The Sharp Starts Tracking Playbook: How I Actually Keep Track of Things

Why Most Systems Fail

I’ve been in healthcare, startups, and tech. In each space, I ran into the same problem: things slipping through the cracks. I’d have notes everywhere—Slack messages, random napkins, half-filled notebooks. For a while, I thought the fix was finding the “right tool.”

That’s when I fell down the productivity rabbit hole. Kanban boards. Jira backlogs. Post-it note flash cards. They all worked for a little while, until they didn’t.

Most systems collapse because they add friction. When maintaining the system is harder than the actual work, you stop using it. You stop trusting it. Once trust is gone, the system is dead.

The test I use now: Would I still use this on my worst day?

• If the answer is no, it’s too fragile.

• If the answer is yes, it becomes part of my playbook.

This playbook is what survived that test.

Play 1: Capture Without Judgment

Rule #1: if something stays in my head, it’s already lost. I need a place to dump it fast—task, idea, reminder, doesn’t matter.

What works for me now:

• Microsoft To Do – Clean, synced across devices, zero fluff. I keep one “inbox” list for raw capture and a few separate lists for projects.

• Confluence action lists – For notes, project documentation, and structured action items that the team can see.

• Notebook – Sometimes pen and paper are faster, especially during calls.

What I ditched:

• Post-it flash cards – At my peak, I had 50+ sticky notes plastered around my desk. Every morning and night, I’d flip through them like flash cards, trying to make sure nothing slipped. It worked for about a week. Then the pile got messy, I started skipping reviews, and it turned into noise. Worse, it burned time and wasted paper.

• Scattering across six apps – I thought using the “best app for the job” was smart. Instead, I created chaos. I’d lose track of what was where.

The key: pick one capture method and stick to it. The discipline of having a single inbox matters more than the tool itself.

For more on why capture is critical, see Getting Things Done.

Play 2: Buckets, Not Boards

Once things are captured, they need structure. Kanban boards looked impressive. Jira boards felt “professional.” But for personal tracking, they were overkill.

I boiled it down to three buckets:

• Today → Must handle today

• This Week → In play soon, but not urgent

• Someday → Good ideas, no pressure

If a task takes more than 30 minutes, I block time for it in Google Calendar. Otherwise, it gets buried. A task without a time slot is just wishful thinking.

This habit—tying tasks to time—changed everything. Suddenly, I wasn’t staring at a bloated list, I was looking at an actual plan.

For a startup-focused take on prioritization, see No-Code vs WordPress: What I Wish I Knew Before Launching My Blog.

Play 3: Highlight for Speed

I write lists in a way that’s easy to scan at a glance:

• Short phrases, not full sentences

• Strong verbs

• Highlighted keywords so the important stuff jumps out

I used to write paragraphs in my notes. Later, I’d open them and feel like I was reading an essay instead of a task list. It slowed me down.

Now, if I can’t scan my list in under 10 seconds, it’s too cluttered.

For more on scanning and visual clarity, see Lifehacker: How to Take Notes You’ll Actually Use.

Play 4: Keep Team Tools Separate

Personal systems are for me. Team systems are for alignment. Mixing the two is a disaster.

Here’s how I handle it now:

• Confluence action lists → Meeting notes, project tasks, and action items all live here. Everyone on the team sees the same thing. Nothing gets lost, and it’s structured enough for accountability.

• Mural → For messy brainstorming or mapping workflows.

• Jira → Sometimes unavoidable in dev or ops environments. I feed it enough to keep the team aligned, but I never use Jira for personal tasks.

Rule: team tools for alignment, personal tools for execution.

For internal reference on scaling team tools, see Why Servant Leadership Is the Only Kind That Actually Works.

For external guidance, see Atlassian: Team Playbook – Action Items.

Play 5: Weekly Reset

This is the glue that holds the system together. Without it, even the best tools collapse.

My reset ritual:

1. Open my capture inbox (To Do, Confluence, notebook)

2. Delete what’s junk

3. Sort the rest into Today / This Week / Someday

4. Block time in Google Calendar for big items

5. Check team tools for follow-ups

It takes 30 minutes. Usually Sunday night or Monday morning. The reset clears mental clutter and makes the week predictable.

For internal reading on managing tools for productivity, see Ubersuggest vs KeySearch: Best SEO Tools Comparison.

For external reading, see Harvard Business Review: The Power of the Weekly Review.

Play 6: Keep It Stupid-Simple

Complexity kills. I used to spend hours setting up labels, categories, automations—then abandon them when things got busy.

Now, my rule: if I can’t use it on my worst, laziest day, it doesn’t make the system.

That means:

• Short lists

• Three buckets

• Highlights for speed

• One calendar

It doesn’t impress anyone on Instagram, but it survives pressure. That’s the point.

Why This Holds Up

Startups are messy. Career pivots are messy. Both demand systems that don’t break under pressure.

Kanban boards looked good in theory, but I wasted time dragging cards instead of doing the work. Jira felt organized but became overhead. Post-it notes were just shuffling 50+ pieces of paper morning and night.

To-do lists, Confluence action lists, highlights, and weekly resets hold up. They survive chaos. That’s why I trust them.

And trust is the whole point. A system you don’t trust isn’t a system—it’s a prop.

Final Note: The Thrill in Control

I used to think tracking was overhead. The right system doesn’t slow you down—it disappears.

That’s when you know it’s working: you’re not thinking about the system anymore. You’re just moving. You’re throwing more at yourself and it still holds.

And that shift—the moment chaos turns into fuel instead of fire—is addictive. It’s why I’ll never go back to post-its and flashy boards.

📚Further Reading

• The One Thing That Really Helps You Stay Productive – A deep dive into prioritization and focus.

• Why Most Productivity Systems Fail – Lessons from common mistakes in personal task management.

• The Science of Habit Formation for Peak Performance – How to build routines that stick.

• Time Blocking: How Top Performers Schedule Their Day – Practical guide to time blocking.

• Digital Minimalism: The Key to Staying Focused – Reducing noise from apps and tools.

TL;DR

• Tried Jira boards, kanban walls, and post-it flash cards — all failed under pressure

• What works: capture fast, organize into buckets, align with team, reset weekly

• Not flashy, not complicated — durable under chaos

• The key: a system you trust to work on your worst day