Tracking Long-Term Progress

It’s Thursday afternoon. You’re staring at your project—that same project you’ve been chipping away at for months. Maybe it’s a business, a book, an app. The calendar insists you’ve been working diligently, but a persistent doubt whispers: “Am I even making progress?”

I’ve navigated this territory repeatedly: building a writing career across 15 years, launching three businesses, completing multiple software projects that each spanned years. The middle is always a wasteland of uncertainty.

Here’s what I’ve learned: your perception of progress is fundamentally unreliable. Memory fails. Emotions distort. And the daily grind blinds you to the distance you’ve actually covered.

Let’s solve this problem systematically.

The Amnesia of Creation

When I was writing my second book, I hit the eight-month mark and had a complete meltdown. I called my editor.

“I’ve made no progress. I’m stuck in the same place I was three months ago.”

She asked me to send my first draft from three months earlier. I did.

“This is completely different from what you have now,” she said. “You’ve rewritten every section, added research, and fixed all the structural problems we discussed.”

I didn’t remember any of it.

This isn’t unusual—it’s the default state. Your brain isn’t wired to accurately gauge progress over months or years. It’s designed for immediate threats, opportunities, and social dynamics. Not long-term pattern recognition across complex projects.

Without external tracking, you will forget what you’ve accomplished. That’s not pessimism—it’s neuroscience.

Three Layers of Progress Tracking

Most people fail because they track at the wrong layer or don’t track at all. Here’s the framework that works:

Layer 1: The Daily Layer

• What it captures: Granular tasks, hours, and immediate outputs
• Tools: Things 3, OmniFocus, Todoist, time trackers
• Function: Maintains momentum and daily focus

Layer 2: The Weekly/Monthly Layer

• What it captures: Progress against defined milestones and metrics
• Tools: Notion, Airtable, project management software
• Function: Enables course correction and identifies emerging trends

Layer 3: The Quarterly/Yearly Layer

• What it captures: Strategic alignment and major evolutions
• Tools: Review documents, versioned artifacts, comparison tools
• Function: Restores perspective and validates strategic direction

Most creators obsess over Layer 1, occasionally touch Layer 2, and completely ignore Layer 3. For long-term projects, this prioritization is precisely backward.

The Comparative Archive Method

Here’s the system that preserved my sanity across multiple major projects:

1. Create versioned snapshots of your work on a fixed schedule
   • For creative work: Save complete versions every 2-4 weeks
   • For businesses: Document key metrics and processes quarterly
   • For software: Maintain build archives with screenshots and feature lists
2. Implement forced retrospectives
   • Schedule 60-minute sessions every month to review previous snapshots
   • Document specific changes, improvements, and evolutions
   • Ask: “What would I have been thrilled to know back then that I take for granted now?”
3. Maintain a progress journal with three sections:
   • Achievements log (completed milestones)
   • Evolution log (how your approach has matured)
   • Learning log (new insights and capabilities acquired)

The power isn’t in sophisticated tools but in the ritual of comparison. Your brain needs to literally see the difference between then and now to believe in progress.

The Measurement Matrix

Projects derail when measuring the wrong things. After experimenting with dozens of tracking systems, I’ve settled on this matrix:

The trap: Focusing exclusively on lagging indicators creates anxiety and tunnel vision. They move too slowly to guide daily work.

The solution: Build your tracking system around leading indicators that predict future success, while monitoring process indicators to maintain productivity.

For my last major writing project, my indicators were:

• Lagging: Manuscript completion percentage
• Leading: Weekly word count, editor feedback scores
• Process: Morning writing sessions completed, research time logged

This matrix gives you a dashboard that separates “feels bad but actually fine” from “feels fine but actually failing”—a crucial distinction for any creative professional.

Navigating the Long Plateau

Every meaningful project hits the plateau—that soul-crushing period where visible progress slows to a crawl. This is precisely where most people abandon ship.

The plateau isn’t the problem. Your response to it is.

I once spent six months rebuilding the backend of my content platform. To users, nothing changed. To me, it represented thousands of hours of work that produced zero visible results—until suddenly everything worked 10x better.

Here’s how to maintain sanity during plateaus:

1. Pre-identify the plateau zones in your project
   • Map out where progress will become invisible before you get there
   • Set expectations with stakeholders (including yourself)
2. Create micro-milestones during plateau phases
   • Break invisible work into visible chunks
   • Celebrate small completions that others might not understand or appreciate
3. Shift your tracking focus during plateaus
   • Move from outcome metrics to process and learning metrics
   • Document capability gains rather than only tangible outputs

“The plateau is where the amateurs and the professionals separate,” as Seth Godin might say. Professionals have systems to see through the fog.

Implementation for Apple Users

Since many creative professionals use Apple products, here’s my specific implementation:

• Daily Layer: Things 3 with custom tags for project categories, synced across devices
• Weekly/Monthly Layer: Notion databases with linked project documents
• Quarterly/Yearly Layer: iCloud folder with dated project snapshots and Keynote review documents

The magic happens in automation:

1. Shortcuts to capture daily metrics into Notion
2. Calendar events that trigger snapshot creation
3. Monthly review reminders with links to previous snapshots

The setup requires about two hours. The payoff arrives when you’re eight months into a project, questioning your sanity and direction.

Beyond Solo Projects

For team leaders, progress visibility becomes even more critical. People need to see their impact to stay motivated.

For team projects:

• Create visual progress walls (digital or physical)
• Hold regular “how far we’ve come” sessions
• Maintain a shared artifact showing evolution

As Reid Hoffman notes, “The most powerful motivator isn’t money; it’s the opportunity to learn, grow and make an impact.” Good tracking systems make that impact undeniable.

Start Now, Regardless of Project Stage

If you’re already deep into a project without proper tracking, don’t wait. Do this today:

1. Create your first snapshot of the current state
2. Document everything you can remember about where the project stood 3-6 months ago
3. Schedule your first retrospective for one month from now

The best progress tracking system is the one you’ll actually use. Don’t overengineer it. Just ensure it covers all three layers and forces regular comparisons.

The Truth About Progress

Progress isn’t a smooth curve. It’s messy, uneven, and often invisible in real-time. Some days you leap forward. Other weeks you circle back to rebuild foundations no one else will ever see.

But here’s what I know after completing multiple multi-year projects: The work compounds. The days accumulate into transformation. The invisible progress eventually becomes undeniable—but only if you’re tracking it properly.

Don’t trust your perception. Trust your system.

Your future self, the one who finishes that seemingly endless project, will thank you for the breadcrumbs you’re leaving today.

Now go make something worth tracking.