Appendices and Templates

A. Five-Year Ideal Life Worksheet Guide

This worksheet helps you define the life your portfolio career is meant to support. Complete it before choosing activities, accepting roles, or building infrastructure. The goal is to describe the future in concrete language rather than vague aspiration.

Future date: Write the month and year that is five years from now.

Opening paragraph: Describe your life as if it already exists. Include where you live, what your typical week feels like, what work you do, who you spend time with, and what gives you energy.

• Geography: Where do you live, travel, work, and spend seasons?
• Compensation: What annual income, cash flow, or asset growth do you want from portfolio activities?
• Health and fitness: What does your body allow you to do? What routines support it?
• Family and friends: Who receives more of your time, attention, and presence?
• Work and contribution: What problems do you solve, for whom, and why?
• Learning and creativity: What are you studying, making, practicing, or exploring?
• Reputation: What do credible people know you for?

Ideal day: Describe a realistic day you would be happy to repeat. Include morning routine, work blocks, exercise, meals, meetings, family time, and evening recovery.

Typical month: List the recurring commitments that should appear in a satisfying month: paid work, board meetings, service, writing, travel, training, family rituals, learning, and unscheduled space.

B. Portfolio Activity Prioritization Scorecard

This scorecard helps you compare attractive portfolio activities without relying only on instinct, prestige, or immediate opportunity. Use it for consulting, board roles, coaching, teaching, investing, nonprofit work, writing, creative pursuits, and other options.

Activity name: State the activity specifically. “Consulting” is too broad. “Advise founder-led B2B services companies on operating cadence” is better.

• Motivation score: Rate from 1 to 5. Are you genuinely interested, or mainly flattered by the invitation?
• Skill fit score: Rate from 1 to 5. Do you have credible strengths for this activity?
• Relationship access score: Rate from 1 to 5. Do you know people who can help you enter or succeed?
• Economic score: Rate from 1 to 5. Does the activity support your income or financial goals?
• Impact score: Rate from 1 to 5. Does it create contributions you value?
• Learning score: Rate from 1 to 5. Will it expand your knowledge, skills, or perspective?
• Lifestyle fit score: Rate from 1 to 5. Does it fit your desired calendar, travel, and energy?
• Cost and risk score: Rate from 1 to 5, with 5 meaning low cost and manageable risk.

Decision note: After scoring, write one paragraph explaining whether the activity belongs in “now,” “next,” “later,” or “no.” The score is not the decision. It is a structured way to reveal trade-offs.

C. Tiny Experiments Design Template

A Tiny Experiment lets you test a portfolio activity before making a major commitment. Use this template when an option feels attractive but uncertain.

Experiment title: Name the test clearly, such as “Three founder coaching sessions,” “One guest lecture,” or “Paid consulting diagnostic.”

Core question: State what you are trying to learn. For example, “Will buyers pay for this advisory offer?” or “Do I enjoy teaching this audience enough to repeat it?”

• Activity: What exactly will you do?
• Duration: When does the experiment start and end?
• Audience or participants: Who is involved?
• Success evidence: What signal would justify continuing?
• Stop evidence: What signal would suggest pausing or rejecting the option?
• Time limit: How many hours will you allow?
• Cost limit: How much money, if any, will you spend?
• Reflection date: When will you review the result?

After-action reflection: Write what happened, what you learned, what energized you, what drained you, and what decision you will make next. Do not let experiments become indefinite commitments.

D. 90-Day Portfolio Career Launch Plan

The first ninety days should create momentum, evidence, and operating discipline. This plan helps you avoid spending too much time on infrastructure before testing real demand and fit.

Launch theme: Write one sentence describing the purpose of the next ninety days. For example, “Test independent advisory work while building the basic operating hub.”

• Outcome 1: Define the first concrete result, such as completing ten relationship conversations.
• Outcome 2: Define the second result, such as testing one consulting offer.
• Outcome 3: Define the third result, such as creating core collateral.
• Outcome 4: Define an optional result, such as joining a community of practice.
• Outcome 5: Define an optional personal result, such as establishing a training routine.

Setup tasks: List the infrastructure needed: accountant, attorney, entity, bank account, bookkeeping software, CRM, LinkedIn update, email address, bio, one-pager, and folder system.

Learning questions: Identify what the launch period must answer. Are buyers interested? Does the work energize you? Is your time allocation realistic? Which relationships are most helpful?

Review cadence: Schedule a weekly review and a final ninety-day reset. The reset should produce a revised “now, next, later” portfolio.

E. LinkedIn Profile Checklist

Your LinkedIn profile should make the portfolio career easy to understand. It should show where you came from, what you do now, and how others can engage you.

• Headline: Does it state your current professional identity, target audience, and expertise?
• About section: Does it begin with your current focus rather than only your past career?
• Prior role: Have you added an end date to your former full-time position?
• New entity or role: Have you added your advisory practice, portfolio role, or new platform?
• Experience entries: Do they emphasize outcomes, expertise, and relevance?
• Featured section: Have you included articles, talks, guides, videos, or proof assets?
• Contact details: Can the right people reach you through an appropriate channel?
• Activity signals: Do recent posts, comments, and shared items reinforce your desired positioning?

