Diverse group of 6-8 adults gathered around a large campfire at night in a forest clearing, faces warmly lit by fire in candid engaged conversation.

THE BEARING

Cut through the noise. Find your bearing.

The Bearing is a 3.5-day retreat for six to ten founders at a time, held on Root Astro's seven-acre property in the Neversink Foothills, 90 minutes from New York City. Guests surrender their phones on arrival and don't get them back until they leave. Founded by Root Astro co-founders Lee Arthur and Marsha Prospere after Lee's own reckoning with burnout on a 240-mile ultramarathon through the Utah desert, The Bearing trades a screen for a fire, a dashboard for a compass, and replaces the always-on habits of running a company with four days of navigation, fire-building, and unscheduled time.

41.4739° N 74.5401° W

ELV 840 FT POLARIS ALT 41°

STILLNESS + STRENGTH · ROOT ASTRO SPECTRUM

The Bearing holds both modes together. Stillness slows a nervous system that has not stopped in years. Strength tests the result against terrain that does not negotiate. The two together are how the instrument gets trued.

THE PROMISE

You’ll leave with clarity you can act on.

The Bearing isn’t a motivational retreat. It’s a calibration. You arrive carrying the accumulated weight of decisions made in isolation. You leave with a peer crew who’ve seen behind the mask, a 90-Day Bearing built from honest self-assessment, and proof that you can think clearly when the noise stops.

90 days later, you return for a weekend to measure what changed: in your leadership, your decisions, and the six dimensions of the Human Return Rubric. This is transformation with a receipt.

Topographic trail map and astrolabe navigation tools laid out for route planning across Root Astrolabe terrain

TERRAIN THAT DOES NOT NEGOTIATE · THE BEARING ROUTE

The Experience3.5 days · +90 day return

An arc, not a checklist.

Four movements, one return. Each waypoint is a coordinate on the arc — not a step in a sequence. Click any to read what happens there.

00Arrival01Body02Challenge03Bearing+90Return
00
ArrivalSurrender
Day 0 · Devices Collected
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Devices collected. Silence begins. The land does what no productivity hack can: it slows you down enough to hear yourself think.

Arrival is the first act of leadership: choosing to stop.

01
The BodyStrip the persona
Day 1 · Physical
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Physical challenge strips away the executive persona. Trail work, cold water, shared labor.

Your body remembers what your calendar made you forget.

02
The ChallengePeer truth-telling
Day 2 · Dialogue
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Facilitated dialogue with your cohort. The Astrolabe Methodology surfaces what's misaligned. Peer truth-telling begins.

This is where the real work happens.

03
The BearingBuild the plan
Day 3 · Commitment
+

You build your 90-Day Bearing. Not a vision board. A concrete map of what changes when you return. Your peer crew witnesses your commitment and holds you to it.

A bearing is useless until you walk it.

+90
The ReturnMeasure the shift
+90 Days · Measurement
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You come back. You measure. The Human Return Rubric captures what shifted across six dimensions: Presence, Connection, Capability, Clarity, Resilience, and Reverence.

This is how we prove the work matters.

Sunrise valley near the Bearing retreat site

WHO THIS IS FOR

You’re a founder or CEO carrying decisions no one else can see.

You've built something real, but the cost is showing. You make decisions in isolation. Your board sees the numbers, not the weight. Your partner sees the absence, not the reason. You've tried executive coaching, mastermind groups, maybe even therapy, but nothing has slowed the world down long enough for you to recalibrate.

The Bearing is for leaders at inflection points: funding rounds, exits, succession, burnout, or simply the quiet realization that the way you've been leading isn't sustainable. You don't need more advice. You need space to hear your own.

WHAT YOU’LL TAKE HOME

Not just insight. Infrastructure.

Your 90-Day Bearing: A concrete, peer-witnessed commitment to specific changes in how you lead, decide, and live. Built from honest self-assessment through the Astrolabe Methodology, not motivational platitudes.

A peer crew of 6–10 founders, funders, and operators who've seen behind the mask. A baseline Human Return Rubric score across six dimensions. And a return date, 90 days out, when you come back to measure what actually changed.

LogisticsWestbrookville, NY · 41.47°N · 74.54°W

The practical details.

Six to ten founders, funders, and operators on the same instrument at the same time. The cohort is the method.

