On Clarity (And Creating Fun)

Last week marked the start of a mini-series detailing the way family and friends have influenced my ongoing journey toward self-discovery (and how yours might, too). Whether it’s work, play, personal, relational, fill-in-the-blank… those closest to us know us best, like it or not. I, for one, am learning how to listen and learn, and the wisdom I’ve garnered has changed my life for the better.


Throughout the past couple of years, two questions have been particularly intriguing to me: what? And why?

It has taken me a long time to answer both, and in the past, I don’t know that I gave much thought to either. I’ve always been able to accomplish whatever I needed to, and there are still plenty of “whats” to get done. Ever a checklist. Entrepreneurial work (and, I suppose, work in general) is a never-ending job. I’ve never had a punch card. Some people envy that, but also fail to realize that if you never punch in, you never punch out.

Last week, I wrote about My One Thing. When my friends and family unanimously affirmed what it is that I do best, it proved not only clarifying, but freeing and invigorating.

“You get shit done and make things happen better than anyone I know.”

Over the past two decades, I’ve worn every hat there is to wear. I’ve been the youth camp guy. I’ve been the marketing director. I’ve been visionary. I’ve been the Wordpress code learner. I’ve been the keynote speaker. I’ve been the changer-of-DNS-settings. I’ve been the blog writer. I’ve been the oh-my-God-how-did-I-accidentally-start-a-tech-company-pastor-guy. I’ve been a social media guru. I’ve been the CEO. I’ve been the overnight driver.

You name it, I’ve done it. Sometimes out of necessity. Sometimes out of pride. Sometimes because I’m a naturally independent person who has always struggled with delegation.

And so when I began to realize that I’d been “sitting on my gift,” I also began to feel free. Here is what I’m good at…

Starting. Launching. Strategizing. Connecting the dots.

I don’t want to set up a server reroute in Cloudflare ever again (and I might just start screaming if someone asks me to).

I finally had a set boundary — something specific — and have been offloading and replacing the work that no longer fits ever since. One new rule I created is if I can’t do it on my iPad Pro, I shouldn’t be doing it in the first place.

In the years that lead up to sitonmygift.com, I moved my family from Pasadena to Huntington Beach. I’ve better-delegated tasks according to the strengths of the people on my team. I joined a mastermind group and launched two of my own. I created betterandbetter.co — a twist on traditional marketing agencies/publishing houses where I connect clients who need help formalizing, launching, and scaling their ideas to trusted subcontractors that I have personal relationships with. I began coaching, counseling people, and hosting strategization workshops. I started Craig Brain: this vodcast/podcast, blog, book, internet-takeover-thing.

And I’ve loved it. This has been, by and large, one of the most fun, most “successful” years of my life.

But, until recently, there has still been a missing component.

The why.

I shared My One Thing with David Tosti — one of my best, longest-standing friends — recently. He thumbed through the narrative and, while agreeable enough, gave it a passing shrug before concluding,

“Yeah, Craig, that’s great and all, but when I think of Craig Gross, I think of a guy creating fun.

That’s when everything clicked for me. The problem is: I still function more from my head than my heart. I might be the best at the things that I do, but what happens if what I’m best at isn’t what I want to be doing? What happens if what I’m best at isn’t fulfilling me?

How do I combine what I do best with why I love to do it?

How can I make fun the mission? The umbrella? How can I use what I do best — practically — to foster fun?

For what it’s worth, I know that life hasn’t promised any of us these words that I keep repeating. Fun. Fulfilled. I can’t just neglect necessary parts of living and working for a 24/7 fun zone, and plenty of our days exists in the mundane. The point is, though, that with fun as both the precursor and the goal, this little epiphany that David sparked has given me a lens through which to view not just my work, but all of life.

More often than not, when a person asks (or is asked) about what one does, the question triggers a work-related response. People always think business, occupation, or career.

Same goes for My One Thing.

“You’re the best preacher ever.”

“Best poet ever.”

“Quarterback, ever.”

What about me as a father? What about me as a husband? A friend?

I’ll put it this way: as a Christian, there are — generally — two styles of seeing God. Two methods of relating to both him and the world. He is a priority, or he is a centerpiece. Sometimes (and perhaps hopefully), he is both. But the two are distinct.

