· personal  · 3 min read

Money, Tech, and Time: How I Decide What to Automate and What to Do by Hand

DRAFT

Outline

Hook: I spent 3 hours automating a 5-minute task I do once a month. Math says this is stupid. Reality says I learned something, own the process, and enjoyed building it. The ROI isn’t always financial.

Core Argument: The decision to automate isn’t pure economics—it’s about money, time, learning, control, and enjoyment. Use a framework that accounts for all factors, not just “will this save time?” Some automations are worth it even if they never pay back in hours.

Key Sections:

  1. The Three Resources

    • Money: Cost of automation (tools, subscriptions, time invested)
    • Time: Hours saved/spent on the task
    • Mental load: Cognitive burden of remembering/doing
    • Traditional calc: Only considers time and money
    • Better calc: Includes learning, control, enjoyment

  2. The Decision Framework

    • Question 1: How often does this happen? (Frequency)
    • Question 2: How long does it take manually? (Duration)
    • Question 3: How annoying is it? (Mental load)
    • Question 4: Will I learn something valuable? (Educational value)
    • Question 5: Do I enjoy building/optimizing? (Intrinsic reward)
    • Question 6: Does it give me more control? (Ownership)
    • Scoring: Not just time saved

  3. When to Automate (Clear Winners)

    • Daily repetitive tasks taking >5 min each
    • Mentally draining tasks (even if quick)
    • Error-prone manual processes
    • Things you keep forgetting to do
    • Examples: Bill payments, backups, report generation

  4. When NOT to Automate (Clear Losers)

    • Rare tasks (<once/month) that are quick
    • Tasks that require judgment/creativity
    • When automation is more complex than task
    • When you don’t own the underlying system
    • Examples: Annual tax filing, creative work

  5. The Gray Zone (Interesting Decisions)

    • Automate despite poor ROI because:
      • You’ll learn valuable skills
      • It’s fun to build
      • You want full control
      • Mental load reduction is worth it
    • Don’t automate despite good ROI because:
      • Process teaches you something
      • Human touch matters
      • System too brittle/fragile

  6. Personal Examples

    • Automated: Photo backups (daily, critical, forgetful)
    • Automated: 99 Minds data exports (learning, control)
    • Automated: Morning coffee (small joy, consistent)
    • NOT automated: Grocery shopping (prefer manual selection)
    • NOT automated: Client communication (human touch matters)

  7. The Learning Investment

    • Some automation never pays time back
    • But: You learned Python, APIs, cloud functions
    • Value: Transferable skills for future projects
    • Example: Spent 10 hours on script that saves 2 hours/year
    • Return: Skills used in paying projects

  8. Money Considerations

    • Free: DIY automation (time investment)
    • Cheap: Zapier, IFTTT ($5-20/month)
    • Expensive: Custom dev, enterprise tools ($$$)
    • Opportunity cost: Could you be earning instead of building?
    • Balance: DIY when learning matters, buy when time matters

  9. The Maintenance Tax

    • All automation requires upkeep
    • APIs change, services shutdown, scripts break
    • Factor in: Ongoing time investment
    • Simple automation > Complex, usually
    • Manual might be more reliable

  10. The Control Factor

    • Some automation: About ownership not efficiency
    • Example: Self-hosted vs. cloud service
    • Trade: Time investment for data control
    • Valid when privacy/control matters to you
    • Not always rational, but sometimes right

Examples/Stories:

  • Personal: Automated blog deployment, saved 30min/post
  • Learning: Built email automation, learned APIs, used in client work
  • Enjoyment: Home Assistant setup took 20 hours, saved 30min/week, but loved building it
  • Failure: Over-automated, system broke, manual was more reliable
  • Wisdom: Friend manually does task in 5 min, I spent 5 hours automating, both happy

Takeaways:

  • Automation decision = Money + Time + Learning + Control + Enjoyment
  • Clear yes: Frequent, annoying, error-prone tasks
  • Clear no: Rare, quick, judgment-based tasks
  • Gray zone: Factor in learning and enjoyment
  • Maintenance tax: All automation requires upkeep
  • Sometimes building is the point, not the output
  • Own your choice: Optimize for your values, not pure ROI

Cross-Links:

  • ← “From Starter Home to Franklin’s Treehouse” (Series 5-36)
  • → “The Invisible Assistant” (Series 5-38)
  • ← “Build Once, Leverage Forever” (Series 2-20)
  • ← “40-Year-Old Brain, New Game” (Series 3-21)
Share:
Back to Blog