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Inner Isles Explorers Club

You Weren't Made to Watch From the Shore

A club for growing in every part of your life. Choose what matters, plan it with Kip, our AI guide, and take it on like an adventure, on your own or alongside fellow explorers.

Start: Tonight
Next Expedition: Tuesday, December 1
Price: $50 a month, with a 75-day refund

See what the club is like. It takes a few minutes. Begin the Crossing

Already sure? Skip to joining.

Mainland Harbour

Conditions This Morning

Visibility: Poor. The days have started to blur together.
Wind: Hardly any. You're busy, but nothing is really moving.
Outlook: The books pile up. The courses go unfinished. The resolutions are gone by February.
Advisory: It isn't more information you're short of. It's somewhere worth heading.

The fog isn't a flaw in you. It thins about a mile out.

Welcome aboard.

I'm Kip, and I'll be your guide on the way out. I don't steer. You choose where we're going, and I help you plot a course you'll actually want to sail: small steps, an honest word when it's hard going, a good question when you're stuck.

I remember where you've been, so you never have to start over with me.

Everyone else aboard is a real person, sailing for an isle of their own, and they're better company than I am.

Kip, your guide

P.S. Kip is an AI guide. What you tell him is used for one thing, which is helping you on your way.

My interactions with ChatGPT were generally bad to neutral at best. This is my first genuinely great experience interacting with an LLM. Kip is the right mix of gentle without pandering, equally supportive and pushing back when necessary. It was like talking to a good friend, and I have to acknowledge how impressive that is.

— John A.

Kip is GREAT with empathy and validation! Better than my friends. But also keeps you on track for the chat purpose, to make the goals. Kip even had a few good things for me to ponder before making my goals. I mean, like it made me think, ‘Oh, I didn’t think of that - good idea, Kip’.

— Anita

Treat Your Growth as an Expedition

Most programs treat growth as a destination, a better self you finally arrive at, so every setback feels like a defeat. Out here, obstacles are terrain, detours lead to discoveries, and rest is part of the route.

~~Certainty~~ Curiosity
You don't need to know how it turns out, only a question worth following into the fog.
~~Perfection~~ Progress
Take the small step today. Switchbacks still climb the mountain.
~~Competition~~ Community
Nobody here is ahead of you, because nobody else is on your trail.
~~Achievement~~ Adventure
Adventure is whatever asks a little more of you than yesterday did. For one explorer that's a mountain. For another, it's a phone call.

Ten Isles. Choose the One You're Sailing For.

Some explorers sail for Ridgeline because work has gone grey. Some sail for Heartwood to mend something, for Idlewild because they've forgotten how to stop, or for Stillwater because the voice in their head is always keeping score.

A painted chart of the Inner Isles: Explorers Island, the home island, at the centre, and ten isles in a ring round it

Meaning

Northlight

Orientation. Purpose, values, faith or philosophy, mortality, and what you are actually aiming at.

Press it to sail for Northlight.

Self-talk & Attention

Stillwater

The voice that keeps score. The running commentary, the stories you tell about who you are, the hiding, and meeting yourself with kindness instead of a grade.

Press it to sail for Stillwater.

Body & Energy

Wellspring

The source. Sleep, movement, food, illness and energy, and the body you have been ignoring.

Press it to sail for Wellspring.

Play & Rest

Idlewild

Unproductive by design. Play, rest, recovery, and remembering how to stop.

Press it to sail for Idlewild.

Craft & Learning

Hammerstone

Where you make things. Creative work, a craft, a skill, and learning for its own sake.

Press it to sail for Hammerstone.

Work & Vocation

Ridgeline

Where you climb. The career question you keep circling, the business, the direction, the work you are paid for.

Press it to sail for Ridgeline.

Money & Resources

Tradewind

What you hold and how it moves. Earning, spending, debt, security and generosity.

Press it to sail for Tradewind.

Home & Surroundings

Anchorage

Where you are moored. Your home, your space, your belongings, your screens, where and how you live.

