The Difference: Living Well vs. Living Great

So many writers advertise their blog by promising ‘a better life’.

On my Dutch website, I used to do the same, feeling increasingly uncomfortable about my pledge.

Reading an essay and thinking about it is one thing, but changing your behavior is a whole different ballgame. I found it hard to imagine that my writings had a significant impact on that level.

What, if anything, would people really do differently after reading my stuff?

Moreover, I couldn’t help feeling that professing life-improvement as a ratherconvenient side-effect of spending time with my essays was unnecessary paternalistic. Most people’s lives — those that read philosophy blogs, anyway — seem just fine.

Nonetheless, when quality of life is the issue at hand, it may be that ‘just fine’ is the wrong point to turn our spades — conceivably, when the topic is of such importance, we shouldn’t settle for anything less than the very best.

For example, in his new book Principles, Ray Dalio insists that having a great life requires “crossing a dangerous jungle” and is not compatible with “staying safe”. Similarly, in Good to Great, Jim Collins argues that few people attain a great life because it’s so easy to settle for a good life.

In this essay, I want to investigate what that means.

Why shouldn’t we be content with a ‘good’ life? What, anyway, is a ‘great’ life? Why do we need to cross a dangerous jungle to get one? Is it worth the risk?

The God-desire

To start our search, perhaps we should look for some kind of arch-want that all humans harbor (deep down) and which we need to actualize to have great lives. Doing this requires crossing a dangerous jungle, because realizing that one has this fundamental desire involves relentless soul-searching or severe hardship and living up to this discovery is even harder because said motive is rather complicated to satisfy.

Sigmund Freud, for instance, has a very spicy theory according to which we are all driven by unconscious sexual desires.

Jean-Paul Sartre, on the other hand, claimed that the true wish of every living human being is to reach toward God. In Being and Nothingness, he declared that “man fundamentally is the desire to be God”.

In response, my eyebrows raise themselves. Sometimes philosophers just say weird things and this was one of those times. An acute reminder of the danger of unjustified generalization from one’s own case, I suppose.

If it leads Freud and Sartre to such implausible-sounding statements, it’s likely that our search for a great life should not take the form of a detective’s hunt for the non-existent Source of Desire.

Playing it safe versus reaching true fulfillment

Next idea: a ‘great life’ does not consist in realizing the magical species-wide desire of desires, but in living the life you truly wantto live.

Regardless of what this exactly comes down to, a life in which one pursues one’s genuine dreams is one that deserves to be labeled as ‘great’.

Indeed, there seems to be an intuitive opposition between choosing the safe option and choosing to chase one’s truest ambition.

This neatly makes sense of the connection between risk-taking and having a great life that many contemporary ‘lifestyle-designers’ are quite keen to emphasize: without entering the dangerous jungle, no one can chase his or her most sincere aspiration.

Still, I’m not really satisfied. Again, most people I know seem to be doing more or less what they want to do and seem to be leading a more or less good life. In many cases, figurative jungle-crossing doesn’t seem to be the proper prescription for life-improvement. The on-or-off conception of either doing what you really want and crossing a dangerous jungle after which you reach “it”, versus not fully chasing your big goals and living a boring life at the mundane side appears to be an exaggeration.

But perhaps I’m mistaken — perhaps this reflection betrays wishful thinking on my side. For, the number one regret of the dying is not living the life theytruly wanted to live. If that is the most common misgiving people have about their lives, it stands to reason that most people I know are not very different.

Are we all cowards?

I’m somewhat puzzled by the disapproval of ordinary, non-risk-taking lives that some theories of living well bring to bear — like people who do not strive to be the next Steve Jobs are doing something wrong.

Yet, given that the number one remorse people have is settling for exactly such a life, it makes sense to emphasize the inadequacy of that approach.

Perhaps writer Marianne Williamson was right in putting forward that:

“Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our light, not our darkness that most frightens us.” — A Return to Love

And when we are about to die, we regret thinking that our light was not bright enough to conquer the jungle.

