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Trusted Circles

Modules &
Reflections

Structured self-reflection tools designed for Trusted Circles sessions. Complete before your meeting, or use the moderator discussion guide to explore these topics live.

22 Reflections · 15–25 minutes each · Printable results · Discussion guides included

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Showing all 22 reflections
All Reflections
00
Ikigai — Purpose Discovery
"Why do you get up in the morning?"

Guides members through the Japanese framework of Ikigai — mapping the intersection of what you love, what you're good at, what the world needs, and what you can be rewarded for — to surface a personal purpose statement.

Expected Insights

Clarity on which quadrants of purpose are strongest and which are underdeveloped. A draft purpose statement. Awareness of where passion and livelihood diverge or align.

Purpose Passion Mission Vocation
01
Post-Exit Identity
"Who are you when the company is gone?"

Helps members who have sold a business or stepped away from a defining role examine how deeply their identity was tied to that role — and what comes next.

Expected Insights

A map of identity anchors beyond professional titles. Awareness of grief patterns around exits. Concrete ideas for rebuilding purpose and daily structure.

Identity Purpose Transition
02
Family Wealth Conversations
"Are you ready for the hardest conversations?"

Assesses a member's readiness to have transparent conversations with family about money — covering disclosure levels, emotional preparedness, and structural planning for intergenerational wealth.

Expected Insights

Identification of conversation gaps within the family. A readiness score for key wealth discussions. Awareness of avoidance patterns and emotional triggers around money talks.

Family Communication Dynamics
03
Philanthropic Clarity
"Is your giving as intentional as your investing?"

Evaluates the intentionality and structure behind a member's charitable giving — from ad hoc donations to strategic philanthropy — and whether giving aligns with personal values.

Expected Insights

A giving intentionality score. Clarity on whether philanthropy is reactive or strategic. Ideas for structuring giving through vehicles like DAFs, family foundations, or impact investing.

Giving Impact Strategy
04
Investor Self-Knowledge
"Do you know how you actually make decisions?"

Uncovers the behavioral patterns, cognitive biases, and emotional triggers that shape a member's investment decisions — moving from instinct to intentional decision-making.

Expected Insights

Identification of dominant investor biases (recency, anchoring, loss aversion). Awareness of emotional vs. analytical decision triggers. A personal investor behavioral profile.

Behavior Bias Psychology
05
Work-Life Architecture
"Is the life you've built the life you chose?"

Examines how members allocate their time and energy across work, family, health, and personal interests — distinguishing between the life they have and the life they want.

Expected Insights

A gap analysis between current time allocation and desired allocation. Identification of energy drains vs. energy sources. A redesign blueprint for the next quarter.

Time Energy Design
06
Next Chapter Planning
"What does a great decade look like from here?"

Helps members approaching or navigating a major life transition — retirement, second career, relocation — build a concrete vision for the next phase rather than drifting into it.

Expected Insights

A vision statement for the next 5–10 years. Identification of fears and excitement around transition. Concrete first steps and accountability commitments.

Retirement Transition Vision
07
Risk Architecture
"Is your portfolio built for the life you want?"

Evaluates whether a member's financial risk profile actually matches their life goals, liquidity needs, and emotional tolerance — beyond what a standard risk questionnaire captures.

Expected Insights

Awareness of concentration risk and liquidity gaps. Alignment (or misalignment) between stated risk tolerance and actual portfolio behavior. A personalized risk architecture map.

Concentration Liquidity Tail Risk
08
Wealth & Identity
"What does money mean to you — really?"

Explores the psychological relationship between a member and their wealth — how money shapes self-perception, relationships, and daily decisions in ways that often go unexamined.

Expected Insights

A wealth identity profile (steward, builder, protector, etc.). Awareness of money scripts inherited from family. Clarity on how wealth affects relationships and self-worth.

Psychology Identity Relationships
09
Legacy & Estate Readiness
"Have you done the hard parts of estate planning?"

Goes beyond checking if documents are in order — assesses whether a member has had the difficult conversations, made the values-based decisions, and prepared heirs emotionally for wealth transfer.

Expected Insights

A readiness score across legal, emotional, and relational dimensions of estate planning. Identification of the conversations you've been avoiding. Clarity on legacy intentions vs. current plan.

Estate Legacy Family
10
The Centenarian Letter
"A letter from your 100-year-old self — back to you, today."

An imaginative exercise where members write a letter from their future 100-year-old self, gaining perspective on what truly matters, what regrets to avoid, and what to prioritize now.

Expected Insights

Perspective shift on current worries vs. long-term regrets. Identification of what your future self would urge you to change. A personal compass for decision-making rooted in end-of-life clarity.

Regret Legacy Clarity Purpose
11
The Decade Map
"A walk through your life, decade by decade — past and future."

