The Curse of Optimization
Vol. XVII of The Weekly Reflection and Recommendations
Happy Sunday, friends.
Welcome to this week’s Path Nine Reflection and Recommendations. Each issue aims to enhance your thinking, lifestyle, and work by sharing distilled reflections and recommendations from the past two weeks.
Don’t feel like scrolling? Here’s the tldr version:
Reflection: The Curse of Optimization.
Rec: Product, Tool, or Framework: Rize App.
Rec: Read: Essentialism: The Disciplined Pursuit of Less by Greg McKeown.
Rec: Watch: Jeff Bezos - Regret Minimization Framework.
Rec: Listen: Ditch Your To-Do List and Do This Instead | Sam Corcos | The Tim Ferriss Show.
Have a calm, productive, and creative week!
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“The ingenuity of self-deception is inexhaustible.”
Hannah More
Reflections
◎ The Curse of OptimizationToday, I write to you with a quiet, peaceful view of the rain-kissed Seattle waterfront. Stereotypical coffee in-hand, books at my side, surrounded by the grey fog. Once again, I find myself nestled amid the familiar rhythms of this city. Having recently returned to the city following a three year stint building a house in central Washington, I’m quickly reminded of the allure of the never-ending optimizations I pursue in work and life. It’s the double-edged sword that tempts me with the promise of increased efficiency, productivity, and progress. Yet, lurking beneath its glossy exterior lies a subtle danger — the curse of over-optimization.
As my wife and I settle back into our 900 square-foot home in downtown Seattle, I’m quickly reminded of the seductive nature of the constant fine-tuning I do in work and in life. At work, it manifests in delegation, optimization, and iteration. At home, though it’s the same process, it seems less insidious. Rearranging books and furniture feels not only productive, but deeply satisfying. And yet, the driving factor of work and personal optimization stems from the same central feeling: fear.
It's easy to get lost in the whirlwind of perfecting our routines and environments, believing that we are moving closer to our goals when, in reality, we may be skirting the hard work that leads to genuine growth and improvement. Eventually, we encounter the law of diminishing marginal returns, exceeding the point of optimal output and risking wasted time and energy with reduced efficiency. Our pull toward the insidious curse of optimization, while offering a facade of productivity, can stifle the very creativity and spontaneity that fuel our most inspired endeavors.
So, as I reacquaint myself with this quite familiar landscape, I remind myself of the importance of balancing creative and productive fulfillment, and embracing the messy and imperfect journey without falling prey to the curse of optimization. For it is in the spaces between the perfectly optimized paths that true creative freedom thrives.
Recommendations
✪ Rec: Product, Tool, or FrameworkRize App
An AI productivity tool that tracks how you spend your time, allowing you to focus on deep work and analyze how you spend your time.
I’ve been intermittently using Rize for a few years. In the beginning, I thought of it as a way to track my time and used it to look for areas where I could continuously optimize and improve my overall productivity. But, I found that left my work feeling hollow, and focused my energy on optimization instead of positive aspects like curiosity, energy, and flow.
Now, I use Rize to help me track and engage with my energy. I look at what tools and tasks help me get into the flow, so I can lean into those more. Instead of trying to squeeze every ounce of work out of myself, I’m trying to fill myself up with what energizes me the most.
✪ Rec: ReadingEssentialism: The Disciplined Pursuit of Less by Greg McKeown
As mentioned above, after three years of living in central Washington, my wife and I just moved back to Seattle. As with any move, it’s a chance to reset and ‘optimize’ our lives for the things we value most. One of the things we’ve been reminded of in the move is that we need—and want—far less than we think.
Essentialism explores the concept of not just having, but wanting less—focusing on what truly matters and eliminating the non-essential. It offers insights into avoiding the trap of over-optimization by prioritizing the vital few over the trivial many. Whether it’s at home, in our work, or through our relationships, sometimes less truly is more. Or, as the author Greg McKeown notes,
You cannot overestimate the unimportance of practically everything.
✪ Rec: WatchingJeff Bezos - Regret Minimization Framework
It’s a cliche to say that ‘life is short’, but cliches always carry some amount of truth. There’s no shortage of people or things to fill our time. We’re constantly bombarded with opportunities and responsibilities that, one by one, fill up the individual units that comprise our life. No matter how you slice it, time marches on. With each passing moment, we’re faced with the option to fast or feed our creativity. One of the easiest ways to do this is to minimize regret.
The framework is simple, yet profound—when faced with a decision, imagine which option would reduce regret for future you. For Bezos, this led him to leave his job and start Amazon, fearing he would regret not participating in the internet boom more than failing at a startup. Essentially, it's about choosing the path that you'll regret the least when you're older, to ensure you embrace opportunities and live without major regrets.
✪ Rec: ListeningDitch Your To-Do List and Do This Instead | Sam Corcos | The Tim Ferriss Show
Everyone I know is looking for the next great to-do app or system. It’s why people like James Clear are so popular: people are desperate for the solution to the overwhelming nature of work.
But better to-do lists usually just feel like re-arranging deck chairs on the Titanic. Instead of relying on an infinite to-do list, try translating tasks directly onto your calendar with estimated time allocations. Remember to create open space: It is important to keep approximately 50% of your time open to accommodate unexpected events or spontaneous activities. This will allow you to improve your estimation skills. Over time, you will become more accurate in estimating the time required for tasks, allowing for better planning and utilization of time.
Pathfinders’ Spotlight
Fellow Pathfinder hype links and shoutouts.
offscript - by Priya Rose (
) - As someone constantly interested in the way we live and work, I’ve always wanted to work at the intersection of technology and architecture, but just haven’t found the right opportunity. Priya has shared and operationalized some of the most interesting ideas about the future of living. If you’re at all interested in the idea of co-living or Scenius, check out her work. I’d recommend starting with her post on How to Live Near Your Friends. Check it out ↗︎Interested in getting a shoutout? Just shoot me a note.
And, just in case you missed it…
Here are some things that I’ve written and shared that people enjoyed.
Until Next Time!
That’s it for this week. As always, if you like the content, please do me a favor and like, share, subscribe — this newsletter runs on overpriced whiskey and reader engagement.
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Thanks for reading, and see you soon,
— Kevin K. (@kkirkpatrick)