10 Lessons I’ve Learned in 10 Years of Tracking Wonder

When I became a father, one October morning I looked into my first infant girl’s sky-wide blue eyes and made a silent two-fold vow: I would learn from her the art of not-knowing, and I would live a life so rich with creativity and wonder that she would want to become a “grown up.”

That was in 2009. The next October we launched the first iteration of Tracking Wonder and of TrackingWonder.com, five years after I had begun my quest to understand the psychology of wonder. 

All of these years later, I’m still on that quest to learn, un-learn, and learn again all of the things I thought I knew and the truths I need to remember. Everything I do – from building a thriving business to writing books to serving as a strategist in branding, creativity at work, and leadership to guiding my two girls’ through childhood – are part and parcel of the same quest for integrity, meaning, and making.

But like most quests, mine has been neither easy nor straightforward. There was never a time in these ten years when I wanted to “throw in the towel.” There certainly were times – especially in the early years – when I thought this all must be folly. There were times when I way overspent our resources on other people, promotions, and events. 

Yet all of it has been worthwhile.

This decade has been such a rich ride of enlightenment that it was hard to choose, but I want to share 10 of the most important lessons I’ve learned in my quest to Track Wonder. First, I’d like to extend an invitation.

An Invitation to You

I extend a deep, genuine thank you to every one of you who has engaged Tracking Wonder during this past ten years. You are what drives me and the entire Tracking Wonder team to do what we do. Every time that you open an email, comment on a post, engage us on social media, or share an article, you inspire us to continue spreading the medicine of wonder among leaders, in workplaces or Work From Home studios, and in the hearts and minds of many. You show us that, together, we can make a real impact on the world.

So in the Comments below I invite you to share a favorite memory of or your own lesson from Tracking Wonder. Deep bow of gratitude.

10 Lessons I’ve Learned in 10 Years of Tracking Wonder

1. A creative life of fulfillment is a quest. 

More than any previous era, knowledge workers today seek a career of feeling: they expect to find meaning and personal fulfillment in their work. But all too often, we make the mistake of looking outside ourselves to find that sense of purpose when in fact, it lies dormant within each of us. Anyone can awaken that purpose – can pursue a meaningful life of fulfillment – if they are willing to adopt a Questing Mindset.

The Questing Mindset begins with a quest. By definition, a quest involves choosing curiosity over closed-mindedness. It means tackling challenges rather than shying away from them. It means embarking on a path defined in part by your own initiative and intentions. A quest also inevitably requires you to step out into the unknown.

As you well know, a creative’s life is full of unknowns because every big idea begets a series of challenges. Whether you flounder or flourish has largely to do with how you respond to these challenges.

This episode of the Tracking Wonder Podcast reinforces this truth. Video game pioneer Tracy Fullerton (Walden, the video game) and twice-Oscar-nominated filmmaker Mark Osborne (Kung Fu Panda, The Little Prince) give perspective on what they and their respective teams did to flourish amidst challenges while they executed projects that took years to complete.

For you: What does your quest look like, and what are some of the biggest obstacles you’ve faced along the way? What could you learn and how might your newfound knowledge bust some biases and well-worn ways of viewing yourself?  

2. Systems matter.

In my work, I speak to highly accomplished professionals, thought leaders, creative entrepreneurs, and service providers who still seem to fly by the seat of their pants. They expend finite time, focus, and emotional energy trying to keep track of all the moving pieces until they find themselves at the brink of burnout. 

If you work in a similar style, my advice to you is this: develop simple business systems. Business systems involve sets of processes, tools, people, partnerships, and strategies that synchronize to help you work smarter. Taking a little time up front to develop these fundamentals will actually help you feel more rested, focused, and fulfilled so you can advance your deep work rather than fret over minor details.

I realized this truth early in launching Tracking Wonder. Two years in, I invested in an advisor to review our existing systems and create an online operations manual. A few years later I invested in an employee to better streamline and automate systems. As a consultant, I quickly learned that if I developed an assignment or framework for two clients that I could develop that framework for multiple clients. So we developed a system for client assignments as well.

If you put some of these business items on near-autopilot, then you free up your mind’s cognitive bandwidth to conceive and execute on some of those great ideas you have that could make a big difference in people’s lives.

For you: What is one business system you or your team could implement or improve upon that would free up time and mind?

3. Ideals and integrity matter. 

You don’t need permission to lead with your ideals, but in a world where cynicism often prevails, it might feel that way at times. I’ve had the honor to work with (and learn from) CEOs, company presidents, city planners of major cities, as well as a host of creative entrepreneurs. Each of them has reinforced my discovery that when you lead with your ideals and keep your integrity, you will find fulfillment in the process. 

A new generation of leaders plus a new generation of consumers demand more business leaders invent radically new business models with new principles – and the integrity to uphold them. 

In 2014, we launched the ArtMark™ branding academy in part to train people to brand with integrity and to shape brand stories with their captivating ideals front and center. Part of that training includes how to craft a brand manifesto with integrity. 

Shortly thereafter, we crafted our own new manifesto on 12 Principles to Do Business as Unusual. #1? GROW WITH INTEGRITY.

