I think it would depend on the degree to which you are prepared to take "contentment" and the extent it is applied to the whole of mankind. It may have worked in preindustrial or prehistoric times but sounds like utopia in this day and age where "self-actualization" (or self-promotion) is all the fashion.

a simple, unremarkable life — Satyesu

Would you prefer a complicated one? Praise and admiration from people you don't know? Or is it a powerful legacy that demands respect alongside a treasure trove of earnest-enough-gotten gains? The sands of time spare very few. Even Caesar, who conquered a large portion of the world, now only lives in the form of internet memes mocking his violent death, and a lackluster salad.

No perhaps I'm assuming again. You care not for recognition of your deeds only for the sorely needed example and influence it could bring, you care not for recognition of your talent other than to enrich, benefit, or entertain as many as possible. The idea of leaving the world a better place ignites a fire in your heart and soul, an adamant gaze of fierce determination in your eyes. The joys, praise, and affluence that come with fame mean absolutely nothing to you for know at the deepest level these things are mere transient distractions from the larger goal, which is the constant state of acknowledgement that you, did something that uplifted and changed the lives of many. They all start that way, yet more often than not, they all end the same. Good luck.

Read some self-help books etc. written by very rich and very influential people, such as those by Arianna Huffington. These people still talk about "going with nature", contentment, and such. (These people aren't crudely ambitious the way poor authors of self-help books and their get-rich theories are.)

I'm not asking how to get famous. I just want life to be interesting, not just adequate, and I wonder if that's wise.

I think you’re right that it does depend on the choice of how one seeks fulfillment, whether to be happy or interesting. One who seeks contentment must seek ways to dull the tribulations of life, while one who seeks to be interesting might embrace them. Perhaps Taoism isn’t the way to go.

I'm not asking how to get famous. I just want life to be interesting, not just adequate, and I wonder if that's wise. — Satyesu

Are you sure it's wise to ask about this at an online forum?

One who seeks contentment must seek ways to dull the tribulations of life — NOS4A2

Now apply this to very rich people: They still seek contentment, and they find it, and it would be hard to call their lives uninteresting. It's just that the tribulations of life have been taken care of by their wealth and power.

who is to say that self actualisation is not @going with the flow” perhaps a goal or achievement is natural to you. That by simply being you, you easily and fluidly gravitate towards a certain path. Going with the flow doesn’t mean that things must always be easy. Flow is turbulent. There are rapids in any stream or river.

For me the Tao is intuitive. Follow what feels right even if it t is a challenge

Wealth and power can come at great effort and cost, and often take entire generations to achieve. Rarely is tribulation absent and contentment fully present. Better to embrace the former to better appreciate the latter.

In the literature of the early classics, there is a distance between the life of the sage and those who have have responsibilities amongst men. But there is also a connection between them. The voice of Tao Te Ching is more absolute in separating the valuable from the useless. The writings of Zhuangzi often show tradespeople and the statesmen learning there is a greater order to their world than the one they impose upon it. The practice of 'not-doing' is not the absence of life coming to be.

We're learning about T/Daoism in my Eastern Philosophy class, and I'm a little disturbed by its prescription of acting "with nature," i.e."going with the flow," "letting what will be, be," etc. I think this can bring contentment with existence, but the individualist in me says I don't want to settle for "chopping wood and carrying water" - leading a simple, unremarkable life. — Satyesu

I assume you've read The Tao Te Ching. It's the best of all the religious/philosophical foundation documents. Why you ask? Because it's short. You can read it in an hour. If you have read it, you've noted that many of the verses are aimed at leaders - princes, generals. It's not primarily aimed at people who "want to settle for chopping wood and carrying water."

Eastern philosophies have often gotten a bad rap from western philosophers. They say that states of heightened awareness are a way of muffling our intellect, living in a hazy state of bliss with no content. That's a complete misunderstanding that highlights the difference between eastern and western approaches. Western philosophy is, generally, about intellect and reason. Eastern philosophy is about awareness. Awareness of the world and awareness of ourselves. Westerners say "think about this rationally." Easterners say "pay attention." The power of paying attention can be hard for westerners to grasp. It seems lazy, sleepy.

Here is my favorite summary of how I understand the eastern approach. It's written by a western writer, Franz Kafka. Not a happy-go-lucky hedonist. I don't know if he was influenced by eastern thought.

It is not necessary that you leave the house. Remain at your table and listen. Do not even listen, only wait. Do not even wait, be wholly still and alone. The world will present itself to you for its unmasking, it can do no other, in ecstasy it will writhe at your feet.

The part of this that always hits me is "Do not even wait."

The concepts of non-action and action-without-action, wu wei, are central to Taoism. They don't mean "go with the flow." They mean to wait until right action arises from within you spontaneously. Don't act from nature, act from your nature. It is possible to act without intention, from the heart if you will. You need to be patient, aware. Pay attention. Then action will arise. I can do this.... sometimes. I'm sure you do too. Very few of our actions come out of rational thought. That's one of the things you need to be aware of.

Have you ever read any self-help books etc. by very rich and influential people?
Much of the advice is commonsensical, or New Age lite. But when you consider this advice against the backdrop of these people's success, wealth, power, it sounds absolutely outlandish, like a bad absurdist play.

Forgot - welcome to the forum. I hope you'll hang around when your class is over.

I haven’t, though I love a good memoir. You’re probably right. But when I think of Eckermann’s Conversations with Goethe I find comfort that not all is lost on the man of wealth and power and genius.

not all is lost on the man of wealth and power and genius. — NOS4A2

What do you mean?

That wealthy, influential people could be shallow, but aren't so necessarily?

When you have reached a point where the both philosophies of life are crossed, it is up to your freedom of choice which you will apply. The option is part of your natural liberty. You can be content with what you have or seek to increase the value of your materials and personal status. When it comes to materialism, you may one-day ask yourself, I have this (x) (car, tv, offspring) do I want more of it, or do I want to increase my asset values? You may answer to yourself, "yes, I have enough, or "no it not good enough", while other things you might want to reach for. In both cases there is room for contentment and happiness. Of course, getting "being" and "having" mixed up is easy, but in one way (the materialist way) they are the same street.

self-actualization — Satyesu

is our nature, I'm not sure.