Activity Set: Lollipop Moments

Activity Set: Lollipop Moments

Lollipop Moments: Quick Overview

Part 1: Lollipop Moments

  • Description: Reflect to see how you’ve helped others in the past.
  • Life Work Activity: List at least 15 times you’ve helped/served others.



Part 1: Lollipop Moments (Based on TED talk Lollipop Moments/Everyday Leadership by Drew Dudley –

This activity focuses on the impactful, positive moments you’ve had on other people.  The Drew Dudley TED Talk is useful in helping you identify life-changing moments, moments where you’ve performed good service to others – whether for one person or 100 people.  We have found that your impactful moments may hold key information to your purpose, mission, meaningful work, and legacy.  This activity will have you identify and write down at least fifteen (15) lollipop moments in your life where you made a positive impact on others.  You may have to stretch to come up with 15 but think hard about the times when you’ve helped others in a positive way.  If you run out of things to list, ask your family, friends, and others that know you for times when/how you’ve helped them for the better.  Note: For this activity, you will focus on the times when you’ve helped others, not when others have helped you.

  • You did or learned something that you were truly interested in/passionate about and shared it with others.
  • You did something where you impacted the life of at least one other person.
  • You were able to overcome a big problem or huge challenge and it inspired others.
  • You did something where you helped a group of people through community service, volunteer work, etc.
  • You were able to help someone else or a group of people solve a problem, get through a tough time, or overcome a challenge.
  • You taught something meaningful/useful to someone else or a group of people.
  • You extended a helping hand to someone in need or less fortunate.
  • You spoke up about or defended someone about an injustice in the world.
  • Others call you about a particular thing (or several things) to get your advice or counsel.
  • You use a specific skill(s), knowledge(s), value(s) or talent(s) to help others be successful.
  • You were engaged in activities when you were in the flow, where time stood still, or when you felt most fulfilled, and it benefited others.
  • You stood for something that was larger than yourself.
  • Specific random acts of kindness/pay it forward activities that made an impact on at least one other person.
  • You were in a job where you’ve impacted clients, customers, colleagues, and/or supervisors in a positive way.
  • You shared information (internet, text, tweet, etc.) with at least one other that made a positive impact – can be big or small.
  • Or anything else you’ve done where you’ve helped others, served others, or made a difference in the life of at least one other person.

As you list your fifteen (or more) lollipop moments, you may also want to write a short sentence that describes how and/or why it made an impact.  Remember, your lollipop moments can be big events or small gestures, it doesn’t matter.  Once you’ve created your list of lollipop moments, review your list and see if you can come up with a theme that describes your help, “To ____________ so that __________.”  The first part of the sentence defines the action part of your contribution – what it is that you do; the second part defines your impact – the result of your action.  If you don’t know what to write, ask for help from someone else – your roommate, a classmate, a spouse, a family member, or friend, etc.  Sometimes, an outside pair of eyes can be useful to see things you might not be able to see.  This activity can help you notice patterns in your experiences – something more than just “helping others.”   How were you helping others?  What was similar in the experiences?  Were there certain issues, situations, and/or problems that you’re drawn to?  Are there specific talents, gifts, strengths, and/or skills that you tend to use more than others, like listening?  Is there a specific population that you seem to help more than others?

Lollipop Moment examples might include some of the following:

  • Mission trips due to disasters, epidemics, helping others in need.
  • Community service activities, such as cleaning up a park, habitat for humanity.
  • Volunteer services, such as food bank, ASPCA, Special Olympics.
  • Captain or coach (or some other leadership position) of sports team/activity.
  • President (or other leadership position) in student group/organization.
  • Inspiring articles, poems, blogs written and/or published.
  • Significant involvement or leadership positions in religious group/organization, such as group leader.
  • Things you organized so that others could participate/be successful.
  • Individuals/groups you’ve led to achieve something greater.
  • Activities you’ve participated in where you helped the group be successful in completing the activity.
  • Presentation/speeches given, workshops/training facilitated, classes taught, debates successfully argued.
  • Performances you have given, such as through music, choir, dance or theater.
  • Art you’ve created that was shared/shown to others.
  • Times when you’ve helped a friend grieve over loss of a family member, friend, pet, etc.
  • Inspiring and helping others pursue and achieve goals and dreams.
  • Impacting others (siblings, friends, parents, other kids and adults) by being a role model.
  • Jobs where you’ve helped/impacted/changed the lives of others
  • Experiences where you’ve helped others succeed in school, such as tutoring, teaching, or mentoring.
  • Involvement in activities such as Boy Scouts and Girl Scouts.
  • Helped a friend get through depression or keep them from attempting suicide.
  • Experienced trauma in your own life and passed on that wisdom to others, such as a break-up.
  • You received an award/recognition for doing a good deed, being kind, etc.

And if it helps, here are a few examples of Lollipop Moments from Bill’s life:

  1. Served as unofficial “captain” in neighborhood of childhood friends against other neighborhood teams.
  2. Served as “Dungeon Master” for many D & D adventures with friends in high school/college.
  3. Served as a personal trainer to help people lose weight and become physically fit.
  4. Led many different groups of riders to complete Multiple Sclerosis Bike Tours rides.
  5. Developed and taught personal growth/self-help exercises and activities for students in various classes.
  6. Presented personal growth/self-help workshops for various on-campus units, i.e. residence life, campus activities, academic departments, leadership and service learning, etc.
  7. Presented personal growth/self-help workshops for international and national organizations, community organizations, and professional organizations.
  8. Created and facilitated Purpose and Vision Navigator Coach Training Program (now called Life Design Catalyst Coach Training Program) for students, faculty, and staff in higher education.
  9. Coached friends and colleagues at institutions I’ve worked at to find their purpose and/or pursue their dreams.
  10. Coach/support my daughters Amanda (sophomore in college) and Bethany (11th grade in high school) as they navigate their paths/directions in life.
  11. Support my wife Rebecca as she continues to develop and grow her art/craft business.
  12. I’m in the “flow” when I’m presenting workshops on self-help/personal growth to others, especially Life Design Catalyst Training Program.
  13. Inspire others by sharing my challenges in college and in life, such as poor SAT scores, poor grades, low graduation ranking, homelessness, physical and sexual abuse, and the death of both parents.
  14. Support charities such as Multiple Sclerosis, American Cancer Society, American Heart Association, and Make a Wish Foundation, especially when they involve fitness/exercise challenges.
  15. Received Golden Key International Advisor of the Year Award in 2004 – and realized how my work really impacted students in a positive way.
  16. Search as life coach for participants in UNCG’s Rites of Passage Minority Male Mentoring Program.
  17. Serve as mentor and confidant to students, staff, faculty, and PVN/LDC colleagues.
  18. Served in various leadership positions in professional organizations, such as the National Academic Advising Association and On Course.
  19. Serve as a comforting soul for people who’ve lost both parents in a short period of time.
  20. Created The Dream Dean blog to share free information on becoming self-experts and personal development resources with others.
  21. Served in various positions in higher education, which has provided me opportunities to serve tens of thousands of students in a positive way for over 27+ years.

Bill’s Statement: “To lead/empower individuals and groups to achieve more than they ever thought possible.”

Again, come up with a statement that describes how you help others, using the template: “To __________ so that __________” to define your lollipop moments in one sentence.  Remember, the first part “To _____” identifies the action and contribution; the second part “so that _____” identifies impact or change.