By Alyssa Gregory

The Five “P” Checklist for Taking the Plunge

By Alyssa Gregory

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

  • bebopdesigner

    Brilliant article! It is indeed really hard to dive and be on your own. It’s been quite rewarding, but it takes a lot of hard / mental work.
    And things are about to get harder as I’ll be moving to another country. Let’s see how that goes. I’ll keep The 5 P list in mind.

    Thanks for sharing so much

  • W2ttsy

    its important not to mix passion and perseverance with denial. If you are in denial that the idea wont fail, then you could end up in some serious strife. Before getting super passionate and betting the farm on anything always make sure that someone else (trustworthy of course) thinks that the idea has legs. Its easy to delude yourself that it will be successful, especially if financial pressure is the motivator for getting it off the ground.

  • Andy Cairns

    This is a nice article. Drilling further into the Purpose section, I think it’s important that the Purpose is the aim of the business and not the individual. If you start a business with the personal purpose of keeping busy, getting rich or impressing an ex-girlfriend, your focus will be completely wrong.


  • If you want to make it 6 “P”‘s, you might want to add “Persuasion”.

    Are you able to convince customers that your product or service has value, and persuade them to pay for it? One of the first things and most important things you need to do when you start a business is find customers and persuade them to buy from you. Once you have a contract or cash in hand, it will be much easier to worry about the details to fill that order and move onto the next.


  • Becky

    Great article. One thing I wanted to point out is that during the planning stage you really need to know what you are doing in order to write up a great business plan. I happened to run across a book titled, “The Ultimate Boomer Business Launch Workbook” by Jeff Williams that does a great job helping people make step-by-step decisions through out the planning process (and beyond). I think that a lot businesses fail because people just do not know what to do next when certain issues arise. The book helps to take out the guessing.

  • Excellent points…and I absolutely think Persuasion would make a good 6th P, @Frank.

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