Friday morning, December 6th. Watching someone optimize their morning routine for the third time this month, tracking every variable, chasing marginal gains. Meanwhile, they haven't called their mom in weeks. You can't optimize what matters.

The Optimizer's Trap

Here's what we've been sold:

Everything can be improved. Measure what matters. Track your habits. Find the best system. Optimize your sleep, your diet, your work, your relationships, your happiness. Data-driven living. Evidence-based everything. The optimized life is the good life.

The promise: If you measure and optimize relentlessly, you'll live better, work smarter, achieve more, and finally have it all figured out.

The reality: The optimization mindset is perfect for well-defined problems and disastrous for everything that makes life worth living. You can optimize your way to an empty, efficient existence.

Thesis: Optimization requires clear, stable objectives. Life's most important things—relationships, creativity, meaning, growth—have objectives that shift as you pursue them. Applying optimization frameworks to these domains doesn't just fail; it actively damages them. The measurable becomes the priority. The meaningful becomes background noise. We've created a generation of people who are exquisitely good at hitting the wrong targets. Stop optimizing. Start experimenting, exploring, and occasionally wasting time on purpose.

Why Optimization Works (Sometimes)

Let's be fair first. Optimization is brilliant for certain things:

Well-defined problems with stable goals:

  • Manufacturing processes (minimize waste, maximize output)
  • Delivery routes (minimize time, maximize coverage)
  • Code performance (minimize runtime, maximize efficiency)
  • Athletic performance for specific events (maximize speed/strength for known demands)

The key criteria:

  1. Clear, measurable objectives
  2. Objectives that remain stable during optimization
  3. All relevant variables can be identified and tracked
  4. The system is relatively closed and predictable

When these conditions hold, optimize away. It's why factories are efficient, why planes stay in the air, why your phone works.

Where Optimization Breaks

But now watch what happens when you apply this mindset to life:

Relationships

The optimizer's approach:

  • Track time spent with friends
  • Measure conversation quality on a scale
  • Optimize for "high-value" interactions
  • Schedule "connection time" in 30-minute blocks
  • Evaluate relationships by ROI

What actually happens:

  • You start seeing people as means to ends
  • Spontaneity dies (it wasn't in the optimization function)
  • Vulnerability becomes risky (might hurt metrics)
  • Relationships become transactional
  • The warmth that makes relationships matter gets optimized away

The problem: The goal of a relationship changes as the relationship develops. What you want from a friendship evolves with the friendship. You can't optimize toward a moving target—you just chase your own tail.

Creativity

The optimizer's approach:

  • Set word count goals
  • Track output per hour
  • Use "proven" formulas
  • Optimize for engagement metrics
  • Schedule creativity in blocks
  • Measure productivity

What actually happens:

  • You produce more and create less
  • The weird, risky ideas get filtered out (they don't fit the optimization function)
  • You copy what works rather than discovering what could work
  • The creative process becomes mechanical
  • Everything starts to feel same-y and safe

The problem: Creative goals emerge during the creative process. You don't know what you're trying to make until you're partway through making it. Optimization requires knowing the target in advance. Creativity requires discovering it along the way.

Meaning and Growth

The optimizer's approach:

  • Define your values
  • Set aligned goals
  • Track progress toward those goals
  • Optimize time allocation
  • Measure life satisfaction
  • Iterate on happiness

What actually happens:

  • You lock yourself into yesterday's values
  • Growth that would challenge your framework gets ignored
  • You optimize toward who you were, not who you're becoming
  • Surprising opportunities get filtered out (they don't match the plan)
  • You measure your life rather than live it

The problem: The point of growth is that you become someone who wants different things. If you optimize for current goals, you prevent the growth that would give you better goals.

The Measurable Takes Over

Here's the mechanism that makes optimization so damaging:

Goodhart's Law: "When a measure becomes a target, it ceases to be a good measure."

Applied to life:

You want meaningful friendships. But "meaningful" is hard to measure, so you track frequency of contact. Now you're optimizing for frequency. You call more but connect less. The metric has replaced the goal.

You want creative fulfillment. But "fulfillment" is fuzzy, so you track output. Now you're optimizing for quantity. You produce more but create less. The metric has replaced the goal.

You want a life well-lived. But "well-lived" is subjective, so you track achievements. Now you're optimizing for visible success. You achieve more but live less. The metric has replaced the goal.

The pattern:

  1. Start with something meaningful but hard to measure
  2. Choose a proxy metric that's easier to track
  3. Optimize for the metric
  4. The proxy becomes the goal
  5. You hit the metric while missing the meaning

The tragedy: You often don't notice until years later. You look up and realize you've been climbing a very efficient ladder leaning against the wrong wall.

What Gets Lost

Optimization systematically filters out some of the best parts of life:

Serendipity

Unplanned encounters, random conversations, accidental discoveries—these don't fit optimization frameworks. They're inefficient. But they're also how most interesting things happen.

The optimizer: "That's off my critical path. Can't afford the time." Reality: The critical path often emerges from the wandering.

Play

True play—not "purposeful play" or "skill-building games," but genuine, pointless play—looks like waste to an optimizer. It has no clear objective. But play is how we explore possibility spaces, develop intuition, and stay human.

The optimizer: "What's the ROI on this activity?" Reality: The best things have no ROI. That's what makes them best.

