Imagine you are 38 year old. You hate your job. You been working in this industry for the past 14 years. Having been in this industry for some time, you realize that you have hit a plateau in your scope of work. If you move on to another job, you be subjected to the same stress, just that the amount of work, responsibilities would be slightly different. If you stay in the current company, 6 months down the road, the management will make the decision on where the regional technical office will be: Singapore or Malaysia. You tell your wife you had enough. Jumping into the healthcare IT industry seems daunting, both in terms of not knowing what you are getting yourself into, and having to rebuild your domain and connections all over again. However, you can take it because you could rely on your $300,000 dividend portfolio giving $18,000/yr ...