Cliff Hakim, 71: Why Kindness and Conversation Can Reset the Internet Age

A natural storyteller and listener, Cliff Hakim, who has worked as a counselor, artist, advisor, and author, is now inspiring connection as a leader of Leap chats. He discusses the power of kindness, going to art school at 69, and pursuing new experiences.

They say that lightning doesn’t strike twice but, for Cliff Hakim, a lifelong inspiration ‘storm chaser,’ it’s hit three times in later life. At 55, he wrote a book on the premise that everyone is actually self-employed now and changed his working life; at 69, he left his business coaching and consultancy career to go to art school and explore new perspectives; and now, at 71, he is part of a movement at Leap changing the way we talk on social media through 20-minute video conversations. 

How old are you and where are you based?
I am 71 years old and share my time between two great cities: Boston, Massachusetts and Portland, Maine.

A few years ago, you wrote a rather prophetic best-selling book, We Are All Self-Employed. Did you foresee the changes that have come to pass with career trajectories? Would you add anything to the book based on what you now know?
I was attending a lecture at Harvard back then and the speaker began with five words: ‘We are all self-employed.’ I knew then that was a book I needed to write. I was finishing a 10-year journey in executive coaching at the time and developing a practice called Rethinking Work. My generation, baby boomers, grew their careers when industries were growing voraciously after WWII to meet consumer demands. With that growth, many workers were told that they would have a job for life. The career promise: the organization will take care of you if you fulfill your work obligations to it. The context of work changed, though; organizations flattened to streamline management, technology began substituting for workers, and organizations adopted just-in-time manufacturing. That former lifetime ‘social contract’ has given way to a new social contract — and that is that we are all ‘self-employed.’ In other words, each of us is responsible for our career and corporations will not be responsible for anyone consistently — or forever. Safety is an illusion; transition is the truth and also where possibility is born, but what people still want is the completion and attachment. If we don’t take responsibility to rethink work as individuals and as organizations, though, we’re going to suffer egregiously, which is something I’d underline in the book if I were adding to it now. 

“Ultimately, kindness nurtures and invigorates the soul”

What do you mean by ‘kindness is a choice’?
In this have-and-have-not world, I believe we are called to awaken our personal awareness and contribute to others’ lives so they feel included and their needs are met. ‘Kindness is a choice’ is my mantra and reminds me to constantly choose caring and empathy, even when others seem unkind. Sometimes I misstep, but kindness is a challenging, imperfect journey, and I give myself permission to keep learning. Ultimately, kindness nurtures and invigorates the soul.

What inspired your book, Walk in My Shoes?
I became interested in drawing shoes, and I saw an opportunity to put together my philosophy of kindness with my ability to write and draw. COVID had just begun, my art class had come to a halt, and I was determined not to let gravity pull me down. I found purpose in interviewing others to uncover and write stories of kindness in a world that was gyrating into unrecognizable twists.

How does one align one’s passion with one’s earnings?
You have to have resilience and tenacity to combine passion and earning and, for me, this has been a sometimes challenging road in my life. But passion and earning are two of my deepest career-life values and I am unhappy when I am not working toward fulfilling the two. Usually when I am clear about my passion and how it might apply as a solution for someone else’s need, they come together. 

How does one discern what one’s passion is?
A passion is something that makes your heart sing. A passion is something that makes your eyes light up. And a passion is something that is tough to let go of in life. Often, I need to still myself to see or hear what is most important to me. Internal and external ‘noise’ can often drown out passion, burying it under layers of have-to-dos and other people’s demands and wishes.

Why is storytelling so important?
We are each making and living one story after another every day of our lives. When I counseled people, they told me their stories and I helped them better understand them so they could use them to move forward in their lives. In my memorial design work, the stones tell peoples’ stories, too; and when we chat with guests on Leap, they also share their narratives. 

“Conversation is one of my passions and I could instantly see Leap as an act of kindness for the world and a new way of connecting online”

How did you get involved with Leap?
My editor, Valerie Andrews, discovered Leap in its infancy, and encouraged me to pick up the phone to founders Caroline and Vishal. Conversation is one of my passions and I could instantly see Leap as an act of kindness for the world and a new way of connecting online. I joined as a Leap Leader as well as sharing my thoughts on the platform with Caroline around kindness-focused facilitation. I also suggested trying a ‘20-minute chat’ format — the short, meaningful interactions between real people on the app today.

What is your favorite sort of Leap chat to lead?
I enjoy chats themed around kindness, as I believe that kindness, empathy, and compassion are the taproot for a better world for all. Without kindness, our spirits are parched for a world that cares a bit more; and guests have mentioned they are amazed by the nuances of kindness that come up in these chats.

