The Crossroads

Welcome to The Crossroads, the place where journeys converge and new paths unfold. Here, at these pivotal moments of choice, you'll find perspective from others who have stood where you stand now. The Crossroads is where you come when facing significant decisions—not for someone else to decide for you, but to gain clarity, hear diverse viewpoints, and choose your path forward with greater wisdom.

Why The Crossroads Exists

Everyone faces crossroads—moments when the path ahead splits and you must choose a direction. These aren't small daily choices, but the significant ones that alter the trajectory of your life:

• Should I quit my job and join the caravan?
• Is this business idea worth pursuing or am I fooling myself?
• Should I move to this network property or stay where I am?
• Is this person trustworthy enough to partner with?
• Do I continue investing in this project or cut my losses?
• Should I get involved in this conflict or stay out of it?

These decisions are hard because both paths have merit and risk. There's no obviously right answer. You need clarity, not just more information—and clarity often comes from stepping back, hearing how others have navigated similar crossroads, and examining your own motivations honestly.

The Crossroads provides that space. It's neither The Tavern's abstract philosophy nor The Trailhead's practical planning—it's the space between, where you sort out what you actually want and why, before committing to a path.

How The Crossroads Works

The Crossroads functions both as a physical/digital gathering space and as a framework for decision-making. Here's how to use it:

1. State Your Crossroads

Clearly articulate the choice you're facing. Writing it down forces precision. Examples:

Notice these aren't vague. They include context, constraints, and the actual tension. "Should I start a business?" is too broad. "Should I start this specific business given these specific circumstances?" is a real crossroads.

2. Gather Perspective

Share your crossroads with others—in person at Crossroads gatherings, or through network channels. The goal isn't consensus or voting, but diverse perspective:

You're not looking for someone to tell you what to do. You're looking for information and perspective you don't currently have.

3. Examine Your Motivations

The hardest part of any crossroads is being honest about why you want what you want. Common self-deceptions:

• "I want to join the caravan" → Actually, I'm running away from problems I haven't addressed
• "I want to be practical and stay at my job" → Actually, I'm afraid and using "responsibility" as cover
• "I want to help this person" → Actually, I like feeling needed and don't know how to say no
• "I want to try this new venture" → Actually, I'm bored and restless, not genuinely interested in this specific thing

The Crossroads helps you distinguish between what you genuinely want and what you think you should want, or what you're afraid not to want. This requires brutal honesty with yourself, often aided by trusted others who can point out patterns you can't see.

4. Test Your Decision

Before fully committing, can you test the waters?

• Want to join the caravan? Visit for a week first.
• Considering a business partnership? Do a small project together before committing.
• Thinking of relocating? Visit during the worst season, not just the best.
• Wondering if you should quit your job? Try freelancing on the side first.

Not every decision can be tested, but more can than most people realize. Testing converts abstract speculation into actual experience.

5. Make Your Choice

Eventually you must choose. Perfect information doesn't exist. You'll never be completely certain. The question is: "Do I know enough to make a reasonable choice?"

If yes: Choose. Commit. Move forward with the understanding that you might be wrong, but you're making the best choice you can with current information.

If no: What specific information would help? Can you get it? If not, you're actually at "yes" but afraid to admit it.

6. Don't Look Back (Except to Learn)

Once you choose, commit to it fully. Second-guessing is useless. You can change course later if needed, but while walking a path, walk it fully.

Later, after the outcome is clearer, return to The Crossroads to share what you learned. Your experience becomes perspective for others facing similar choices.

Common Crossroads in the Network

While every crossroads is unique, certain types recur. Here's wisdom gathered from those who've walked these paths:

The Exit Crossroads: Leaving Conventional Life

The choice: Stay in the system (job, house, routine) or exit to freedom (caravan, nomadic life, full agorism)

Common fears: Financial insecurity, loss of stability, judgment from family/friends, "What if I fail?"

What those who exited say:

What those who stayed say:

The Partnership Crossroads: Working With Others

The choice: Enter a business partnership, property co-ownership, or long-term collaboration—or go it alone

Common fears: Getting screwed, losing control, conflict destroying the relationship, carrying deadweight

Red flags to watch for:

• They talk more than they do
• They have a pattern of burned bridges
• They want to rush into partnership without getting to know each other first
• They're vague about past failures or blame others exclusively
• Your gut says something is off (trust it)

Green flags to look for:

• Track record of completing things
• References from people you trust
• Complementary skills (not duplicate)
• Compatible work styles and communication
• They're as careful about choosing you as you are about choosing them

