Am I Sabotaging Myself?

You are always hearing, "Follow your dreams and they will come true" and "hard work pays off." Seems simple enough. If I want to make a living as an artist- the kind that paints and draws, not the kind I currently am that sits behind a computer and does boring stuff (but at least doesn't totally suck at it and once in a while does get an opportunity to inject a teeny, tiny bit of creative flair), all I have to do is keep my dreams at the forefront (dream = make enough selling art to pay the bills and I'm not talking platinum diamond encrusted toilet seats here) and then work hard to achieve said dreams.

Seems like a realistic formula for success, no?

Yet I think I might be sabotaging it. I do.

I'm not sure why. Maybe because if I keep the job I have now, and continue to work for the man rather than myself, there's sooooo much less pressure. I know what's expected of me. I get up and do my work for X amount of hours and then I go on a website and log my hours and I get a paycheck every 2 weeks. 

If I go into business for myself, it's alllllllll up to me. I will have to constantly actively look for opportunities and take the ones that let me have a chance. And maybe even out of those, only a couple will be successful. Art shows for example. I may apply to many. I may get into a few. I may make a profit at ONE.

Not such good odds when going into business.

Right now I'm Eric Cartman. Someone wants a picture done in light, mellow colors and I scream, "Wha-Evah! Wha-EVAH!! ...I do what I WANT!" I paint what I want when I want how I want. I will keep painting in bright, obnoxious colors because that's what I do.  Once in a while if there is an ungodly demand for a certain subject matter (like poppies or sunflowers), I will paint it, even if it doesn't particularly interest me.

If I want to be successful, I'll probably at least have to start out doing paintings of things other people like. Like lighthouses and boats and barns. I have been avoiding that for as long as possible and will continue to do so until I am about to go bankrupt. I am not THAT much of a whore.

I am scared to death of the phone and email. I'm not one of those people that (in business matters) composes a simple email, quickly checks for spelling/grammar errors and sends it away. No, I sit there and analyze each and every sentence. Do I sound mean? Do I sound demanding? I am neither of those things, and have had some pretty bad experiences through letters and art associations in the past (I was on the receiving end) and the last thing I want is any sort of miscommunication. So I put off emailing people (art-related) almost indefinitely.
I am scared.

At art shows I have this terrible habit of "how bout you call me." It's awful, I know. If someone is interested in a certain size print that I don't have available, instead of taking an order and giving them a price and taking a deposit and then fulfilling said order (which is the easiest part), I give them a business card and sometimes write on the card what it was they wanted, to remind them, and then ask them to email me and we can work out the details of the order. UGH, DUMBASS!!! That is NOT the way it's done! Why have I not learned by now!
(Answer: Because I'm so unsure of myself that I'm absolutely positive that if I take the order and deposit, by the time I get home, I'll have received a phone call or email saying the customer changed his or her mind and wishes to cancel the order and get their deposit back because my art isn't worth it. OR even worse I'll forget to do it and then the person is pissed and thinking I ripped them off, which technically I would have not totally not on purpose, I am human. I am SO scared of that happening! But of course I'd go out of my way to rush the stuff to them as soon as possible...)

So I'm putting it all out there.... some of you who read this are artists. Do you find yourself sabotaging your efforts, too?

I am scared of failure.
I'm scared of trying really hard to do something I love and then finding out... it won't work.
I'm scared of investing more money into this business since it takes money to make money, and coming up short, and not carrying my fair share of the load since my dear husband already makes way more than I do, and no matter what job I'm doing I won't ever even come close. But I would like to contribute a significant amount of money to the household rather than just wasting time and money on a hobby.
I'm scared of someone buying an expensive piece of my art and getting it home and changing their mind and having to face rejection.... because that would be way worse than someone just not wanting it in the first place.
I am scared if I DO become successful, my art might actually be in demand (a little) and I won't be able to fulfill someone's order quickly enough, leaving them disappointed in me.
Or that I'll get an order for a few prints and that day my printer will decide to blow its load on my last few remaining sheets of sugar cane paper and I will have to order more paper and then when the paper comes the print heads have dried out and now I have to do 45 head cleanings and go through a bunch of ink that I don't have so then I have to order that too and wait for it to come and 2 weeks later I finally might get to make one print.