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Freestyling, by Kevin Williams

Freestyling, by Kevin Williams

FEBRUARY 11, 2021

/ Articles / Freestyling, by Kevin Williams


My son Terry and I have the same competitive gene. It only takes one comment, like, “I can slide across the kitchen in my socks farther than you can,” and boom! The contest begins: juggling tennis balls, balancing a cup on one finger; you name it. It doesn’t matter what the challenge is. Competition almost always ensues.

On one family excursion to New York City, we rented bikes to ride through Central Park. When we came up to Columbus Circle, I had the bright idea to let Terry know the race was on by smoking past him on my bike. I’m willing to admit that challenging a sixteen-year-old wasn’t the wisest thing for a grown man to do, but I told you I’m competitive! He had just started to catch up as the area got more congested, which caused us to ride closer together while pedaling as fast as we could. In an instant, our pedals smacked together, and we both came crashing down in the middle of a mob of people. It was not a pretty sight. Sprawled out and disoriented, we checked to see that we were both still alive and that we hadn’t mortally wounded any innocent bystanders. Somehow neither of us or anyone else was hurt or had any broken bones. It was only my pride that had been badly bruised. I felt drenched in the embarrassment of my Bad Dad moment as my wife and daughters shook their heads at us. So, we got back on our bikes and went for the only thing that could soothe a near-death experience: pizza.

We all have some sense of competition that can lead to unhealthy outcomes. An infatuation with competition can create a ripple effect throughout our lives and cause us to move in directions we never intended—like being laid out in the middle of a Central Park crowd. The unhealthy habit of competing with or comparing ourselves to others can suck the life out of our joy; and trying to measure up to other people we think are smarter, more athletic, funnier, or better looking than us isn’t much fun. It’s easy to fall into the trap of feeling like others’ agendas, opinions, and actions should shape the way we feel or guide the steps we take. That’s why exploring the idea of freestyling is so important for me and you.

Traditionally, freestyling has been about improvising activities and interests—such as skateboarding, music, or clothes—on the fly. For example, Bluegrass musician Earl Scruggs will often take classic hits in all kinds of new directions by freestyling musical breaks, and the group Gangstagrass combines the unlikely mashup of bluegrass and rap to create a unique take on each musical genre.

My friend Chad Teague brought new meaning to the word while we were planning a college-reunion weekend. When I gave him an outline for one of the day’s activities, he said I shouldn’t count him in on my structured itinerary. He was going to be freestyling. Chad told me he wanted to go with no agenda. “Just because the world says we need a master plan, doesn’t mean I do,” he explained. Witnessing his willingness to embrace unexpected opportunities was like taking a breath of fresh air we didn’t know we needed.

Since then, I’ve come to embrace freestyling as a simple mindset that suggests we are all in charge of our own lives. We often feel controlled by comparisons we make around money, position, and challenges—all of which can crush our freestyle spirit—and it’s easy to get stuck in the mindset that we don’t have the ability to embrace unexpected opportunities. We can easily get sucked into the lie that we are prisoners of someone else’s agenda. In fact, you may be an actual prisoner as you read this. But I’m here to tell you that you have the option to freestyle your very next steps. Every one of us can freestyle. In the counsel of my friend Henry Cloud, we must remember that “we are all ridiculously in charge of our life and decisions.” Yep, if you are alive, breathing, and reading this, then you, too, have the freedom to freestyle!

Listen to our Interview with Kevin Williams here.

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