The Clarity of the Grave

“The successful warrior is the average man, with laser-like focus.” — Bruce Lee

Have you ever noticed how much you can learn about someone from which store they obsess over? We are defined by what we consume. As a wide-eyed child, I would dart through the aisles of Toys R Us, my heart racing with each new discovery. I jumped for joy when I got my first Optimus Prime or the Teenage Mutant Ninja Turtle Pizza Thrower vehicle (with real pizza-tossing action)!

As the years passed, my obsessions evolved. The bright colors and plastic figurines of the toy store gave way to the sleek gadgets and cutting-edge technology of Best Buy. I found myself entranced by the latest computers, gaming systems, and big-screen TVs, each one promising an immersive escape into digital worlds. I geeked out over specs and features, dreaming of the ultimate gaming setup with mind-blowing graphics and heart-pounding surround sound.

At some point, the store I got most excited about was the office supply store. My eyes lit up as I walked in. I envisioned the perfect workspace, one that would liberate me from clutter and anxiety. The feel of a perfectly-balanced ballpoint pen would inspire me to write something brilliant. I was sure of it. The smell of a leather organizer holding a fresh notepad would lend gravitas as I captured critical notes in a meeting. The Zen beauty of the perfect desk organizer would mirror my soul as everything was nestled in its proper place.

If you haven’t realized how nerdy I am by this point, you have now. I was obsessed. I couldn’t rest until I had the perfect tools.

Obsession, when harnessed properly, is the engine behind meaningful achievement. It will push you past obstacles and roadblocks and the inevitable losses life throws at you.

My obsession with productivity artifacts led directly to writing this substack. My hunt for the perfect set of tools was never satisfied. Searching for the ultimate journal became a particular fixation. I wanted a journal I could easily carry with me, that would lay open perfectly on my desk, and would have just enough direction to keep me organized while giving me room to be creative.

I couldn’t find it. Some wouldn’t lay open right. Others were too bulky. Most had subsections and labels that made no sense to me. I started creating my own journal using a rubber band and note cards. Each day, I jotted down my three most important tasks for the day, listed my three core habits, and wrote three things I was grateful for. The three-by-five note cards fit in my pocket perfectly and easily laid flat on a desk.

I continued to refine my note cards until I eventually transformed them into the Level Up Journal, which included early versions of many of the principles I write about here. Feedback from the thousands of readers who used the journal helped me to refine the principles and make them more useful to a wide range of people. By leveraging my own peculiar obsession, I transformed my passion for productivity and my annoying tool search into a creative mission. The recipe of “scratching your own itch” and diving deeply into the details of your obsessions shaped some of the most iconic products in the world and it is a strategy you can use too.

Steve Jobs embodied obsession as a superpower. When developing the first Macintosh, he insisted the computer greet users with a friendly face rather than a cold command line, a revolutionary concept at the time. He drove his team relentlessly toward this vision of making computers intuitive and inviting.

His perfectionism extended beyond what customers would see. Jobs demanded even the internal circuit boards be elegantly designed, telling his team that true artistry meant caring about parts no one would ever look at. “When you’re a carpenter making a beautiful chest of drawers,” he would say, “you’re not going to use plywood on the back, even though it faces the wall.”

This obsessive attention to detail shaped everything he touched. His product keynotes became legendary performances that he would spend weeks rehearsing down to the minute. When creating the iPhone, he rejected dozens of prototypes until his vision of a true pocket computer was realized, ultimately transforming the entire mobile industry.

While others scattered their attention, he channeled all his energy into the most important, transformative work he could do. He spent time on minutiae, because when you are working on the right things, it’s the minutiae that matters. What Jobs understood is that how you spend your attention is how you spend your life. Every choice about where to focus is also a choice about what you love enough to give your limited time to.

You don’t need to be Steve Jobs to harness this power. To cultivate a healthy obsession, we need to be clear about what is worth obsessing over and what gets in the way.

In our modern world, distractions wage a constant war for our focus. Advertisements, social media notifications, emails and cat videos fragment our attention into a thousand pieces. We bounce from task to task, never fully present, never diving deep.

The result? Our ability to focus on what matters has grown weak, like a muscle that’s atrophied from lack of use. To do truly meaningful work, we find projects worthy of deep, sustained attention. Once we have that clarity, focus will follow.

And there’s nothing like death to provide that clarity.

The Clarity of the Grave

“Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life.” -Steve Jobs

In any game, knowing the timer is running out changes how you play. Life works the same way. Most people would rather not look at the clock. But ignoring your mortality doesn’t make you live longer. It just makes you live less.

We waste our lives distracted by minutiae. We wander through the world in a waking trance of consuming, posturing, and numbing. The recent death of my good friend Alex (which I wrote more about here), brought this insight front and center for me. Don’t wait until you’re on your deathbed to realize your life was spent poorly.

Exercise—Write Your Eulogy

This exercise transformed my life when I first did it twenty years ago. It helps cultivate a healthy awareness of mortality and separate the trivial from the triumphant.

Imagine your funeral, many years from now. You lived your dream life and now get to watch people eulogize you. Take a moment to picture it. Where are you? Who is there? What are they saying? Are you praised as a loving partner, parent, or friend? Did you inspire others or accomplish great deeds? Were you known in your community for being charitable and good? Let the scene come to life before you start writing.

Now write the eulogy. Spend ten to fifteen minutes writing from the perspective of someone who loved you deeply: a partner, a child, a lifelong friend. Write about the legacy you want to leave, not the titles you held or the money you made. Focus on impact, relationships, and how you made people feel. What stories will they tell? What did they learn from you? What were your defining qualities?

When you are done, sit with what you wrote and ask yourself three questions:

1. Will the path I am on today lead to the life described in that eulogy?

2. What do I need to focus on now to close the gap?

3. What distractions or trivial concerns can I let go of starting today?

When thinking through the path you are on today, if it does not align with the vision of your ideal eulogy, imagine the worst case scenario outcomes of continuing on your current path. Imagine the lost opportunity and regret you might have. Only then, come back to the present, and imagine that though you lived your life incorrectly the first time around, you have been given a second chance to make things right. Answer questions two and three from that frame.

The Eulogy exercise helps you transform your passions into the type of focus needed to achieve great things in any field.

Identify the path you want to be on.

Maintain your focus relentlessly on that path.

Remove everything else that gets in the way.

Our attention will get spent one way or another. You now have a picture of what your life can be if you obsessively point it at the things that matter. The only question left is whether you are willing to aim it there now, while you still have time.