Questions to Ask Before You Quit Your Day Job for Good

Some readers of John Chow dot Com likely have regular day jobs of one sort or another. Some of you may work on your blogs and Internet marketing efforts as something that you do “on the side” for “extra money” now and then. And some of you dream of the day when your online income is high enough to replace your regular paycheck altogether.

While there are certainly going to be exceptions, the fact of the matter is that you’ll have a really hard time growing your online business to that level while still holding down a regular full-time job. If you aspire to live the dot com lifestyle, at some point you’ll need to quit your job. But how can you know that you are ready? Here are a few questions you’ll want to ask yourself.

Am I self-motivated? Am I a self-starter?

When it’s just you, sitting in front of your computer, staring at your web browser, there is no one else there who is going to motivate or push you to keep going. A big part of the dot com lifestyle is the freedom of time, not being bound to a traditional work schedule. What this also means is that you need to have the self-discipline to stay focused and get things done, even when you are presented with infinite opportunities for distraction and procrastination. You are your own boss and you are responsible for everything.


Can I survive the first few months without positive cash flow?

Let’s be perfectly frank. Most people who embark on this endeavor probably aren’t going to make a full-time income right away. That’s just a fact. Even when John first set out to monetize this blog years ago, it took him several months to get to what would be considered full-time money. And during those first several months (or even longer), you still need to keep a roof over your head and food on the table.

You have to be prepared to play the long game and stay dedicated to the cause (see the first question). That’s why it’s a very good idea to have a decent nest egg saved up that can help you cover your regular living expenses until your online income catches up. And that’s just a good rule to have in general, as your online income may not be as regular and predictable as a traditional paycheck.

Will I be committed to investing in my business?

If you want to succeed, you need to be prepared to invest in your business. This includes investing your time and energy, as well as your money. When you look at how much it costs to run this blog, it’s far less than what it’d cost to run a brick-and-mortar business with the same kind of monthly income. That’s true. But it didn’t get here overnight either.

Depending on what you want to do, you will need to spend your time, your money, or both. You’ll want to invest in a custom blog theme, for example, or you may need to invest in affiliate marketing software. You may need to invest in hiring a freelance writer or a graphic designer. It takes money to make money, even if you don’t see a direct 1:1 ROI right away.

Who are my mentors and supporters?

No man is an island, and no man really does it “on his own.” Seek out the people who have already achieved success and are accessible. Seek out mentors who can help you with your questions, while also recognizing that you need to provide them with value too. The philosophy of “what’s in it for me?” definitely applies.

And on the flip side, your friends and family may not really understand what you’re trying to do and what you’re trying to accomplish, but you need at least a few of them to support you. I’m not talking about supporting you financially; I’m talking about moral support and encouragement. As they say, behind every successful man

Do I have a positive mindset?

You’re going to be sorely disappointed if you think that you’ll achieve massive success overnight. You’re going to face disappointing failures. You’re going to get disheartened when you go in to check your Analytics account, only to see that your blog just isn’t getting the traffic you were hoping for. But you need to see the bigger picture and you need to stay positive.

Given these kinds of questions, you might come up with a whole universe of excuses for why you shouldn’t quit your job today and dedicate yourself full-time to your online business. You could tell yourself that you’ll wait until you have this or until the situation has that. You could tell yourself that you’ll do this “someday,” but the hard truth is that “someday” never comes. At some point, you’ll just need to take a leap of faith and believe that you can do it.

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