The hardest place to be is in the middle. It lacks clarity that either pole, either end of the spectrum, definitely has.
Hard, however, does not mean 'bad'. Hard just means hard.
A lot of us are in the middle on a lot of stuff. We used to not be all the much. And by we, I mean everyone in the world. But here I'm specifically talking about anyone who lives close to a city that has restaurant options or niche coffee shops, and works on a laptop for their job.
When we lived in small groups and tribes, with specific orders and limited options, there wasn't really a middle. Life was closer to either pole -- safety on one side, death by bigger animals on the other side (h/t Tim Urban's Social Survival Mammoth). This may have been true even up to pre-WW2 and suburbanizing.
Those concerns, for significant part of the developed world, are no longer concerns. Going to the grocery store is an experience, not a means of survival. Aside from social dismemberment or isolation, if we experience it, we're not really on the extreme end of any major concerns for our daily, basic well-being.
Now, we do have a Middle. It's quite large and touches most things. If the poles were characterized by extremities -- emotionally and physically -- the middle is characterized by something like not knowing which show to start after you stream Game of Thrones for the third time. My friend Daniel calls this a "showpocalypse."
Materially, we're managing a lot of what we want, or think we want, rather than what we need. Now, if you're raising kids, raising a farm, trying to cultivate something bigger than yourself, or care-taking for someone or some delicate thing, then yes, you are managing needs. And good for you! That's real human work. It's tough to come by and even when we have it, we're still in the Middle of many other things.
Two pieces of difficult news
Because we drive instead of sail, eat oranges in the winter instead of hunt, and labor over how to email our bosses back instead of speak to a warring tribe next door, our vehicles for growth come through softer realities than our ancestors.
Meaning, if you want to build a muscle for sticking up for yourself or your boundaries, odds are the opportunity is in something like not answering that work email on Saturday. If I want to be more self-assure, that'll happen as I stop apologizing for little everything that's not in my control.
One final thought
This post is a thought, a model, in progress. Paul Graham wrote an essay called "The Best Essay" and in part of it says that the best essay would involve thinking about a question and exploring it:
"An essay should ordinarily start with what I'm going to call a question, though I mean this in a very general sense: it doesn't have to be a question grammatically, just something that acts like one in the sense that it spurs some response.... You don't need to have a complete thesis; you just need some kind of gap you can explore."
This, to me, is the fun in writing.