Rule 7: Plan for the Long Term Top
Having noted the current situation in Rule 6, it's important also to say that a career decision should be made with the long haul in mind. The business cycle will eventually reverse itself, and while the business model may need to change irrevocably, the aging population alone dictates that healthcare will be an increasing global priority. Likewise, history shows that growth in government funding for science waxes and wanes, with a time constant somewhat longer than a decade. Trying to optimize a career decision based on current conditions is a bit like trying to time the stock market—you are sure to be overtaken by events.
One approach is to choose some reasonably long time frame, perhaps a decade, and ask yourself whether you'd be content to have lived through the average ups and downs you'd experience in a given job over that period. In academia, that would include a tenure decision (rate your chances), a lot of grant applications with mixed success at best, and maybe some great students and really significant scientific contributions. In pharma or large biotech, it would encompass a couple of promotions, your own group and maybe a department, at least one merger or other big disruption, and several rounds of layoffs. In small business, it might include a failed startup (or two, or three), an IPO if you're lucky, and a lucrative exit strategy or long-term growth if you're really lucky.
If you game these scenarios with various probabilities, and use your imagination, it just might become clear which ones you have no stomach for, and which ones really hold your interest.
via PLoS Computational Biology: Ten Simple Rules for Choosing between Industry and Academia.

There was an aha moment when I got this. I used to plan. In planning I count myself as topnotch. I coupled this with an extremely frank, honest evaluation after. Repeatedly doing this It hit me that as Dwight Eisenhower said

“In preparing for battle I have always found that plans are useless, but planning is indispensable.”

“Plans are nothing; planning is everything.”

See, it hit me that as things become more complicated the more useless plans become. To be really rational about something what you need to do is develop a personality of adaptability. To be a person that can face most of anything. To train yourself to be quick on your feet, and great at improvisation.  We can guess a lot of things about the future we can see trends and have a feel for what is happening, But in a sense predicting the future is simply impossible. This help wean me from believing that there is a yellow brick road to a happy/successful life. I’m no longer blind to believing that anything is a sure thing. Most things for me are probable or improbable.
Life is not as clean as that of science or math.  Yes you can use some optimization, game theory and stuff but the complexity in life sometimes mean that even if you optimize from start to finish you end up somewhere not so good, whilst even if you made so many mistakes and bad decisions you still end up someplace great. Life is choatic.
Does this mean I don’t plan? No, I still plan during times when I don’t have anything better to do. This is because planning is everything. It is aform of play acting. It’s probably my excuse for perusing science fiction, to put myself in situations where making decisions does not follow simple rules.
If all things fail, cheer up always remember that the human mind has an extreme ability to be okay with most things. Just ask Dan Ariely(In his 2005 TED Talk I think.)