Kathleen Megan wrote a sidebar to her article entitled “Taking the Leap: They Quit Their Day Jobs to Follow Their Dreams” (See the blog entry for January 13, 2006) entitled “Advice From Those Who Have Been There.” The advice offered is either to do your dream work while still holding down a day job until you are comfortable taking the financial risks involved in making a complete transition, or to set a time-limit (six months is the amount of time suggested by an example) on how long you will give the dream job before you quit it unless it begins generating enough income to provide for a satisfactory middle-class existence.

Both pieces of advice are attempts to deal with the dilemma most middle-class workers face in making a transition from doing work that pays well but is not all that exciting to doing work that is exciting but that may not generate a satisfactory income. The problem is that stepping off a career track is a jump-off-a-cliff move. Once you step off, it’s hard to get back on at the same place if you determine that it was a mistake to hand in the resignation. You need to be sure before pursuing your dream job, but it’s hard to be sure without having done the new work for some time. The two strategies noted are ways to hedge your bets, to lessen the risk a bit.

The strategies are sensible ones, and they are ones that I considered before making my own jump to soul-satisfying work. I don’t find them entirely satisfactory, however.

The problem with working at both a day job and your dream job is that there is a good chance that you will not know for sure whether the dream job can ever generate a significant income if you do not devote your full-time energies to it.

It took me a long time to write the book Passion Saving in the way that I wanted it written. If I had been working a full-time safe job at the same time, it would have taken a lot longer. It would have taken so long to get the book completed that way that I worry that I would have made compromises in the research I did to support the book’s claims or in the efforts I put into the task of organizing the material so that the arguments flow logically and clearly. Had I done that, the book would not have provided as strong a reading experience. If it had failed to sell, would the reason have been that there was not sufficient demand for a book on the topic of Passion Saving, or that I simply had not done the best job that I was capable of doing? I never would have known, and the question would have troubled me for the remainder of my days.

What about the idea of a six-month trial? That strategy too makes a good bit of practical sense but that strategy too is seriously flawed, in my view.

If I had left my corporate job with a promise to my wife to return to safe employment if the fling at doing soul-satisfying work did not pay off financially within six months or a year, I would have been required to continue writing reports on financial freedom rather than move up to the harder task of constructing a book-length manuscript on the topic.

I earned $15,000 in six months selling my Secrets of Retiring Early report from an internet site. I presumably could have increased the income amount by publishing another two or three reports per year. My sense, though, after six months of selling the report, was that selling only internet reports was too limited an approach to building a business. There are many people interested in the topic of financial freedom who have never purchased an internet-published report. I concluded that it was important to write a “real book” to reach as many people as I wanted to reach with my writing. Since I had set up my plan so that financial concerns would not be an issue for a lot longer than six months, I was able to take the time to write the book of my dreams as the foundation stone of my move to gaining the ability to spend the rest of my life doing the work of my dreams.

Near the end of completion of the book, the Great Safe Withdrawal Rate Debate broke out on the first of the Financial Freedom Community boards (the Motley Fool board). I participated actively, and that took up several additional years of time for which I have so far received zero compensation. That was a risky financial move, by anyone’s estimation. The other side of the story is that we learned things about investing during the safe withdrawal rate discussions that very few others on Planet Earth know. I hope to be able to turn that learning experience into a second book, one providing a reading experience of roughly equal power as the first.

It’s possible that neither book will pay off in a financial sense. I have hopes that both will, but we’ll just have to wait and see how that all turns out. My point here is that I couldn’t have taken the chances I did had I not set up my plan with enough financial backing to permit me to go for several years without generating any income at all from my writing business.

Different people are in different sorts of circumstances. I of course have no problem at all with seeing other community members employ the strategies outlined in the article linked to above. There are many ways to skin the financial freedom cat.

Still, I think it is better when possible to go with a plan that calls for sufficient financial backing to permit you to engage in your vision of soul-satisfying work on a full-time basis. I question whether a test in which much of your time is directed to work being done to pay the bills is a real test of the dream-job concept. I also think that there are big advantages to plans that permit you to continue doing your dream work for a long period of time before needing to reverse course because of financial pressures. To make soul-satisfying work pay, you need to become really good at it. That takes time.

Please give consideration to the benefits of the strategies noted in the article linked to above. But please give consideration to the downsides of these strategies as well.