Fools and their Money Metaphors

I have a boatload of financial problems, which I do fret about constantly, but my debts have bought me and my sons good health. Most folks with the diagnosis I and my oldest son have are also drowning, financially, and getting nothing but sicker. In contrast, we are on an upward trend (both financially and health-wise). The amount I owe is the equivalent of one or two hospital stays for this condition. It's a drop in the bucket. So I kept doing what I was doing, in spite of going wildly deeply in debt at a fast pace, because it wasn't simply my best hope, it was my only hope. It was clear to me that getting well was the only hope I had of ever getting my finances straightened out. Whenever I feel like I just can't keep going, I inevitably wind up talking with someone who is also under enormous financial stress but for whom there is no fix because the financial problems are rooted in their health problems and they can't fix the health problems.

I can relate to your remarks in that as long as I had more income, I kept making some of the same choices. I don't regret that because it was making me well, but when I hit a wall financially I gave up my car (which has been a wonderful experience and something I always wanted to do but wouldn't have done without a financial crisis to motivate it). And I have had other occasions where excellent solutions that resulted in overall improvements in how we did things grew out of the fact that I simply lacked the money to do what I had been doing for x issue so I had to think up something workable but cheaper.

So maybe you could find some means to get perspective on your worries so you can fret less? Perhaps doing a couple of hours a week of volunteer work at a homeless shelter or some such? And perhaps you can work on the issue of "not compromising your grand vision" so you can try to get out of a rut and make it profitable BEFORE the money runs out and financial catastrophe finally motivates you to do something else? Since this is a known issue, perhaps working on some "creativity" things (workshops, reading books on the topic, etc) and re-examining the idea with an eye towards keeping its soul but also making it profitable so you don't have to go back to bigco? If you haven't done so already, maybe you need to crunch the numbers and figure out when the money is likely to run out so you have some idea of what your timeline is for making this work? Maybe that would help make it less nebulous?

I started some websites and didn't want them to "be commercial". Then noticed that a) some of the webmasters I knew who were similarly idealistic were bitter as hell about the time and energy they put into their websites and the fact that they weren't getting the recognition and money they wanted and b) other webmasters who started similarly idealistic sites later turned their sites into an ad for a paid service because it was popular and they couldn't do this for free anymore. I ultimately decided that I wanted to keep my sites "free to the public" but also make money. I added ads, donate buttons, and have joined a few affiliates. I am not making much money but it at least pays for costs of webhosting and domain names, something that came out of my own pocket for years. It shows promise for doing more than that. So I decided that the "soul" of my idealistic ideas was keeping the information free to the public and I began looking at models which achieved that but also adequately monetized the work for the person behind it. It is clear to me that the bitter webmasters I know are causing the problem themselves. One individual has forum members practically begging for the chance to give him money and all he does is spit in their faces and turn them down while at the same time whining about the site not making enough money. He has a strangle-hold on the income-potential of the site and won't loosen his grip. And no one can tell him anything. So, in short, I would suggest you work on YOU -- your attitudes, your mental models, your stumbling blocks in terms of feeling like making money would somehow compromise your vision.

Good luck with this.

If you'd asked me 3 months ago what I'd do with a windfall, I'd have said something like 'enjoy 10%, share 10%, use 30% for a project, put the other 50% in some savings vehicle, then get back to work'. In actuality I've got option paralysis because the consequences of such decisions loom larger than I'm used to.

You have the means to generate money, both in your self-discipline and experience, so in the Chris Rock dichotomy you're a wealthy person.