10 Questions To Ask Before Quitting Your Job To Start A Business

Hey there,

My guess is, if you’re reading this article, you’re thinking about starting your own business.

I’m no Sherlock Holmes, but I’m guessing that you feel like you have a great idea, that can make some money and hopefully provide some freedom from the 9-5 rat race for you to enjoy life, and finally spend more time with friends and family.

Right?

You might have even taken some baby steps towards starting your own business like thinking of a name or registering a website.

Maybe you’re even further along than that and have been working on your new business after work and on weekends but now you’re faced with a difficult decision.

Should you quit your job, to start your own business?

I’m not going to pretend it’s an easy decision to make. In 2008, I left the company I had worked for over 4 years and earned a healthy six figure income with to start my own business.

I didn’t make the decision to do this easily, it took a lot of soul searching and advice from others.

See I was due to speak at a conference in Las Vegas and if I quit I wasn’t sure I was going to go there at all.

But right before I made that decision I sat down first alone and then with some trusted friends and mentors and asked some BIG questions.

The answers to these questions lead me to starting my own successful business which is currently in it’s 7th profitable year.  I even ended up speaking in Vegas still, so everybody won.

The exact same 10 Questions I asked myself are here now, to help you make your decision.

1. Do I have to quit now?

The first question you should ask yourself is if you have to quit right now. If you’re just getting started you’re almost always better off keeping your job and working on your business during nights and weekends.

My friend Scotty Nelson created the multimillion dollar brand  “On The Mat” while working his day job.

2. Does my business have sales?

In his awesome book “Ready, Fire Aim” Michael Masterson repeatedly makes the point that until your business grosses a million dollars in sales, everyone’s job is to make more sales.

I cannot stress this enough, you should not quit your job until your business either has sales or is about to release a product or service that can make sales within the next few weeks. If you don’t have sales, you’re not in business.

There are a few exceptions with the types of businesses that attract angel investors, but even those guys want to see sales or other forms of income.

As I always say people saying they like your idea doesn’t pay the rent.

Related: 10 Signs You Are Born To Be An Entrepreneur

3. How do I deal with uncertainty?

Starting your own business is going to require a large amount of confidence in yourself in order to deal with all the uncertainty.

You have to be able to keep yourself steady emotionally and psychologically in order to push through and get things done!

If you’re the type of person who needs someone to tell you everything is going to be alright, starting a business may not be for you.

4. What do successful people think of my business?

Before you quit your job to start your own business, you should talk to the most successful business owners you know. If you don’t know any business owners, you should try talking to a manager or employee of a business in the same area as yours.

If successful people or people who work in the same area of your business don’t think it’s a good idea, you may want to reconsider quitting your job.

5. How much money is needed to start the business?

This might be the most important question to ask yourself before you quit your job. You have to factor in not just the start up costs (offices, insurance, websites), but also the ongoing costs of salaries for employees, advertising and other unexpected fees and costs.

In my experience everything always ends up being about 25-30% more than you expect it to be starting out, so I recommend factoring a 25-30% cushion just in case.

6. How should I spend my time in the business

If you quit your job, you have a lot more hours in the day to dedicate to your business.

But what should you be doing to create value for your company and what can you delegate to other people?

You have to answer these questions in order to be efficient and not waste valuable time doing things that don’t generate money for your business.

Related: 21 Reasons You Should Start A Business Online

7. What happens if the business fails?

Lastly, you have to ask yourself the dreaded worst case scenario question. If you have a job now, you will be able to get a job again, if your business fails.

Plus as almost every millionaire and successful person can attest to, you meet a lot of interesting people and get a lot of opportunities during failed businesses.

Now that you’ve gone through all of these questions, I suggest you take a full hour and write out your answers to these questions.

By answering these questions, you will get a through idea of whether or not now is a good time for you to quit your job to start your own business.

If it is you’ll have already done a lot of the hard brainstorming, and you’ll know exactly what steps you need to take next and what to expect.

If these questions have made you realize now is not the right time to quit your job and start your own business, that’s good too, because by thinking about all of this stuff that goes into a business you’ve seen what you’re missing and could do now without quitting your job.

Best,
Jon Lee