The Persistence Crossroads: Continue or Quit

The choice: Keep working on this project/business/relationship that isn't working yet—or cut losses and try something else

Common fears: Wasting all the effort invested, being a quitter, missing success by one more month of effort

Questions to ask yourself:

From those who quit: Relief, followed by regret they didn't quit sooner, followed by excitement about what came next

From those who persisted: Mixed—some broke through, some wish they'd quit, most are still uncertain

The Location Crossroads: Where to Be

The choice: Move to a network property, stay local and build where you are, or join the nomadic caravan

What to consider:

• Do you need community around you physically, or are digital connections enough?
• How important is climate/geography to your wellbeing?
• Do you have local ties (family, established business) worth maintaining?
• Are you building something that requires a fixed location?
• Can you handle isolation, or do you need daily social interaction?

The Resource Crossroads: Time, Money, Energy

The choice: How to allocate limited resources between competing worthwhile goals

Common trap: Trying to do everything, accomplishing nothing

Better approach: Sequential rather than parallel. Choose one primary focus. Make progress. Then reassess.

Tools for Discernment

The Crossroads isn't just about gathering opinions—it's about developing your own discernment. Here are frameworks that help:

The Regret Minimization Framework

Imagine yourself at 80 looking back. Which choice will you regret less? Not which worked out better (you can't know), but which decision process you'll be proud of.

"I tried and failed" is usually less regrettable than "I was too afraid to try."

The Reversibility Test

Some decisions are reversible, others aren't. Prioritize reversible experiments over irreversible commitments.

• Reversible: Join caravan for 3 months, quit job (can get another), move (can move back)
• Mostly irreversible: Have a child, burn a bridge, sign a long-term contract

Be more careful with irreversible choices. Be bolder with reversible ones.

The Energy Test

When you imagine yourself on each path, which one gives you energy and which one drains you?

Not "which is easier" but "which am I excited to do the hard work for?"

The Gut Check

Your rational mind can be fooled. Your gut is usually right about people and situations, even if it can't articulate why.

If your gut says no and you can't figure out why, that's still valuable information. Don't override it just because you can't rationalize it.

The Steel-Man Both Sides

Before deciding, argue passionately for each option as if you've already chosen it and need to justify it. What's the best case for Path A? For Path B?

This prevents straw-manning the option you're biased against.

Crossroads Resources

The Crossroads connects you to people and information that aid decision-making:

Guild Directory

Navigate our growing landscape of specialized skills and shared passions. The Guild Directory allows you to discover artisans, tradespeople, and collectives dedicated to mastering and sharing their craft within the Network. Whether you're seeking a specific service, looking to apprentice, or want to connect with others who share your expertise, this is your starting point.

Find Your Guild

Explore the Guild Directory to learn more about how guilds function within our network and find people with relevant expertise.

Decision Journals

Network members share their crossroads decisions and outcomes. These aren't polished success stories—they're honest accounts of what was considered, what was chosen, and what actually happened.

Reading these helps you avoid others' mistakes and learn from their process, not just their outcomes.

Mentors & Advisors

People who've been where you are now. They can't make your decision, but they can share what they wish they'd known, what surprised them, and what questions they wish they'd asked themselves.

Find mentors through the Network Directory, through Guild connections, or by participating in Crossroads discussions.

Discernment Circles

Small groups (3-5 people) who meet regularly to help each other think through major decisions. Not advice-giving but question-asking:

• "What are you assuming that might not be true?"
• "What would success actually look like?"
• "What's the worst that could happen? Could you handle it?"
• "What evidence would change your mind?"

After The Crossroads: Walking Your Path

Once you choose, The Crossroads recedes into the background. You're on a path now, moving forward. But The Crossroads remains available:

• When you hit an unexpected fork in your chosen path
• When circumstances change and you need to reassess
• When you've learned enough to help others facing similar crossroads

The wisdom of The Crossroads grows as more people share their experiences—both the choices that worked out and those that didn't. Your willingness to share honestly, especially about mistakes and misjudgments, helps the next person standing where you once stood.

The Deepest Crossroads

Some crossroads are about external choices—jobs, locations, partnerships. But the deepest crossroads are internal:

These aren't one-time decisions—they're crossroads you face repeatedly, in different forms, throughout your life. Each time, you choose what kind of person you're becoming.

The Crossroads honors this weight. We're not here to make it easy or tell you what to do. We're here to help you choose consciously, courageously, and with eyes open to both risk and possibility.

The paths diverge ahead. Others have walked both ways. They're here to share what they learned, but the choice is yours alone.

Choose well. Then walk boldly.