do your duties as assigned and explained to you, and if you don't there will be penalties" - because I'm tired of covering for all these lazy bastards who can't come in on time and can't do their jobs correctly. The only time employees get disciplined is when a customer gets a burr up their *** and sends in a cranky survey result. Even if they're unreasonable - or flat out LYING - the employee in question is disciplined. But come in late? Don't show up at all? Don't do paperwork right? Eh, don't worry about it. I'm not here to hold your hand and make you feel safe; I'm here to fix your car. And management fails to understand that cars don't get fixed when employees aren't at work for their shift.
So yea. I think it's about time to go work for myself. I'm handy. I can build, fix, paint, wire, plumb...I can fix n flip houses, or get more rentals going...I can do more concerts and pick up more gigs...it's just ME (sole proprietor), no employees to trash my gear or my company image...