You know that project you keep moving forward that never actually arrives?
You’re doing the work. You’re adding steps. And the finish line stays put. If you don’t know what done looks like, taking steps toward a project is like walking toward the horizon. You aren’t getting closer. You’re treading water.
Write the end state before you break the work down. One to three sentences. That’s your Definition of Done. Then reverse-engineer the steps from it. Breaking a project into tasks doesn’t help when those tasks have no finish line to point at.
Could someone else read your sentences and tell you whether the project is finished? If they’d have to guess, you don’t have a Definition of Done yet. Write those sentences before you open a task app.
Plan in a doc first
The stall hits while you’re breaking the work into pieces. The project is unfamiliar. You start listing steps, and a task manager turns every one of them into a commitment before you’ve decided they belong.
Task managers feel permanent. Every line looks like a promise. Leave one undone and it feels like you failed a to-do. You want a place where you can scratch an idea without that guilt.
Use a document or a mind map at the start. A Google Doc or a Notion page is enough. Documents feel fluid. You can scratch a step, reorder a section, or throw out part of the plan, and none of it sits on a list as a failure.
Stay in the doc while the plan is still moving. When it settles, move the real work into your task app. Next project you plan, open the Google Doc or the Notion page before you touch the task manager.
Does a list you’ve barely started already make you feel behind? Keep that early pass somewhere you’re allowed to rearrange it.
Who has done this before
Some projects you have no experience with. Implementing new software is a typical one. Don’t try to figure out the how by yourself.
Find out who has done it before. Who, not how. Hire an expert by the minute and let them break it down for you. Clarity.fm is one place to book that call. Buying the expertise saves time and prevents costly mistakes. On a project you’ve never done, it is often more efficient than learning from scratch.
You can also get the breakdown from ChatGPT. I have a custom GPT for project management, and I use it when a project is unfamiliar. Regular ChatGPT will do this.
Put your project description in. Ask the AI to act as an expert who has done this hundreds of times. Have it give you the steps, the risks, and the considerations you might miss. It shortcuts the learning curve.
Paste this:
You are an expert who has done this kind of project hundreds of times. Here is the project, and here is my Definition of Done:. Give me the steps, the risks, and the considerations I am likely to miss.
Read the answer in your doc. Keep what serves the Definition of Done. Scratch the rest. In a doc, a scratched line is just an edit.
One more ChatGPT move, for the questions that are smaller than a project. The mobile app has a camera. Use it to identify an object, translate text, or analyze ingredients. Take a photo of a supplement label and ask whether it’s safe to take before bed. That can save 30 minutes of manual research. Try the camera the next time you want a quick fact-check or a translation.
What would have to be true
Your stakeholders still have to approve something. Sometimes a presentation. Sometimes the project plan.
Ask this while you plan: What would have to be true for my stakeholders to approve this?
Every point you keep has to serve that decision. Asking “What slides do I need?” is how feature dumping happens. Apply the approval question to your next big deliverable and filter out anything that doesn’t help them decide.
What would have to be true for the stakeholders on the project you’re in right now? Write those conditions under your Definition of Done. Keep the points that make one of those conditions true.
After the project, thirty minutes
Hold a retrospective after every project. Block 30 minutes. Ask:
What went well?
What didn’t?
What can we do better?
This is Kaizen. You’re looking at the project you just finished, and you’re building a database of team strengths and weaknesses. That database tells you how to allocate people on future projects, including projects that aren’t related to this one.
A retrospective after a customer event can inform how you run a software rollout later.
Schedule a 30-minute retro for the last project you completed. Do it while you still remember what happened.
Open a Google Doc or a Notion page. Write the Definition of Done for the project you’re stuck on, in one to three sentences. Don’t add a task until those sentences describe an end state you can reverse-engineer.
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