One of the biggest changes I've made over the years as a recovering overachiever has been to rely on installing systems to guide my behavior rather than attempt to hold myself to high expectations.

For whatever reason, I've always held the assumption that outcomes were solely tied to effort, and it's been a long road to understand how that's a flawed maximalist view.

There's a related concept in building and designing products that you can't blame the user if they don't behave as desired.  

Rather, you have to change how the product is designed.  Their behavior is accepted to be outside of your control.  Instead, you have control over the conditions: do you put the button on the left or the right; what words do you use to label a control; what options do you present vs. what do you decide to be the defaults?  These are your levers, and you accept that it'll be a long iterative process to achieve the objective.  You're focused on a designing and building a system vs. simply placing expectations on the user and blaming them if they failed to behave as desired.

At the time, I understood this to solely be a localized aspect of my job.  I didn't quite understand the broader importance.

This came up again when I began teaching.  

Inevitably, you'll have a normal distribution of outcomes in a class, and some students will be deemed as under-performers.  In the workplace, it was (then) customary to assume that you simply needed to cut them loose.  You blamed the employee for not being a good worker and didn't consider the design of the system.  It took me a few years of teaching to realize that I was carrying these workplace biases into the classroom.  And that, if a student isn't performing, it is important to interrogate and talk to the student to understand why, but with the lens of fixing the design of the course, rather than thinking that your job is to fix the student.  Is the course designed to glorify what you know in your head, or is it truly designed for the user—someone who can truly fill a knowledge or skill gap by going through the obstacle course that you designed.

It's only been within the past few years that I've started to apply this at a personal level—to how I live and work.  But in order to get there, I had to first free myself from the responsibility of my own exceptionalist expectations.  Implicit in the previous examples of designing for users and teaching students is a fundamental notion of both meeting people where they are at.  You want to design for that, not the end state.  But it's such a common mistake.

And so, it's just as important to consider this when you're designing for yourself.  

It's a much harder challenge than the other two scenarios, because, well you're designing for yourself.  Have you acknowledged and accepted your flaws or do you pretend they don't actually exist?  If you haven't you'll fail simply because you won't know where you need to start from.  And, it's likely you'll fall into the trap of mimicking behavior you see and hear about on social media because it simply maps to how you imagine your future (best) self, rather than getting started on iterating on a system that will work for you.

For example, I will forget to eat or will often overeat, which can lead to bad things.  I've tried some blend of keto and paleo and found them difficult to sustain.  What's worked better for me is the 16/8 intermittent fasting regimen, because it's easy to remember (don't eat before noon and finish dinner before 8pm) and doesn't place any onerous constraints on shopping and cooking, which are now pertinent details.    This has had an added affect on helping to impose a consistent schedule, which contributes to my sanity.

Sleep is another thing, and here I could definitely be better.  However, years ago, I was fairly undisciplined around getting enough sleep and saw it as a problem of being able to sleep in later. Eventually I realized that the issue is really about whether you are going to bed at a regular hour.  It's kind of like treating yourself as your own kid who needs to be put down at a certain time.  That framing has helped me get over the tendancy to stay up as late as possible for fear that I'm going to miss something great happening.

I've talked about my practice of daily writing before.  The combination of freewriting at Daily Words Club, and writing a morning blog post here has helped me clear my head from the chaos of the world, rather than simply waking up and getting engulfed in Twitter.  That ritual, too, contributes to a consistent regular schedule, while helping me improve my writing game.

All of this sounds perfectly straight forward, but the challenges here, especially when you are designing for yourself is that you don't always know what your own irrational hurdles really are until you repeatedly stumble over them a few times.  

How can you meet yourself where you are, if you don't have an accurate picture?

For example, a blind spot I uncovered in recent years was my belief of my own exceptionalism.  That is, there's a narrative that starts when you're young with being in gifted education programs, attending elite universities, getting a job at impressive companies that creates a compounding of exceptionalism which disconnects you from your own humanity.  It's easy to miss in particular if you're gaining more power and prestige along with a bigger bank account, because it seems like everything is going up and to the right.

This is a problem because it means that you see systems (rituals, support networks, etc.) as crutches that signal a flaw to the world, rather than as superpowers that enable you to be more effective.

And so, part of the journey of designing an effective system for yourself may involve uncovering your own biases, much in the same way that a phase of research and discovery often precedes the product design process.

Without that, you'd simply be throwing darts rather than iterating towards something that will eventually work.

In my case, Orbital was a blunt but effective screening method, and the end result was that it helped me see that I had to first "clean out the garage" of unrealistic self-imposed expectations I'd been hoarding my whole career before I could have the clarity to get started.