Why Greatness Can’t Be Planned: The Case for Following the Interesting
I didn’t go to law school to become an entrepreneur. In fact, for most of my time there, I was laser-focused on the next obvious step: clerkships, law firms, maybe eventually a path into public service. But life has a funny way of unfolding—not by sticking to a carefully laid plan, but by veering into the unexpected.
For me, it was a negotiation workshop during my second year that planted the seed. One of my professors shared an offhand anecdote that struck a chord, though I couldn’t have told you why at the time. Several years later, I found myself at lunch with some of my parents’ friends while on vacation, and that anecdote bubbled back up. That conversation, entirely unplanned, became the foundation of my first company, VacationFutures.
From there, one thing led to the next—not through a tidy strategic plan, but through a series of meandering, curiosity-fueled steps. VacationFutures led to Rented Capital. Learnings from that led to Rented.com. None of it was straight. None of it was predicted. But each step, fueled by genuine interest, created the momentum for something new. That’s the thing about greatness: it doesn’t arrive by request. It emerges when you’re following what feels worth chasing—even if the destination isn’t clear.
The Trap of the Plan
This might sound counterintuitive. After all, we live in a world that worships plans. We set goals, chart paths, optimize for outcomes. But as Joel Lehman and Kenneth Stanley argue in Why Greatness Cannot Be Planned, that mindset can actually limit us. When we focus too much on achieving a specific objective, we often restrict ourselves to what feels like the next logical, incremental step.
But true greatness? It’s rarely logical—and almost never incremental.
Take computers, for example. They didn’t evolve from some straight line starting at Charles Babbage. The vacuum tube, an essential part of early computing, wasn’t invented to help build computers. It came from a completely different field. You could never have charted a course from Babbage to the laptop you’re reading this on, not without walking through dozens of other disciplines and accidental discoveries.
It’s the same with flight. The Wright brothers relied on internal combustion engines—another unrelated invention—to bring their vision to life. Innovation is often less like climbing a ladder and more like crossing a river by jumping from stone to stone. The path isn’t visible until you look back.
Even Evolution Isn’t Straightforward
Stephen Jay Gould, one of my former professors, had a term for this in evolutionary biology: punctuated equilibrium. Rather than slow, continuous change, species often evolve in bursts—long periods of stasis followed by dramatic, sudden leaps. It’s messy. It’s unpredictable. And it’s how nature works.
So why would we think that human creativity, innovation, or personal growth would be any different?
When Metrics Mislead
Sometimes, what we believe is progress actually moves us further from our goals. Ben Azadi, in his new book Metabolic Freedom, tells the story of a client who wanted to lose weight. Every morning, this person dragged themselves out of bed at 5am to hit the gym, determined to burn off the pounds. But they were also deeply sleep-deprived. The scale wouldn’t budge.
The fix? Sleep more. Work out less.
As counterintuitive as it sounds, shifting that focus led to real weight loss. The problem wasn’t discipline—it was direction. The client wasn’t lazy. They were just following the wrong metric.
And this isn’t just a health issue. It’s a human issue. We chase what’s measurable—money, hours worked, followers, output—because it’s easier to track. But not everything that counts can be counted.
A Holistic View of Health—and Greatness
At Alively, we believe health isn’t a single number or habit. It’s built across five interconnected pillars. You can’t neglect sleep to chase fitness. You can’t grind through stress and expect resilience to magically hold. The system works best when you care for all of it.
Greatness is the same way. You don’t achieve it by hammering one narrow objective. You achieve it by cultivating an ecosystem of ideas, experiences, and interests—and then following the paths that genuinely light you up.
Follow the Interesting
In Why Greatness Cannot Be Planned, the authors emphasize the importance of pursuing the interesting. Not the strategic. Not the efficient. The interesting.
That’s how I built my companies—not through carefully calculated business school frameworks, but by paying attention to what sparked my curiosity. That unplanned class anecdote. That conversation over lunch. A pattern I noticed in an existing business that begged to be explored. I didn’t know what I was building until I built it. I just knew it was worth exploring.
Curiosity isn’t frivolous. It’s foundational.
The Risk of Easy Metrics
The danger is when we let ourselves get hypnotized by easy metrics. Revenue. Growth charts. Round numbers. These are tempting because they’re tangible. But they can pull us off course.
The truth is, not everything meaningful can be captured in a KPI. Sometimes progress looks like slowing down. Sometimes innovation looks like stepping sideways. And sometimes, the best decision you’ll make will seem, in the moment, completely irrational.
That’s how greatness works. It doesn’t follow your plan—it rewards your attention.
Leave Room for the Unexpected
If there’s one takeaway I’ve learned, it’s this: make space for what you didn’t expect. Don’t let your calendar or your metrics crowd out your curiosity. If something feels interesting—even if it makes no sense right now—give it room.
Because you never know. That conversation at dinner? That class you almost skipped? That itch you can’t quite name?
It might just be the start of something great.