Press it to sail for Anchorage.

Close Bonds

Heartwood

The people you already have. A partner, family, dating, old friends, the conversation you need to have, and the repair.

Press it to sail for Heartwood.

The Wider Circle

Commonweal

Widening the circle. Belonging, making new friends, community, service, and showing up for a place.

Press it to sail for Commonweal.

Turn Anything Into an Adventure

Point the lens at the thing you've been putting off. Kip helps you plot the course: a role to play while you do it, a first step for tonight, and a plan for when it goes sideways. On your own, any day you like.

A Day on an Expedition

Once a month the club sets out for four weeks, each member working on one part of their life. Most days look like this and take a few minutes, and what you write stays yours unless you choose to share it.

The Daily Dispatch

Day 12 of 28 · Fair winds

Good morning. Yesterday was a rest day in your log, and a good one. You'd been at the hard part of this for three days straight, and stopping for one is how a month goes the distance.

Your step forward for today

Write the first paragraph of the email to your sister. Just the first one.

Around the campfire

Rosa, on your Expedition, finally made the phone call she'd been circling for a week.

Kip writes it every morning: your step, a tale from your Expedition, a question to carry.

Field Note Day 12

Didn't want to start today. Did the first ten minutes anyway and the rest came easier than I expected. Note to self: the wall is always at the beginning, never in the middle.

evening, if you feel like it. Only you and Kip read it.

Check-in

Day 12

Did you take a step forward today?

any time before bed. Sign it either way: an off day goes in the log too.

that's a mark in the log.

Four Weeks, One Mark a Day

Trail Log

Bound for an isle of your choosing

Week 1

Week 2

Week 3

Week 4

On trail

Off trail, and it stays in the log

Each day you check in, a stamp goes in your Trail Log: footprints for a day on trail, a cup for a day off it.

Miss a week and nothing piles up while you're away. The log is right where you left it.

At the start I was worried about burnout, but by allowing myself easy days, I never struggled.

— T. Benson

What You Bring Home

Usually something smaller than a new life, and better: a project finally started, a habit that held, a phone call made. The club has set out on 15 Expeditions since July 2025, and these are a few postcards from explorers who've been out here.

Someone You'll Meet Out Here

A version of you who doesn't flinch at the hard conversation, who starts the thing without a week of circling. Kip helps you give them a name, a story and a passport, and you step into them when a moment asks more of you than you feel you have.

Explorer Identity · Passport

Kelly Redmond

Moves with intention through spacious terrain

Pronouns he / him

Traits

Unhurried Restorative Intentional

Crossings

Said the true thing 14 MAR 26

Rested without guilt 02 APR 26

Set out unhurried 27 APR 26

Went first, quietly 19 MAY 26

I am Kelly Redmond, moving with intention through spacious terrain, trusting that my unhurried pace and restorative spirit are the very foundation of my boldest explorations.

Kelly Redmond

That Was the Club in a Few Minutes

The real one starts tonight: tell Kip what you've been putting off and take the first step. Once a month there's a four-week Expedition to join, when you want company.

Inner Isles Explorers Club

Passage

The Inner Isles

Passenger: You
Sets out: Tonight
Bound for: Any of the ten isles
Passage: A guide, and every Expedition

Fare

$50 a month, or $500 a year. One membership covers all of it, every Expedition included. Cancel any time, and a 75-day refund of everything you've paid, no questions. If the price is a barrier, makes it half, or free.

Admit
One

No. 0042

Join the Club

Start tonight: sit down with Kip and plan the thing you've been putting off. Every Expedition is included, and the next sets out on December 1.

Monthly

$50

a month, as you go

The year

$500

twelve months for the price of ten

Not sure it's for you? Talk it over with Kip first. It's free, and he'll tell you straight.

Nobody loses their place here because of money. If the price is a barrier, makes it half, or free, and asking is the whole process.

Inner Isles Explorers Club

Questions

Before you join

What if I'm not very adventurous?

