The Spreadsheet Artist

Creative work is a whole different animal.

I wrote the epilogue of my book three times.

Not three drafts. Three completely different versions, from scratch, each with its own angle, structure, and emotional arc. Each one took weeks. I’d finish a version, sit with it, and realize it wasn’t saying what I actually wanted to say, so I’d start over and try to find it again.

Version two felt closer but still not right. Then I talked it through on a walk with Claire, and something clicked. That conversation became version three.

And then came round after round of edits. Some of those edits made it worse before they made it better. Sentences that flowed got choppy. Paragraphs that worked got torn apart. I had to trust that the mess was part of the process, even when every instinct I had told me I was going backward.

You’re wasting time. This is inefficient. You should be done by now.

But I wasn’t going backward. I was doing creative work.

***

I recorded a podcast episode with AJ Harper this morning, and I was reminded of all this. If you don’t know AJ, she’s ghostwritten some of the biggest business books of the past decade. She’s Mike Michalowicz’s writing partner for ten books, including his hit Profit First. She also wrote Write a Must-Read, which has become the book on writing books.

I sat with our conversation all day. It got me thinking about the transition I’ve been living for the past few years: from entrepreneur to author. Or really, from entrepreneur to creative. Because I think this applies whether you’re writing a book, starting a podcast, painting, building something new, or pursuing anything that requires you to make something that didn’t exist before.

I’ve learned there are two paths. Most entrepreneurs only know how to walk one of them.

***

The Hard Path is the one you’ve been on: Clear problems. Measurable outcomes. You know what success looks like, and you can work toward it with a plan. Get the promotion. Close the deal. Hit the number. The feedback loop is tight, so you can see whether you’re winning or losing in something close to real time.

The Uncertain Path is different: The problem isn’t clear. The outcome isn’t measurable, at least not while you’re in it. You don’t know if what you’re making is good until you’ve made it, and sometimes not even then. The feedback loop is long, foggy, and often silent.

Creative work runs on the Uncertain Path.

Because you’ve spent decades on the Hard Path (successfully!) you’re going to have some advantages… and also some serious unlearning to do.

***

Three Advantages I’ve Had as an Entrepreneur

1. I know how to show up. Blocking a daily 90-minute appointment on my calendar to write? Easy. I’ve been managing my time for decades, and I already know that waiting for inspiration or the right mood is a losing game. I just need a calendar invite and the discipline to treat it like any other non-negotiable commitment.
2. I know how to take feedback. Years of performance reviews, client pushback, and collaborative projects taught me that feedback isn’t personal. Its information. I already know how to separate my ego from my work, hear hard feedback without falling apart, and actually use it to make the thing better.
3. I know how to manage a project. Breaking a massive undertaking into phases, setting milestones, tracking progress, adjusting when things slip. This is second nature to anyone who’s managed complex work. I already know that creative work isn’t just about inspiration. So much of it is logistics and follow-through over a long period of time.

***

Three Things I Had to Learn as a Creative

1. I had to be willing to make it worse before making it better.

This is the epilogue story. I wrote it three times from scratch, talked it through on long walks, and then edited it in more rounds than I can count. Some of those rounds genuinely made it worse. I’d tighten a sentence and lose the rhythm. I’d cut a paragraph for efficiency and gut the emotional core. I had to learn to sit in that discomfort, to trust that breaking something down was sometimes the only way to rebuild it stronger. Creative work isn’t linear, and the path forward often looks like going backward. The entrepreneur brain resists this with everything it has, because we’re trained to measure progress, and “I made it worse today” doesn’t feel like progress. But it is.

2. I had to let go of efficiency.

My brain wants to optimize, and seek out the shortest path to the best outcome. Find the maximum output per unit of input. I was trained to eliminate waste and streamline everything.

Creative work laughs at this.

Sometimes the scenic route is the only route. Sometimes you need the “bad” draft to discover what the good one wants to be. Sometimes you need to write ten pages to find the one paragraph that matters, and then delete the other nine without regret. This isn’t waste. This is the creative process. But it feels like waste to someone trained in efficiency, and learning to be okay with that feeling took me longer than I expected.

3. I had to trust that connections would emerge.

On the Hard Path, you plan the work and work the plan. You know the destination before you start moving, and you can measure your progress against it.

On the Uncertain Path, you often don’t know what you’re really making until you’re deep into it. The best insight, the surprising connection, the line that makes it sing. These reveal themselves through the work, not before it. This requires a different kind of faith. Not faith that you’ll hit a predetermined target, but faith that if you keep going and stay open, something worth finding is waiting out there for you to discover it.

***

I’m still learning this. I’m not writing from the mountaintop. I’m writing from the middle of it, still catching myself trying to optimize my way through something that cant be optimized.

The transition from entrepreneur to creative isn’t about starting over. It’s about keeping what serves you and releasing what doesn’t.

Show up like an entrepreneur. Let go like an artist.

That epilogue I rewrote three times? Its the part of the book I’m most proud of now. I never would have found it if I’d been efficient.