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Caroline Middlebrook has written a very interesting post about making the decision to quit her day job to work full time on her business efforts. She analyzes the traditional advice given to would-be entrepreneurs with a job, and why this advice usually results in failure all around. She also explains how she was able to quit her job without being reckless about it.

While I believe Caroline’s decision was right for her, I’m taking the opposite approach: being an entrepreneur in my free time while keeping the day job. There’s no right or wrong here, as this is a highly individualized decision that needs to be considered from your own perspective. What’s important is that you decide based on careful evaluation of what makes sense for you.

In my case, I have a day job as a software developer that provides plenty of challenge. I also have a business that’s a significant part time effort, some miscellaneous income-producing activities, and now I have this blog, which I’m treating not as a hobby but as a personal development business. That’s quite a lot for me, and that’s just on the work front—obviously I have other things going on in my life too. I know that I ultimately don’t want to be an employee, so the question I had to ask myself was whether I should quit my day job in order to devote more time to the business activities that I eventually want to do full time (by which I mainly mean this blog, as that’s what currently suffers the most from my lack of time).

You always want to be true to yourself. In my case, I know that I’m very conservative, and that had to taken into account. Although I could quit my job and be fine for a few years, I know I would be very stressed by the thought of all the money I’d be losing. Not just the salary I’d be giving up, but all the money that could be generated as that money compounded in the stock market. Just to give you an idea, $100,000 compounded at 10% annually for 30 years is $1.7 million. Being 32 years old, I need to look that far ahead and consider what I’d be giving up for a blog-based business in which I have no track record and no basis on which to determine what the results might be.

On the other hand, I know that I would be vastly more productive with my blog if I didn’t have my job. Not only would I have much more time available, but I’d be able to work on it when inspiration strikes instead of when I’m drained. I can’t even begin to explain how much creative energy I’m wasting when I spend all this time entertaining ideas during the day that I can’t take action on until night. By then, the ideas are just phantoms that have lost their substance, if I even remember them at all, and if I even have time to try.

As I write this, my blog is in an early alpha version. This is only my second post, I have a huge backlog of posts in my head that I want to get out, I still have the default About page and the default theme, I don’t know how to use WordPress, and so forth. I know my blog’s growth is going to be greatly hampered by my decision to keep my day job. For that reason, and for the fantastic lifestyle that comes with being happily jobless, I do understand why some people would decide to quit their job and go for it. Like I said, it’s a highly individualized decision.

One thing I will caution against though, is being overly optimistic and quitting your day job without considering the consequences. Caroline ran the numbers and thought everything through. She brings some business experience to the table, knows what she’s working for, and takes consistent action. I can’t tell you how many people I’ve seen who get a business idea and think the money will start rolling in right away, despite their initial lack of skill, experience, and willingness to take action.

I’m fortunate to currently have the best job I’ve ever had, in that the people give me a great deal of flexibility and don’t micromanage me. However, if I were to lose that job for whatever reason, I think I would first take a quick vacation and then start blogging like a banshee. Then I could lay a foundation more quickly and get a better idea of how things would play out. Even if the money was only trickling in by the time I went back to work, having a track record to speak of would mean much less uncertainty about making projections into the future.

To quit or not to quit, that is the question. What is your answer?

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