To Quit or Not to Quit

Who hasn’t ever fantasized with quitting the day job to start their own business? I often imagine how wonderful it would be to have the freedom to work on what I want, when I feel like it, while making money in the process.

Unfortunately, the reality isn’t necessarily as rosy as the dream. When you start your own business, you will very rarely do what you enjoy most, and will certainly have very little free time.

If you start on your own, you will be responsible not only for performing your business’s main activity, but also for every other chore, no matter how dull -from bookkeeping to cleaning your home office.

You may hire employees, in which case you will add to your main task that of supervision, and you will be liable, among other things, for paying their wages, providing health insurance, or withholding employment taxes.

If you’ve read up to this point and, despite all the drawbacks, are able to see the appealing side of being your own boss, you will find some books out there that encourage you to take the plunge, such as Ian Sanders’ LEAP! Ditch Your Job, Start Your Own Business & Set Yourself Free

Chances are, however, that you’ll want some insurance before you trade a wage for uncertain profits. Ditching the 9-to-5 routine is tricky, and most of us will be too risk-averse to do it at once. The question, then, becomes whether it has to be a stark transition. Isn’t there a middle way?

Starting your business while you’re still employed seems like the perfect compromise. You can use your wage to finance the start-up phase and delay the crucial jump until you’re sure of the business’s viability.

But there’s a reason why I suspect this idea rarely works: who would have the time to juggle a job and a side business, let alone the rest of life’s responsibilities -shopping, exercising, taking care of the kids, spending quality time with your partner … The list is endless. This route would seem apt only for those with top notch management skills -and hopefully an understanding spouse!

Nevertheless, in the course of reading books about making money and, in the process, finding the freedom to follow your life vision, I’ve come across plenty of examples of people who started in this precise way and ended up not only quitting their job, but exceedingly succeeding at their new ventures.


In her book Cash Machine for Life, Laurel Langemeir -the creator of the Wealth Cycle, whom you may know from the Dr. Phil show, talks about how she built her company Live Out Loud while working for a large corporation.


Ewen Chia describes in How I Made My First Million on the Internet and How You Can Too! his own experience working at a large telecommunications company in Singapore while dedicating all his free time to learning the secrets of online money-making. He experimented with different strategies for 5 hours a day during 5 whole years, at the end of which not only had he not made any money, but was actually $50,000 in debt. His breakthrough came with an affiliate marketing site that would provide him with considerable earnings and kick-start his way to riches.


My much admired Tim Ferriss, of The 4-Hour Workweek fame, reminisces in the book about starting his dietary supplement company while still employed –in his case, it wasn’t long before he got fired.

I imagine that for each successful story there may be several others of people who discovered that self-employment was not for them, who got tired of trying, or never managed to take their business idea off the ground. But I remain hopeful in view of the previous examples. If they teach us anything it’s that, if we have the courage and the determination to follow our dream, we may just manage to pull it through!


  • Do you have an experience relating to this topic?

  • Are you running a small business on the side while working full time?

  • Did you start your business while employed but have now left your job and become self-employed?

  • What problems have you faced incubating your business idea while still working for somebody else?