Profile test: Ask a trusted colleague to read your profile for thirty seconds and explain what they think you do now. If they cannot explain it clearly, revise.
  

F. Portfolio Collateral Checklist

Collateral helps relationships convert into opportunities. Keep a small, current set of materials ready so you can respond quickly and professionally.

• Short bio: A 100- to 150-word version for introductions, events, podcasts, and newsletters.
• Long bio: A 300- to 500-word version for speaking, academic, board, or advisory contexts.
• Resume: A current document that includes professional history, board roles, education, and selected accomplishments.
• Project list: Sanitized examples of representative work, organized by problem type or sector.
• One-pager: A concise overview of your advisory, consulting, speaking, coaching, or board value proposition.
• Headshot: A professional photo suitable for event pages, bios, and media use.
• Speaker assets: Topic list, sample titles, prior talks, and video clips if available.
• Proof assets: Articles, podcasts, videos, case examples, testimonials, or public resources.

Version control: Store editable and PDF versions in a clean folder system. Use file names with document type, your name, and date. Archive outdated materials rather than letting multiple “final” versions circulate.

G. Personal CRM Setup Checklist

A personal CRM helps you remember conversations, track opportunities, and follow up reliably. Set it up before the relationship system becomes too complex for memory or spreadsheets.

• Tool choice: Choose a lightweight CRM such as HubSpot, Pipedrive, or another tool you will actually use.
• Email integration: Connect email if appropriate so conversations can be logged efficiently.
• Calendar integration: Connect calendar if it helps capture meetings and reminders.
• Contact import: Add priority contacts first rather than importing every address you have.
• Company records: Add organizations connected to clients, boards, investors, nonprofits, and communities.
• Pipeline setup: Create one simple opportunity pipeline before adding complexity.
• Task reminders: Use reminders for every important next action.
• Weekly review: Schedule a recurring CRM review to update notes, move opportunities, and close stale items.

Minimum habit: After every meaningful conversation, add a note, capture the next action, and set a follow-up date before moving on.

H. Sample CRM Fields and Pipeline Stages

A CRM works best when fields are useful but not excessive. Begin with a simple structure and add detail only when repeated use proves it is necessary.

Sample contact fields:

• Relationship category: Client, former colleague, board contact, investor, founder, nonprofit leader, academic, media contact, peer, or friend.
• Priority level: High, medium, or low based on relevance and relationship strength.
• Portfolio relevance: Consulting, board, speaking, teaching, investing, service, writing, community, or personal.
• Relationship source: How you met or who introduced you.
• Last contact date: The date of the most recent meaningful interaction.
• Next action date: The date you plan to follow up.
• Personal notes: Appropriate details that help you be thoughtful and human.

Sample pipeline stages:

• Identified: Opportunity noticed but not yet qualified.
• Introduction requested: Waiting for or pursuing a warm introduction.
• Conversation scheduled: First discussion is on the calendar.
• Needs discussed: Problem, buyer, urgency, and fit have been explored.
• Proposal or next step: A concrete follow-up, scope, or decision is pending.
• Active: Work, role, or commitment is underway.
• Nurture: Not active now but worth future follow-up.
• Closed: Opportunity completed, declined, lost, or no longer relevant.
  
  

I. Contract Review Checklist

This checklist helps you slow down before signing agreements. It does not replace legal advice, but it helps you identify issues to discuss with counsel.

• Parties: Are the correct legal names used for you, your entity, and the client?
• Scope: Is the work clearly defined, including what is excluded?
• Deliverables: Are outputs, formats, deadlines, and assumptions stated?
• Fees: Are pricing, payment timing, retainers, expenses, and taxes clear?
• Availability: Are meetings, response times, travel, and access expectations bounded?
• Confidentiality: Are obligations reasonable, clear, and consistent with your other commitments?
• Conflicts: Are restrictions on other clients, sectors, or roles acceptable?
• Intellectual property: Is your background IP protected?
• Liability: Are indemnities, warranties, caps, and exclusions reviewed?
• Termination: Can either party end the relationship under clear conditions?

Escalation rule: Ask an attorney to review any agreement involving meaningful fees, equity, board duties, regulated industries, unusual liability, restrictive covenants, or unclear ownership of work product.

J. Weekly Relationship Cadence Template

The weekly relationship cadence turns networking into thoughtful relationship stewardship. Use it as a recurring operating habit, not as a sales sprint.

Weekly review block: Schedule sixty to ninety minutes each week. Protect this time as part of the portfolio operating model.

• Review recent conversations: Add notes, commitments, and next actions to the CRM.
• Check overdue follow-ups: Send promised notes, resources, introductions, or thank-yous.
• Advance open opportunities: Move active items to the correct stage and define the next step.
• Reconnect with priority relationships: Choose three to five people for thoughtful outreach.
• Make useful introductions: Connect people when there is clear mutual value.
• Share useful material: Send an article, event, idea, or resource that fits the recipient’s interests.
• Update newsletter ideas: Capture themes, questions, or observations that may become a future update.
• Close stale items: Remove or archive opportunities that no longer deserve attention.

Weekly reflection: End by asking what relationship work created energy, what felt transactional, and which relationships deserve more deliberate attention. A strong portfolio career grows through trust, and trust grows through repeated, thoughtful contact over time.