Trusted Circles

Workshop
Assessments

Structured self-reflection tools designed for Trusted Circles sessions. Complete before your meeting to surface the conversations that matter most.

10 Assessments · 15–25 minutes each · Printable results

All Assessments
00
Ikigai — Purpose Discovery
"Why do you get up in the morning?"
Passion Mission Vocation Purpose
01
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Post-Exit Identity
"Who are you when the company is gone?"
Identity Purpose Transition
02
Family Wealth Conversations
"Are you ready for the hardest conversations?"
Family Communication Dynamics
03
Philanthropic Clarity
"Is your giving as intentional as your investing?"
Giving Impact Strategy
04
Investor Self-Knowledge
"Do you know how you actually make decisions?"
Behavior Bias Psychology
05
Work-Life Architecture
"Is the life you've built the life you chose?"
Time Energy Design
06
Next Chapter Planning
"What does a great decade look like from here?"
Retirement Transition Vision
07
Risk Architecture
"Is your portfolio built for the life you want?"
Concentration Liquidity Tail Risk
08
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Wealth & Identity
"What does money mean to you — really?"
Psychology Identity Relationships
09
Legacy & Estate Readiness
"Have you done the hard parts of estate planning?"
Estate Legacy Family
+
Raising Financially Grounded Children
"Are you preparing your children — or protecting them from reality?"
Parenting Education Values

Designed for your Circle

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

Complete an assessment before your session. Bring your results. Use the discussion prompts to go deeper than you would otherwise.

How to use them

  • 1Choose the assessment 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.
  • 4Use the built-in discussion prompts to open the conversation.