What TODO When You Have 99 TODOs

Exec Article Summary

• Many people have mile-long TODO lists.

• This results in analysis paralysis, procrastination

• Without a plan, prioritization is difficult.

• Product manager frameworks have already solved this.

• Here’s one I use for myself and teams I coach.

Quickstart

Scoring System

Process:

1. Create a spreadsheet with each TODO item.

2. Rate each item over each dimension (go fast, don’t overthink)

3. Add up the total score.

4. Sort by highest score

5. Pick 1-2 items in the top 5 and go.

Alternative Process:

1. Send the prioritization skill to your AI chatbot.

2. Work through an existing TODO list interactively.

3. Review the ranked results.

4. Pick 1-3 items in the top 5 and go.

When Things Show Up In 3’s

A teacher of mine told me to pay special attention to things that show up in your life in 3’s.

In the last month, how to prioritize has come up 8 times with the following archetypes:

• 2 Startup founders

• 2 SMB CEOs

• 2 coaching clients

• 2 CTO colleagues

So clearly, people are struggling to figure out where to spend their time and energy.

Hell, I’ve had to re-run these exercises for myself on any given day! I have 30+ TODOs and 8-10 hours in my workday. It’s not going to all fit, so I have to be aggressive about sorting my daily targets to make sure the most important things get done.

Sounds Nice, But How?

The fix is simple, but don’t let its simplicity fool you.

Most people (including me) struggle to mentally sort all of this on the fly across multiple issues. By getting it out of your head and quantifying, you can help yourself zero in on the items with the biggest impact.

So get started by doing the following:

• Get a spreadsheet.

• Column 1: TODO label

• Column 2: What is done?

• Columns 3-7: Sorting across the following dimensions.

Effort is inverted on purpose. Cheaper is better, so 5 is cheap, and 1 is expensive. Impact, Reach, and Recurring follow intuition; the higher is better.

You’ll know two key things about scoring.

• Integers only. No 3.5s. The moment you split the difference, you’ve reintroduced the illusion of precision that the coarseness was designed to strip away. You can’t hide behind 4.3 versus 4.4. You have to decide: is this a 4 or a 5? That forced choice is the point.

• Orders of Magnitude. Points matter because they represent big jumps. For something to go from a 4 to a 5 on effort, you have to 10x the speed. For something to go from 4 to 5 on recurring, you have to 10x the frequency you benefit from it.

This makes 5 very hard, and 4s the highly desirable floor.

You can tolerate 3s, but only if the other categories are 4s and 5s.

1s and 2s should be avoided whenever possible. Or you should redefine the task to get a better score. If something of incredible value (5) takes a quarter (1), perhaps you find a way to get great impact (4) but in a week (3). A score of 7 beats a 6, so you should try to find those optimizations.

Don’t Let the Math and Numbers Scare You

This sounds like a lot of work, but it isn’t.

I’ve worked with teams of >10 people, and we’ve been able to rip through and score >20 items in less than an hour.

That’s way better than running with scissors and wasting days or weeks of time on a low-value item.

And if you want, you can use AI to do the scoring for you. Just have it interview on each item, and it’ll assess and spit out the scores.

An AI-era footnote

One axis has been quietly shifting on everyone: Effort.

What was a “1 week build” (score 3) in 2023 is often a “1 day build” (score 4) in 2026. AI tooling has compressed the Effort axis hard, and your rankings will systematically undervalue small, fast, high-leverage work until you recalibrate the legend.

The other three axes are stable. Only Effort drifts. Recalibrate quarterly.

Try It as a Claude Code Skill

I built this as an interactive Claude Code skill. It picks dimensions with you, calibrates the legend against your domain, scores each item, and produces a ranked table you can paste straight into a doc.

Install once:

/plugin marketplace add rickmanelius/skills

/plugin install save-your-startup

Then run it on whatever’s on your desk:

/sys:prioritize 8 features for our Q3 roadmap

It works equally well on startup features, AI experiments, side projects, or life decisions. Pick the hard list you’re avoiding right now and run it through.