How is Leap creating a more empathetic and compassionate world?
There are five or six ‘blue zones’ in the world, recognized places where people live the longest and healthiest lives, and one of the characteristics of those environments is that people engage in conversation, belonging and community. I believe Leap will become the digital Blue Zone connecting curious minds and open hearts. Our chats offer guests community, a place to belong, and are based upon the sharing of ideas and thoughts and the opportunity to grow individually and together. 

“I started art school a year before the pandemic, when I was 69, to reignite my spirit and discover different parts of myself”

When did you go to art school and why?
I started art school a year before the pandemic, when I was 69, to reignite my spirit and discover different parts of myself. I was ready to open myself to other possibilities. I left the world of coaching because it was just getting boring to me, and I could see my life moving on. My mother was an artist and I always felt this was part of me, so I just wanted to put myself into an environment I loved and with people that were unfamiliar. I didn’t want to say, ‘I’m an executive coach’ because that’s a ‘safe’ thing to say. All I did was sat down with hope that I would look at things with fresh eyes. And with my teacher and the Museum of Fine Arts in Boston as a studio, I learned to see from different perspectives, draw and paint, and in the end wrote and illustrated a book on shoes, which eventually led me to Leap.

What advice would you give someone over 50 looking to go back to school?
School is everywhere so try something new, stick with it for a while and assess if you feel connected to it. If not, try something else, but never stop pursuing purpose and things that are meaningful to you. What is meaningful to you can become a gift to another. If you’re thinking about going back to formal school, take a class at a community college or a lifelong extension program — engagement with others and interests is life supporting and giving.

Do you feel any setbacks from being in school with younger students?
I like being with all ages; each person brings a different perspective and contributes regardless of age. I never felt old and I never felt young going back to school. I just loved the process, and I was there to learn to figure out whether I could I do this. The students in my art classes ranged from mid-twenties to mid-seventies and were all supportive of me. I always felt our different generations and experiences were an asset. I feel the same spirit at Leap.

“The students in my art classes ranged from mid-twenties to mid-seventies and were all supportive of me.”

Shoes are an unexpected choice for a subject. Tell us about that…
Shoes found me! I was learning to draw different objects in class and one day I started to notice people’s feet, and that we were all wearing different forms of the same object. After that, I began to think about all the shoes in the world — how they are different, yet perform similar functions, and how we all wear them to get to where we want to go. I noticed all the nuances, ranging from fashions to the ways that people would walk in their shoes. The question then for me was: ‘How do you walk in your shoes?’ — literally and metaphorically — and: ‘How do you walk in the shoes of the other?’

You also make memorial stones. What inspired you to do this work?
I am inspired by natural things, and I’ve been attracted to stone since I was a teenager. When I was transitioning from career coaching into art, I began to experiment with stone forms in our back yard. I had built some benches and a bird bath or two when a landscape architect neighbor visited and saw my creations and told me my work was inspiring; from that encouragement, my business Inspired Stones and my gallery were born. I let myself be led by the natural shapes in the stone but also the stories that people tell me about the person. When I started, I realized I had spent my life interpreting people’s stories, but now I was doing that in a different form.

You’ve worn many professional hats in your life: teacher, counselor, artist, advisor, author. What’s next for you?
I am not pursuing title or ‘a noun’, but experience. When I connect the dots of my life, I can see how storytelling and listening to others, creating, writing, and facilitating have all been important verbs in my life. I’m letting myself enjoy the verbs in my life now and watching where they might lead.

What are your three life non-negotiables?
Hope, health, and freedom for the self and the other. 

Click here to join one of Cliff’s Leap chats and to explore this week’s calendar of 20-minute conversations.

Connect with Cliff:
Walk in My Shoes Book
We Are All Self-Employed Book

Connect with Leap:

Photography by: Boris Zharkov

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The ideas expressed here are solely the opinions of the author and are not researched or verified by AGEIST LLC, or anyone associated with AGEIST LLC. This material should not be construed as medical advice or recommendation, it is for informational use only. We encourage all readers to discuss with your qualified practitioners the relevance of the application of any of these ideas to your life. The recommendations contained herein are not intended to diagnose, treat, cure or prevent any disease. You should always consult your physician or other qualified health provider before starting any new treatment or stopping any treatment that has been prescribed for you by your physician or other qualified health provider. Please call your doctor or 911 immediately if you think you may have a medical or psychiatric emergency.


David Stewart
David is the founder and face of AGEIST. He is an expert on, and a passionate champion of the emerging global over-50 lifestyle. A dynamic speaker, he is available for panels, keynotes and informational talks at david@agei.st.


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