Last year's gathering: a courtyard in Mexico City with a painted mural, ivy-covered brick, and mats laid out for a session

Un Poco de Planning

Eight days in San Juan with forty friends, and a plan for the year you want.

  • Dec 27 to Jan 3
  • 40 friends
  • San Juan, Puerto Rico
  • Kids welcome
  • Invite only
Reserve a spot$500 depositSee the week

The idea

Clarity comes easier in the company of people you admire.

Most of us have tried doing this alone: a notebook, a quiet morning somewhere between Christmas and New Year, and an honest attempt to work out what the year meant and what should come next. It helps, but only so far. On your own you see what you already know how to see, and you often land on the same conclusions as last year.

Doing it with other people helps, especially people whose lives you admire and whose judgment you trust. Some of them know your history well enough to notice when you are talking yourself into something. Others are meeting you for the first time and bring none of your context and a different way of reaching an answer, and that helps too. Saying what you want out loud in front of both makes you more honest about it, and you get asked questions you would not have thought to ask yourself.

Over eight days we look back at the year honestly, work out what we want from the next one, and leave with intentions specific enough to act on. The calendar turns over in the middle of the week, which makes a natural line to step across.

The week has a clear arc, and small pods of attendees design and run each session, so everyone is responsible for something.

A letterboard reading Un Poco de Planning among potted plants
Everyone working at long tables under the greenhouse roof
A friend leading a session for the group

Who comes

Forty people worth the trip

Everyone here is very good at something. What we look for on top of that is people who are as thoughtful about how they live as they are about what they build. They ask good questions, they can sit with something difficult without rushing to fix it, and they will tell you the truth kindly. That combination is what we select for.

Every invitation comes through someone who knows the person, and the organizers talk it over before it goes out. We also pick the mix on purpose: left brain and right brain, different fields and cultural backgrounds, and a group balanced across genders. The week runs on being asked questions you would not have asked yourself, and people who work the way you do tend to ask the ones you have already answered.

Eight days is long enough for a guest list to become a small community, and it tends to last well past the airport. People from past years have built things together, stayed at each other's houses, and shown up for each other through hard years.

You will already know some of the people here, and you will get to know the rest quickly.

  • Artists, musicians, founders, and engineers, plus the ones whose work resists a tidy job title
  • Academics and researchers who think for a living and argue well
  • Leaders carrying real responsibility, and honest about what it costs
  • Community builders, and the ones who always end up organizing dinner
  • People trying to build a life that fits who they are
  • Friends who value honest conversation and are comfortable in the quiet

Focus, then rest

Working blocks in the morning, downtime in the afternoon, and dinners with no set end time.

Nerding out on how you plan

Some people arrive with an elaborate setup and strong opinions about it, and plenty arrive with nothing. Both are fine, and everyone leaves with a few new ideas to try.

Nobody leads it

Small pods design and run each session, so the people in the room shape the week.

Leave with it written down

You go home with a written vision, goals with dates attached, and systems that still hold up in February.

Bring the kids

We built this one for families

We want families here. Childcare runs on site all week, so parents can give the sessions their full attention.

Parents rarely get a long stretch of focused time for this kind of thinking, and they deserve one. We also love the idea of kids watching adults they love sit down and think honestly about their lives, which most of us never got to see growing up.

Childcare, covered
On site during the working blocks and already sorted. Nothing extra for you to arrange.
Uninterrupted sessions
The morning and afternoon sessions are yours to focus on.
Kids in the room for the rest
Kids join for meals, evenings, and the closing circle.

Tell us ages when you reserve and we will size the care to the group.

The week

Eight days, each with its own focus

December 27, 2026 to January 3, 2027. The week moves from looking back, to deciding what you want, to building the systems that support it, and ends with everyone teaching what they know.

  1. Dec 27

    Sunday

    Arrivals

    Land, drop your bags wherever you are staying, and come find us. Dinner together, introductions, and no agenda beyond starting to settle in.

  2. Dec 28

    Monday

    Context and Reflection

    Group agreements and intentions, then a session on why we are all here. We start from the work you already did at home and give the whole day to the year behind you: the highs, the lows, a walk back through your own calendar, and small groups where people who know you well catch what you glossed over. Evening circle and a letting go ritual.

  3. Dec 29

    Tuesday

    Vision Crafting

    Values, purpose, and the long view. Map the domains of your life and look honestly at the one you have been avoiding. Peer coaching in small groups, focused on asking each other better questions.

  4. Dec 30

    Wednesday

    Adventure Day

    No sessions. El Yunque and the waterfalls, the old city walls, the coffee, the beach, and a great deal of food. For anyone who would rather go inward, there is an optional plant ceremony in the afternoon with musical facilitation, and quiet space held around it.

  5. Dec 31

    Thursday

    Direction and New Year's Eve

    Back to the vision with more room to get specific about direction, and a good day to sit with whatever Wednesday surfaced. Then the New Year's Eve party, and intentions set together at midnight.

  6. Jan 1

    Friday

    Strategic Mapping

    A slow start, then turn the vision into goals with dates attached. OKRs, habit stacking, a personal Life Dashboard. Get it into one document that survives the trip home, and pair up with someone who will check in on you come April.

  7. Jan 2

    Saturday

    Unconference

    Everyone teaches something. Sessions get proposed in the morning and run through the day, on whatever people here know well: the craft, the tools, the hard-won stuff you cannot get from a book. Closing dinner and a gratitude circle that runs long.