When God is a priority, perhaps he comes first in the day. For those of us who grew up like me, that means quiet times first thing in the morning. Maybe it means prayer and meditation before we go on with our day. But it also tends to say that — once we’ve gotten on with our day — his time is over, and it’s on to the next thing. He is reduced to a checkbox.

What I mean by God as a centerpiece, however, is that he the fountain from which all things — throughout the day, in all of life — flow. To eat a bowl of cereal following your quiet time, from this perspective, is just as holy an act as the moments spent in prayer, prior because the lifeblood of God is central to the whole. He is the heart, pumping oxygen to the body. The lens through which we look. He has transcended the “first moments” of the day and entered into all moments. “In Him, we live and move and have our being…”

I’ll be the first to admit: I’ve only recently begun to learn how to function from the latter perspective, and I use this analogy as an explanation because I think “Craig, the Creator of Fun” is the fruit of that shift as much as it is its own lens through which to look at work and life.

There are certain people I want to work with simply because it’s fun to work with them. Most of the time, I could care less about what we’re working on, as long as I know that we’re having fun together, and creating fun for others. It’s not the equivalent of a hedonistic search for instant gratification — and “fun” might work itself out directly or indirectly — but it has helped me temper my “yesses” with an ever-fine filter.

To put fun in front of everything I do — the why in front of my what: My One Thing — has made all of the difference.

And it’s definitely not just work-related.

My family members have bucket lists, and I’ve been trying to make their dreams come true. Last year I discovered that — for some ungodly reason — Jeanette has always wanted to spend New Year’s Eve in New York, watching the ball drop in Manhattan. That sounded like a nightmare to me, but we rang in 2019 doing just that.

My son turned sixteen this year. I wrote him a letter for his birthday, detailing some of what I’ve written about here. I bought him a watch that was on his list, even though I know Jeanette and I agreed upon experience type gifts only. We still had a fun trip, too, but I broke my own rule because it was fun for me to gift something from Nolan’s bucket list and it was fun for him to receive it, and cross it off of his list.

Once again, it’s not so much the what but the why.

I’ve never had a bucket list, and I never wondered why until recently.

In part (and however haughty this sounds, it’s not my intent), I’ve always just been able to buy whatever I wanted to buy. Somehow, the Lord has given our family the privilege of a life where the money is not an issue, and while we seek to be generous and sacrificial, I’ve also never had much need for a wish list that I couldn’t just go out and fulfill on my own.

In part, though, I think it’s also because I’m not good at merely receiving. I always want to reciprocate. I still feel indebted to the giver, and perhaps that also accounts for much of why it has taken me a lifetime to be with God simply, as opposed to continually drowning beneath the weight of doing something for him.

Nevertheless, I’m changing. My family sees it. My friends see it. Levi kicked off this entire project with a foreword that details the shifts.

I’m trying to partner with God in giving the ones that I love an abundant life because it’s fun. Abundance in work, life, marriage, opportunity, parenthood, friendship…doesn’t matter.

In my Collide Mastermind group, I built a room of CEO’s, business owners, and solopreneurs under the guise of spurring one another on in our own respective companies. But at the end of the day, the most fulfilling aspects of our time together are spent on the deep work of relationship. Work is not all of life (and I’ve learned that the hard way), and if it used to be fun before the passion became a poison, then we’ve got to remember why we started in the first place.

In my home, I’m trying to teach my kids to accept better than I have ever been able to, but I’m also trying to show them that it truly is better — more fun — to give than it is to receive. I’m trying to hear my wife tell me how fun her life is again…how much she loves being alive. She said that during one of our last trips together, and my heart just about exploded for joy.

I’m learning a little bit more, day in and day out, about what it means to function less from the head that I’ve bashed through walls to keep up the grind for twenty years, and more from that beating center.

The last chapter, I asked you to define your what?

Today, I want to ask you why?

Craig

P.S. It has been a while since I started this experiment and as I hit publish on this episode here in June of 2019, I thought I would add something to this entry. One thing I found was the thing people told me I do the best is not the thing or the things that I enjoy the most. So, the last few months I have been on a journey to really connect some more dots. I wrote this the other day and put it on my website and thought I would leave you with it.

I enjoy creating fun, connecting people and launching products. I believe anything is possible and love instilling that belief in others.

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