Thought(ful) Leader Series: Author & Productive Flourishing Founder Charlie Gilkey


I have asked leaders in different fields whom I respect their views on leadership today and what conversations they think we need to be having.

This week’s guest is ally and colleague Charlie Gilkey. A former Army officer in Iraq with a philosopher’s reflection and a productivity hack’s action, Charlie often raises questions & checks assumptions about the field of digital entrepreneurship and business itself.  An influential soul more prone to questions than answers is, in my book, a thoughtful leader.

In this Thought(ful) Leader interview, Charlie shares when he realized he was leading his field, how to face the hard, and whom he looks up to.

– Jeffrey

Jeffrey: When you “look around” the world and within your field, where do you see a need for a bold or new kind of leadership?

CharlieI’m seeing a need for more focus on true conversations and insights. With the proliferation of social media and blogging, we’ve co-created a situation in which controversies and clickbait are becoming more of the norm than actual transformative discourse that helps us become better people.

What traits define for you a “thoughtful leader”? What is a “thought leader”?

Not all thoughtful leaders are thought leaders and not all thought leaders are thoughtful leaders. ‘Thoughtful’ brings to my mind compassion and empathy, as in “that was really thoughtful of you.” Thought leaders, though, are individuals whose livelihoods depend on their ability to lead and contribute to conversations about a focused set of topics that others care about.

When did you realize you were a leader in your field, a leader of ideas, or a leader of a conversation?

It didn’t occur to me that I was leading my field until 2008 or so when my email, comments, and in-person questions were mostly about the topics I was interested in and writing about. In my view, you don’t get to be a thought leader merely because you say you are – you become a thought leader because others interact with you as one.

I still didn’t really own my thought leadership until April 2010 when I was voted Wealthy Thought Leader of the Future by other thought leaders at Andrea Lee’s 2010 Wealthy Thought Leader event. Apparently the Universe needed to send me a bigger message. (Why many of us won’t own what’s right in front of us is a conversation for another day.)

What’s the conversation you hope more people will have or the question you hope more people will consider this year?

Am I making the best of these beautiful moments I have in front of me? It’s not just about getting more done or taking things to the next level, but simultaneously owning where we are while building better tomorrows, today.

If you could change or influence more people’s perceptions or notions of something, what would it be?

That something being hard is a sign to avoid it. Reaching mastery, fulfillment, and prosperity normally requires working through and embracing hard work, conversations, and decisions. We often wish to be at the top of the mountain more than we take the next step to climb up it.

To be clear, I’m not advocating playing life on hard mode all the time or making things harder than they need to be, either. The universe provides ample challenges on its own.

It’s how we respond to adversity and cherish the magic of life that makes us who we are.

As an author, what has been one of the most rewarding responses to one of your books that lets you know you’re making the kind of difference you want to? 

Many of my readers tell me they return to my book several times per year and use it to navigate their growth as an entrepreneur and their business’s growth. Praise like that always seems to show up precisely when I need to hear them. To know that your book changed someone once is amazing, but that people know that they’ll be able to come back to it and be changed again is just indescribable. I don’t want my work to sit on a shelf; I want it to be a catalyst for the change people are trying to make in themselves and the world.

Who is someone you have looked up to or looked back to as an exemplar for how you hope you lead?

Seth Godin. A lot of people know Seth because of his brilliance AND there’s such heart in him. At this point in his life, he’s change-making not because he has to, but because he both wants to and feels responsible to do so. All the while, he demands excellence and growth from himself every day. He’s a great mentor.

What one thing or idea or wisdom do you hope people remember you for?

I hope I’m remembered for reminding people that they have what it takes to flourish and playing a part in their taking action on and finishing the stuff that matters most to them.


Small Business Life CycleCharlie Gilkey
is a champion of and catalyst for Creative Giants – talented Renaissance souls with a compassion-fueled bias towards action. He’s the brain and heart behind Productive Flourishing, best-selling author of The Small Business Life Cycle (JETLAUNCH 2014), Ph.D. candidate in philosophy, and a former Army Logistics Officer. He’s driven to figure out how to help Creative Giants be their best selves in the world. Find out more at



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