  8. Jan 3

    Sunday

    Departure and Re-entry

    One last morning ritual, goodbyes that take longer than anyone plans for, and home with a plan you intend to follow.

A normal day

8:00 to 10:00
Optional movement or mindfulness, then coffee
10:00 to 12:00
Focused working session at the venue
12:00 to 2:00
Lunch out, which tends to run long
2:00 to 5:00
Afternoon working block
Evening
Dinner, wandering, or wherever the evening goes
El Morro on the headland from the air, with Old San Juan and the bay stretching out behind it

The setting

San Juan, Puerto Rico

San Juan sits in the low eighties all week, five hundred years old on one side of the bay and a working Caribbean city on the other. We gather around Old San Juan & Condado: walkable, full of good coffee, ten minutes from the water and an hour from the rainforest. Everyone books their own place to stay, and we will cluster close enough to walk to each other.

No passport

A domestic flight from the US. Dollars, and a phone that just works.

Old city

Blue cobblestones, painted facades, and two forts on the water.

Green

El Yunque an hour east, and the beach fifteen minutes north.

A canopy of colored umbrellas strung above Calle Fortaleza in Old San Juan
A sunlit street of pastel colonial houses and wrought iron balconies in Old San Juan
A sentry box on the ramparts of El Morro looking out over the water
The forested peaks of El Yunque under low cloud
The turquoise curve of Flamenco Beach on Culebra from the air

Last year in Mexico City

What the week looks like

This year moves to Puerto Rico, with the same kind of people.

The whole group piled together for a photo in the greenhouse
A friend playing during an evening session
Two friends co-leading a session in the greenhouse
Long tables and laptops seen from above
Three friends sharing with the group in front of the greenery
Friends playing music together during an afternoon session in the courtyard

Shared costs

Roughly $700 per person for the week

A shared bill, split evenly. Everyone books their own place to stay this year, which keeps the number small and lets you pick your own budget. The final figure lands on Dec 1, once we know how many of us there are.

What the money covers

The venue
Where we meet each day
A local event producer
Someone San Juan-based and well connected, running logistics all week and opening doors we would not find on our own
Production and materials
Sound, staging, session supplies, and whatever the pods need
Hired talent
Musicians and facilitators brought in for the evenings
Childcare
On site during the working blocks
Coffee and snacks
Stocked daily at the venue
A few group dinners
Opening and closing nights

What is on you

Flights
Book your own
Lodging
Book your own for the eight days
Most meals
Pay as we go around the city
Getting around
Uber and taxis, and a lot of it on foot

If you need to pull out

Costs are split evenly, so when someone drops out late, their share falls on everyone else. That is why the policy below exists.

Before Dec 1
Your deposit comes back in full, no questions asked. Nothing is locked in until then.
Dec 1 onward
The deposit is not refundable. The venue, the producer, and childcare are all booked against headcount by that point, and your share of it is already spent. We will not come after you for the remainder.
Any time
You can hand your spot to someone else, as long as the organizers know them. Settle up between yourselves and nobody is out of pocket.

Key dates

  1. Oct 1

    Flights and stays shared

    Post when you land and which neighborhood you are leaning toward, so anyone who wants to split a place can find each other.

  2. Oct 10

    Accommodation booked

    Book your stay. Holiday week in San Juan fills up earlier than most people expect.

  3. Dec 1

    Final contribution confirmed

    The number lands once we know headcount and which space we book.

  4. Dec 15

    Homework goes out

    Two to three hours of reflection to do before you travel, so the days together can go to each other.

  5. Dec 27

    Arrivals in San Juan

    Settle in, dinner together, introductions.

Hold your place

$500 holds one spot

Forty spots, first come. Your deposit holds your place while you sort out flights and a room, and comes off your total. The rest is settled on Dec 1.

Payment is handled securely through Stripe.

Questions

The things people ask

Is this a retreat or a program?

It is closer to a gathering of friends. Nobody makes money on it, and there is no curriculum to complete.

Can I bring my kids?

Yes. Childcare runs on site during the working blocks and is already covered, so there is nothing extra for you to arrange. Tell us ages when you reserve and we will size the care to the group.

Do you book lodging for me?

No. Everyone books their own place this year, which lets you pick your own budget, your own room, and how much privacy you want. We will coordinate so people end up close together.

Where should I stay?

Old San Juan and Condado are the two easy answers, and both are a short ride from wherever we gather. Santurce is the third, quieter and more residential, with the best food in the city. We will share a shortlist of places people liked. Plans go into the group thread on October 1 and most people book by October 10, so there is a real window to find someone to split a place with.

Do I need a passport?

Not if you are flying from the United States. Puerto Rico is a US territory, so it is a domestic flight, the money is dollars, your phone plan works, and you can drink the water. If you are coming from outside the US, check your own entry requirements early.

What is the homework?

A set of reflection prompts, sent December 15. Plan for two to three hours. Past years taught us that the solo work is best done before you arrive, so the days in San Juan can go to conversations, feedback, and time with each other.

Can I invite friends?

It is invite only, though that is less rigid than it sounds. If there is someone you think belongs here, run it by one of us.

What should I bring?

A journal you like writing in, comfortable clothes, swimwear, and a rain shell for the ten minutes a day it pours. San Juan sits in the low eighties all week, so you can leave the coat at home.

How structured is the week?

Loosely. A morning session, an afternoon session, and dinner together, with a lot of room in between to rest or wander.

What happens after I put down a deposit?

You get a receipt and a spot on the list, and we add you to the group thread where lodging and travel get sorted through the October window.