Environment
One owned home in a base city. Two international stays of 4-8 weeks every year. Roots in one place, adventure in two more.
One base city. Owned home. Two international stays a year.
Stop the nomadic chaos. Own a home in one base city. Then every year, 2 stays of 4-8 weeks in international cities I keep returning to. Same gyms, same friends, same coffee shops in each.
Deadline · Home by Dec 2030 · Rotation ongoing- Q4 2026Base city locked. Test 2 international stays this year.
- Q4 20272 rotation cities chosen. Property search active in base city.
- Q4 2028Property shortlisted. Sustained 2-stay rhythm.
- Q4 2030Own home in base city. 2 international stays / year, locked.
Finish the 100. Write the book.
The series becomes a body of work — a published field guide for working from anywhere.
Deadline · By Dec 2030- Q4 2026City 60 (current pace + intentional new cities)
- Q4 2028City 85 + book outline + 30% draft
- Q4 2030City 100 + book published
Career
Build the ecosystem so it compounds without me. Marketplace, media, advisory, products. Each fuels the others. Each measurable. Each dated. The biggest compounders land by 2032.
10,000+ listings. The global front door for coliving.
BookMyColiving is the trusted global directory. Listings and reach come first — revenue model layers in later. Operators list. Residents discover. The default place the world searches for coliving.
Deadline · By Q4 2032- End 20261,500 listings · 150 cities · reach foundation set
- End 20273,000 listings · 1L+ annual inquiries
- End 20285,000 listings · category brand recognition
- End 20307,500 listings · global default for coliving search
- End 203210,000+ listings · 1L+ inquiries / month
100K+ subscribers. Required reading.
The definitive voice of the category. When operators, investors, or journalists want to understand coliving, they start here.
Deadline · By Dec 2032- End 202645K subs · weekly newsletter cadence locked
- End 202755K subs · 50 podcast episodes shipped
- End 202870K subs · 1M monthly reads
- End 203085K subs · paid tier launched
- End 2032100K subs · industry's front page
150+ operators across 30+ countries.
Strategic partner to operators worldwide — brand, growth, tech, the full stack.
Deadline · By Dec 2032- End 202670 operators served · 16 countries
- End 202790 operators · 20 countries
- End 2028110 operators · 25 countries
- End 2030130 operators · 28 countries
- End 2032150+ operators · 30+ countries
2 products. $500K combined ARR.
JumboTiger (PMS for coliving operators) and Everything Coliving (media + tools). Two products that run while I sleep — built once, sold many times.
Deadline · By Dec 2032- End 2026Both products live and earning · $50K combined ARR
- End 2027$120K combined ARR
- End 2028$220K combined ARR
- End 2030$360K combined ARR
- End 2032$500K combined ARR
Two books published.
One on coliving (the frameworks). One on building solo with AI (the playbook).
Deadline · Book 1 by 2027 · Book 2 by 2031- Q4 2026Book 1 outline + 30% draft (coliving frameworks)
- Q4 2027Book 1 published
- Q4 2029Book 2 outline + draft (AI playbook)
- Q4 2031Book 2 published
On stage at the 4 conferences that matter. Every year.
Not 'wherever I'm invited'. Pick the 4 events I want to be on stage at. Earn the invitations. Show up every year.
Deadline · From 2027 · every year- 20262 talks at events I picked · introductions for 2027
- 20274 talks at the chosen events
- 2028 →4 talks / year · the rooms are familiar now
Finances
Money stops being the question. Build income across media, marketplace, advisory, and products so I only do work that energizes. Net-worth target lands by 2032.
$5M+ personal net worth.
Built across business equity, real estate, and invested savings. The buffer that buys freedom — a projection, not a promise. The mechanism matters more than the ladder.
Deadline · By Dec 2032- End 2027$1.5M · base built · habits proven
- End 2030$4M · equity + real estate + invested savings
- End 2032$5M+ · the number that makes work optional
$10K / month passive.
Recurring income that hits the account whether I work that month or not. Rent, dividends, royalties, SaaS.
Deadline · By Dec 2029- End 2026$2K/mo passive · 1 source
- End 2027$5K/mo · 2 sources
- End 2028$7K/mo · 2-3 sources
- End 2029$10K/mo · 3+ sources
24-month runway, ready.