Depth

Going deep into something with no clear payoff, following curiosity into weird corners, spending years on a project that might not work—optimization frameworks filter all of this out. But depth is where mastery lives. Where original thinking happens. Where you become someone interesting.

The optimizer: "That's not the fastest path to the goal." Reality: The fastest path often isn't the best path. Sometimes it isn't even a path at all.

Presence

When you're optimizing, you're always in meta-mode. Always tracking, measuring, evaluating. You're never just doing the thing—you're doing the thing while monitoring your doing of the thing. This creates a subtle distance from experience.

The optimizer: "I'm being mindful about my productivity." Reality: You're not present. You're performing presence for your tracking system.

The Alternative Framework

So if not optimization, then what?

Satisficing (Not Maximizing)

Satisficing: Choose the first option that meets your criteria, then stop searching.

For most decisions, good enough is actually optimal.

  • Dating: You can't optimize for the "perfect" partner. Find someone great, commit, build something together.
  • Career: Don't hold out for the optimal job. Take something good, learn fast, iterate from there.
  • Creative work: Don't polish endlessly. Ship when it's good enough, learn from the response, make the next thing.

Why this works: It frees enormous energy from optimization itself. That energy can go toward actually doing the thing rather than perfecting your approach to the thing.

Experimentation (Not Iteration)

Optimization is about getting better at what you're doing. Experimentation is about discovering what to do.

  • Try things with no clear purpose
  • Follow curiosity into dead ends
  • Give yourself permission to waste time productively
  • Pursue multiple threads without forcing them to converge
  • Accept that most experiments fail—that's the point

Why this works: You discover goals worth pursuing rather than efficiently pursuing mediocre goals.

Principles (Not Systems)

Systems are brittle. They break when conditions change. Principles are flexible. They adapt to context.

Instead of:

  • "I wake at 5am, meditate for 20 minutes, exercise for 45 minutes, then work on my priority project for 90 minutes"

Try:

  • "I do my hardest work when I'm freshest, I move my body regularly, I protect time for what matters"

The first is optimized but fragile. Miss one step and the system fails. The second is resilient. It works in hotels, during illness, through life changes.

Why this works: Principles guide without constraining. Systems optimize while removing judgment.

Slack (Not Efficiency)

Slack is the opposite of optimization—it's deliberate looseness in the system.

  • Unscheduled time that stays unscheduled
  • Energy reserves you don't deploy
  • Money you don't optimize for returns
  • Space in your calendar that stays empty

Why this works: Slack is where opportunities live. When you optimize for 100% utilization, you have no capacity for the unexpected. Slack is expensive in the short term and essential in the long term.

What To Actually Do

Practical advice for escaping the optimization trap:

1. Identify Where Optimization Works

Use it for:

  • Genuinely technical problems (build systems, data pipelines, manufacturing)
  • Tasks where the goal is stable and clear (commute time, budget allocation)
  • Things you've already decided to do (optimize execution, not decision)

Rule: If you can write down the objective function completely, you can optimize. If you can't, you shouldn't try.

2. Protect The Unmeasurable

Actively guard domains from optimization pressure:

  • Have friendships where you never track frequency or "quality"
  • Do creative work without measuring output
  • Spend time with no productivity goal
  • Let some decisions be made on gut feel
  • Keep some parts of life off the spreadsheet

These aren't failures of optimization. They're refuges from it.

3. Build In Waste

Deliberately schedule:

  • Time to wander with no goal
  • Conversations that "aren't necessary"
  • Projects that might not work
  • Activities with no clear benefit
  • Space that stays empty

This feels irresponsible. It's actually essential. The "waste" is where life happens.

4. Use "Good Enough" As Default

For most decisions:

  • Spend 10% of the time you think you need
  • Choose the first genuinely good option
  • Move on before "optimizing"
  • Let good enough be good enough

Save deep optimization for the 5% of decisions that actually matter. Guess what: you probably can't identify those in advance, so don't optimize the optimization either.

5. Check Your Metrics Regularly

Ask:

  • Am I measuring because it helps, or because I can?
  • Has this metric become my goal?
  • Am I hitting numbers while missing meaning?
  • What am I not measuring that might matter more?

When a metric starts driving behavior, kill it. Find a different way to track, or stop tracking entirely.

The Real Optimization

Here's the paradox:

The actual optimization is to stop optimizing most things.

Optimize for:

  • More unstructured time
  • Deeper relationships (without tracking them)
  • Greater capacity for surprise
  • Resilience over efficiency
  • Exploration over exploitation

These can't be directly optimized. You create conditions and see what emerges. You tend rather than force. You guide rather than control.

This is harder than optimization. It requires judgment, not just measurement. Taste, not just tracking. Presence, not just performance.

But it's the only way to avoid spending your life getting incredibly good at the wrong things.

The Takeaway

Stop asking "How can I optimize this?"

Start asking:

  • Does this need optimizing at all?
  • What am I losing by optimizing it?
  • Am I solving the right problem?
  • Would good enough be better than optimal?
  • What would I do if I couldn't measure this?

The optimization mindset is a tool. A powerful one. But it's not the only tool, and it's definitely not the right tool for everything.

Life isn't a problem to solve. It's a process to experience.

You can't optimize your way to a life well-lived. You can only live it, mess it up, adjust, and try again.

The goal isn't to find the optimal path. It's to walk a good-enough path with enough slack to notice when it's time for a different path entirely.

Stop optimizing. Start living.

Today's Sketch

December 06, 2025