The most popular entry on this blog is about large, medium, and small businesses. However, all of those choices assume that you wish to be an employee. Being an individual contractor, consultant, proprietor, or CEO is something else. For the purposes of this blog, I’ll stick with going off on your own as a contractor/consultant (as opposed to starting a company with more than one employee).

Advantages:
Freedom! Can’t stress this enough because it’s why I’d rather struggle my way than be content doing it someone else’s way. Assuming you’re working from home or at a coworking site, you can set your own hours, pay rate (subject to negotiation), working hours, sleep time, and dress code.

You can get chores done during regular business hours, when a lot of things are open and the lines aren’t as long. You don’t have to “ask the boss” if you can take time off for a doctor’s appointment. You choose–again, within reason–your days off. Perhaps the most satisfying aspect of working for yourself is choosing the types of work you do and the types of customers you choose as your target market.

Disadvantages:
It’s all on you, bub: marketing, writing, editing, layout, negotiating, bill paying, finding insurance, networking, and so forth. You might think it’s great to take a day off whenever you want, but you’re never really off duty. If a customer calls, you need to take that call–unless you set hard limits. A day not working is a day money isn’t being made.

Yes, you can farm out some things, like going to H&R Block or using TurboTax to work on your taxes or hiring a lawyer for legal issues, if any. And you might find a graphic designer to partner with on more visual pieces. But you’ll need to be a lot more conscious about estimating your hours, ensuring that cash flows when it should, and that you’re bringing in new business (or trying) when other projects end. You need to have cash reserves or backup plans in case work dries up.

Coin Tosses:
Actually, both items above–freedom and responsibility–have their ups and downs. When things are going well, you’re the one who gets to enjoy it; when things are going awry, you’ve got to take it on the chin. Also, working alone is not for everyone. You either dig it or you don’t.

You might find that you feel more comfortable with a large organizational support system around you. (I won’t lie–there are times I miss “the bureaucracy.”) If you don’t, there’s always coworking, but again, you have to have a budget for that. Or, if the money’s just not coming in, you might have to beg off freelancing and take a steady job for a while to keep the bills paid.

Other Thoughts/Issues:
Before you go off on your own, it’s important to have clients and types of work in mind. You need to have a good network of potential customers, advisers, and references. You need to have a good idea of what your expenses are and how long you’ll have to work to make those bills.

And those “financial reserves” I mentioned? You’ll need them, especially when starting out because odds are maybe 50/50 that you’ll be working the first day you hang out your shingle. And even if you are working on day one, odds are that you won’t be invoicing that day and that you won’t be getting paid that day.

Lastly: you have to love what you do. As a one-person show, you have to keep yourself motivated to do all the things you need to do to ensure products are produced and bills are paid. If getting up and facing a pile of specific types of work fills you with dread–whether you’re on your own or working for corporate America–that’s a problem. We all spend too much time at work as it is. If you don’t like what you’re doing and you’re doing it for yourself, you need to seriously rethink what you’re doing.

Of course as “an army of one,” you’re more nimble than a large organization, and you can make the decision that day to look for different work, look for a steady job, change your rates, or whatever. The choices, as an independent contractor, are yours. That’s the glory and the hurt of it.