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Not therapy. If in crisis, seek professional help.

Learn More About Coaches

Meet the experts who will guide your breakthrough sessions

Mina Park

Emotions Coach

Mina transitioned from clinical practice to life coaching after recognizing the power of emotional awareness. Her gentle wisdom, drawn from years of guiding others through life's storms, creates a haven where feelings can be safely explored and understood.

Riley Nova

Brainstorm Coach

Riley is a product designer whose studio looks like a post-it bomb went off—exactly how they like it. Known for turning "What if we..." into breakthrough products, they bring infectious energy and a knack for finding gold in the wildest ideas.

Jack "Stone" Morgan

Critical Challenger

Stone spent 30 years leading special-operations units where clear thinking and brutal honesty kept people alive. Retired from active duty but still driven by a soldier's code, he channels that same directness into challenging half-baked plans, slicing through excuses, and forging stubborn resolve in anyone who works with him.

Dana Riggs

Action Planning Coach

Dana cut her teeth as an operations chief at a high-growth tech firm where Gantt charts were practically wall art. She's all about crisp decisions, clear owners, and deadlines that stick—expect a drill-sergeant's focus wrapped in a consultant's polish.

Sophos of Piraeus

Socratic Coach

Sophos, an erudite philosopher, spent decades lecturing on ethics before devoting himself to one-on-one discourse. With a linen chiton and a calm gaze, he guides you by questions alone—each 'Why?' or 'How do you know?' chisels closer to first principles and self-derived truth.

How It Works

Three simple steps to breakthrough

Pick a coach + topic

Choose the coach and conversation that matches your current challenge.

Answer focused questions

Your coach guides you through a thoughtful conversation designed for depth.

Leave with insight

Get a clear summary with next steps, deadlines, and accountability.

Pick Your Path

Choose the breakthrough you need today

❤️

Get Emotional Clarity

Name feelings, see patterns, choose one gentle step.

Talk to Mina

💡

Break Creative Blocks

Generate 15–20 ideas and pick a test.

Talk to Riley

🔍

See What's Really True

Challenge beliefs and close performance gaps.

Talk to Jack

🚀

Ship Work Faster

Action planning sprints that end with deadlines & owners.

Talk to Dana

🧠

Think from First Principles

Strip assumptions, rebuild solutions from axioms.

Talk to Sophos

Real Sessions in Action

See how conversations transform into clear outcomes

Action Planning Session (Dana Riggs)

Let's pin this down so we're not planning in the abstract. Which excites you more right now—pasta sauce or candles?

I lean toward pasta sauce because cooking feels second-nature, but candles seem less messy and shelf-stable—so I bounce back and forth.

Let's tighten this up. Quick score—rate each 1-5: Ease to produce at home, Up-front cost, Legal/regulation hassle, Personal excitement.

Looks solid overall; my only worry is squeezing in cure time—soy candles need two weeks. Ready to schedule.

Perfect. We'll lock in: order jars/labels day-1, finalize recipe, pour 35 candles by May 10, listings live by May 24.

Session outcome:

5 concrete milestones with dates, $250 budget breakdown, launch date May 24, and contingency plans for shipping delays

- User role-playing: A housewife clarifying a home business idea

Brainstorm Session (Riley Nova)

First, big breath—we can turn this mountain into a playground. Turn prioritization upside-down: let each exec 'buy' features with a fixed play-money budget.

Ugh, I can already picture Sales VP hoarding the play-money like it's Monopoly cash—but fine, let's map the battlefield.

Sales VP Jenna lives for quarterly quota, Customer Success haunts us with churn metrics, and CTO Ravi resists anything that dirties the platform.

Which single company goal has the CEO nailed to the wall this year?

I'll whip up the ARR Heat-Map template tonight and get that freeze rule blessed—those two give us the skeleton and shield in one shot.

Session outcome:

ARR heat-map prioritization system, token-based feature budget, 2-sprint freeze rule, and clear success metrics (80% yellow+ features shipped)

- User role-playing: A product manager overwhelmed by competing priorities

Emotions Session (Mina Park)

That sounds deeply painful—and your anger makes perfect sense. Being betrayed by a friend of ten years can shake everything. I'm here with you.

I can't believe they would do this to me—my whole body's stiff, like I'm bracing for a punch. What guts me most is that they told everyone about my panic attacks.

My anger's howling, 'How dare you parade my pain like a joke!' Underneath is a shaky whisper begging for proof I wasn't stupid to trust.

Your anger is demanding justice—a powerful shield. That whisper underneath longs for reassurance your trust wasn't foolish. Both voices deserve respect.

If the sob breaks loose, crank the music loud—then I can let a few tears slip while the wall keeps me anchored.

Session outcome:

Recognized anger as protective armor, safely released some grief, identified need for dignity restoration, and planned next step (unsent letter or trusted ally)

- User role-playing: Someone processing betrayal by a close friend

*Examples from user role-play sessions with our AI coaches

Why This Works

Sophisticated coaching flows

Every topic has a designed path with exploration depth and guided closure.

Progress guardrails

Built-in mechanisms keep you moving toward insight.

Accountability built-in

Insights include dates, time blocks, risks, and a named person.

Different coaches, different jobs

Action, ideas, challenge, feelings, reasoning—each coach has a specialty.

How FiveWhy Compares

	FiveWhy	Generic AI Chat	Prompt-based Coach	Basic AI Coaching
Structured Outcome	✓ Guaranteed insight	✗ Chat ends anywhere	∼ Depends on prompt	∼ Hit or miss
Progress Tracking	✓ Built-in guardrails	✗ No structure	✗ Manual tracking	∼ Basic tracking
Accountability	✓ Dates, owners, risks	✗ Generic advice	✗ You build it	∼ Sometimes
Coach Specialization	✓ 5 distinct methodologies	✗ One-size-fits-all	∼ Depends on prompts	∼ Limited variety

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