Stage 5: Daily Practice | Project Planner

Some experiments from Stage 4 will grow into proper projects. A side hustle might become an actual business launch, a "try cooking at home for a month" experiment might turn into "redesign my entire relationship with food." If and when that happens, you'll need a way to manage such projects.

This planner is for personal life design projects: things with a clear outcome, multiple steps, and a timeline longer than a week. Use it for anything from "build a morning routine" to "launch a freelance consulting practice."

-HOW TO PLAN

Start with the minimum viable version

Eric Ries popularised the Minimum Viable Product in "The Lean Startup", and the idea transfers perfectly to personal projects: build the smallest version that lets you learn whether this is worth pursuing at all.

If your project is "start a newsletter," the MVP is writing three issues and sending them to twenty people you know. You don't need a custom website, a logo, or a content calendar. You need to find out whether you enjoy the writing and whether anyone reads it.

Most personal projects die from over-planning, not under-planning. You spend six weeks building the perfect system and never actually do the thing. So the planner below asks you to define both "done" and "good enough." Start with good enough. You can always iterate.

Work backwards from the outcome

Amazon's "Working Backwards" process, described by Colin Bryar and Bill Carr, starts with the end state and reasons back to today. Before building anything, Amazon teams write a mock press release for the finished product. This exercise forces brutal clarity about what you're actually trying to create, before you've spent any money or time finding out what you didn't know.

For personal projects, the equivalent is answering two questions: How will I know this is done? What does it look like when it's working? Then trace backwards from that picture to your first concrete action. The clearer the end state, the more obvious the path.

Milestones for orientation, dates for momentum

Personal projects don't follow predictable schedules because life gets in the way, you get sick, work dumps extra work on you, or your energy dips for a fortnight.

This is where a lot of advice tells you to abandon dates entirely. Don't. Dan Ariely and Klaus Wertenbroch found that people who set their own deadlines perform better than people working with none at all. Deadlines aren't the problem. The problem is arbitrary, borrowed, externally-shaped deadlines, because missing one of those produces guilt.

So define your milestones as the waypoints that tell you where you are: "prototype built," "ten people tested it," "decision made about whether to continue." Then give yourself dates you chose, because a project with no dates becomes a project you're not doing.

The vital few (and the useful many)

Vilfredo Pareto observed that roughly 80% of the land in Italy was owned by 20% of the population. Then Joseph Juran, an engineer working in quality management, read it and realised the same showed up everywhere: a small number of causes producing most of the effects. Juran coined the phrase "the vital few and the trivial many," and then named the whole principle after Pareto.

He regretted it. Juran later published a paper titled "The Non-Pareto Principle: Mea Culpa," confessing that he'd mistakenly attached the wrong man's name to a principle he had actually been the first to articulate. Buuut the name stuck anyway, and you're probably already aware of it.

Jurian also softened his own phrase over time, from "the trivial many" to "the useful many," because the other 80% isn't worthless - it's just not where the leverage lives. Which is exactly the point for your project. Before you start, ask: what are the two or three activities that will create most of the result? For a side business, it's probably making something and talking to potential customers. Everything else (the logo, the business cards, the Instagram presence, the beautiful Notion database) is just useful to have (not the vital few). Do the high-value work first, while you still have energy for it.

Run a premortem before you commit

You already have a tool for this from Decision Making, and it's far better than a list of risks.

So before you fill in a single milestone, ask yourself: it's six months from now and this project died. How did it happen?

Then look at your list and ask which of those causes you could defuse today, and which you'll simply have to watch for.

Scope creep

Every personal project wants to grow. You start with "redesign my morning routine," and within a fortnight you're researching circadian biology, buying a sunrise alarm, overhauling your bedroom, and four books deep into sleep science (hello, that's me 👋). The project doubled in scope before you changed a single thing about your actual mornings. Not great.

The fix is simple and quite easy. Write down the scope at the start and treat it as a contract with yourself. When new ideas arrive, and they will arrive, put them on a "later" list rather than into the project. Finish the original scope first. Then, and only then, decide whether the additions still look good and should be pursued.

Know your off-ramp before you need it

Your experiments have exit criteria and your projects should too. Before you start, decide what would tell you to stop, and what would tell you it's working. Write both down while you're clear-headed, because the version of you six weeks in, tired and slightly embarrassed, is not the right person to be renegotiating that decision from scratch.

Then at each review, you're not asking "do I feel like continuing?" You're asking the same three-way question we discussed earlier: quit, adjust, or continue? Quit if you've hit your stop criteria, adjust if the direction is right but the design is wrong (most "failed" projects are just badly scoped ones), continue if it's working, or if it's merely uncomfortable.

-THE PROJECT PLANNER TEMPLATE

Fill this in before you start working, not after.

Project overview

Project name:
One sentence description: What is this project, in plain language?
Connected to: Which focus area, goal, or experiment does this come from?
Why this matters to you: What value does this connect to? Why do you care?

Defining done

What does 'done' look like? Be specific. Add the full version.
What does 'good enough' look like?: The MVP. The smallest version worth doing.

Resources needed

Time: Hours per week? Total?
Money: Budget needed?
Skills: What do you need to learn?
People: Who can help you?

The premortem

It's six months from now and this project failed. Write the story of what happened. Then, for each cause: was it preventable, and what could you do now to reduce it?

The vital few

What are the two or three activities that will produce most of the result? Do these first. Everything else is the useful many.

First three actions (this week)

Not "research options." Something physical, something you'd know exactly how to start if you sat down right now. "Email Sarah to ask about her experience with X." "Write 500 words of the first draft." "Sign up for the free trial."

Write the action and add a deadline.

Scope boundary

Write down what this project includes and what it doesn't (for now). When new ideas come up, they go in the right-hand column, not into the project.

Review the schedule and off-ramp

• How often will I review this?

• Next review date:

• What will I evaluate?

• What would tell me this is working?

• What would tell me to stop or change direction? (Your exit criteria. Write them now, while you're clear-headed.)

At each review, ask: quit, adjust, or continue?

Key milestones

The waypoints that tell you where you are. Give each a date you chose. When you miss one, move it and notice why.

Milestone name:
Target date:
Status:
Notes:

AI companion (optional):

How to use: Share the project you're planning, why it matters to you, and any relevant context from the experiment it grew out of. The AI will help you scope it down to something doable and plan your first concrete actions. 15 to 20 minutes.

Copy and paste the prompt below into Claude, ChatGPT, or any AI assistant alongside the project you're planning, why it matters, and relevant context:

You are a project planning coach helping me scope and plan a personal life design project. I'll describe the project I want to take on.

Your job:

(1) Help me define a clear, specific outcome. If my description is vague ("get healthier"), push for specifics ("cook dinner at home 4 nights a week and walk 30 minutes daily").

(2) Help me define the MVP version. What's the smallest version of this project that would still be worth doing? Most personal projects fail because the scope is too big.

(3) Ask me to identify the 2 to 3 activities that will produce most of the results. Help me see what's essential versus what's busywork disguised as progress.

(4) Help me set milestones as waypoints, with dates I choose myself. Ask how I'll know I'm making progress.

(5) Run a proper premortem with me: ask me to imagine it's six months from now and the project failed, then tell you why. Push for specific causes, not vague worries. Then help me plan for the ones I can prevent.

(6) Help me set exit criteria before I start: what would tell me this is working, and what would tell me to stop or change direction?

(7) End by helping me write 3 concrete first actions for this week. Each one should be specific enough that I'd know exactly what to do if I sat down right now.

One question at a time. Be practical. If my plan sounds over-engineered for a personal project, say so.

My project and context: [INSERT HERE]

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