A boy and his mom on a mission for good...


In September 2014, 11 year-old Jaden Winn and his mother, Amanda Winn, set out on a “voluntourism” adventure across the United States, where they took Life Vest Inside’s vision of sharing meaningful and tangible acts of kindness and compassion out on the road for a whole year.

They carried the powerful message of the Life Vest Inside mission within the communities of each city they visited and engaged them in conversations and activities to inspire greater kindness and compassion in the world. Their intention was to encourage those they met along their journey to join the #kindnessmovement and to help raise awareness and funding for Life Vest Inside.

Jaden became Life Vest Inside’s youngest Kindness Ambassador during the year-long US tour and he spoke to kids about what The Kindness Journey meant to him personally and how kids can inspire meaningful change in the world.

Amanda was proud to officially step into the role as a Life Vest Inside Kindness Activist, where she focused her social giving efforts in meeting with School Administrators, Teachers and Parent Activists about the value and benefits of the Life Vest Inside’s Kindness Curriculum and especially how participating in giving-forward programs with her son have enriched their relationship.

See the Journey!




Kindness breaks down the barriers that all too often keep us apart. Kindness goes both
ways equally – to the giver and the receiver. Kindness is good for your whole being and
makes for healthy, happy people, families and communities.

Early on in 2014, before having the idea for the Kindness Journey, Amanda had woken up in the middle of the night and couldn’t go back to sleep. She laid there wide awake thinking about the life that was unfolding for her and her son and then something pretty magical happened: she dared to ask this life altering question, “IS THIS MY LIFE I’M LIVING?” and “Does the way we live, provide the kind of example that I’d most like to set for my son?”

After getting clear NO’s to both questions, she laid there for the rest of that night and
pondered what she might do to completely rewrite the story, so that for at least some
period of time they could have the experience of what it would be like to just say YES
and put the status quo on pause. The Kindness Journey was their conscious choice to live a life of giving back.

Jaden and Amanda decided it was time to take the focus off of themselves and look out to the world around them to learn about others, to learn about themselves, their values and the great difference that can be created by simply giving.


See where they went!



  1. Missoula, Montana – September 15th – October 15th
  2. Boulder, Colorado – October 26th – November 30th
  3. Miami, Florida – December 1st – December 15th
  4. Santa Fe, New Mexico – December 18th – January 15th
  5. Austin, Texas – January 15th – February 15th
  6. New Orleans, Louisiana – February 15th through March 15th
  7. Atlanta, Georgia – April 5th – May 3rd
  8. Chicago, Illinois – May 5th – June 5th
  9. Philadelphia, Pennsylvania – June 5th – June 30th
  10. Washington DC – July 1st – August 4th
  11. New York, New York – August 4th – August 26th


How the journey began...

meet-jaden “Kindness isn’t about how old or young you
are but by the contribution you have made. When
you are seven years old you can participate in the
same kindness movement as a seventy year old.
Kindness acts are easy for kids to complete be-
cause you don’t need to be a certain age. I hope
that more people participate in acts of kindness at young ages.”

– Jaden Winn

3 years ago, Jaden Winn was given a 3rd grade writing assignment where he was asked
to consider what he might like to do when he grew up. He asked his mom, “What’s it
called when you find money for people who need it and get it to them?” His mom re-
sponded, “Go look up the word, ‘philanthropist’. Jaden returned enthusiastically informing his mom, “I’m going to be a philanthropist when I grow up.”

Since Jaden’s mighty declaration, he assisted in raising funding to help preserve his teach-
er’s job, danced in a Flash mob right along-side his mom to bring awareness to ending
violence against women and launched his own giving program to raise money for the ONE Campaign.

When Jaden’s not involved with community service programs, he’s a pretty normal
11 year old boy and has a variety of interests. He has a love for dance, is a competitive
soccer player, is crazy for the drums, and enjoys the outdoors, especially sailing and
hiking. Jaden is also an enthusiastic student, loves to cook and enjoys learning about
what being a caring and effective leader really means. Above all, Jaden is a big-spirited
boy, full of light and life whose smile you can’t help but return.

Jaden is thrilled to be setting out on this Kindness Journey, which he sees in three parts:
one, the physical journey and adventure of traveling throughout the United States, two,
the experience of contributing to an organization that he thinks is cool #kindnessiscool
and three, the personal spiritual journey for himself and what he imagines will happen
for him by giving to others – and how that will likely help him to be even more con-
scious of his actions. Jaden is also looking forward to experiencing more joy in his al-
ready close relationship with his mother, Amanda.

Jaden believes “kindness is a whole other language”; that you can speak through kind ac-
tions. Receiving kindness makes him want to give back to others because “it feels so
good”. He is beyond excited to be making this journey in honor of Life Vest Inside and
hopes his work will help replenish the big pool of kindness that we all create with our

meet-amanda“Kindness isn’t always comfortable. Often times it’s not our first inclination. Sometimes it can even be a real stretch for us, but what’s profound to me is that any act of kindness we choose to initiate or participate in, we are changed for the better. Even through our smallest gestures, “we” as in you + me can leave love and goodness in our wake. Kindness ripples and boomerangs.”

– Amanda Winn


Amanda Winn is a Wholehearted Business Development professional, a passionate
parent, an at-times shy creative, a heart-on-her-sleeve Humanitarian and a committed
and loyal friend.

She is honored to be a part of Life Vest Inside and beyond grateful to be providing her
son with this amazing experience to follow his instincts of bringing kindness everywhere
he goes. She is so proud to be Jaden’s mom and learns from him every day. She hopes
to meet you in one of their stops along the way and is overwhelmingly happy to be part
of The Kindness Journey.

In her professional life, she is the founder of Wholehearted Business Development: a
boutique agency of dedicated marketing, PR, design and operations professionals who
care about holding the space for businesses to become all they are meant to be.
Wholehearted Business Development specializes in people using their life and their
work for good.

In her free time, you might find her dancing in a flash mob she organized to raise aware-
ness for a cause she believes in, cooking up a storm with Jaden or enjoying an evening of
deep connection with her closest friends. What she most loves to do is share the good-
ness, build enduring bridges, connect people to resources that open doors wide open,
and hold a quiet space in her heart for the path of healing to love.