I cannot tell you how many times I have spoken to entrepreneurs and colleagues who told me that they wanted to start a new company, or even looking to join a new, young company, because they "hate their job." Let me say this up front: if you are going to go and take the risk associated with a young company, please, please, please make sure you are doing it for the right reasons.

The very first question I ask someone when they come to me with that glimmer in their eye, the wanderlust effusing from within, spouting off about how great it’s going to be at this new company, or starting their own thing, is "are you running to something or from something?" It’s a pretty simple question, and one that is easy to misunderstand. The core principle is to determine if you have thought through what you are doing and understand the situation into which you plan to insert yourself.

The common fallacy about a new or young company is that you do only what you want to do. This is especially true if this new company is your own. Admit it. You’ve thought the same things:

1. I’ll get to make my own schedule
2. I’ll work on only the things that interest me
3. I won’t have to deal with anyone else’s shit

Unfortunately, these are all very, very wrong. So very wrong. One of the first things you will discover when you venture out on your own is that there is all this other "stuff" that needs to get done. Seemingly, all the time. Stuff that you don’t want to do, and will never find interesting.

What is it that you hate about your job so much? Ask yourself that. Then, be completely honest with yourself, and ask if those things will still exist in your new gig. If you get over that hump, ask yourself how much you think you will enjoy doing the following:

Not getting through when you call

The first job that I had when I got out of college was working for Microsoft. In the early 90s, this meant quite a bit more than it does today in terms of what attributes people ascribed to you by virtue of your association with the company. Whenever I had to call a company for a contact, I would either get through, or my calls were returned quickly. Seeing as this was my first job out of college, I just assumed that’s how people in business conducted themselves.

It turns out that people were responding to "Microsoft" and not "Brandon Watson." People didn’t give a hoot who I was, but they did care that I worked for Microsoft. When I switched jobs to working for AskMe.com from Microsoft, I got a very, very rude introduction to the realities of being at a small company. No returned calls. In fact, when I got the admins of people that I knew, I would have a tough time getting through those gate-keepers. Getting your calls through, much less returned, has a somewhat inverse relationship to the age and size of your company.

Getting rejected 99% of the time

Even if you do get your calls through, get ready for the word "no." A simple fact of life is that people are simply not going to be interested in whatever it is you are selling. You will be fighting an uphill battle on many fronts. They don’t know who you are, what you are selling, why it’s important, why they need it, why your company is the best at solving whatever problem you are solving, and, most importantly, whether or not they want to give you money for it. That’s if you are trying to sell them something. It’s a completely different bag of "no" when you are looking to raise money, and yet another when you are trying to hire someone.

There are so many different reasons why someone is going to tell you "no." Worse, the inertia of saying "no" far outstrips that of saying "yes." Saying "no" is easy. It’s safe. Most importantly, it costs them nothing. It’s not personal, generally, and you need to keep that in mind as you work your way through the gauntlet of "no"s that will accompany you on your journey.

Dealing with the myriad of government forms and processes to ensure that your business is in good standing

Do you know what forms you need to fill out with your State Comptroller’s office to start your business? What about with the county registrar? Which tax forms do you need? What kind of legal entity are you going to create for your new company? Do you know whether or not you have to pay taxes on the furniture and other capitalized equipment that you have in your office?

The answers to these questions will vary based on the location of your business, and this book is not about trying to help you answer those questions. I am merely trying to point out that there’s plenty of these sorts of questions waiting for you, and they are going to occupy a large portion of your time, which will obviously take you away from the very thing you want to be doing – working on your product/service. If you join a new company, this is probably already done, but if you are going out on your own, invest the time to ensure that you get this one right.

Quickbooks, or dealing with accounting in general

I make it no secret that I hate Quickbooks. It’s not that I have a blood feud with Intuit per se, but rather a severe distaste accounting and accounting software. Everything has to be just so, and if you screw something up, it’s difficult to back track and figure out what you did wrong. The software has a direct link to your bank account, so you can forget feeling comfortable about the whole check writing process. Me personally – well, every time I used Quckbooks, I felt like I was going to blow up my bank accounts and never recover the data file.

Your basic bookkeeping is certainly something that you can contract out, and I would strongly encourage you to do so. If you use Quickbooks, you can even give your contract accountant access to the file and they can do your bookkeeping remotely. In the early days of your company you will most likely not have the revenue base to support someone full time handling the accounting, and if you have a transaction intensive business (even something as simple as an eBay business), you will be interacting with the accounting software quite a bit.

Have fun. I hated it. Even when I was working as an investment banker, I didn’t ever have to deal with the nuts and bolts accounting, and certainly not the accounting software.

Asking people who owe you money to pay you the money they owe you when they owe it to you

So you got the sale? Congratulations! That’s awesome. You’re only part of the way there. Now comes the part where you have to actually ask for the money. You may have sent out the invoice, and you are probably dealing with someone who handles their vendors on a net 30 or net 45 basis (meaning you get paid 30 or 45 days after they receive the invoice). What do you do when they don’t pay you? How comfortable are you going to be when you have to call and ask for the money?

At larger companies, you never think about this sort of thing. You probably have an Accounts Receivable department who handled all of that for you. Now you are the AR department. You will hear all sorts of excuses. Yes, you will even hear "the check is in the mail." If you are selling to small companies, you will find that they are just as cash strapped as you, and are also probably waiting on getting paid from another vendor who owes them money. It’s a tough cycle to get caught in, and your little company goes to the back of the line. Who do you think your customer is going to pay first? No name, young company with whom they have a short working relationship, or large, well known corporation with an army of lawyers?

As you can see, there’s no shortage of suck work that goes into a new company. In all probability, you have never given much thought to any of these things, and therefore don’t really have an appreciation for all the various departments within your current company that handle these items. I know I certainly hadn’t.

I mostly wanted to paint you a picture of some of the harsher realities of a new company. In having something that you are running to, these other issues won’t be the show stoppers they often times end up being. Knowing what it is you are looking to get out of your new gig, and knowing with certainty why you are doing it, will create for you a sense of purpose which will override the voice in your brain asking you why you got yourself into this mess. Starting a new company because your current job sucks is just trading in one bad situation for a new set of pain and drama.

The moral? Know whether you are running to something or away from something. Running to something will get you through the rough times when you are dealing with all of the fun subtleties that come with being a new company.