Software Developer, Media Nut, and Proud Father of Two

Over the last year, heck, the last six months, I've been told by a few people that I should start my own business. The thought of starting and running my own business does not sound like the kind of challenge I'm up for. There's create the company, properly handling the finances so that the company money is separate from my personal money, lawyers for the overly and meticulously worded contracts, fees, registrations, filing, and then, enter a boat load of sarcasm, my most favorite part of all: finding new work. My other option is going with a sole proprietorship, which pretty much avoids all of that nonsense. However, as an employee of a company that has their own sales staff, I don't have to worry about that kind of stuff. I don't have to be worried about whether or not I can find the work to live my life. I can rest assured that as long as I deliver, I'm not going anywhere. My conundrum, however, is that I am actively trying to get away.

Lately I have been feeling pretty overwhelmed with the number of things on my plate for my side work. The amount of pending side work greatly overshadows what I have left over from my day job, and it seems to have no end in site. It's almost weekly that something comes up and requires my attention; the icing on the cake is that I'm a nice guy and have already donated countless hours to things I never have been compensated for, or if paid, not nearly what I'm worth. Being such an easy going guy, I'm not the type to demand money that I have earned and deserve, and typically I feel trepidatious about bringing up money or how much I really want to be paid. Lately I have gotten better about stating my rate and sticking to it. Still, though, I can't help but be apprehensive about going to my former church and charging them the same rate as I would for a business. I could maintain two different rates: one for businesses and another for non-profits or some kind of preferred customer discount. I don't like being a business man, despite having done plenty side work for a few years now. It's just not in my nature, darn it!

With that said, do I start a business or go with a sole proprietorship? As a sole proprietor, or freelance developer, I could save myself both time and money by having more simplistic contracts between clients and myself. This is almost what I'm doing now, except no contracts have been signed and all agreements have been verbal. Thankfully, all but one client have lived up to their word. The money I bring in would be filed as a 1099 instead of having to pay fees that a business would pay. As a sole proprietor, however, I'm opening myself up to liability, whereas with at least a limited liability company, I would have some protection. My contracts could free me or my business from any such liabilities, but throw a lawyer into the mix and I may find myself hard pressed to not be liable any more. Still, a contract is a contract and if worded properly and clearly, without leaving room for a loophole, then I should be okay. By now I either sound like a babbling fool or someone who has a decent grasp on this situation, but I'm utterly bewildered, lost, and confused. So now I'm left with a few choices, do I:

• Continue my current trend and work all day and all night?
• Leave my employer and aggressively pursue more potential work?
• Shut my mouth and continue dealing with my current employer until a full time position opens up?
• Do none of the above?

I make decent money right now and I'm convinced that I won't find the amount of work needed to make up for what I would lose by leaving my current job (I would make a horrible PR person). I have a pretty good opportunity with a good friend of mine, but that job initially was going for a starting date of August and has been pushed back to September; who's to say it would be pushed further until October, November or 2009? I can't bank on that opportunity, as promising as it is. I do, however, have a part time job opportunity that has come up, which would be as an employee, thus freeing me from both the crap that is 1099 and the headache that is running my own business. A part of me feels like I need to step out in faith and become aggressive with my side work. Becky made an interesting point tonight that all of the work I have gotten so far has been from word of mouth; none of it has been from me putting my name out, so what would happen if I did suddenly pursue more work? I can't help but think I'd fail; not miserably, but just fail at acquiring the work that I would want. In the end, I will do what is most beneficial from my family and what Becky and I believe God is calling us to do through lots of prayer. Hey, if you would like to pray for us, please do!