The Perils of Over-Optimization
Three Perfection Traps Killing Your Productivity
Image: Geocentric model of the orbits of the Sun, Mercury, and Venus, from The Encyclopædia Britannica (1771).
In a classic case of “maintain appearances at all costs," 18th-century astronomers had to depict the [solar] system in an increasingly complex fashion in order to account for phenomena such as Mercury appearing to move backward (!) at certain points in its cycle.
They ended up with a bunch of convoluted diagrams like this one, refusing to even try putting the sun at the center.
I suppose their hesitance to shift paradigms was understandable. Galileo had already figured out heliocentrism in 1633 and the Roman Catholic church imprisoned him for heresy.
Missing: Nothing
When I first landed in New York in 2013, I arrived ready to optimize. I submitted myself to the cult of personal development and joined the masses, trying to reverse engineer the processes of successful people. I crafted a schedule that carefully tracked my levels of daily productivity against the prolific outliers in their fields.
How did I measure productivity? In the time spent optimizing my mousetrap, of course. I fantasized about the day in the not-too-distant future where I would finally have all the pieces in place and realize my dormant potential.
I treated productivity as a source of entertainment, bouncing from one quick fix to the next. Each new round left me feeling like my work was finally done. I would say to myself, “Now I’ve finally found it!” or “This changes everything!”
In truth, my work had not even begun. While improving my processes and routines proved valuable, trying to fully optimize them quickly became counterproductive.
Now, after years of consultations with underachieving high achievers, I’ve realized that over-optimization is the most dangerous trap of all.
We’re constantly being sold the lie that we’re not enough. That we’re not there yet. That something is missing. That progress would come easier and faster if only we optimized ourselves a little more—with a better system, the right tool, and a meticulously crafted day.
Perfect is the enemy of good.
The Over-Optimization Traps
The reality is that the perfect system, the perfect tool, and the perfect day do not exist. They are traps. Anyone who tells you otherwise has a hand in your pocket. You already have everything you need.
Remember: productivity is something to be done, not something to be solved. You can only win the game if you treat every single day as Game Day.
Rather than setting your sights on achieving the unattainable 100%, concentrate on hitting 70%+ consistently.
If you are reading this, you are probably the type of person who falls into one of these three traps:
The Perfect System
The Perfect Tool
The Perfect Day
For each trap, I will outline the symptoms of a person who regularly repeats these self-defeating patterns along with a case study, and then share principles, or antidotes, to prevent these traps from killing your productivity.
Falling into these traps may be a recurring theme in your life. The same attributes which help high-achievers outperform become dangerous when indulged to extremes.
All strengths, when inverted, emerge as weaknesses:
Ambition → Narcissism
Self-confidence → Blindness to change
High standards → Low tolerance for failure
Sensitivity to opportunities → Micromanaging, shiny-object syndrome
As you read, be aware of your own internal narrative and past experiences.
Do you recognize any of these symptoms in yourself? What form does your self-sabotage take?
Over-Optimization Trap #1: The Perfect System
“An important function of almost every system is to ensure its own perpetuation.”
—Donella Meadows
The pursuit of a perfect system is a trap because over-optimization breeds FRAGILITY.
A Case Study on Fragility:
My client is a top executive at one of the major tech firms. He considered himself a model of productivity success, with a systematic approach to everything he did. Yet while his systems all showed constant upward trajectories, my impression is that his growth had plateaued. Over time, he kept adding new systems, and the systems he had became increasingly complex.
“It all felt like homework,” he told me. “I had lost confidence in my systems.”
He had to completely abandon the infrastructure that he had built around himself, temporarily killing his productivity, in order to save it.
Symptoms of System Fragility:
Irrelevance. You overfit to your current systems by seeking additional uses for them, rather than working backward from the problem to be solved. You lose sight of why you created the system in the first place.
Rigidity. You prematurely optimize your systems before the current iteration has proven its usefulness. When goals or values change in the future, your system cannot pivot to accommodate the change.
Overcomplexity. You have reached the inevitable point in the optimization of your system where utility increases sublinearly while complexity increases exponentially. You are forced to expend more and more resources just to maintain a steady state.
Intolerance. Your systems are unaccommodating of the inevitable lapses in adherence when life gets in the way. With no room for slack, a single failure risks wholesale abandonment.
Antidotes to The Perfect System:
Simple is beautiful. Simple systems have less downtime because they minimize ongoing maintenance costs. Start with a Minimum Viable Product and see which system parts help you make better decisions. Strip away anything not actionable.
