Starting a Business: 3 Questions Entrepreneurs Must Answer

So you want to be your own boss, huh? Set your own schedule, make all the rules, sail your own ship, and, come the end of they day, be like Sinatra and say, “I did it my way.”

Well, you’re not the only one. Millions of people chase the “my business, my way” dream every year, and, sadly, the great majority of them fail.

It’s not because they aren’t bright, or didn’t read the right books. It's because they just don’t have the mentality for it.

If you’re thinking about running your own business, do a bit of soul-searching before you plunk down your hard-earned cash on seminars, workshops, or how-tos. Even if you follow an exhaustive checklist of best practices, if you don’t have the personality required to run your own business, when the going gets tough--and it will at some point-- you will fail.

Here are three questions you should answer honestly before taking your dream one step further:

1. Are you willing to be called crazy?

Because people are definitely going to treat you like you are.

I don’t mean crazy as in certifiable, wandering the streets with a jarred goldfish tied around your neck, declaring the end of days. I mean crazy for bucking the status quo.

Most people are risk-averse when it comes to gambling their financial future on the very risky dream of a doughnut shop, a dog treat bakery, or, in my case, a software startup. Routines are a big part of our existence and many people find safety and comfort within them. If you’re not a risk-averse person, you’ll single yourself out for ridicule and skepticism by the majority who are. Oh, and if your startup struggles, expect that sentiment to only get worse.

I started my business when I was just out of college, engaged, with no savings, living in a busted-up old house with mushrooms growing on the shower floor. Seriously. I told my dad that, despite all this, I still had a passion to run my own business. He replied with the obvious: “You’re broke, you’re about to be the head of a household--one that’s falling down around you--and you want to start a what? You’re crazy!”

Crazy indeed. But sometimes you have to be or you'll never get started. Instead of shirking from that label, I embraced it. Thirty years of blood, sweat, and tears later, I’m the CEO of Patriot Software, Inc., a multi-million dollar company that helps other passionate entrepreneurs chase and realize their own crazy dreams.

The point here is, if you’re not ready to be called nuts for chasing your dream, you may end up doubting yourself to the point of backing down or bowing out. An entrepreneur has to have an iron will and a thick skin. Do you?

2. Are you willing to work harder than everyone else and NOT get paid for it?

Slogans about outworking the competition have become cliche. You can find them everywhere, from marketing offices to locker room walls. They’re supposed to instill a sense of drive and inspiration, but they only work because we inject them with the following assumption: if we outwork everyone else, we’ll be rewarded more than everyone else.

When starting your own business, however, this effort to reward equation is not always true.

When my partner and I left our corporate engineering jobs to start Patriot Software. Inc., we were both making $40,000 a year. Not bad for 1980. In my first year as an entrepreneur, my earnings dropped to $12,000. Keep in mind that I worked 40 hours a week as an engineer to make that $40,000 while I worked 80 hours a week at my startup to make that $12,000. Then, in year two at my startup, I made $0 and worked nearly 100 hours--100 hours of the hardest work I’d ever done.

My big payoff came years later, but, even then it wasn’t guaranteed year over year. This highlights an important part of business ownership: you must always be willing to outwork everyone else and not get paid for it. Are you?

3. Are you willing to give up your life for your business?

No, I don’t mean throw yourself in front of a car or rush into a burning building. I mean, are you willing to give up your nights, your hobbies, your social life, and family life for your business?

Remember when I said I worked nearly 100 hours a week during the second year with Patriot Software, Inc.? You don’t rack up 100 hours by working during traditional times, let me tell ya!

Your small business is like a child, and you’ll need to be there for it morning, day, and night, 24/7, 365. What’s more, you are everything to your child: its protector, its provider, and the person who wipes its bottom when it has an accident. There are no diapers for small businesses--unless, of course, that’s the business you plan on starting.

Many start businesses based on their solid grasp of a key functional skill, like baking, roofing, or designing diapers. But a business is much more than using that skill to make a wage. There are taxes, accounting, payroll, insurance, fixed costs, risks, employee drama, and just about anything else you can think of. All that stuff equals extra work, work that you’ll do because off-loading it means paying someone else to do it and most small businesses can’t even pay themselves.

This is why time is money. If you didn’t understand this concept before, you will after you start your small business and discover how much time you have to invest just to make sure you have enough money to keep your business going. Time with friends, family, kids. Are you willing to make that sacrifice?

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If you answered "no" to any one of these questions, you may want to rethink your dream lest it turn into a nightmare. I don’t want to discourage you, but, if I have, that in itself might be telling.

However, if you are mentally tough, willing to push on when others say to pull back, and make tough sacrifices, then you definitely have what it takes, and I wish you all the luck and success as you chase down your dream of being the boss.