Self-Observation Discovering and Living Your Deepest Gifts Page 1

Self-Observation: Discovering and Living Your Deepest

Gifts
This is a multi-hour exercise. Work through this exercise once a month for 3 months.
Each time you do this exercise add more milestones to your lifeline as you remember
them and try to find answers to the questions from deeper inside you.

Part 1: The Past

Complete this inventory through observation and research. Stay focused on what you
have experienced in life. Don’t slip in to fantasy or life design.

1. Construct a lifeline of “important milestones” (e.g. family events, school,

relationships, conflicts, achievements, memorable moments, synchronicities,
funny things, major events, etc.) in your life. On your first pass through this
exercise name no more than 4 milestones per year to keep things simple.
Don’t sweat it if nothing comes to mind for a given year. If you can’t recall
exactly when a milestone occurred, estimate the year. Don’t sweat it. The
effectiveness of this exercise doesn’t depend on precise dates. E.g.,
a. 1980
i. milestone 1 - what happened?
ii. milestone 2 - what happened?
iii. milestone 3 - what happened?
b. 1982
i. milestone 1 - what happened?
2. As you reflect on your life, what were the things that came easily and
naturally for you? What were the things that were hardest for you? Notice any
patterns.
3. Where were the moments of greatest joy? Deepest respect? Heartfelt love,
appreciation, and gratitude? Deepest fulfillment? Notice any patterns.
4. What obstacles have you overcome in relationships with others and the world?
What obstacles have you created in relationships with others and the world?
Notice any patterns.
5. What have you left incomplete? Notice any patterns.
6. What are the fears, frustrations, problems, worries, regrets, and needs that you
empathize with most? What actions have you taken to alleviate these in
yourself and others?
7. When were you most passive? Most proactive? Notice any patterns.
8. When did you most allow natural unfoldment? When did you most try to fight
and control what was happening to you? If you can recall, what were you
feeling at the time? Notice any patterns.
9. From your life experiences, what have you earned the right to do or to talk
about as an expert?

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Self-Observation Discovering and Living Your Deepest Gifts Page 2

10. What does your experience position you to offer to others right now (without
any further preparation or study)? What ways are open to you? What ways are
closed to you?
11. Often people wait for something specific to be done or be different in some
fundamental way before following their life’s passion. What are you waiting
on?
12. Where does your deepest gladness meet the world’s deep need?
13. What else are you learning about yourself in this exercise?

Part 2: The Future

1. What actions will you take from what you are learning/observing?
2. What relationships (or types of relationships) will you build or strengthen?
3. How do you want to be known by others?
4. What do you want to learn more about?
5. What are the contributions that you want to be sure you make with your life?
To whom? When?
6. What are your plans for the …?
a. Next year?
b. Next five years?
c. Next ten years?
d. Next fifteen years?
e. Next twenty years?
7. What processes, procedures, routines, resources, and tools will you need to
follow your plans?
14. What resources can you draw on in life? Money, relationships, tools,
equipment, education, experience? Be as exact in quantity and quality as you
can.
8. How will you allot the 168 hours (7 days * 24 hours/day) each week to life in
accordance with your life design?
9. How will you adapt your life design to respond to what is happening in your
life moment by moment, day by day, week by week, month by month, year by
year?

Part 3: The Present

1. What are your current, unresolved breakdowns in life? Where are you failing
to meet your commitments to yourself and others critical to your life design?
Where are you stuck?
2. What are you doing to learn from these breakdowns and feelings of being
stuck?
3. What action are you taking?
4. Who is supporting you right now?
5. What is your overall mood?

Compassionate Coaching
rd
527 23 Avenue Suite 212 • Oakland, CA 94606
http://www.compassionate-coaching.com