One of the biggest appeals of opening a small business is the prospect of being your own boss. I know a lot of entrepreneurs, and the majority of them are restless, independent, do-it-yourself types. Throwing off the shackles of a nine-to-five existence and striking out on your own is exciting.

With that freedom, though, comes the responsibility of making decisions that can mean the difference between paying the bills and having the utilities shut off. It's impossible to understand the pressure that brings until you actually experience it.

During my early years as a full-time entrepreneur, there were nights when I went to bed so stressed that I'd waking up the morning wondering if I'd ever slept. My dreams would be full of failure--failure to make payroll, cover my bills, finish a job--and these fears were magnified tenfold by the fact that I had a growing family to take care of.

It's important to think carefully before committing. Once you do, remember that there are effective ways to alleviate stress and put yourself in the best possible mindset for all the decisions that lie ahead.

These five principles worked for me, and they can do the same for you with a little practice:

1. Learn how to be firm.

Haste makes waste, and nowhere is that more true than when you're calling the shots. It's one thing to goof up when you're on salary, and another when you've got a client to satisfy who can just as easily hire someone more competent.

The stakes are higher now; the environment less forgiving. Often, you'll be tasked with quick choices regarding a range of critical transactions within a short period of time.

My first hundred thousand dollar contract resulted from just such a moment of off-the-cuff reasoning. I'd created a series of billboards for a new client, and the day I completed the job he asked me if I manufactured awnings as well.

The answer was no--I'd never done an awning in my life. I didn't have the equipment or experience. I said yes regardless, because it was an incredible opportunity and I was certain I could handle it.

This certainty existed because I'd prepared for the occasion by forcing myself to make hundreds of snap judgements in the years leading up to it. It sounds crazy, but you can train yourself to do this.

Start small, but be purposeful and systematic. Practice in low-pressure situations, where the subject is as seemingly trivial as your plans for the weekend or a shopping list. Don't deliberate--choose, and stick with your choice. Do it again and again and again. Decisiveness is a habit you can master.

2. Learn how to plan.

Far too many would-be entrepreneurs leap into the fray without planning their next steps, and the result is almost always dismal failure. It's easy to get worked up about an idea; it's hard to turn that idea into reality. A business plan is a bridge from one side to the other.

Consider a friend of mine who started a small business with his wife a few years ago. They were both smart, talented, creative people; they had an appealing product, as evinced by a bunch of sales right out of the gate; yet they closed up shop within about eight months of incorporating.

"We did everything but think it through," my friend told me later. "If we'd even roughed out a roadmap at the beginning, we'd have saved a bunch of money and headache. We'd have built traction from our initial success. Instead, we winged it and got in over our heads."

The internet is thick with resources eager to help you avoid a similar fate. Use them. The U.S. Small Business Small Business Administration provides a killer introduction to the hows and whys of producing a business plan.

3. Learn how to get feedback.

My friend from above made another mistake, which in my opinion was more serious than his lack of planning. It was one of those all-too-human errors to which each of us are prone and which can sink us fast if we're not careful.

When he and his wife decided to try entrepreneurship, they went to friends and family for advice. The advice they received was uniformly encouraging. It was long on "we believe in you" rah-rahing, but short on actual substance.

This kind of feedback is usually well-meant and always dangerous. Your friends and family believe you're wonderful. Their love and affection for you act as blinders, preventing them from spotting potential weaknesses in your decisions.

 Seek counsel from people who can step back and form an objective opinion. You want tough love in this scenario--the toughest you can find. If you can win a thumbs-up from someone who's (a) been in your shoes, (b) has nothing to gain by flattering you, and (c) is able distinguish a solid business proposal from a castle in the air, you can move forward with confidence.  

Published on: Jan 11, 2019
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