design is iterative

· 6 min read

This essay explores an idea already written about by Henrik Karlsson’s Everything that turned out well in my life followed the same design process.

In fact, go read that instead of this, because he has said everything I’m going to say, with 1000x more tact and elegance.

It’s actually one of the most important realisations I’ve had, and one that I’ve learned through experience, but I feel compelled to write about it so I can deeply internalise it.

Good design is iterative, bottom up ‘unfolding’

What you can plan is too small for you to live. What you can live wholeheartedly will make plans enough for the vitality hidden in your sleep David Whyte

There are two approaches to design.

Top-down design starts with a complete vision of the endpoint. You imagine the finished state: the perfect career, the ideal relationship, the complete product, and then work backwards to create a plan to get there. It’s architectural: blueprint first, then build to spec. The assumption is that you can know what you want before you’ve experienced it, and that the world will remain stable enough for your plan to stay relevant.

Bottom-up design starts with curiosity and immediate experience. Instead of a grand vision, you begin with small experiments, paying attention to what genuinely engages you. Each step reveals information that shapes the next step. It’s biological: like a plant growing toward light, constantly adjusting based on real feedback. The path emerges from the walking.

The fundamental difference isn’t just about planning versus improvisation. It’s about where knowledge comes from. Top-down assumes you can know through thinking; bottom-up insists you can only know through living. Top-down treats life like a problem to be solved; bottom-up treats it like a mystery to be explored.

A few differences I’ve observed.

Abstract vs Embodied

  • Top-down: Relies on abstract, secondhand information—“what I think being a lawyer is like.” Assumes you can know through thinking. Suffers from planning fallacy: underestimating complexity, overestimating control. - see Adam Mastrionni’s essay : Face it, you’re a crazy person
  • Bottom-up: Generates embodied knowledge through direct experience. Hidden constraints and opportunities reveal themselves only through practice. You can only know through living.

Ego vs curiosity

  • Top-down: Fuelled by ego and the search for security—which is really the fear of insecurity. You have this vision you’re hurtling towards, especially if you’re a Type A person.
  • Bottom-up: Fuelled by curiosity and genuine interest. Each experiment is intrinsically interesting, not just instrumentally useful.

Coercion vs joy

  • Top-down: Falls prey to the “once I get there” fallacy. You’re forcing yourself through tasks, like jamming a square peg into a round hole. The process feels like something to endure rather than enjoy.
  • Bottom-up: Allows for joy and engagement in the process itself. Each step reveals something new. The journey becomes as important as any destination. It’s like moulding a piece of clay slowly, letting the environment and context shape it into the perfect fit.

Fragile vs anti-fragile

  • Top-down: Feels secure. You have a clear vision and plan. But this security is an illusion. The design is fragile because it hasn’t been tested in reality.
  • Bottom-up: Feels insecure initially—the option space is wider, the path unclear. But through constant trialing and error-correcting, you build something anti-fragile, moulded by real experience.

Certainty vs uncertainty

  • Top-down: Assumes a stable, predictable future where your initial vision remains relevant. When reality doesn’t match the plan, you face sunk cost fallacy—reluctant to abandon what isn’t working.
  • Bottom-up: Embraces uncertainty. Each small experiment opens new doors rather than closing them. Pivoting isn’t failure; it’s the method.

Failure vs error correction

  • Top-down: Failures feel catastrophic. You’ve invested so much in the vision that any deviation threatens your identity.
  • Bottom-up: Failures are data points. The whole point is to preserve methods of error correction. You’re meant to try and fail—each failure shapes the design.

Narrative arc vs messy unfolding

  • Top-down: Creates a neat narrative structure. “I’m becoming a doctor.” It’s the traditional career ladder where you can cleanly explain your trajectory.
  • Bottom-up: Can be messier but more authentic. “I studied philosophy, explored meditation for a decade, became fascinated with neuroscience, and now run a media company.” (This is Sam Harris). The funny thing is we always retrospectively create narratives anyways to justify how it happened. Just notice when you are creating a narrative before even doing the thing!

Let’s take a look at some examples of top down versus bottom up approaches to design.

Examples

  • Startups: Pivot-based success stories (Twitter, Instagram) vs. rigid business plans

  • Cities: Planned cities like Brasília vs. organically grown cities like Tokyo

  • Learning: Following a rigid curriculum vs. project-based/curiosity-driven learning

  • Writing: Outlining everything vs. discovering what you think through writing

  • Exercise: Following a rigid 12-week program vs. exploring different activities until you find what you genuinely enjoy and stick with

  • Reading: Working through a “100 books you must read” list vs. following your curiosity from book to book, creating organic knowledge chains

  • Hobbies: Deciding to “become a painter” and buying all the equipment vs. doodling → sketching → gradually acquiring tools as needed

  • Scientific research: Grant proposals with predetermined outcomes vs. following unexpected results (like penicillin’s accidental discovery). Actually a big problem of science (see David Deutsch talking about this : https://youtu.be/6nN-L3DO0-o?si=J5VdGZ2jsp2iW0wG&t=852) ’this grant application always includes a statement of what you are going to discover… and that is fatal to research. Because genuine research…is incompatible with knowing what you are going to discover. Discovery is an open ended problem solving process. The first problem you are going to address is… just the beginning.'

  • Career: deciding you want to be ‘X’. The trap is that you don’t actually know what ‘X’ does all day, you just have an idea of what ‘X’ does. See Adam Mastroianni - Face it, you’re a crazy person

  • Dating : having a long checklist of traits you want you’re partner to be like

  • Product design: Feature-complete launch vs. MVP and iteration based on user feedback

  • Friendship: Networking with agenda vs. genuine connections that deepen naturally

  • Community building: Creating elaborate structures/rules vs. letting culture emerge from member interactions

  • Language learning: memorising grammar rules vs. immersion and conversation

  • Cooking: Following recipes exactly vs. tasting and adjusting as you go

  • Gardening: Designing the perfect garden layout vs. planting things and seeing what thrives in your specific conditions

  • Economic systems: Central planning vs. market emergence

  • Fashion trends: Designer-dictated seasons vs. street style bubbling up

TLDR : Follow your genuine curiosity in everything that you do.