Going out on your own - starting your own business.You’ve already determined that you’d like to, at a minimum, supplement your main income with an online side business, and now you’re wondering if it’s time to strike out on your own, take the plunge, quit the 9-to-5, free yourself from your corporate masters… You get the idea.

But when is that ‘right time’? Is there such a thing? No. Like any such major life decision, it’s very personal and specific to you. Your situation is different from ours - your finances, social life, aversion/comfort to/with risk are all different. What if you have a family (wife and/or kids and/or even extended family responsibilities) and a mortgage, auto loans and other financial commitments? This is a very important question that may take some time to make. It’s not to be rushed.

However, having said that, this may be an itch you need to scratch, because you will remain unsatisfied until you do. You will constantly wonder and think about what could have happened. You will go to your grave wondering ‘what if’. Any motivational speaker worth his/her salt will tell you to take the leap. After all, you only have one life to
live.

‘Older’ types that have been in a corporate culture most/all of their lives tend to advise others not to take such chances, but to leave it to youth. Youth that don’t have any financial or family commitments. We don’t agree with that. Despite the proverbial inability of old dogs to learn new tricks, we say humans have the ability to adjust at any age. The mass buzzing with billions of neurons between their ears can achieve anything.

Now there are some basic guidelines that will be true for most people. Sit down and work out your month to month financial obligations (rent/mortgage, insurance, loans, utilities, food, entertainment, etc.). Don’t underestimate. Then ask yourself how long you’re going to give yourself for your shot at your own business. 3 months? 6 months? 1 year? Be sure to tie this to a realistic estimate of how long it will take to build your business up to a level that can sustain you financially. Now, ask yourself how you’re going to fund this. Will it be out of your savings, a loan, or perhaps angel and/or venture capital?

As two budding entrepreneurs ourselves, we’ve wrestled with this very idea for a few years now, and we’ve been slowly drifting to the (inevitable?) conclusion that if we wait for the perfect time to take the full plunge, we’ll never do it. There is no ‘perfect time’.

If you would like some additional inspiration as well as very solid mechanics on how to go about transitioning to a shorter work week based entirely on your income from an online business, we recommend Tim Ferriss’ book The 4-Hour WorkWeek. The first third alone of this book is quite inspiring even if you decided not to go this route, as it has ideas that are worth considering.

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