Good. You're the person this was built for. Adventure here isn't cliffs and passports; it's whatever asks a little more of you than yesterday did. For one explorer that's a mountain. For another it's a phone call. The journey starts where you're standing.

Do I have to wait for an Expedition to start?

No. You start the evening you join: tell Kip what you've been putting off, and he'll help you plan it and take the first step that night.

Expeditions set out on the first of the month. The next one leaves on December 1, and you can join that one or any after it.

What's the monthly Expedition, and do I have to go?

Once a month the club sets out together for four weeks, each member working on one part of their life, like work, rest or the people they love. You get a short letter each morning, a check-in that takes a couple of minutes, and other members going through it alongside you.

You don't have to go. Join the months you want company. Kip is there every day either way, and your membership covers every Expedition you do take.

How much time does this take?

Whatever you give it. A plan with Kip can start with one small step tonight, and a conversation with him takes as long as you want it to. On an Expedition the daily check-in is a couple of minutes. Step away for two weeks and everything is where you left it.

I've tried things like this before. Why would this be different?

Then you know the pattern: a burst of motivation, a plan, and a few weeks later the quiet guilt of having fallen behind. Most tools run on willpower and punish you the moment it dips. This is built the other way around. Nothing piles up while you're away, an off day is just an off day, and rest is part of the route.

And you're not doing it alone. Kip remembers where you are and picks up where you left off, and once a month you can set out with other members.

Do I have to share what I write?

No. What you write is private: only you and Kip read it. Sharing is a second step you take on purpose, and you choose who reads it, the members on your Expedition or the whole club, and whether your name goes on it.

What you share with your Expedition stays with them. Nothing is ever opened up later to people it wasn't written for.

Do I have to be into AI for this to work?

Not at all. The other members are people, not algorithms. Where AI helps, in a conversation with Kip, it's in service of your own course and your connection to other members, never the point in itself.

What you write here is used to support your own experience. Our privacy policy spells it out.

What does it cost?

$50 a month, or $500 for the year. One membership covers all of it: Kip, every plan you make with him, and every Expedition.

Nobody loses their place here because of money. If the price is a barrier, makes it half, or free, and asking is the whole process.

What if I join and it's not for me?

You're covered by a 75-day refund of everything you've paid, no questions asked. That's long enough to settle in on your own and go on a whole Expedition, whenever in the month you join. And you can cancel any time, in a couple of clicks.

Still wondering? Email [email protected]. Matt reads every note.

One Last Question

How would you live your life, your everyday life, if you had the perspective of Indiana Jones?

Not the boulders and the whip. The way Indy meets the unknown: curious, driven, certain the map is incomplete and glad about it. That question has been driving me for years. Inner Isles is my answer.

You see, I'm not the adventurer you'd picture. I'm a homebody. I get homesick, crowds make me nervous, and I've spent big stretches of my life indoors, mired in depression.

For the past five years I've lived in an RV, traveling the country with my partner. The anxiety didn't disappear. What changed is that I stopped waiting to feel ready, and started treating the whole messy thing as an adventure.

Have a question, or an answer to mine? Write to me. I read every note that comes in.

Matt

There was a time when I thought success looked like a spouse, a mortgage, a business degree, and a dependable rotation of 30-minute weekday dinner recipes. I chased all of that with sincere effort and very little questioning, until the day I realized I'd built a life that didn't feel like mine at all.

What followed wasn't a grand reinvention so much as a series of rebellions. I left a long-term relationship. I decided against the MBA I thought I was supposed to get. I left the office job and started consulting. I started asking myself, what if this isn't failure, but just the next chapter? And to my surprise, the world didn't collapse.

I co-founded Inner Isles because I want to share this mindset. Not as a fix-all, but as a way to get unstuck, to feel more alive, and to remember that this is your life and you get to explore it.

Madelinne, co-founder

Whenever you're ready

You can start tonight. The next Expedition sets out Tuesday, December 1.

Back to Joining