Make updates, not additions. Are some parts of your system not working as intended? Have the requirements of your system shifted? Make the necessary changes to your current system rather than adding new layers on top.
Increase slack. Anticipate future contingencies and create built-in buffers so that your systems can sustain them.
Assume failures. Everything tends towards disarray. All systems will fail. Knowing you will eventually fall off, make your system trivial to pick back up when you do.
The best systems address bottlenecks, utilize feedback loops, and target the points of greatest leverage. To explore how to apply these three core principles to your own systems, check out Systems Thinking—The Essential Mental Models Needed for Growth.
Fragile systems hate uncertainty, variability, incomplete knowledge, and randomness. The arrow of time culminates at the entropic heat death of the universe. In a dynamic world in which accelerating change is the only constant (sorry, it’s true), we need systems in place which are robustly built to last.
Keep It Simple, Systems.
Over-Optimization Trap #2: The Perfect Tool
“That is the risk of any tool. A hammer is good only if you stop pounding after the nail is all the way in. Keep pounding and you break the wood.”
—Scott Adams
The pursuit of a perfect tool is a trap because over-optimizing your tools is a SUBSTITUTE for actual progress.
A Case Study on Substitution:
“One of my worst habits is changing my productivity setup when I hit the limitations of my tools. I think I’ve used almost every popular productivity app at some point in the last few years.
The cycle is predictable. I’ll use one stack for a period until I hit a roadblock, causing me to feel unproductive. Then, to feel productive again, I’ll play with the surface-level problem by changing the tools I’m using.”
Symptoms of Tool Substitution:
Early adopter syndrome. You identify strongly with your choices of productivity tools and love being among the first to master and share opinions about them. The potential of finding the “next big thing” is a continual distraction.
Dependency. Your tools become a prerequisite, their imperfections serving as ready-made excuses for lack of progress. You conveniently forget that you, the tool operator, are the common denominator in all your productivity challenges.
Diminishing returns. Your initial big wins from improving workflow come quickly and you often procrastinate by scrounging small efficiency increases when you would be better off simply getting to work.
Consumerism. Tools masquerade as quick solutions. You conflate the installation of a new tool with progress towards your goals themselves.
Antidotes to The Perfect Tool:
Intentionality is everything. Whenever you find yourself unsure about the next course of action, ask yourself, “What is the most important thing I could be doing right now?”
Identify your true bottleneck. If you feel stuck and want to make yourself feel better by adopting a new tool, ask yourself, “What is actually preventing me from making progress?”
Use only tools that bring you net benefits. All tools can be handy, but don’t overlook what you need to invest or give up to unlock that usefulness. Be relentless about cutting any tools that don’t exceed this bar.
Start analog. Almost every tool can be at least partially replicated using pen and paper. Invest in digital tools only once you have seen benefits from an analog version.
I’m often asked my stance on divisive topics such as the pros and cons of using one task manager over another. It’s a fair question. Tools can be very useful for reducing friction (i.e. making what you want to do, easier to do) so presumably, some tools are better at accomplishing this than others.
Don’t worry, I didn’t return from the dark side of shortcut-seeking without at least a hundred opinions. [Read: My 100+ Resources For Optimizing Productivity and Performance.]
But here’s the secret—it doesn’t matter.
I like to think of myself as tool agnostic. Which task manager, you ask? Who cares? As long as you have some way of keeping track of your commitments, everything else is just icing.
No tool is as important as its operator. The best-designed tool in the world will be worthless if you do not have the right intentionality behind it.
Think less about what you are using, more about how you are using it.
Over-Optimization Trap #3: The Perfect Day
“There is no perfection. It's really the world's greatest con game; it promises riches and delivers misery. The harder you strive for perfection, the worse your disappointment will become because it's only an abstraction, a concept that doesn't fit reality.”
—David Burns
The pursuit of a perfect day is a trap because over-optimizing your day creates cognitive distortions, negatively filtering your perception and expectations.
Symptoms of Day Distortion:
All-or-nothing thinking. Your days either go exactly as planned or are “ruined.” This, of course, becomes a self-fulfilling prophecy. A day that starts slightly off-track quickly goes off the rails and has negative spillover effects to the next day.
Catastrophizing. You hide behind the perceived strength of your routines, only to shatter at the first real obstacle to them. You bury your head in the sand in avoidance and shame. Minor setbacks become personal tragedies, creating a negative spiral that can last days or weeks.
Discounting the positive. All your actions are viewed from a half-empty perspective. Any fleeting victories are reminders of how far you still have to go. Since you aren’t perfect, you’re not great. Not a very fulfilling way to go through life.
