In his 2017 interview at the University of Michigan, Charlie Munger responded as such when asked about advice for success in one’s career:

"It’s amazing how if you just get up every morning and keep plugging and have some discipline and keep learning. It’s amazing how it works out okay. I don’t think it’s wise to have an ambition to be President of the United States or a billionaire or something like that because the odds are too much against you. Much better to aim low. I did not intend to get rich. I wanted to get independent, I just overshot!”

Quite the overshooting by the billionaire investor. This made me think about how people tend to set goals and think about if there is a prescription.

It reminds me of another saying that if you want to be happy, live around those less off than you and if you want to be successful, live around those better off than you. There are obvious exceptions but the message stings on the element of compare and contrasting we do as people.

Yes, success and happiness aren’t mutually exclusive. They are also extremely subjective per the individual. What appears to be misery from the outside may be happiness and vice versa.

"The secret to happiness is to lower your expectations. ...that is what you compare your experience with. If your expectations and standards are very high and only allow yourself to be happy when things are exquisite, you'll never be happy and grateful. There will always be some flaw. But compare your experience with lower expectations, especially something not as good, and you'll find much in your experience of the world to love, cherish and enjoy, every single moment.” - Charlie Munger

My first thought was about the alternative to low expectations. To set high ones so that you still do better than if you had set low ones. It just seemed a requirement that one would need to have one’s goals/aspirations/expectations set high if it was to achieve something truly remarkable.

“If you set your goals ridiculously high and its a failure, you will fail above everyone else's success” - James Cameron

Winston Churchill had dreamed of being the prime minister (rather leading England) since he was a child, as that is what he had written down at an early age. Elon Musk seems to have been rather obsessed with the idea of space and Mars for a long time and Bezos seemed quite focused on making Amazon the everything store even when focusing on books to start.

Yet, I imagine there are plenty of other famous entrepreneurs and leaders who did not have massive ambitions to start. At least I haven’t heard of such tales from Zuck, Brin & Paige, Jobs, Hastings, etc…

It is true that to build a habit one should have easy goals to create a cycle of positive reinforcement to continue the action until it becomes a habit. Maybe this is required to have people continuously persevere through the hard times. To have low expectations to begin with to build a work ethic and then to reach for the skies afterward.

A possible staged development where one needs to start with low expectations to begin with and earn the right to set high ones after showing a track record of execution. Obviously, one’s personality will play a big factor too as some are more confident in themselves than others. Such a development in confidence will probably come in different strides. I for one am quite over-confident in myself while I have a great many friends who aren’t despite their abilities.

Even the concept of high or low expectations seems rather arbitrary to the individual. Quite frankly, my dream life seems like a high expectation at times…but also quite achievable. It’s something within the realm of possibility I’m confident in. But this could be a joke to someone with ambitions of being a billionaire entrepreneur.

This is all a trite way of saying, it probably doesn’t matter whether one has high or low expectations. The important thing is to even have one. Which many don’t seem to. To set a goal/aspiration/expectation for the self and to strive for it.

However, in the spirit of picking a side, I think low expectations would be better. Because it’ll reinforce the feeling of achievement over time….and it’ll make one happy. A happier person will probably be more inclined to push the agenda further. If one doesn’t, no matter since the person is already happy and that will probably influence those around the individual to seek such happiness too.

I’d rather be around 100 happy people who had low expectations than 100 disgruntled people who had high expectations of themselves.