1. Considering the cost of a Master's degree (tuition, foregone wages, and foregone investment earnings), what is the probability that I will earn more money over my lifetime with a Master's degree than without one?
(Mean, Median, Standard Deviation)
Overall (N=25): 62%, 60%, 23%
People who have or plan to get Master's or higher (N=19): 61%, 60%, 23%
People who do not have nor plan to get Master's or higher (N=6): 62%, 60%, 16%
2. What is the probability that I will be more successful as an entrepreneur with a Master's degree than without one?
(Mean, Median, Standard Deviation)
Overall (N=25): 34%, 25%, 25%
People who have or plan to get Master's or higher (N=19): 33%, 25%, 25%
People who do not have nor plan to get Master's or higher (N=6): 36%, 35%, 28%
3. What is the probability that I would eventually regret not getting a Master's degree?
(Mean, Median, Standard Deviation)
Overall (N=25): 46%, 45%, 30%
People who have or plan to get Master's or higher (N=19): 48%, 45%, 29%
People who do not have nor plan to get Master's or higher (N=6): 45%, 45%, 30%
The charts below display the individual responses. Blue bars represent people who have or plan to get a Master's or higher, and green bars represent people who do not. (Click to enlarge.)


Bottom line: The data clearly show wide-ranging opinions, but on average, there is a remarkable similarity in estimations between people who have or plan to get a Master's or higher versus people who do not. And for each question, the average response is close enough to 50% that I think it is safe to call it a toss-up. If it truly is a toss-up, then my decision comes down to whether I would rather work for a couple of years or go to school for a couple of years. The answer to that is pretty obvious.
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Regarding the question about lifetime earnings, here is a statistic from a brief 12/30 NYT article called Ten Master's of the New Universe: (Thanks, Phil.)
On average, a master’s degree results in 20 percent more pay than does a bachelor’s, according to the Bureau of Labor Statistics.