For you: What are your top 3 core values or virtues you live out each week? How do they or could they inform the decisions you make when you advance your endeavor – be it business, brand, creative, personal.

4. Movements matter.

In 2014, I was feeling a restlessness in myself and among the numerous people around the globe I was having conversations with. The restlessness had to do with our broken frames of “business” and what “doing business” in the world had meant throughout much of the twentieth century. We still have residues of the “business as usual” mentality – feed the bottom line for executives at the expense of others, compete to defeat, bluff your way to fill your pockets. 

But the restlessness I sensed was among smart, attuned business people, executives, professionals, entrepreneurs, creatives, and other mindful change-makers who were hungry for something else.

They were hungry for business as unusual that gave precedence to integrity, creativity, and community.

What would such people call themselves other than “business people”?

Hence, the birth of a piece of writing that I thought might turn into a micro-book. Once my team and I pared it down, we had in essence a manifesto poem. So I collaborated with Dom, our videographer, and we produced the Be A Business Artist video.

It struck a chord. We were taken aback by the immediate response from people around the globe. “That’s what I am! A business artist!” we heard over and over again. 

We knew we had to give space to this growing movement. 

For you: If you could organically start a movement, what would it be?

5. Do-It-Together beats DIY.

I savor slow days of creative solitude where I can pursue complex projects and reach meaningful goals. But the do-it-yourself approach to work, brand development, thought leadership, and – well –life gets exhausting and old.

When my goals – for myself, my family, my business, my creative projects – were not being fully realized, I knew I needed to be part of a bigger conversation and a community that shared my vision of doing business in a radically different way – one imbued with caring, creativity, and integrity.

And I knew I couldn’t be the only one feeling this way. So in 2014, after realizing we were leading an organic movement of sorts, I knew we needed to create a space for business artists to convene. 

That year we designed the first-ever month-long Quest Experience throughout all of December. I invited 12 visionaries – from Seth Godin to Tara Mohr to National Geographic “Shots of Awe” tv host Jason Silva – to inspire our new Tracking Wonder Quest Community with wondrous questions and prompts that helped us envision our best year ahead. The experience integrated evidence-based ways to reach your goals and fulfill your vision together in an international community of mindful change-makers.

The response again floored me. Our community exploded. All of us saw that social media could be used for the good and for real connection. Our Tracking Wonder Quest Community in turn has spawned hundreds of collaborations that we call Business Artist Alliances and has helped countless business artists develop their own communities.

Thousands of people have gone through the Quest Experience, and our community includes mindful change-makers from 37 countries and growing.

The creativity, inspiration, and encouragement of this community took me from lone wolf to pack leader, and this experience made me realize that DIY is a myth for the modern entrepreneur. We’re stronger when we Do-It-Together.

For you: Who are three people you could connect with regularly for mutual support and inspiration?

6. Why we fear standing out – and why we need to stop.

I work and speak with brilliant, accomplished professionals every day, but even they hesitate to stand out with their ideas or exercise their influence. Why?

A few years ago, I thought that lack of time or resources might be the perceived culprit. I was wrong. When we informally polled our community of mindful change-makers on what holds them back, their responses surprised me.

Much of their resistance stems from fear. Fear of what people will say. Fear of failing in public. Fear of looking incompetent. 

Every one of these fears I have contended with and continue to do so because I often push myself and Tracking Wonder to the edge – that is, until 2020. But facing fear is an inevitable part of branding with integrity. It’s essential to recognize the power and importance of leaning into the stances you’re willing to take and living the story you want to tell.

For you: What do you stand for? What do you stand against? What fear holds you down? What truth do you know that will help you override that fear?

7. You are not your work.
   
   I love good work, and I love helping people discover how work can be “love made manifest,” in the words of one poet. But our work in the world is not who we are.
   
   This fact gets tricky when some of us public figures are seen in relation to our work. It’s tricky for employees and knowledge workers and service providers who get rewarded and who get creative satisfaction from work.
   
   Basing your life’s meaning on your work is not the same as crafting meaning in your work. You can enjoy purpose-fueled work without losing yourself in the process. 

One year when our first born was only five years old, I was supposedly playing with her in her room, but my mind was elsewhere spinning about business issues. “Papa,” she said softly, “Are you here?”

Busted.

“No, angel,” I confessed, “I’m not. I’m sorry. I’ll do better.”

It’s taken me several years of obsessive working not only to realize this but to put this knowledge into practice. I do that by noting how many hours a week I’m paying attention to work-related items while talking to my girls (no!), if I’m bringing my computer to the beach vacation (did not happen!), and if I’ve reversed my mind’s stress habits of checking email 153 times a day (not anymore).

For you: Who are you at your best and most natural and free outside of your work? What activities do you regularly engage in to remind yourself of this fact?

8. Follow your curiosities, not your passions. 

“Follow your passion” is misleading advice. As psychologist Carol Dweck found in her studies on growth mindset, this mentality of pursuing a singular vocation can narrow focus and imply an easy path to success that only discourages students when they inevitably encounter failure.