Duration
3.5 days, plus the 90-Day Return Weekend.
Arrive Friday afternoon, 1–4 pm. Depart Monday evening.
Location
Westbrookville, NY.
90 minutes from Manhattan.
Cohort
6–10 leaders. Curated by application.
Founders, funders, and operators.
Investment
Inquire for current pricing.
Includes lodging, meals, facilitation, and the return weekend.
Bring
Comfortable clothing, hiking boots, a journal.
Phone
Gets you there.
We hold it on arrival and return it when you leave.
Leave behind
A laptop, or any expectation of a spa retreat.

Biologists have a name for what The Bearing is built on: hormesis, a stressor delivered in the right dose, with adequate recovery, that leaves the system stronger than it found it. Four days of navigation, fire-building, and unscheduled time are not an escape from the work of running a company. They are a controlled dose of the thing your nervous system has been missing.

Not ready to book? Stay close to it.

Cohorts fill slowly on purpose. Tell us you're circling this one.

Thank you! Your submission has been received!
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Ready to cut through the noise?

The Bearing begins with an application. Tell us where you are, and we’ll tell you if this cohort is right for you.

Apply for The Bearing

Frequently Asked Questions

What actually happens during The Bearing, day to day?+
3.5 days, Friday evening to Monday morning. Day 0 is Arrival and Surrender: devices collected, land orientation, first fire that night. Day 1 is the Body: guided trail, bushcraft, and the first introduction to the Astrolabe Methodology's three Bearings (Truth, Health, Wealth). Day 2 is the Challenge: a longer shared endeavor with no assigned roles, then a facilitated debrief and paired peer dialogue. Day 3 is the Bearing itself: you finish your 90-Day Bearing, read out your top bearing to the group, and depart with a peer Circle formed through the experience. Ninety days later, that same cohort returns for the Return Weekend.
How much does The Bearing cost, and what's included?+
Pricing is by inquiry; reach out through the application and current rates are confirmed there. It includes lodging, all meals, and facilitation, plus the full 90-Day Integration Program: two field prompts by post, a 1:1 Recalibration Call at Day 14, two self-facilitated Circle checks (Day 30 and Day 60), and the Return Weekend at Day 90.
Do I need to be physically fit to do this?+
There's a physical component (trail work, a shared endeavor, full days outdoors) but it's built as a stressor with recovery, not an athletic test. Highland's expedition asks more of the body; The Bearing asks more of your honesty. If you can manage a full day on your feet outdoors, you're prepared for it.
I'm genuinely unreachable with my phone gone. What if there's an emergency?+
Your device is collected on arrival and returned after the closing circle, no exceptions, but the property isn't unsupervised: medical intake is reviewed before every cohort arrives, first aid certified staff are on-property at all times, and emergency contacts are held on file throughout. If something genuinely needs you, Root Astro can reach you.
How is The Bearing different from Still Point or Highland?+
Still Point is solo: no cohort, no agenda, complete rest and silence. Highland is a single company's own leadership team, tested together on a harder physical expedition. The Bearing sits between them: a curated cohort of 6 to 10 founders, funders, and operators who don't know each other going in, built for individual clarity rather than either total solitude or team dynamics.
Can I just book, or is there an application process?+
The Bearing begins with an application, not a booking form. Cohorts are curated by Marsha or Lee directly and fill slowly on purpose; the mix of eight to ten leaders is part of the method, so who's in the room matters. Apply and you'll hear whether the cohort is right for you.
What happens at the 90-Day Return?+
You come back to Root Astro for a weekend, ninety days after you leave, with the same cohort. The arrival ritual holds again: devices surrendered, more deliberately this time, since the crossing carries more weight the second time. Each person lays out what held and what broke against their 90-Day Bearing; the Circle leads that conversation, not the facilitator. It isn't scored, but Root Astro tracks the shift across six dimensions (Presence, Connection, Capability, Clarity, Resilience, Reverence) through what participants and facilitators observe. You leave with a recalibrated plan, and the Circle decides together what it becomes next: an ongoing fellowship, a seasonal reconvene, or something quieter.

Further reading

Solo leadership retreat: is it right for you?Leadership retreat vs. team offsiteWhat most leadership retreats get wrongThe 7 best leadership retreat programs for senior executivesPricing, answered straight