A Case Study on Distortions:
My client is among the most successful poker players in the world, regularly playing for stakes that would truly make your nose bleed. He (over)analyzes every aspect of his daily routines, constantly on the lookout for incremental improvement to his performance. This quest for perfection occasionally becomes all-consuming and self-destructive.
Me: “What does a good day look like for you?”
Client: “I work out for at least two hours. I eat no calories outside my meal plan. I meditate and read for one hour each and never turn on the TV.”
That became the bar he had to hit every day.
If he slipped up by having a slice of pizza or missing a workout, he felt like a total failure. He would go into a shame spiral for days afterward, “eating trash, not getting out of bed, avoiding work, not seeing my friends.” He was so embarrassed by continuously falling short that he couldn’t see the vicious cycle he had created.
Antidotes to The Perfect Day:
Raise the floor. Your total productivity is the sum of all days. The most effective way to bring up the average is to make your “worst days” not so bad. With the right habits and routines in place, every day will be at least a 6/10.
Reset to zero. If the day is going off the rails, rather than writing it off completely, close the container. Forget about your original expectations and start again. Find a way to be slightly more productive than you would have been. [Read: A Guide to Getting Unstuck for my tactical recommendations!]
Practice gratitude. Celebrate your wins, no matter how small. Making a conscious choice to emphasize the good primes your perception to focus on the positive. Positive thoughts lead to positive actions.
Be kind. Left unchecked, we can abuse ourselves in ways we would never tolerate from others. Cultivate an awareness of your self-talk and actively reframe any narratives which are not serving you.
Conservation of energy. Productivity is not created, it is just shifted from one day to another. A 10/10 day is simply the harvest of previous planting days. If today is just not your day, plant some seeds for a successful tomorrow. Setting tomorrow up for success could be as straightforward as writing out tomorrow’s to-do list, avoiding electronics to replenish your mental energy, or getting to bed early to begin recovering.
There is nothing wrong with having a perfect day to strive towards. Having an ideal is useful for identifying opportunities to better align your time with your priorities. However, keep in mind the glaring omission from any perfect day—all the messiness.
Achieving the perfect day makes some major assumptions. Unlimited energy and willpower. Flawless planning and decision-making. Nothing unanticipated and everything under your own control.
Put another way, the expectations are completely ungrounded in the messiness of reality.
A habit missed. Undershooting productivity goals. Something urgent coming up. Distractions. Circumstances outside of our control. These are the normal constraints of daily life.
We get caught up in harmful narratives when we evaluate today, still in progress, against an impossible standard. These unrealistic expectations drag down our performance even further on days when we fall short. Worse, we deal our future self a poor hand, making it unlikely that tomorrow will be any better.
In poker, the media obsesses about who is the best, the player with the most skill. The player with the best “A+ Game.” But this is rarely the player who has the best long-term results. The biggest winners may not be the best, but they are always among the most consistent.
The strength of your A+ Game pales in importance to how often you play it.
The Case for Consistency
“Rather than trying to make yourself perfect, you relax into your natural perfection.”
—Susan Piver
The mirage of perfection has seduced countless seekers toward an unattainable horizon.
There was a persistent illusion that, if only I could optimize myself a little more, I would be magically catapulted into greatness. Optimization is only useful as a force multiplier, but we act like it is the end game. In a culture obsessed with personal exceptionalism, optimal has become the standard, while consistency has become vulgar.
In four years of working with high-performing executives, what truths have I learned?
If you are consistent in your output, results will follow. Great work does not stem from optimization. Committing to consistent execution over time yields lasting results, period.
This truth is quite inconvenient. I wish the data led to a different conclusion. Gym time is not sexy. Consistency doesn’t sell courses. There is a reason training scenes in movies are compressed into montages.
Learn the difference between feeling productive and being productive.
If you’ve tinkered with your systems like a mechanic tinkers in a garage…STOP!
If you’ve tried more than three tools to solve the same problem…STOP!
If you’ve held yourself to an impossible standard and you keep self-sabotaging…STOP!
If you’re just now realizing how much you’re missing and how far behind you are and how you’re never going to be good enough…
STOP.
Breathe.
Smile.
We’re all going to be just fine.
You already have everything you need to start taking imperfect action.
Being consistent means knowing you don’t have everything quite figured out yet.
You probably never will.
But keep pushing forward nonetheless.
Special thanks to Marianna Phillips for pulling a first draft out of me and translating these ideas into an intelligible form.
Shoutout to Khe Hy, James Wang, Chris Williamson, Donza Worden, Fred Terenas, and Natasha Conti for their invaluable feedback, edits, and suggestions. You guys are the best.