Is it Time to Quit Your Day Job?
You’ve been doing freelance work on the side for the last couple years. Going out completely on your own often crosses your mind, especially after a rough day at work. How do you know when it’s time to cut the cord, take a leap of faith, and go to work for… you? No one can be certain the time is right, but you can take a lot of the guess work out of your decision.

As I’ve mentioned before, in the summer of 2008, I left my job of over ten years and went out on my own as a freelance consultant. I had the top three keys in my favor — funds to match my income (savings and severance), insurance for 18 months (COBRA), and the complete support of my family.

How Can You Take the Guess Work Out of It?

• Set aside enough income to match your current full time pay for as long as you believe it will take your new venture to replace that income (minimum of nine to twelve months). If you’re not in that position, my best advice is to start saving.

• Consider your family. If you don’t have 100% support from your family, don’t do it. If it could put your family in immediate jeopardy, you’re not ready.

• Replace benefits. The income needed to pay for insurance needs to be part of your plan. If you can’t replace it, wait until you can. You and your family need insurance.

• Have work contracted or pre-ordered for at least three months in advance. You don’t want to begin your solo career with the pressure of having to sell, sell, sell. Release the pressure by being ahead of the game.

• Take a vacation. Who knows when the next one will be? It certainly won’t be paid time off, will it?

• Think about your health. How will the stress and pressure of owning your own business affect you? How is your current health and mental state? Are you ready for the physical and mental rigors you will face?

• Is it your true calling? Is this what you’re supposed to be doing? Are you passionate about the opportunity? If not, what are you passionate about?

• Do you know your competition? Whoever you’re competing with has a foothold — they’re ahead of you from the start. Is there room for you? Do you have a unique position in the market that solves prospects’ problems?

• Will you have any fun? Work can’t be fun all the time (or can it?), but it needs to be fun some of the time.

Are you ready to take on the challenge? If you aren’t prepared to handle the first three bullet points, you aren’t ready. Instead of quitting your day job, make a plan to meet the first three points. The other seven points will help you be successful sooner, happier, and longer.

I have several friends who have disregarded all or most of these bullet points and, despite themselves, are successful. Have you broken the rules and made a go of it? If so, tell us how — we’d like to hear from you.

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