Designing a deep life: how David Dewane uses space, scores, and slow planning

Executive overview

Most people drift through their days at zero — not miserable, but not flourishing either. David Dewane, architect and longtime friend of Cal Newport, has spent a decade systematically engineering his life toward what he calls plus-one and plus-two days.

The conversation covers two interlocking ideas: how physical space shapes the quality of thought, and how personal metrics can guide life decisions. The Collins score — a daily rating from −2 to +2 — is the central tool, used to identify what drains energy, what generates it, and whether a life change is worth making.

The deep life is not one grand radical decision; it's a slow accumulation of evidence-based choices that compound over time.

The eudaemonia machine and designing for depth

• David sketched the eudaemonia machine — a theoretical office optimised for deep work — on a napkin at lunch with a mutual friend; Cal Newport included it in Deep Work.
• The design became a minor sensation; a version was built in Chelsea, New York; press coverage led directly to David's current role as Chief Experience Officer at Geniant.
• His day job now is making these ideas real: designing workplaces that shift organisations from functional to performative — not just spaces that work, but spaces that put people in the right state of mind.
• Key distinction: a trailer can function as a school; Georgetown's campus performs as one — the architecture shapes mindset, relationships, and creativity.
• Remote work fails not because home is bad, but because most home setups optimise for languishing; flourishing at home is harder without reciprocal, energising dialogue.
• Zoom is a poor proxy for in-person conversation; the quality of this interview, David argues, would have been measurably lower on a call.

Space, virtual reality, and the screen-first path

• Early VR failed as a deep-work environment because resolution was too low and friction was too high — people wouldn't put on a headset to replicate something they could do on their laptop.
• Apple Vision Pro impressed David; peripheral vision stays intact, and immersion is close to 80–90% of the real experience for familiar places.
• The winning entry point for virtual workspaces was not full immersion but screens: the app Immersed gave remote workers four virtual monitors instead of one physical one — useful first, immersive second.
• David's personal bar: the moment you forget you're in a headset and believe you're somewhere else. That bar remains high.

The Collins score

• Jim Collins, in a Tim Ferriss interview, described tracking three things daily: a brief bullet log of what happened, hours of creative (deep) work, and a subjective daily rating.
• The rating scale is −2, −1, 0, +1, +2. Zero is languishing — not bad, but nothing got you fired up. Negative territory is actively draining. Positive territory is flourishing.
• David has tracked this for six years, initially with a mentor via daily text check-ins.
• The scale is deliberately small: it forces you to notice whether you're actually flourishing or just not suffering.
• Two immediate effects of tracking:
  • He identified what reliably pushed him into negative territory (confrontational interactions, meetings that misaligned with his goals) and cut them.
  • He started asking each morning: what would get me to +1 today? What would it take to reach +2?
• His personal refinements after six years: he dropped −2 (never experienced it) and added +1.5 to create more resolution at the high end; he now reserves +2 for genuinely exceptional days.
• The day he signed the contract on the farm: +3 — the only one he's ever recorded.
• His hypothesis for broader use: anonymised, pooled Collins scores across an office could replace subjective guesses about whether a workplace intervention worked.

What pushes scores negative

• Confrontational interactions and pushing back aggressively on colleagues — emotionally draining even when habitual.
• Spending time on activities misaligned with stated quarterly goals.
• Certain people or interaction types that reliably trigger negative states — he now avoids asking them for the wrong things.
• Letting time bleed away: no sense of accomplishment at day's end from a master task list.

What pushes scores positive

• Making non-trivial progress on a specific item from a master task list.
• Carefully segmenting creative time from shallow work and protecting it.
• Setting realistic daily goals and containing scope: he aims for two or three important things per day, not more.
• Weekly planning done thoroughly — David identifies the Monday morning planning session as the critical, often undercooked link in multi-scale planning.
• Quarterly goal review embedded into the daily planner: goals are reviewed briefly each morning so nothing drifts.

The farm: lifestyle-first planning in practice

• David and his wife, both from a small Wisconsin town, wanted a country complement to their Chicago row house — not a house on a lake they couldn't afford, but a way to connect to roots, slow the pace, and give their kids proximity to ageing parents and family history.
• The vision crystallised during COVID but had been forming since 2010, when they discovered Norman cider apples in rural France on a study-abroad trip.
• They used their 20th wedding anniversary as a forcing mechanism — committing to host a reunion at a country property by that date.
• Found five acres near Lake Michigan for $170,000 — an 1870s barn with a two-car garage attached. Converted the garage; put in a well, gas, and electricity themselves.
• Funded it by cashing out a 401(k) early, absorbing the penalties — a deliberate trade of future-retirement capital for the next twenty years of life quality.
• Airbnb both properties to make the arrangement financially sustainable: when a big Chicago event inflates demand, they rent the city house and retreat to the farm.
• David planted an apple orchard (hard cider varieties) and built an octagonal writer's cottage for ~$2,000 in materials — modelled on Mark Twain's writing cabin, sitting in a field beyond the orchard with a view of Lake Michigan.
• Every day at the farm in the first month, regardless of 10-degree Wisconsin winter: +2. He had not anticipated how reliably it would generate high scores.

Life engineering: principles David applies

• Take on less, do it better. More commitments means more administrative overhead, which is time not spent doing things — an ironic cycle.
• Slow productivity applied to identity. Depth of commitment to a few things compounds into something authentically interesting; breadth reads as busy but rarely becomes rare or valuable.
• Evidence before the leap. His early failure — a design-build project in Central America without the skills to execute — taught him to build career capital first. Discovering So Good They Can't Ignore You reframed that failure as a sequencing error, not a values error.
• Systems get things out of your head. The time block planner is, in his words, "the most essential mental health tool I've ever had" — not for productivity theatre, but for presence. When the plan is clear, he can be fully inside the current task.
• Calendar emptiness is not a signal. He deliberately does not fill Google Calendar with everything he does; his physical planner holds it. He does not equate a full calendar with value.
• Consistency over intensity. The early project failure was intensity without consistency. The farm, the book, the Collins score research — all are slow, sustained commitments.

On deep work, email, and collaboration tools

• Deep work is not hustle culture; it is the mechanism for earning enough autonomy to go to the farm on weekends.
• The open office is the physical correlate of an inbox: both assume a blended, always-on hive-mind produces better output. Neither matches how human cognition actually works.
• David pays a social cost for checking Slack once a day; he accepts it because the tool is solving a collaboration problem he doesn't have at his current role.
• His preferred alternative: project-based email accounts rather than personal inboxes. The interpersonal dynamics of "you saw my message and ignored me" disappear when the recipient is a project, not a person.
• Cal's framing: Slack is the right tool for the wrong way to work. If constant conversation is your collaboration model, Slack does it better than email — but the model itself is the problem.

On the deep life as a concept

• Eudaimonia — flourishing — is not moment-to-moment happiness but a trend. The Collins score measures whether you are on the right trend.
• The meaningful vignettes David wrote in letters to his daughter were all mundane: working in the orchard, an early-morning writing session interrupted by a child, a child's birth. Nothing about professional accomplishments or brushing against fame.
• The deep life is not one radical decision (moving to a sailboat, quitting everything). It is a slow accumulation of evidence-based choices: tracking what works, cutting what drains, and protecting what generates the highest scores.
• Architecture as metaphor: you learn the tools first, then use them to build something great. Expecting immediate results misunderstands the timeline — in architecture, as in life, significant work typically matures in your fifties.