Cash equivalent of 24 months of personal expenses. Untouchable. Refilled if drawn down.
Deadline · By Dec 2026- Q2 202612 months funded
- Q4 202624 months funded · auto top-up rule set
Relationships
Anywhere I land, someone I love is one call away. Family, partner, friends, community. Cadence over crisis.
50 humans I actively show up for.
Not 5,000 followers. 50 people I check in on with intent. Birthdays, milestones, hard days.
Deadline · Ongoing · audit every year- Monthly5 deep conversations (not text — call or in-person)
- Quarterly15 catch-ups across the 50
- YearlyAll 50 have at least 4 touchpoints / year
60+ days a year with parents.
Fixed visits. Not 'whenever I'm in town'. Quarterly visit. Festivals together. One long trip.
Deadline · Starting 2026 · every year- Q1 202615 days (visit + festivals)
- Q2 202615 days (birthdays + long weekend)
- Q3 202615 days (festival + family trip)
- Q4 202615 days (year-end + holidays)
Active in 3 communities.
Coliving (the industry), AI builders (the craft), and a fitness community (the body — a run club or training group).
Deadline · By Dec 2027- End 2026Active in coliving + AI-builder communities
- End 2027Joined + showing up at a fitness community (run club / training group)
Personal Growth
Become the person who can pull this off. Sharper focus. Deeper curiosity. The work that's hardest because no one assigns it.
Write down what I know about coliving — in a form someone can use.
Take the frameworks, mental models, and patterns I've collected from inside the industry and put them into shareable shape. When a new operator asks 'how does this actually work', there's a real answer to point them to.
Deadline · By Dec 2027- Q2 20265 core frameworks documented in the newsletter
- Q4 202610+ operators using the frameworks in their own writing
- Q4 2027Book 1 published. The frameworks are reference material.
30 books a year. Notes that compound.
Philosophy, biography, technical, fiction. Read with a pen. Notes go into a system I revisit, not a Notion graveyard.
Deadline · Every year · starting 2026- Quarterly~7-8 books with written notes
- Year-end30 logged · top 5 written up publicly
Learn 1 new skill a year.
Something unrelated to work. Forces a beginner's mind. Builds neuroplasticity.
Deadline · Every year- 2026AI (advanced agents, custom systems, fine-tuning)
- 2027Photography (portfolio worth showing)
- 2028Cooking (master 20 dishes)
- 2029Music (guitar, 10 songs)
Mental Health
The inner game. Calm hustle is the goal — high output without burning the operator running it. Practice, not performance.
20 min / day. 365 days a year.
Not a streak hack — an actual practice. Sit, count breath, get up. Even on the worst days.
Deadline · Locked in by Dec 2027- Q2 20265 min / day · 30-day streak
- Q4 202610 min / day · 90-day streak
- Q2 202715 min / day · 180-day streak
- Q4 202720 min / day · 365 days
Daily journaling.
Not bullet-journaling. Real prose. Process the day, the wins, the patterns I keep falling into.
Deadline · Hit 365-day streak by end 2026- Q2 2026100-day streak
- Q4 2026365-day streak — locked-in habit
Monthly session, always.
An outside voice that sees blind spots. Coach or therapist (or both), monthly minimum.
Deadline · Ongoing · starting Q1 2026- Q1 2026Pick a coach + commit to 6 months
- Q2 2026Biweekly during onboarding period
- Q3 2026 →Monthly cadence, locked in
Physical Health
The body has to carry all of this. Specific lifts, specific distances, specific dates. No vague 'get fit'.
Full marathon. 42.2 km. Under 4:30.
Train through 2026-2027. Run a half first. Run a full in spring 2028. Not vague — picked a race city, picked a time.
Deadline · By April 2028- Q4 202610K race · sub-50 min
- Q2 2027Half marathon · sub-2:00
- Q4 202730K training run · sub-3:00
- Apr 2028Full marathon · sub-4:30 (pick race city by Q2 2027)
Century ride. 100 km.
Hundred kilometres in one ride. Picked a route. Picked a date. Trained for it.
