I was recently asked, “what advice would you give other entrepreneurs about quitting their day job?”  It’s a great question.  And there’s not one correct answer.  But here’s my attempt to answer it, and some of my thoughts on related questions.

First of all, mentally prepare yourself for a long journey.  Success doesn’t happen over night, and more often then not, it takes about a decade.

You will be tired.  But it will be worth it.

There is nothing more rewarding than building a success story, a legacy of your own.

Until you’ve lived it, others won’t get it. You will be misunderstood. Others will doubt you. You will even question yourself. A lot.

You can’t doubt yourself because plenty of others will. You and you alone is the only person’s approval that you need.
Acknowledging ahead of time that it will be a tough journey is one of the best ways to sooth your soul for what lies ahead.

I’d like to walk you through a time when I had to make this decision.  Would I do anything differently, and what did I get right?

For me, the timing felt right when I knew that I made enough on the side that I could at least pay my bills. That was in 2006. And I formally registered my company in February, 2007.

I reached a point where my side work was producing as much income as my day job. Each were nearly an equal 50% of my income. However, my day job was 80% of my time.

It wasn’t easy acknowledging that I’d cut my income in half by quitting my day job. But the appeal of freeing up 80% of my time to further pursue my own line of work was too hard to resist. So I made the jump.

Fortunately for me, I was able to make my income back up in less than two months.

when should I quit my job

Make the jump (Pixabay / geralt)

What is some of the best advice I’ve gotten about quitting a day job?


No one ever encouraged the jump for me (except my wife). And the same goes for many others. You have to be accept that you are 100% responsible for the success or failure of what you’re about to pursue.

So many others are/were scared to pursue their dreams. And they reflect that regret in their conversations with their lack of supporting others braving that decision.

However, for me, that lack of support was a driving factor. Use others’ negativity as motivation to prove them wrong.

Similarly, what is some of the worst advice I’ve gotten about quitting a day job? Why wasn’t it good advice?

The worst advice was “don’t do it.” 11 years later I’m supported by a talented team, and maintaining a comfortable lifestyle while spending time with my family.

What are some common misconceptions about the right time to quit your day job in pursuit of a venture?

There will never be a perfect time.

Between saving money, preparing for future expenses, and investing in supplies, some people say, “there is never a ‘perfect time’ to have a kid.” The same goes for quitting your job.

You will always be concerned about money. You will be nervous about the upcoming workload.

Do it.

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