Q&A: When to Quit the Day Job and Start On My Own

This Q&A post is different. Usually I highlight questions here for my answer, meaning I’m answering a question I think others are asking, for which I’m hoping my answer might be useful. In this case, however, I’m posting because of the question itself: It’s extremely common, very important, and doesn’t have any obvious single answer I can think of.

This question came through my ask me form on timberry.com:

I am at a crossroads in my working life. The company I am working for is going through retrenchments and no-ones job is secure. I have good experience in the industry and was aproached by a former employer who suggested that start my own business and sub contract to them. I do not have capital and because of the problems that the company I am working for have had my finicial situation is not looking good. I have always wanted my own small business and this seems a great opportunity except I am worried about the finances. My question is simply this: Do i take the risk and go on my own or find a another better paying job and sort out my finances at the risk of loosing this opportunity?

Your advice would be greatly appreciated.

My first reaction to this is not to answer out of respect for the importance of the question, and how little information I have.  Yes, this is one of the most important questions I get, and I get it a lot, although not often as well worded as this one. And in my case respecting the question means I’m afraid to answer it simply. It’s a life-changing decision and no thoughtful person should answer it from afar, with an email answer.

My follow-on reaction is easy answers that are cliches: things like follow your gut that sound good but don’t really help.

My best answer is you should do a business plan. Not a formal written business plan, a plan-as-you-go business plan, a simple practical plan that’s just big enough to reduce the uncertainty; that may never get printed; that may be as simple as a target market and business offering, key milestones, and projected sales, costs, expenses, and cash flow.

The right kind of business planning is the best way to break the huge fear and doubt down into more manageable pieces.

(Image: shutterstock.com)


  • Andrew Rondeau says:

    I agree…do a business plan like you outline.

    And I would asnswer the question with a questin myself…Could you do both?

    FInd another job and and ‘go on your own’ part-time.

    That’s how I started my own on-line business. It took 3 years before I was ready to make the leap.


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