Tuesday Email: Innovating Yourself

Read time: ~5.30 minutes

Happy Tuesday!

Every Tuesday I'd like to offer strategies for the week ahead and a thought to fuel your action.

The safest boat is often the one willing to rock itself.

I once read that the most dangerous threat to a ship isn't the storm – it's the still water that allows barnacles to accumulate. Small creatures, over time, create enough drag to slow even the mightiest vessel.

Our careers, routines, and thinking accumulate their own version of barnacles when left undisturbed for too long.

I know this because I've lived it.

I sat staring at my screen, split between two windows—Trello cards stacked neatly on the left, half-built Notion pages on the right. Three weeks into my "gradual transition," my productivity had ground to a halt.

My phone buzzed: a notification about a deadline I'd missed yesterday.

I felt that familiar tightness in my chest as I frantically clicked between tabs, trying to remember where I'd stored that particular task information. Was it in the old system or the new one? The calendar appointment said one thing, my email another.

That's when I recognized the absurdity. I'd created this transition to reduce anxiety, yet here I was, paralyzed by it. My fingertip hovered over the delete button next to my Trello bookmark.

"This is ridiculous," I muttered and clicked. Gone.

The relief was immediate – not because the new system was perfect, but because the decision was made. I'd jumped from the diving board instead of shivering at its edge.

By Friday, I'd rebuilt only what I actually needed in Notion. The clutter from years of digital hoarding never made the journey, and I discovered I didn't miss it.

This is more than a story about productivity tools. It's about the paradox that sits at the heart of personal innovation: the things that made us successful become the very anchors that prevent us from evolving.

Economist Joseph Schumpeter coined the term "creative destruction" in the 1940s to describe how economies progress—new businesses must replace old ones for growth to continue. But he might as well have been describing our personal growth.

Consider the typewriter manufacturers of the 1980s. Most failed not because they made bad typewriters but because they were too successful at making great ones. Their excellence became their blind spot. While they polished their ribbons and perfected their keys, the word processor arrived and changed everything.

We do the same thing with our habits, skills, and thinking patterns.

The reason is brutally simple: success creates an asymmetric risk calculation. Once we've built something that works – a career, a skill set, a daily routine – the potential downside of change feels vastly larger than the potential upside.

This is why doctors who graduated at the top of their class in 1980 might still practice medicine as if it were 1980. Their early success confirmed that their approach works, so why risk changing?

But the world changes whether we like it or not. The question isn't if we'll need to adapt but whether we'll do it proactively or be forced to do it reactively.

Three barriers prevent us from innovating ourselves:

First, success creates its own gravity.

When what you've been doing has worked well enough to create success, the logical conclusion is: keep doing exactly that. It's the equivalent of returning to the same fishing spot where you caught a big fish yesterday.

The problem is that success isn't just a destination – it's also a potential trap. As the saying goes, what got you here won't get you there. Yet our brains are wired to believe that past success predicts future success, even when the conditions have completely changed.

Second, innovation requires social courage.

A friend who lost 50 pounds once told me the most challenging part wasn't the diet or exercise – it was explaining to everyone why he was suddenly ordering salads instead of burgers at lunch. "Every change you make," he said, "requires dozens of explanations to people who prefer the old you."

We underestimate how much social friction even small changes create. Changing yourself means temporarily becoming a stranger to those who know you. It means answering the same questions repeatedly: "Why are you doing this new thing?" "What was wrong with the old way?" "Are you going through something?"

The anticipated exhaustion of these conversations keeps many of us on the path of least resistance.

Third, we confuse big innovation with small evolution.

We tend to think of innovation as big, dramatic breakthroughs—the iPhone, the Internet, the electric light. But most innovation, especially personal innovation, happens through what Silicon Valley calls "iteration"—small, continuous improvements that compound over time.

James Clear captured this perfectly in Atomic Habits when he wrote about the power of being 1% better each day. Tiny changes, consistently applied, lead to remarkable transformations.

In 1976, a computer engineer named Seymour Cray was asked what the secret was to his company building the world's fastest supercomputers. His answer wasn't about technology – it was about psychology.

"We waste three months of the year thinking about how things might be different," he said. "Most people just try to protect what they have."

Those three months of contemplation—of imagining different approaches and questioning assumptions—were the source of Cray's competitive advantage—not the execution but the willingness to regularly rock his own boat.

Most of us never give ourselves those three months, metaphorically speaking. We're too busy rowing.

Innovation on yourself doesn't need to be dramatic to be effective. Some of the most powerful personal innovations I've seen came from small experiments:

• A CEO who started reading fiction after 20 years of only reading business books and found it dramatically improved his empathy and communication

• A lawyer who began writing a daily haiku about her cases, which transformed how she constructed arguments

• A teacher who swapped his lecture format to start every class with a question instead of an answer

The pattern in each case was the same: small change, unexpected insights, compounding results.

The paradox is that while these innovations seem minor, they signal something powerful to everyone around you. They show you're willing to question your assumptions, even when things are going well.

Nothing inspires a team like a leader who's willing to evolve. Nothing builds trust like someone who acknowledges they're still learning. Nothing creates psychological safety like seeing the boss try something new and sometimes fail.

The Blockbuster executive team famously passed on buying Netflix for $50 million in 2000. It's easy to mock this decision in hindsight, but they were making a rational choice from their perspective—protecting what works rather than risking something new.

The tragedy isn't that they made the wrong call. The tragedy is that they had stopped building the mental muscles needed to evaluate transformative opportunities. They had been right for so long that they lost the ability to question their own thinking.

We risk the same calcification in our personal lives when we stop questioning our assumptions, when we stop experimenting with how we work, how we think, how we live.

If you had to choose whether to stay the same and let the world change around you or to be part of the change, the comfortable answer is "stay the same."

But comfort is often the enemy of growth. And in a world that's constantly evolving, standing still is its own form of risk.

The irony is that our human instinct for belonging – for being part of the tribe – actually requires us to change. Because the tribe itself is always changing. The only way to stay relevant is to evolve alongside it.

So rock your own boat before someone else does it for you. Start with something small. Test a new approach. Question an old assumption.

The waters may feel choppy at first, but you'll be sailing when others are still stuck at the dock, scraping off their barnacles and wondering where everyone went.

The best is ahead!

-Matt