Optimizing Into Fragility

Life Tools + Systems + Mental Models

For years my underlying obsession was finding a way to optimize my life and break away from needing to hold down a normal job. To live outside the rigid parameters that corporate culture defines for us. Looking to people I had envied, I identified skills and accolades they carried and worked backwards to assign a daily task for myself. I was convinced that in creating this perfect list of requirements, through sheer Grit, I would be able to quickly and effectively rewire all my habits and mindset and be on a path to my new life.

And then something doesn’t go according to plan. My delicate sleep schedule gets thrown off by something innocuous like a catch up on the phone running 30 minutes longer than expected or working on something too late. Then the house of cards starts to see pieces blown away – I try to wake-up at the same time with significantly less sleep and end up sleeping far past any “acceptable” time, because of this I can’t do a full workout so why do one at all?  And if I’m already being “unhealthy”, why make time to meditate? So, the day descends into mental chaos.

A critical error I was making – and have to stop myself making to this day – is architecting inherently fragile goals and systems. I don’t align to my long term goals but instead focus on unreasonable battles of scarcity – losing both in the process. This idea of fragility is something that I have grown to naturally think about more and more without necessarily appreciating the actual concept itself. I think that is a natural progression when you are trying to improve and change yourself – you have to explore what isn’t working and what pulls you back to the place you are trying to get away from.

Nassim Nicholas Taleb defines and expands upon the concept of fragility (more accurately, the concept of antifragility) in his book Antifragile. I will not attempt to reference this book as I have not had the chance to read it yet – it is high on the list though. The Farnam Street team has a great piece succinctly outlining this concept from Taleb to lead into their 10 principles to living an antifragile life. I just stumbled across that article this morning and thing it is an absolute must read for anyone trying to “redesign” their daily life.

When examining my own actions, the over commitment and binary approach to goals was me setting myself up for failure before I even got started. I designed oppressively rigid expectations for myself that I would never have recommended to another person as it was unreasonable and unsustainable. I was so focused on the how I would execute each goal, I lost my connection to the reason I was doing it in the first place. Without that tether and devotion to the why, the motivation to foster discipline was increasingly fleeting.

With the goals I have for myself now, I focus on keeping them as simple as possible and keep in mind that I am in a very long term game. The only responsibility for each day is to do the following:

  • Meditate
  • Read
  • Workout
  • Eat healthy
  • Write
  • Get to bed early so I can wake up early
  • Bonus: Do another creative or learning activity



That’s it. That’s the ‘requirement’. I still have detailed plans around all these things, but I don’t fall to pieces and spiral if things don’t go according to plan – because there is no “right” way to do everything. Sure, I have a workout plan and a reading target, and a preferred way each of these things will happen – but all that actually matters is that they happen.

Yesterday I had a lot more work than I appreciated for my day job. On top of that I had somehow strained my neck. Easy situation to write up the day as a loss. Instead I went to bare minimum execution – I read one page of my current book. I read. I stretched and did 1 pull up so as not to aggravate my neck further and to ensure I did some training. I trained. I edited yesterday’s article before publishing and white boarded some notes for today. I wrote. I got to bed as early as I could and after missing my morning meditation, I switched to a wind down nighttime meditation. I meditated.

In this way, I accomplished what I wanted to do. Of course none of those things went how I wanted. Not a single one. But they all got done. Progress was made. And looking back, I feel great about yesterday and am looking forward to today.

Even as I write this, I wish it would have been out by my personal goal of having something posted by 6am CST each day – but I’m just focused on getting something meaningful and of good quality out there. To push myself to be better but show myself grace when I inevitably falter. And I’m making more progress than I ever had with my “optimized” model which turned out to be the most fragile of them all.

See you tomorrow.

Inspirations: Nassim Taleb, Farnam Street, Being kind to yourself

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