This post uses Annie Duke's "time travel" technique from her appearance on the a16z podcast. Rather than focusing on how to succeed, I'm conducting a pre-mortem—imagining complete, catastrophic failure five years from now and working backward to identify the preventable pitfalls that led there.
A pre-mortem differs from a post-mortem in a crucial way. Post-mortems happen after failure, when hindsight bias makes everything seem obvious. Pre-mortems happen before failure, when you can still change course. The exercise forces you to take failure seriously rather than assuming success is inevitable.
So: it's 2024. This blog is dead. No new posts in years. Traffic has flatlined. The domain will expire without renewal. What happened?
The Goals That Didn't Materialize
First, let me articulate what this blog was supposed to achieve. Clarity about goals makes failure easier to diagnose.
Goal 1: Generate meaningful dialogue on topics of interest. I wanted to write things that made people think, respond, and engage. Not viral traffic for its own sake, but genuine intellectual exchange. Comments, emails, conversations stemming from ideas I put into the world.
Goal 2: Connect with influential thought leaders. Writing publicly is a way to attract attention from people you admire. If you write thoughtfully about topics they care about, sometimes they notice. Sometimes they respond. Sometimes relationships form. I wanted to use the blog as a networking tool in the best sense—connecting through ideas.
Goal 3: Develop writing skills through practice. Writing is a skill that improves with repetition. The more you write, the clearer your thinking becomes. The blog was meant to be a forcing function for regular practice, a commitment device that would make me a better writer over time.
If I fail at these goals, it won't be because of external factors. It will be because of identifiable bad habits that I can prevent now—if I'm honest enough to name them.
Failure Habit One: Not Showing Up
The most common way blogs die is simple abandonment. Life gets busy. Other priorities emerge. A week without posting becomes a month becomes a year becomes forever.
The insidious thing about not showing up is how it compounds. Fewer articles mean a narrower audience, which means less feedback, which means less motivation to write. Less writing practice results in lower quality work, which makes writing harder and more unpleasant, which makes avoidance more tempting. Each day you don't write makes the next day harder.
Long-term success depends on consistent habits rather than momentary motivation. Motivation is unreliable. Habits carry you through the days when you don't feel like it.
I know my own tendencies. When something is difficult or frustrating, my instinct is avoidance. Checking email instead of writing. Doing research instead of producing. Any activity that feels productive while actually procrastinating.
The countermeasure is simple but not easy: schedule writing time and protect it ruthlessly. Treat it like a meeting that cannot be rescheduled. Show up even when you don't feel like it, especially when you don't feel like it. The habit matters more than any individual session.
Failure Habit Two: Perfection Paralysis
A famous ceramics study divided students into two groups. One group would be graded solely on the quality of their best pot. The other would be graded solely on the quantity of pots produced. At the end of the semester, an interesting pattern emerged: all the highest quality pots came from the quantity group.
Why? The quantity group produced more work, and through iteration, developed their skills faster. They learned from mistakes because they made more mistakes. The quality group spent so much time theorizing about the perfect pot that they never developed the practical skills to actually make one.
This study haunts me because I recognize the tendency. I can spend hours perfecting a paragraph instead of finishing a draft. I can research endlessly instead of writing imperfectly. Perfectionism feels like high standards, but it's actually a form of fear—fear of putting something imperfect into the world.
Publishing volume matters more than perpetual revision. Ship it. A published post that's 80% as good as it could be does infinitely more than a perfect post that never exists. You can always write better pieces later. You can't retroactively produce the pieces you never published.
The countermeasure: set deadlines and respect them. Publish on schedule even if the piece isn't perfect. Trust that iteration will improve quality over time. Done is better than perfect because perfect is never done.
Failure Habit Three: Misaligned Priorities
It's tempting to confuse personal wants with reader needs. They're not the same thing.
I might want to spend time building a custom blog platform, tweaking the design, optimizing the infrastructure. These activities feel productive because they're tangible and satisfying. But they don't serve readers. Readers don't care what CMS you use or how clever your CSS is. They care about the ideas.
Creating custom solutions often prioritizes personal preferences over reader needs. It feels like working on the blog while actually avoiding the hard part—the writing itself. This is procrastination disguised as productivity, and it's dangerous precisely because it feels legitimate.
Similarly, I might write about topics that interest me but don't resonate with anyone else. Self-indulgent writing has its place, but if the goal is dialogue and connection, I need to consider what readers want—not just what I want to say.
The countermeasure: ruthlessly ask whether each activity serves the goals. Does this help me produce better writing? Does this help readers find and enjoy my work? If not, it's probably avoidance. Cut it and get back to writing.
Failure Habit Four: Failing to Differentiate
The blogging landscape is crowded. There are millions of blogs, most of them abandoned. Even among active blogs, there are thousands writing about the topics I care about—technology, business, culture, ideas.
Competing against professionally-designed platforms and established industry voices requires finding a unique angle. Without differentiation, even good writing disappears into the noise. The internet rewards distinctive voices and punishes generic ones.
What makes this blog different from the alternatives? If I can't answer that question clearly, readers have no reason to choose me over everyone else. "Good writing about interesting topics" isn't differentiation—that's table stakes.
The differentiation might be perspective: my specific background, experiences, and viewpoint that no one else shares. It might be format: a distinctive approach to how ideas are presented. It might be focus: going deeper on specific niches rather than broad surface coverage. But it has to be something.
The countermeasure: develop and articulate a clear positioning. What do I write about that others don't? What perspective do I bring that's unique? What would readers miss if this blog didn't exist? If I can't answer these questions, I need to figure them out before the market does it for me.
Using the Pre-Mortem
The point of this exercise isn't to be pessimistic. It's to be prepared. Now that I've identified these failure modes, I can watch for them.
When I notice myself avoiding writing, I'll recognize it as Habit One and recommit to showing up. When I'm endlessly revising instead of publishing, I'll recognize it as Habit Two and ship the piece. When I'm tinkering with design instead of writing, I'll recognize it as Habit Three and redirect my energy. When my writing feels generic, I'll recognize it as Habit Four and sharpen my angle.
Pre-mortems work because they make failure concrete and specific. Abstract goals are easy to abandon. Specific failure modes are easy to recognize and avoid. "I want this blog to succeed" is vague. "I will not let perfection paralysis stop me from publishing" is actionable.
The best time to prevent failure is before it starts. The pre-mortem makes invisible threats visible, turning unknown unknowns into known quantities you can plan around.
Will I follow through on all of this? History suggests I'll struggle. The whole point is that these habits are hard to break. But at least now I've named them. I've made failure less abstract and more recognizable. When I see myself drifting toward one of these patterns, I'll have the language to diagnose what's happening.
That's the best I can do. The rest is execution.