Why it’s so hard to write about yourself

You’d think it would be a snap..

After all, it’s your life. You were there for all of it. You remember the key players, the big turning points, the bad haircuts. You’ve probably told some of these stories at conferences, dinners, or over a bottle of wine. And yet, when you sit down to write about yourself—really write—it’s as if someone’s poured glue into your brain and handed you a broken keyboard.

You’re not alone. I work with a lot of smart, accomplished people—founders, executives, doctors, lawyers, even the occasional retired race car driver—and most of them struggle with the exact same thing: translating a rich, complex life into a clear, compelling, readable story.

And it’s not for lack of effort. Many clients come to me with a folder labeled “Book” that’s been collecting digital dust since the Obama administration. It’s filled with promising starts, voice memos, late-night notes-to-self, and a half-written prologue that trails off mid-sentence.

So what’s going on? Why do capable, confident people falter when the subject is themselves?

Let’s break it down.

1. “I’m Too Busy” Syndrome

You’ve built a successful life by staying focused on what’s urgent. Writing a memoir feels like a luxury project—something you’ll get to after the next deal, the next quarter, the next vacation that turns into a board call in Cabo. But memoirs aren’t weekend projects. They require time and structure. Left to chance, the process stretches out like George R. R. Martin’s publishing schedule.

Here’s the truth: you don’t need a sabbatical. You need a system. And probably someone—hint, hint—to keep you accountable and on track.

2. “I’m Too Close to It” Fog

This is the big one. When you’ve lived through something—especially a full, nonlinear, occasionally chaotic life—you’re inside the jar. You can’t read the label. You remember everything, which makes it hard to know what matters. You’re tempted to include every job title, every turning point, every character who once shared a cab with you to LAX.

But readers don’t want a résumé. They want a story. A collaborator can help you find the pulse—the emotional throughline that gives your life its shape. Think of it like therapy, but with footnotes.

3. You Know Too Much

This may sound like a compliment. (And it is!) But knowing too much makes it harder to write for readers who know none of it. You forget what needs explaining. You summarize things that should be scenes. You assume emotional resonance when you’ve only delivered bullet points.

It’s like the Simpsons episode where Homer becomes an astronaut and casually mentions to Marge, “Oh yeah, we landed on the moon today. Anyway, what’s for dinner?” You’re Homer. You’ve lived through moon landings. But the rest of us want the details—the lift-off, the G-forces, the view out the window.

4. “It’s Too Late” Myth

This one usually shows up in people’s 60s or 70s: The kids are grown. The business is sold. The window has closed. Nonsense.

You’re just now getting good at this. You have the distance. The clarity. The perspective that turns anecdotes into insight. Frankly, your younger self probably would’ve written a boring book full of chest-puffing and buzzwords. Now? You’ve got wisdom—and stories worth passing on.

5. You’re Not Wired to Look Back

High-achievers are future-oriented. You plan. You solve. You pivot. Reflection feels unproductive, like driving with the rearview mirror taped over. But memoir requires exactly that: slowing down, circling back, looking inward. It’s not a quarterly report—it’s a reckoning.

The irony? That rearview reflection often reveals the most valuable parts of your story—the mistakes, the pivots, the unexpected grace.

That’s a lot, I know. You started out thinking about telling a few good stories—and now you’re staring down questions of perspective, structure, narrative arc, and the emotional resonance of your moon landing. No wonder people stall out. But here’s the thing: none of this means your story isn’t worth telling. It just means you need a different approach.

So What’s the Fix?

Start by giving yourself a break. This isn’t supposed to be easy. Memoir is the literary equivalent of performing surgery on yourself—with no anesthesia and a typewriter in your lap. The solution isn’t grinding it out alone. It’s inviting someone else into the operating room.

A good collaborator helps you step outside yourself. They ask the questions you’ve forgotten to ask. They notice the pattern hiding in the chaos. They listen for what makes your story human—then help you bring that to the page.

Because in the end, that’s what makes a memoir sing. Not the success. Not the chronology. But the reflection. The honesty. The moments that made you flinch, laugh, or change direction.

So if you’ve been stuck on your memoir—or never quite started—know this: you’re not the problem. The process is. You just need a better one.

And maybe someone who knows what questions to ask.

If you're ready to turn that dusty folder into a finished book, let's talk about what that process actually looks like.