Takes members on a structured journey through their life in ten-year increments — reflecting on defining moments, relationships, and lessons — then projecting that arc forward intentionally.

Expected Insights

A narrative arc of life themes and turning points. Patterns in what brings fulfillment vs. regret. A deliberate vision for the decades ahead based on lived experience.

Life Arc Reflection Design Legacy
12
Wealth, Values & Children
"What do you want money to do for your children — and what values alongside it?"

Examines the tension between providing financial security for children and instilling the values, work ethic, and resilience that wealth can sometimes erode.

Expected Insights

Clarity on inheritance philosophy (how much, when, under what conditions). Alignment between stated values and financial structures. A framework for age-appropriate wealth education.

Trusts Inheritance Values Letter of Intent
13
The Values Inventory
"Sort, test, and own the values you actually live by."

Moves beyond aspirational values to identify the values members actually live by — through a structured sorting, ranking, and stress-testing exercise that reveals alignment gaps.

Expected Insights

A ranked list of core values with evidence of how they show up in daily life. Identification of values conflicts and trade-offs. Awareness of gaps between espoused and enacted values.

Values Alignment Identity Commitments
14
Relationship Capital
"Who really has your back — and whose back do you have?"

Audits the depth and quality of a member's personal and professional relationships — revealing over-reliance on transactional connections and under-investment in meaningful ones.

Expected Insights

A relationship portfolio map showing depth vs. breadth. Identification of neglected relationships and over-indexed ones. Concrete steps to deepen the connections that matter most.

Relationships Community Networking
15
Time & Energy Allocation
"Where does your week actually go?"

A granular audit of how members spend their time and energy week to week — distinguishing between obligation, habit, and choice — to identify where reclaimed hours could transform quality of life.

Expected Insights

A time audit revealing the gap between perceived and actual allocation. Identification of energy-draining obligations that could be delegated or eliminated. A redesigned ideal week template.

Time Energy Balance
16
Partnership Audit
"Is this partnership still serving both of you?"

Evaluates the health of a member's key partnerships — business, spousal, or co-investor — across dimensions of trust, alignment, communication, and shared vision.

Expected Insights

A partnership health score across trust, vision alignment, and communication quality. Identification of unspoken tensions or role drift. A framework for re-negotiating partnership terms.

Partnerships Trust Communication
17
Health & Longevity
"Are you building a body that lasts as long as your wealth?"

Assesses whether members are investing in their health with the same rigor they apply to their finances — covering physical health, mental wellness, preventive care, and longevity habits.

Expected Insights

A health investment score comparing financial planning rigor to health planning rigor. Identification of blind spots in preventive care. A personalized longevity action plan.

Health Longevity Wellbeing
18
Continuity Blueprint
"If you were gone tomorrow, would everything hold together?"

Stress-tests whether a member's financial, legal, and family systems would function if they were suddenly incapacitated — exposing single points of failure in their life infrastructure.

Expected Insights

A continuity readiness score across financial, legal, digital, and relational dimensions. Identification of single points of failure. A priority checklist for closing critical gaps.

Continuity Planning Risk
19
Opportunity Cost
"What are you saying no to — without realizing it?"

Helps members examine the hidden costs of their current commitments — every yes is a no to something else — revealing where time, capital, and energy are being silently consumed.

Expected Insights

A map of current commitments and their hidden opportunity costs. Awareness of sunk cost traps. A framework for evaluating new opportunities against what must be released.

Opportunity Strategy Investing
20
Scenario Planning
"What would you do if everything changed overnight?"

Walks members through multiple life and market scenarios — market crash, health crisis, family emergency, windfall — to test the resilience of their current plans and emotional preparedness.

Expected Insights

Clarity on which scenarios you're prepared for and which would destabilize you. A stress-tested financial and emotional resilience profile. Contingency plans for the three most likely disruptions.

Scenarios Risk Planning
+
Raising Financially Grounded Children
"Are you preparing your children — or protecting them from reality?"

Assesses a member's approach to raising children who understand money, value work, and develop resilience — without the entitlement or detachment that wealth can inadvertently create.

Expected Insights

A parenting-wealth alignment score. Awareness of which financial lessons are being taught implicitly vs. explicitly. Age-appropriate strategies for building financial literacy and character.

Parenting Education Values

Designed for your Circle

These reflections are preparation tools — not tests. Each one surfaces language and insight around topics that are rarely discussed openly, even among people who know each other well.

Complete a reflection before your session, or use the Moderator Discussion Guide to explore the topic live during your meeting when members haven't completed the reflection in advance.

How to use them

  • 1Choose the reflection most relevant to your current moment or your Circle's agenda.
  • 2Complete it privately — answer honestly, not how you think you should.
  • 3Print or save your results to bring to your session.
  • 4Or use the Discussion Guide for a live, moderator-led conversation.