265: What's the Point?

All great outcomes emerge from focus, strategy and sustained effort over a long period of time. None of those things are possible if you aren't motivated by or drawn to some aspect of the work you're doing.

You need to be compelled. You need to feel like all of this has a point—that there's a purpose to it all.

This is especially true for outliers who aren't just following conventional scripts and founders who need to drive not just themselves but their entire organization toward a very difficult challenge.

Knowing why you do something matters a lot. When people stop feeling like there's a point, things can go sideways very quickly. Sometimes this emerges from struggle.

Losing Purpose From Struggle

One of my clients, Kevin, was a senior marketing manager at a Series D unicorn company. He had hired me to advance his executive presence, but more and more I saw that his behavior was telling me something different. He was getting constantly bogged down in meetings and drowning in Slack messages and fire drills. He had less and less time for his family or for the actual marketing and messaging strategy work he was most passionate about.

"If your boss quit and you were offered her job starting tomorrow," I asked him point-blank, "would you take it?"

"Hell no," he said without hesitation. "You couldn't pay me enough to deal with what she has to deal with."

"Then what are we doing here?"

Kevin no longer saw the point of climbing the ladder. That's When we started working on his real change: building a highly sought-after strategic messaging agency that has done more than seven figures in revenue in its first year of business.

Losing Purpose From Success

Kevin lost his purpose from increased struggle that wasn't his chosen suffering. sometimes success can also cause you to wonder, what's the point?

One of my other clients, Edmar, had built a company to 400 people and tens millions of dollars in revenue. But he no longer felt excited by it. The problems were no longer technical—they were marketing, business, and financially oriented.

As long as they kept acquiring their competitors, they could grow market share and rinse and repeat. In his success, he had lost sight of his purpose.

So he sold his shares and traveled the world for a year. After that, he decided he was too young to retire and needed to find a new purpose. That's how we worked together, step by step, to help him get back to what he loved: coding and working with new technology, including the generative AI advances that had emerged in the last couple of years while he was wrapping up his time as CEO and traveling the world. We helped him find a new point for what he was doing.

Know the Point

So what does this mean for you? It means you need to constantly interrogate your own sense of purpose.

Not in a way that paralyzes you, but in a way that propels you forward. Ask yourself: What am I truly trying to accomplish? Where is the energy in my work? What makes me lean in, rather than check out?

Purpose isn't static. It shifts and evolves.

Michael Jordan decided, at the height of his basketball prowess, that playing ball no longer felt meaningful. He wanted to fulfill a different dream, one his recently deceased father had had for him—to play professional baseball. And he threw himself into it, showing up for batting practice at 7 am every single day. If the MLB player's strike hadn't derailed his baseball career, who knows if he would have ever returned to the NBA.

Purpose is a winding path, not a straight line.

The point isn't to have a perfect, immutable mission, but to stay curious about what drives you. Sometimes that means walking away from something that no longer serves you. Sometimes it means radically reimagining your path. But it always means paying attention to the signals your work and your body are sending you.