An entrepreneur is sometimes described as someone who jumps off a cliff and builds a plane on the way down.

It is true that it is impossible to prepare for every single twist and turn in starting your own business. But, preparation can make the road a little less curvy.

Think you’re ready to be boss? Here are 5 things to consider before taking the leap.

(1) What is your WHY?

“Very few people or companies can clearly articulate WHY they do WHAT they do. By WHY I mean your purpose, cause or belief – WHY does your company exist? WHY do you get out of bed every morning? And WHY should anyone care?” – Simon Sinek

Starting a business is easy. Staying focused on your business and making it grow is the difficult part. Carefully explore WHY you want to start your own business or launch a new product or blog. Are you passionate about the work you do? Do you love helping people? Do you want to give a portion of your profits to a charity that you care about? Your WHY will drive you forward on the tough days and attract customers to your business.

(2) Do you have a plan?

A dream written down with a date becomes a goal, a goal broken down into steps becomes a plan and a plan backed by action makes it happen. It is imperative that you write out your business plan. You will, of course, pivot at times as your business grows. However, at the very minimum, have a detailed outline of a business plan before getting started.

 (3) What is your financial health?

Starting a business can be stressful enough without adding financial stressors and it also involves a certain degree of risk. Determine how much money you will need to invest in the startup of your business. Do you want to take on debt or are you able to set aside your own funds for this purpose? Do you have debt that needs to be paid off prior to starting a new business? Will the new business have a financial impact on you and your family? Keep personal and business funds separate and make sure you have enough funds to cover your monthly expenses for at least 6 – 12 months should your business take a while to become profitable.

(4) How will the work get done?

Determine what you are good at and delegate the rest.  You may be able to start your new business with just you. However, at least think about what sort of assistance you will need as you set up and grow your business. Do you need a full time assistant or will a virtual assistant suffice? Do you need an IT person or bookkeeper? Are there legal or accounting issues to address? Before hiring someone, determine whether they are truly needed and will serve as an asset to your business.

(5) How will you define success?

Always start with the end in mind. When starting a new business, it can be easy to get caught up in the new of it all – the branding, the office space, the new business cards. Determine what defines success for you. What are your personal and financial goals?  How long are you willing to work to make your business a success? Will the business transition forward without you? Your definition of success should be unique and personal to you.

Still want to be boss? Then the only thing left to do is to get started.

Anna Freeman Greer describes herself as “entrepreneur first, attorney second.” After starting and building her own law practice in 2009, she quickly realized her passion for helping other entrepreneurs and small business owners launch and grow their respective businesses. Visit her at