Deadline · By Oct 2027- Q2 202630 km · consistent weekend ride
- Q4 202660 km
- Q2 202780 km
- Oct 2027100 km — completed
90 kg. 20% body fat.
Walking-around weight that supports the marathon training without being a chore to maintain.
Deadline · By Dec 2026- Q2 202694 kg · 23% body fat (transition phase)
- Q4 202690 kg · 20% body fat · sustainable habits
8 hours. 11 PM to 7 AM.
Boring goal. Highest leverage. Track every night. Don't break it for late calls.
Deadline · Starting now · audit weekly- Q1 2026Tracked every night · baseline measured
- Q2 202680%+ nights hitting 8 hours
- Q4 2026Sleep score locked above 85
5 workouts a week. Forever.
3 strength sessions. 2 cardio. Non-negotiable like brushing teeth. Travels with me.
Deadline · Locked by Q3 2026- Q1 20263x/week consistent
- Q2 20264x/week consistent
- Q3 20265x/week locked in · travel routines built
Spirituality & Meaning
Not religion — the practice of sitting with the hard questions. What do I believe? What do I owe the world? What do I do when nothing's working?
Put down on paper how I think about how to live.
A long essay (or short book) on the principles I actually use to make hard decisions — money, work, relationships, when to walk away. Not a manifesto. Just what I've learned, written down.
Deadline · By Dec 2027- Q2 2026Outline + 10 core principles drafted
- Q4 2026First draft (5,000+ words)
- Q4 2027Published as long-form essay
One silent week, every year.
No phone, no inputs, no outputs. The world keeps spinning. So do I. Annual non-negotiable from 2026.
Deadline · Starting 2026 · every year- 20263-day silent retreat (entry version)
- 202710-day vipassana
- 2028 →7-10 days every year, locked in
Write the year down. Every December.
Three questions, every December: what went well, what didn't, what I learned. Stored where future-me can read it back.
Deadline · Starting Dec 2026- Dec 2026First written review · template locked in
- Dec each yearPublished or private — but written down
Contribution
Build the ecosystem and then give some of it away. Free help where it changes a life. Money where it changes a system.
Help 30 operators in emerging markets — for free.
Pick founders building coliving in places where capital is scarce: South Asia, Southeast Asia, Africa, LATAM. Strategy, intros, frameworks. No invoice.
Deadline · By Dec 2030- End 20265 operators mentored (1 hour / month each)
- End 202710 operators · case studies written up
- End 202818 operators · 2 of them now hiring
- End 203030 operators · a community formed across regions
$25K / year donated. Sustained.
Picked causes, recurring transfers, not one-off virtue signals. Build the habit before the income makes it easy.
Deadline · By Dec 2028 · then yearly- End 2026$5K donated · 2 causes picked
- End 2027$12K donated
- End 2028 →$25K / year · sustained
Fund one student through college.
Pick a partner org. Sponsor one student fully — tuition, books, costs. Stay in touch for the duration.
Deadline · Sponsorship starts 2027- Q4 2026Partner org chosen · first student identified
- 2027 →Funded annually until completion
Fun, Play & Adventure
The category ambitious people skip. The one whose absence predicts burnout. Concerts, festivals, no-laptop trips, the shock of beginner's mind.
Two weeks. No laptop. Every year.
One trip a year where work doesn't exist. Phone for navigation, that's it. Family, friends, or solo — but no inbox, no slack, no notion.
Deadline · Starting 2026 · every year- 20262 weeks · zero work
- 20273 weeks · same rule
- 2028 →A month-long every other year
Four big experiences. Every year.
Concerts, sporting events, festivals, performances. Tickets bought ahead, dates blocked, no work cancellations.
Deadline · Starting 2026 · every year- 20261 concert · 1 sporting event · 2 festivals
- 2027 →4 experiences / year · variety preserved
Learn to surf.
Pick one physical skill that has nothing to do with work. Be terrible at it on purpose. Get the shock of being a beginner again.
Deadline · By Dec 2027- Q2 2026First 5-day surf camp
- Q4 202610 sessions logged
- Q4 2027Catch and ride a wave clean, start to finish