Ian Daniel Stewart

What does Ray Dalio, super-investor and author of Principles for Life and Work think your greatest challenge is? It’s mastering the part of you that won’t be mastered.

Your greatest challenge will be having your thoughtful higher-level you manage your emotional lower-level you. The best way to do that is to consciously develop habits that will make doing the things that are good for you habitual.
— Ray Dalio in Principles for Life and Work

I’ve been thinking of this as more like a struggle. The struggle for your (somewhat) free will — your conscious thought — to control and tame your (mostly) chained will — or unconscious mind. If you’ve ever tried to break a bad habit, a really, really ingrained one — for Ray Dalio it’s close-mindedness or something like narcissistic conversation — you can probably relate to the metaphor of a struggle. It’s not easy.

That struggle is well-expressed in a thread from one of my favourite Bob Dylan songs: Where Are You Tonight? (Journey Through Dark Heat).

The truth was obscure, too profound and too pure
To live it you have to explode
In that last hour of need, we entirely agreed
Sacrifice was the code of the road

…

I fought with my twin, that enemy within
’Til both of us fell by the way
Horseplay and disease is killing me by degrees
While the law looks the other way

…

There’s a white diamond gloom on the dark side of this room
And a pathway that leads up to the stars
If you don’t believe there’s a price for this sweet paradise
Remind me to show you the scars

There’s a new day at dawn and I’ve finally arrived

If I’m there in the morning, baby, you’ll know I’ve survived

I can’t believe it, I can’t believe I’m alive

Your greatest challenge:

You have to do things that seem too hard and face much discomfort. (It’s uncomfortable developing good habits and breaking bad ones.) The discomfort is in doing things that the “lower-level you” doesn’t want to do. You have to explode an old way of doing things. There will be sacrifice. The struggle between you and your twin (the “lower-level you” or enemy within that’s easily misled by horseplay and dis-ease) will lead to both combatants falling. There are going to be scars but you’ll arrive at your destination even though you might find you can’t believe it.