Design thinking for life

Why: This book provides the foundational framework of applying design thinking to life and career choices.

How:

• Focus on the chapters regarding 'Wayfinding' and 'Odyssey Planning'.
• Take notes on the 'Gravity Problems' concept to avoid wasting energy on unchangeable facts.
• Use the 'Workview' and 'Lifeview' exercises as your primary compass.

Done when: Book read and core principles summarized in your notes.

Why: To visualize where your life is currently out of balance before making major changes.

How:

• Draw four gauges representing Health, Work, Play, and Love.
• Mark each from 0 to 100% full based on your current satisfaction.
• Write one sentence for each explaining why it is at that level.

Done when: A completed visual dashboard with four marked gauges and brief explanations.

Why: To define what work means to you and what its purpose is in your life.

How:

• Answer: Why work? What’s work for? What defines good or worthwhile work?
• Focus on your philosophy of work, not just your current job description.
• Keep it under one page to ensure clarity.

Done when: A written statement of approximately 250 words reflecting your work philosophy.

Why: To clarify your core values and what gives your life meaning.

How:

• Answer: Why are we here? What is the meaning of life? What is the role of others in your life?
• Reflect on your personal beliefs and worldview.
• Ensure it is distinct from your Workview but potentially complementary.

Done when: A written statement of approximately 250 words reflecting your life philosophy.

Why: To ensure your career goals don't conflict with your personal values, creating 'Coherency'.

How:

• Read both statements side-by-side.
• Identify where they complement each other and where they clash.
• Adjust your statements until you feel they represent a unified 'you'.

Done when: A short paragraph describing the alignment or necessary adjustments between the two views.

Why: To identify which specific activities in your current life drain you and which energize you.

How:

• Record daily activities for one week.
• Rate each activity on a scale of 1-10 for 'Engagement' and 'Energy'.
• Note 'Flow' states—times when you lost track of time because you were so involved.

Done when: A completed 7-day log with at least 5 entries per day.

Why: To stop wasting time trying to solve things that are actually 'circumstances' (like the economy or your age).

How:

• List all the things currently frustrating you in your career.
• Circle the ones you cannot change through individual action.
• Reframe these as 'facts of life' to be navigated rather than problems to be solved.

Done when: A list of 3-5 'Gravity Problems' that you commit to accepting.

Why: To find patterns and creative connections between the things that energize you.

How:

• Put a high-energy activity in the center of a page.
• Branch out with related concepts, tools, and environments.
• Create three separate mind maps for your top three energizing activities.

Done when: Three distinct mind maps showing potential career directions.

Why: To visualize where your life is headed if you continue on your current trajectory.

How:

• Map out the next 5 years of your current career/life.
• Include professional milestones and personal goals.
• Give this plan a descriptive title.

Done when: A 5-year timeline for your current path.

Why: To explore what you would do if your current career path suddenly became unavailable.

How:

• Imagine your current industry disappears.
• Map out a 5-year plan for your 'Plan B'.
• Focus on transferable skills identified in your mind maps.

Done when: A 5-year timeline for a realistic alternative path.

Why: To explore what you would do if money and image were no object.

How:

• Map out a 5-year plan for your most 'daring' or 'crazy' idea.
• Don't censor yourself; focus on pure interest and joy.
• Give this plan a bold title.

Done when: A 5-year timeline for your 'Wild Card' path.

Why: To objectively evaluate which path is most viable and exciting.

How:

• Rate each plan (1-10) on: Resources (Do you have what you need?), Likability (Do you want it?), Confidence (Can you do it?), and Coherence (Does it fit your Work/Lifeview?).
• Identify which plan has the highest overall score.

Done when: A completed ranking table for all three Odyssey Plans.

Why: To turn vague curiosity into specific questions that can be answered through action.

How:

• Example: 'What is the daily reality of a freelance UX designer?'
• Example: 'Can I earn a living doing X while living in Y?'
• Ensure questions are open-ended and testable.

Done when: A list of 5 specific questions you need to answer to validate your plan.

Why: To find people who are already living the life you are curious about.

How:

• Use LinkedIn to find people in your target roles or industries.
• Look for 2nd-degree connections or alumni from your school.
• Focus on people who have made a similar transition.

