The Five “P” Checklist for Taking the Plunge

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diveWhile this is the last post in my business start-up series, it could arguably be the most important because it focuses on one of the biggest challenges business owners face when they start a business — knowing when it’s time to leave the relative security of a steady paycheck, ditch employee status, and focus on their business full-time.

Until you’re ready to take that step, your goal of being a successful business owner will never be fully realized. Of course, you can maintain both a full-time or part-time job while running your own business, but in most cases, you will eventually have to pick one (or burnout!). And however you do it, it’s a scary and sometimes progress-stopping judgment call.

I have boiled the decision of whether or not the time is right to take the plunge down to these five factors. This admittedly simplified checklist may not tell you with complete certainty that you are ready to go, but it will give you some areas to gauge your readiness against.


Every other post in this series focused on one overriding theme – planning. You need a plan for your business in terms of the work you will do, how and where you will do it, how you will market your products/services, what your budget will look like and how you will control your finances. Without a plan for your business, it can be impossible to find your way and create success.

And what happens if your business grows quickly? Takes an unplanned turn? Has to keep running without you behind the helm? Or faces collapse? Along with planning each of the important elements in starting a business, you should plan for as many contingencies as possible. Not only will thinking through a plan B help you rebound quickly, but it can also give you confidence in your business and ability to keep it alive.


I have never met a successful, long-term business owner who didn’t have an undeniable passion for their work. If you don’t love what you’re doing, why do it? It’s the passion that keeps you going when you face a challenge; makes it easier to make sacrifices and compromises; and gives you a feeling of satisfaction at the end of the day.

This passion also translates into being able to identify the things you don’t enjoy doing so you can outsource and delegate them as your business grows over time.


You are starting your business with an intention, and your goals, happiness and financial success are entwined with that objective. Sure, the principles behind your business may not remain static, but they should be something you maintain an awareness of. If you don’t have a clear and measurable purpose for your business, it will be difficult to continue to move it forward.


Starting and running a business is demanding and frequently requires a decent measure of resolve. To be successful, you need determination and the desire to persevere through challenges.

You won’t be successful all of the time in every aspect of your business, and if you can’t pick yourself up and dust yourself off when you face a setback, you won’t grow as a business owner or as a person. And this growth can be the foundation of success.


Successful business owners share some common traits – confidence, determination, self-discipline, creativity, a desire to learn, good communication skills and the ability to work under pressure, just to name a few. You may not have an abundance of all of these characteristics (very few people do), but you need an appreciation of their importance and a desire to improve areas where you may be deficient. And you need to be able to reach for outside help when you need it.

And those are the five “P’s” you need before taking the plunge. I hope you have enjoyed this series on starting a business; I know I’ve enjoyed writing it. As you move ahead in your journey, no matter how hard things get, stay true to yourself. Be authentic. Be helpful. Be honest with your clients, your vendors and yourself. And work really hard. Harder than you ever worked before. It will all be worth it.

Image credit: zizzy0104

Alyssa GregoryAlyssa Gregory
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Alyssa Gregory is a digital and content marketer, small business consultant, and the founder of the Small Business Bonfire — a social, educational and collaborative community for entrepreneurs.

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