10 Questions to Ask Before Quitting Your Job to Start a Business


Quitting your full-time employment to start your own business is very stressful. When I decided in 1997 to strike out on my own, I was financially strapped and the only solution I saw was to take a leap of faith in myself and go freelance. It was the best and the worst decision of my life – more about that later.

Before you tell your boss to go jump in a river because you have decided that you wanted to open that grass hut pub on the beach, you need to ask yourself some questions and you need to be honest about the answers. Going it alone is difficult, but do-able. Take the case of Ivan Salztman and his wife Lynette. Who, do I hear? Only the founder of Dis-Chem, the most successful privately owned pharmacy retail company in South Africa. He started out with a good idea and as little as R10 000.00 capital back in 1978. To buy a Dis-Chem franchise today will cost you in the region of R18mil!

Back to those questions:

  • Are you just miserable in your current job?

Many people who think they want to become entrepreneurs are just plain bored or unhappy with their current situation. While you are making up your mind, write down a business plan. You have to have a viable business idea and an effective marketing and operations plan. Do you? Write it down, do research, look into the possibility of changing jobs or studying for another qualification. Don’t resign before you are ready, willing and able to take on the new role of entrepreneur.

  • What will your new day-to-day routine be like?

Your worst enemy when you start your own business is all that ‘free time’. You think it’s free time. It is not. It’s time that you need to spend advertising, networking, pounding on doors… It only feels free because all of a sudden you don’t have a boss cracking the whip and set tea breaks. ‘Oh, I’ll do it later’ is not a great recipe to success. Set yourself a routine and stick to it.

  • How will you raise money to keep the business going?

Come up with realistic projections regarding cash flow as part of your business plan before deciding whether you can afford to leave your job. Keep in mind that many businesses take 3 to 5 years before they become profitable. Will you be able to support yourself or your family financially for a period of that duration?

  • Have you taken into account possible unforeseen costs?

It does not help looking at your new business through rose-tinted glasses only. You are going to make mistakes. Your fax machine will die on you. Your transport company may go on strike. A dozen unforeseen things can go wrong. Factor in an emergency fund or plan when drawing up a business plan. Supplementing your income through freelance or part-time work can alleviate some of the strain.

  • Are you willing to take on multiple roles?

You will need to leave your ego at the front door of your new business. One day you will be the chairman and the next day you will need to be the janitor. Ask yourself if you are willing to don many hats. If not, don’t even start!

  • What are your strengths and weaknesses?

Be honest with yourself. If you are going to try a web-based business, you need to be more than just computer literate. If you want to open a school for dogs, you must at least like animals. Beef up your weak points or consider taking on a partner with the desired skills.

  • Who are your future customers and competitors?

Although it is sometimes difficult to predict your customer base, you need to have at least an idea of who you are going to target with your new venture. You also need to do some research to see who your competitors will be. Rather start up the business on a part time basis to test the water before you commit yourself fully and perhaps disastrously.

  • Will your support network back you?

When you start a new business, your whole support network  is affected. A lot of changes regarding lifestyle, income and leisure time may happen. If your family unit is reluctant to come on board, it is perhaps better to cancel your plans.

  • Do you have a plan B?

You need to have a fall-back option if your new business does not start making you money as soon as you hoped. Do you have enough goodwill from ex-employers, friends and the like who will be willing to give you part time work, for instance? Keep your options open and do not lose contact with people who can be of help.

  • How will you avoid those burning bridges?

If you quit your job, do it correctly. As tempting as it is to tell your boss what you really think of him or her, remember that your employer could be helpful to you as you launch your new venture. Figure out a way to leave in good standing. Give plenty of notice to help your employer handle the transition. Be open about your future entrepreneurial plans; quite often, previous employers may offer help or send clients your way.

Once you have addressed these questions, you may just be ready to take that big step. Good luck and don’t give up on your dream.

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