The dichotomy of best/worst — or, as I often think of it, acceptable versus available — is a tricky one, and it's not one which I feel I've yet solved. But I can certainly see how areas of my life tend towards the latter.
Take my dotfiles, for example. I spent ages writing a vimrc which sets up key bindings just so, the way I like them. Then one day I have to SSH onto a remote server and make a hotfix, and I start vimming files and get instantly confused when my muscle memory betrays me. I tried out Dvorak for a while, but then every time I had to help someone with their computer, or go to a client site, I was struggling to adjust to the 'normal' QWERTY layout. Eventually I realized it was better to learn the vim defaults like a pro, and then extend them without overriding them.
We can get very comfortable in environments we create for ourselves, expending huge quantities of energy to build a nest suited just for us. But Stoicism teaches us that fate is a lot more powerful than our nesting activities. One day a flood comes tearing through your house, or your hard drive fails, or you miss a credit card payment, and if you've wired your brain to only be happy in the environment you created, you are going to have a breakdown. In my childhood alone, I was evicted twice, moved countries several times, and had times when we were very well-off and times when we couldn't afford food. These things happen to all of us.
Nevertheless, in the Poisson distribution of cataclysms, before disruptive events, the Best approach may render you far more productive than the Worst. I consider this penalty to be my insurance policy; others have a different risk tolerance.
Just my $0.02.