My $.02 (crossing my fingers and hoping I have fixed the formatting problems -- apologies if I haven't):

I'm a former homemaker. I got my first full-time paid job post divorce, when my oldest child was 19. I was also a top
student at my high school, with lots of academic awards, and had visions of having a very egalitarian marriage, staying home briefly with my kids while they were little and then pursuing my own career goals. Things didn't exactly go like that and I've read lots of books, articles, and statistics trying to figure out a) what went wrong and b) how to avoid similar pitfalls in the future so I don't end up bitter about my life.

Some stats about the lives of American women, some of which may not be up to date but should give a general idea of the situation women find themselves in, often in spite of their best efforts and best intentions:

The majority of poor people in America are women (and their children) who were solidly middle class until one of
three things happened: They got pregnant. They got divorced. Or their husband died.

About half of all American marriages end in divorce and 90% of the time, when one spouse buries the other, it is a woman
burying her husband. As best I can figure, this means that about 95% of American women will face the need to start their lives over without their spouse at some point. In most cases, even men who were excellent providers while alive don't do a great job of planning for her needs in the event of their death. Alimony and child support laws have eroded overthe years so that women are typically entitled to relatively little financial support post-divorce. To make matters worse: One third of divorced fathers pay their child support obligation in full. One third make partial payments. One third skip town and stop making payments.

Women who have no children and no spouse make, on average, about 98% of what men make who have similar education and work experience. Once they either marry or have kids, they are highly likely to fall into the majority of women who make 2/3 of what men make (or, said another way, men make on average 1.5 times what women make). Some of the reasons for this include:

Women are much more likely than men to take time off from their career to raise kids, care for elderly parents and so on. Even in a two career couple, it is typically the wife who takes time off from her job to take kids to the doctor, attend parent-teacher conferences and so forth. Most of the time, when a couple relocates for the sake of a better job, they are following him to a better job and she is quitting her job to do so. Most of the time, relocating because you accepted a job elsewhere involves a step up in your career but quitting your job to follow your spouse typically means that your next job is a career setback. Women frequently choose "pink collar ghetto" jobs which leave sufficient energy and mental focus at the end of the day to pull their "second shift" of housework and childrearing. Homemakers typically spend 60 hours a week on housework. Women with full-time jobs typically still spend 40 hours a week. Men have tried to take up some of the slack at home and do, on average, about 10% more at home than they used to do. This amounts to about 10 minutes a day or an hour and ten minutes a week, which doesn't begin to make up the difference in the 20 hours of work no longer being done by her. Studies typically indicate that women are chronically short of sleep and often cannot afford to take the demanding, physically exhausting jobs which pay better.

Generally speaking, time taken off from pursuing a paid career will hurt your earning capacity. The one exception that I am aware of is when you take time off to pursue an education. I found that going to college part-time, even with health problems and special needs kids, was very do-able. Lots of colleges today cater to working adults and have online classes, condensed classes, evening and weekend classes. Such things worked really well for me.

Mihaly Csikszentmihalyi did research into the psychological relationship people have to time. I read one of his books when my oldest son was between 5 and 8 years old. They had people do timelines of their lives. Women, especially homemakers, were very prone to listing nothing but endings: All their kids would graduate high school and move away, their husband would retire and then die and then they would die. This profile had a high correlation with depression. In contrast, men would write things like "I'm going to retire -- and finally get that boat I always wanted and go fishing every weekend!" This was correlated with a much more positive outlook on life. I swore to myself right then and there that I would go to college and make plans for my future and not set myself up for "empty nest syndrome". I'm content with the outcome so far.

My understanding is that one of the biggest fears that women with small kids have is that their spouse will die. Given the statistics listed above, this isn't exactly irrational. Adequate life insurance can help calm such fears. So can a resource packet and plan for what she would need to do if you died. In my marriage, a phone call to let me know when he was going to be late from work would have made a huge difference in my sense of security. He was really bad about not calling and there were way too many nights that I spent 2 or more hours worrying myself sick that any minute now there would be a knock at the door and it would be a police officer informing me he died in a car wreck or his commanding officer informing me he died in a training accident. My husband knew that but was very slow to change his habits. It was a big point of contention in the marriage.

Since women do typically make a good deal less money than men, a level of debt that a man is comfortable with can be very intimidating and problematic for a woman. Reducing debt is generally a good idea if you hope to go out on a limb and start a startup and will also generally make a financially dependent wife feel more secure. When I was married, more income never helped increase my feeling of security. It only seemed to go towards financing a higher debt load and this made me really crazy. It was another really major point of contention in my marriage.

Women are psychologically risk-averse due to the above financial realities. Shoring up her actual security by having adequate life insurance and similar measures can go a long way towards making a woman more risk-tolerant. It is a tactic used by the American military, which provides a generous benefits package, including free medical care, life insurance,and so on. Also, look at info on how women typically start a business. They usually do it in much the same way others in this thread have suggested: Work from home, part-time, don't borrow money for it, etc. Pursuing that type of busines model is likely to involve a great deal less actual risk and be far more psychologically tolerable and practically supportable.