If everyone is finding a calling or a hidden talent, it implies that pursuing a passion is easy work. You come to believe that if you haven’t found yours, you must be doing something wrong. Yet, in actuality, you are stuck in this one-track mindset and so you work harder with the same frustration, leading to anxiety, disappointment, and inevitable burnout.

While passion is fickle and high-voltage, curiosity is deep and abiding.

When you approach something with a curious mindset, you are seeking growth and newness for the sake of novelty. Stay curious by pursuing topics that intrigue you, or consciously searching for gaps in your knowledge.

For you: Maybe you aren’t sure what you want to achieve in your work, or just need time to recharge. Maybe you don’t know how to bring your project to life, or which of your ideas to pursue. In any case, when you find yourself feeling stuck, taking time to transition creates fertile ground to do the deep work of defining your intrinsic values and trajectory.

9. Expand by contraction.

As our business and impact grew during the past decade, I realized I had to develop new principles to live and work by. I needed to keep my sanity and serenity, but I also ultimately had to allow the goodness we had created at Tracking Wonder to continue growing. How to work with the paradox of growing by simplicity?

The first part of this lesson was learning something about saying no. I have since trained numerous leaders and entrepreneurs at what stage of growth and how to “Say Yes to Less and No to More” – How to say no to grow.

Here’s the tricky psychology of saying “no”: Whether it’s turning down a dinner invitation or denying a colleague your time to help on a project, the social risks of saying no seem to outweigh the perceived “lower” cost of attending a boring dinner or working late. In other words, we’d rather give up hours of our time to an endeavor we aren’t invested in than risk scorn for setting a healthy boundary. 

Learning how to say no is an essential skill in order to preserve a strong sense of self, and stay on track in advancing your personal goals, all the while maintaining strong relationships with the friends, family, and coworkers who rely on you for support.

Last year I wanted to take this practice further: Focus on less, better and deeper. That’s been a motto of mine and Tracking Wonder for the past year, even before the year of years began.

The year before the COVID-19 pandemic struck, I had decided to expand by contraction. That meant I would radically simplify business services and operations in order to expand our impact and return.

This past year we took on very few new online branding story clients as a team, and we paused the next season of the Tracking Wonder Podcast.

In the spirit of radical pausing, this fall was the first time I’ve suspended the weekly email list Dispatch to refine my focus on what really matters: My curated private clients. The Tracking Wonder Inner Circle MasterMind. The Quest Community. My friends. Actions in the community, local and global. My next book manuscript deadline. 

And especially my wife and two young girls – who were home much more than usual. For our family, I call 2020 “The Year We Reloved Home” because that is in part what we did. We fostered more ways to be present together and really relish it.

I could be all the more present to the occasional beauty and magic of the most ordinary moments. 

The results? I was able to allocate resources more judiciously and because I lessened my and the team’s duress, I could serve clients and community who were suffering greater distress. In other words, for the most part I had more reserve to give without feeling depleted.

For you: Where in your life can you contract in order to deepen your work, or your relationships, and advance what matters most?

10. We can foster a wondrous mindset to navigate rampant uncertainty.

In times of crisis, when uncertainty abounds, we seek mental order amidst the chaos. But a number of business leaders, entrepreneurs, and freelancers are discovering what poets, artists, and writers have known for centuries: we can cultivate wonder in tumultuous times to drive creative innovation and personal break-through.

You see, when we hit a wall or find ourselves overwhelmed by unknowns, we usually respond in one of three ways: We react, we surrender, we get curious. React and you cognitively shut down. Surrender and you disempower yourself by denying yourself the opportunity to creatively problem solve. Curiosity and its close cousin, wonder, allow you to reframe the problem so you can crack yourself open to new possibilities and novel solutions.

When deeply confused or paralyzingly uncertain, you want to glimpse the big picture. While reactivity and negative emotions constrict thinking and narrow perception, positive emotions like wonder and curiosity can broaden our perspective. Wonder is the singular experience that momentarily dissolves our habits and biases so we can see what is real and true, beautiful and possible right here today. 

This creative act is more essential than ever in times of crisis because often you can’t resort to the same tried and true methods to get you out of your predicament. You need to find novel solutions or reimagine what’s possible to overcome whatever hurdles you face. You want resourcefulness, inventiveness, openness. You want wonder.

For you: Think back to the last time you truly experienced wonder. Maybe it was when you marvelled at the kaleidoscope of autumn leaves changing color, or maybe it was a eureka moment that unlocked a work dilemma you’d been puzzling over for weeks. Now ask yourself: How can I cultivate more wonder in my day-to-day life? What got me to that place of open, yet focused attention?

From there you can design your own daily practices to create more awe and openness in your work and in your life.

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Maybe you’re in the process of growing your own dream or endeavor. Maybe you’re trying to build your business or your family with a little more wondrous of a mindset. If so, I hope you find value here. I hope that my reflections can help to give you perspective on your own dreams or endeavors.

Now, I want to hear from you. What are some of your favorite Tracking Wonder memories, moments, collaborations, gratitudes? Reply below to share, or tag us on social media with your own insights and reflections.