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May 19, 2014

Are you ready to be your own boss?

By work from home

It’s living the dream —fighting and scraping your way until you can go it on your own. Start your own business or freelance from your home office. You’re the boss; you work at your own pace, on your own time and in the “uniform” of your own design (pajamas, anyone?). It sounds ideal — everything you’ve ever wanted.

You can finally go for an afternoon bike ride, without being questioned. You’ll have a boss who’ll never block social websites or stuff your khaki-clad self into a cubicle. But wait, hold up just a moment. Have you bothered to ask yourself this one, simple question: Are you actually ready to be your own boss?

It’s not a trick question, but it’s one filled with nuances that many aren’t ready to address. And to answer it, you have to first answer these five key questions I have laid out for you. Once you’ve thought them through, you should have the key to unlock the door to your future.

1. Can you work through distractions? This is the easiest question on the block. When you are your own boss, or you’re working from home, there are so many distractions to deal with. Family, beautiful weather, outdoor activities, social networking, television and sleep…the list goes on. It takes a very resolute mind to get through a work day knowing you could blow it all off for something more fun. Over time, this becomes less and less of an issue — but at first, the pull to procrastinate is incredibly strong.

2. Can you manage finances? There are so many issues involved with working on your own. The biggest financial issue is taxes. You don’t have the luxury of a company taking out funds to pay the various government entities, so you must pay quarterly taxes. That means building up a flush fund so you have your payments ready in time. If you don’t pay quarterly taxes, you’ll be fined and, come tax time, you’ll end up with sticker-shock over how much you owe! But it’s not just taxes. Freelancing means that your income will vary, so you must learn how to budget accordingly.

3.  Are you ready to take the blame? When work isn’t done in time, or is subpar, you only have one person to blame; you. Are you ready to shoulder that blame? When you’re working for a company, you have departments and fellow co-workers to help take the fall  for shoddy work (not that we’re looking to lay blame). But when it’s just you, it’s literally just you. It’s quite a burden to take on. If you have strong shoulders and a thick skin, you may be ready. But don’t jump to any conclusions without giving this one some serious thought. When you work for yourself and something fails, it becomes an imperative to right the wrong. If you cannot do so, that will not only reflect badly with the client in question, and word will spread.

4.  Are you financially sound? Do you have a contingency plan in the bank in case of a slow month? Calculate what you bring in per month and then multiply that by three; this is the figure you should try to have in the bank in case of emergency. When you work from home, the amount you pull in is completely dependent upon the work you do. If you have a slow period, it’s not like you’re working for a salary or hourly wage. You’re not ready to be your own boss until you can soundly handle your finances.

5.  Can you market yourself? I’m not talking about just taking out an ad in the Yellow Pages (do people even still use the phonebook?). What I mean is, are you ready, willing and able to attack social networking, send out mailing lists, handle your own PR, network, pass out cards and fliers? Are you okay with that? Or does the idea of marketing make you want to curl up in a ball and hide? A solid marketing plan is tantamount to success even when you don’t work for yourself, but even more so now.

Adding it all up. What are your answers? A resounding yes, a half-hearted meh, or a definite no? Based on this, you should now be able to approach the final and most important question: Are you ready to be your own boss? To really enjoy a successful start on your own, all of the above questions should receive an affirmative. If not, don’t quit your day job until the time comes when you can give them each a confident yes.

About the Author

is an award winning writer of technical content and fiction. He has been covering Linux and open source since the late '90s and just about every conceivable topic since. His fiction breaks ground in the post apocalyptic genre as well as horror, thriller, and science fiction. For more information on Jack, check out his site, Get Jack'd at