Done when: A list of 10 names, their current roles, and why you want to talk to them.

Why: To lower the barrier to reaching out and ensure a professional first impression.

How:

• Keep it short: 3-4 sentences.
• Mention how you found them and why their specific path is interesting.
• Ask for a '15-minute virtual coffee' to hear their story, not to ask for a job.

Done when: A reusable template for email or LinkedIn outreach.

Why: To move from theory to real-world data collection.

How:

• Send out your outreach script to at least 5 people from your list.
• Aim to book three 20-minute slots.
• Use a scheduling tool to minimize back-and-forth emails.

Done when: Three confirmed calendar invites for informational interviews.

Why: To immerse yourself in a new professional environment and meet people organically.

How:

• Find a coworking space or industry-specific hub in your area.
• Book a day pass or attend an open event.
• Aim to have at least one spontaneous conversation about your career transition.

Done when: A physical visit completed and one new contact made.

Why: To gather 'insider' knowledge that isn't available in job descriptions.

How:

• Ask: 'What is a typical day like?' and 'What was the most surprising thing about this role?'
• Do not ask for a job; ask for advice and other people you should talk to.
• Take notes immediately after the call.

Done when: A one-page summary of the interview and one new referral name.

Why: To compare different perspectives within the same industry or role.

How:

• Use the same core questions as Interview #1 for consistency.
• Look for conflicting information—this is where the real 'nuance' lies.
• Ask about the 'unwritten rules' of the industry.

Done when: A one-page summary and comparison with Interview #1.

Why: To reach a 'saturation point' where you start hearing similar themes.

How:

• Focus on the 'Prototype Questions' you drafted in the Preparation phase.
• Ask for a specific recommendation for a 'small bet' (e.g., a specific course or project).
• Thank the person and offer to help them in the future.

Done when: A one-page summary and a clear idea for a 'Small Bet' project.

Why: To test your actual interest and skill in a low-risk environment.

How:

• Choose a short course (e.g., on Coursera, edX, or Udemy) or a weekend volunteer project.
• Spend at least 10 hours actively doing the work, not just watching videos.
• Evaluate if the 'doing' matches your 'imagining'.

Done when: Completion certificate or a finished project artifact.

Why: To signal your new direction to your network and recruiters.

How:

• Rewrite your headline to include keywords from your target industry.
• Update your 'About' section to tell a story of transition and transferable skills.
• Add the 'Small Bet' project or course to your profile.

Done when: A refreshed LinkedIn profile that reflects your new Odyssey Plan.

Why: To maintain your new network and show that you valued their time.

How:

• Send these to your interview partners.
• Mention one specific piece of advice you have already acted upon.
• Keep the door open for future updates.

Done when: Three sent emails or LinkedIn messages.

Why: To decide which path to commit to based on real data rather than assumptions.

How:

• Review your interview notes and 'Small Bet' experience.
• Re-rank your Odyssey Plans using the same metrics (Resources, Likability, etc.).
• Notice if your 'Wild Card' has become more realistic or if your 'Current Path' has lost appeal.

Done when: A final decision on which path to pursue for the next 6-12 months.

Why: To ensure you have accountability and diverse perspectives as you implement your change.

How:

• Identify 3-5 friends, mentors, or peers who are supportive but honest.
• Ask them if they would be willing to meet once a month for a 'Life Design' check-in.
• Share your chosen Odyssey Plan with them.

Done when: A confirmed group of 3-5 people and a scheduled first meeting.

Why: To reframe setbacks as data points rather than personal failures.

How:

• Write down 3 potential 'failures' that could happen in your new path.
• For each, write down what you would learn and how you would pivot.
• Practice the 'Fail Fast, Fail Forward' mantra.

Done when: A written 'Failure Plan' for your top 3 risks.

Why: To ensure you don't fall back into 'autopilot' and continue to iterate on your life.

How:

• Set a recurring 2-hour appointment every 3 months.
• Use this time to update your Health/Work/Play/Love dashboard.
• Adjust your Odyssey Plan based on the previous quarter's experiences.

Done when: A recurring calendar event for the next 12 months.