In comparable vein, psychologist Brené Brown describes her decision to “live in the arena” like this:

“We all have shame triggers, things that you could overhear someone saying about you that would be so painful that you don’t know if you could survive it. For me, these things really used to dictate my life. I engineered my career to be small and safe. I wanted to play right under the radar because I wasn’t willing to get myself out there and get criticized. The problem with staying small, however, is that it’s always connected to resentment. When we’re not using our gifts, and being in our powers, there’s always a price for that.When I realized this, I decided that I do want to live a brave life, that do want to live in the arena.

It’s not just that a great life is, well, more great than a normal life, but also the thing is that we are effectively paying a price if we don’t strive for it.

So, let’s enter the jungle?


So far, the idea seems to be this: everyone wants different things, but whatever your deepest desire is, you must “live in the arena” or “cross a jungle” to fulfill it.

The question that suggests itself is how we should understand these metaphors.

On one way of cashing them out, their message is that everyone’s true ambitions necessarily require a heroic crusade to be reached.

In my opinion, this is overblown.

I don’t think that doing what one wishes to do involves such “big” things for all of us. Not everyone secretly desires to be the next Elon Musk.

If living great means doing what you truly want, not all ways of living great require winning your personal holy war or completing any such extremely high-flown challenge.

It’s not that difficult.

Or rather, it’s not difficult in that way.

However, I do believe that a quest for a ‘great life’ cannot go together with a commitment to “staying safe”.

It’s not that easy.

At some point, these two aims are going to conflict.

If failing doesn’t make you unhappy, stop doing it

The correct reading of the metaphors is, I think, that a great life involves being vulnerable.

More precisely, a great life calls for exposure to two different kinds of vulnerability.

The first way in which a great life requires vulnerability is that doing what we really want means that our happiness cannot be independent of our ability to engage in this activity and of our success in doing so.

When you do something you care about, your results will affect your happiness — failure will make you unhappy.

When I was young, I wanted to be like Dexter: completely emotionally independent. As Dexter eventually learned (I’m still learning), however, emotional detachment is not compatible with living well.

When we pursue something we deeply care about, we are going to be miserable when we fail or when we can no longer engage in the chase.

To live great, you’re going to have to expose yourself to those risks.

That is the truth of the jungle-crossing metaphor.

However, these risks manifest themselves differently for everyone.

A very good friend of mine finds true joy in helping people. He enjoys working in service-related jobs, is truly disappointed when he hasn’t been able to provide the help a fellow human being needed and positive, personal contact with a customer makes his day.

Elon Musk, on the other hand, wants to ensure that the human race will survive a disaster on planetary scale. I don’t know Elon, but I assume he is devastated when a rocket launch fails and elated when it succeeds.

Both are emotionally invested in the enterprise on which they spend the majority of their waking hours.

That means that they are both living in the arena.

Introspection isn’t always fun

The second way in which a great life requires vulnerability is that we are going to need to be radically honest with ourselves.

Before acknowledging that he was more like a true Samaritan than like an elbowing fancy-pants, my friend unsuccessfully tried to find happiness in “higher” jobs that by some are considered to be more socially acceptable for the educated person he is.

I admire him for quitting that search.

It takes courage to deviate from these expectations and do what you actually want to do.

When we dig deep in ourselves and to discover what really makes us happy (at this point in our lives), we must be open to the possibility that we might not be living by our personal values; we must be open to the possibility that we have to change direction.

And we must take action accordingly.

The paradox of life

All this means that how you should live, depends on how you are.

This is what I have come to call ‘the paradox of life’: risk-taking and struggle are only required to the extent that doing what you truly want requires it, whereas these desires are not under our direct control: we cannot always explain, let alone decide, what we want deep down.

Each of us has his own deep-seated needs and each of us needs to decide what he values the most.

Saying that a great life calls for monumental endeavors is, again, an unjustified generalization from one’s own case, probably a consequence of a narrow diet of examples regarding “successful” people, leading to an unhelpful idea of what success really means (that unfortunately is all too prevalent in our society).

By contrast, having the basics — a good bed to sleep in, good relationships, good food— is most important, and those things don’t get much better when you achieve a lot or much worse when you achieve less.

An intense life filled with accomplishments is not necessarily better than a relaxed life filled with savoring.

I can’t tell you which one is best for you. That’s for you to figure out.

So go and figure it out.

Like to read?

Join my Thinking Together newsletter for a free weekly dose of similarly high-quality mind-expanding ideas.

Spread the love