How do you plan?

I am a visual person, so I tend to lean towards rough wireframes to plan a project. My favorite system for wireframes is https://balsamiq.com/.

As for task management, I use https://clickup.com/ with a project for each of my ideas and different lists for dev, marketing, and business tasks under each project.

May have seen my other threads on this out there, but I'm an ol' paper and pen kind of guy.

Earlier this year, after many apps, many google docs, lists out the ass, perpetual lists that are never ending, I came up with a method that works for me.

Every Sunday I plan out my up coming week, in up to but not exceeding 25 items. This list includes personal / work / side hustle.... everything.

Then during the week, I try to get everything on that list done. Which honestly, never happens. That's why I have a second column, which I consider "next week's list" but mostly includes new ideas, any work that just came out, etc.

I don't hesitate to work on "next week's" tasks if they are P1 type stuff, but ideally, I'd like to never touch those until the next week. That second list is ALSO limited to 25 items, never exceeding that.

These limits on the number of tasks allow me to be hyper focused on what's important. I don't list out everything under the sun, just the important stuff. Most of my side hustle stuff is based around conversations I've had with users, specifically things that keep coming up, or pain points in my process that I'm just sick and tired of doing manually.

Then, at the end of the week, I sit down and make a new list of 25 items. It's mostly based on what I didn't get done the previous week. I consider this to be the equivalent of backlog grooming, and definitely will throw tasks out if I find them to no longer be important or relevant.

That's not to say I won't add those items back in the future, but I try to keep everything neat and tidy for the coming week.

That's also not to say that I don't have long term vision or goals, this is just how I plan my week to week efforts. Moon shots and the like SOMETIMES are written down, but usually just hang out in my head, and I will come up with tasks to help me chip away at them.

Because I do this all on a pad (steno pad, exactly 25 lines, split down the middle) I get that satisfaction by crossing stuff off. The split columns allow me to easily see if I'm focusing on the right tasks (this week's stuff, vs the one off stuff for the coming week).

Been going strong on this for about 6 months now. It's been one of the only systems I've been able to stick to, and because I'm focusing on small tasks, I've been able to snow ball a ton of work into shorter amounts of time.

Brainstorming: Mindmaps or Dynalist
Planning: Agantty and/or Trello
Operational work with a team: Trello & Slack
Copy and documents: Google Docs
Time management: PomoDone App

I've got some long-term goals with Indie Hackers. At Stripe we call these "charter metrics". For IH these are: (1) inspire people to start companies, (2) help people succeed, and (3) expand our reach to as many founders as possible without sacrificing #1 or #2. Everything we do is, ultimately, to help move these metrics.

Every quarter I put together a document that runs through a few things:

• progress on charter metrics and some other metrics
• some paragraphs about how I felt about last quarter
• list of things I shipped last quarter + things I'll ship this quarter
• list of goals I had last quarter and their progress + goals for this quarter; often these goals are aligned with metrics and/or ships
• list of things you guys are asking for

Just the process of putting this together every quarter is helpful. You don't want to go too long without looking at big picture stuff and reflecting on your past performance.

I also have a roadmap document that continues some strategic tasks with explanations and due dates. Almost all the strategies on here are in support of hitting the goals from the previous doc. I review this once a week on Monday.

Finally, I have daily task lists. I try to fill out my task list for each day of the week on Monday when I review my overall roadmap. I mostly don't want to waste time rejiggering my tasks every day, but I end up doing that anyway. I also think a lot about setting a realistic workload for myself. I try to schedule 4-5 hours of tasks per day, but it almost always ends up taking me twice that long to work through it.

It sounds like a lot, but overall it's probably a couple days of planning per quarter + 2 hours of planning on Mondays + 10 minutes of planning per day.

Org-mode for code. https://orgmode.org/
Frenzy for non-code. https://frenzyplan.com/

My planning strategy is pretty high level at first and then gets more granular as I progress through the project.

Let's assume the project is for a client looking to build a web app...

• First, write 5-10 bullet points on goals, questions, etc
• Second, create a "model" of what data or information I need (think database model with fields and types but this can be used for anything really... such as a meeting or business plan)
• Third, run it by someone to see if it makes any sense.

From there if the project sprouts wings and gets off the ground, I then provide the client with a software requirements specification (SRS). This outlines the project in more detail with API docs, architecture charts, etc....

Once all of that is complete I grab a beer and exhale.

Product ideas:

I tend to capture ideas with Trello. If something stands out I head to Notion to create an outline of what an MVP for a product/resource might look like. Those things might be logic, data maps, monetization strategies and more. It's just a place to dump any idea even if it's a bad one.

Blog posts/writing/tutorials:

I use Trello to capture feedback from my audience about what they might want to see. Being a YouTuber, I use the new polling feature to help determine the next series of videos to produce. Time permitting, I prioritize those first.

Other than that I try to explore avenues most gloss over with regards to tutorials and resources related to web development and design (the topic of my blog). I write everything in markdown files which get saved to either icloud or dropbox. My favorite markdown editor is typora at the moment. It stays out of my way and allows me to preview markdown inline rather than a whole new view.

When I come up with a new project, I start by writing out everything I can think of, relevant resources and all ideas about it in Evernote. Found this really helpful with coming up with great ideas on how to do things / what do to.

Then I start organizing it all, removing some things and adding some others. Then I break down each part into actionable sections, like 'Updates to the website', 'Marketing strategies' and others...