5 Questions To Make Starting Your Own Business Easier

should i start a business

I had worked at the company since I was 20 years old as an intern.

I had a great relationship with my boss Nick, who was also one of my close friends.

Together we had grown the business from running out of his living room into a real company.

I had just told Nick I wanted to talk about my future, but as soon as we sat down at the Starbucks in Hollywood, I knew I was going to quit.

Before he arrived I quickly checked my notes to re-affirm the reasons I needed to run my own shop. I had been going back and forth before then about whether I really wanted all the responsibility of being the boss or not.

On my notes I had written out five questions about why I wanted to start my own company. The answers to those questions were all I needed to know I made the right decision.

I quit calmly and left on good terms with Nick professionally and personally. For me it was the right choice.

But what about you?

If you’re reading this, you might have that annoying itch in the back of your mind. You think you might sorta, kinda, maybe like to start your own business.

But you’re not sure where to start. You’ve always had a job, and you don’t know what you should do in what order to end up successfully self-employed.

So I’m going to share the questions I asked myself to make my transition easier that I have shared with several aspiring entrepreneurs since.

1. Do You Need To Quit Your Job?

This was the first question I asked myself. Did I actually need to quit, or could I continue to draw a regular paycheck and work on my business on the side?

Obviously that’s the best case scenario, but in my situation it wasn’t an option because I’d be going into the exact same field as my former boss.

If you can, try to get started on nights and weekends before making the switch to full time, as it will let you get an idea of how viable the business is.

2. Who Are Your Customers?

This is the second most important question you can ask yourself. I was lucky enough to have gained a following due to my old blog and social media posts.

When I left my old job, I was able to use my blog to create a list of about 1500 interested prospects I could market to. If I didn’t know who my customers were, or how to find them cheaply, I would not have quit my job.

A lot of entrepreneurs live by what I call the “Field of Dreams” delusion. They think “If they build it, they will come,” but in reality you need to know who your customers are — at least broadly — before you start your own business.

3. How Soon Can I Make My First Sale?

No matter what your business idea is, it will live or die based on its sales. Michael Masterson said in his great book Ready, Fire, Aim that until your business is grossing a million dollars a year, sales is your only job.

Don’t be discouraged if you can’t make your first sale for a few months or even, in the case of businesses like real estate, for more than a year. The key is to  focus on your sales process.

I recommend creating a sales funnel, which is an easy and preset way to guide your prospects to the sale.

4. What’s Most Important To You?

A lot of times when I talk to aspiring entrepreneurs they want to start their own business for the totally wrong reasons. I hate to burst your bubble, but if you start your own business, you’re going to be working more, not less.

Especially in the beginning.

Ever since The 4 Hour Work Week, a lot of people want to start their own business for the “lifestyle” benefits. While you will have more control over your time and can probably ditch your commute, you will always be on call.

When something goes wrong at work, you can call your boss or someone else in charge. When it goes wrong in your business, you’re the person they call.

Make sure that, like a contestant on The Bachelorette, you are doing it for the right reasons.

5. Are You Willing To Work Super Hard?

When you start your own business, you are signing up for 18 to 24 months of really hard work. I have successfully started three different businesses and helped launch countless others, so I know this — that’s the reality of starting a business.

Yes, some people(mostly in tech)get lucky and sell for a kajillion dollars, but that’s the exception not the rule. Listen to any successful entrepreneur, and they will talk

about the hard days and nights, grinding away, before they became successful.

If you’re not willing to work really hard for 18 to 24 months, like most people won’t, you will not be successful and live like most people can’t.

If you ask yourself those five questions and are really honest with yourself, you will get all the answers you need about whether or not you’re ready to start your own business.   

Good luck!

(Photo by tvol / CC BY)

Jon Lee is a full stack marketer who specializes in helping small businesses grow to seven figures. He also blogs about career development and hosts the A Player Podcast where he interviews A Players from various fields as diverse as cage fighting and neurobiology. Find out more at www.Aplayerpodcast.com.


  1. Corstiaan on the 28th August

    Great list. Short and to the point. I consider number 3 the most important. It’s important to get the financials wheels turning asap in the beginning.

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