# My Daily Planning System If you're an early stage founder, you have to do everything and everyone wants a piece of you. It's really easy to get distracted by the wrong shit or absorbed by the loudest problem, and suddenly you've helped everyone else but the job that only you can do, is in the toilet. I tried every system (GTD, Pomodoro, Eisenhower) and app (To-Doist, Things, Akiflow, ClickUp, etc.. You get the idea). The systems demand too much overhead that I had to think about the system itself, and the apps either didn't collect all my tasks. It's 2025, and tasks don't just come at me from an assistant. They're hiding in email, ClickUp, Jira, Github, Linear, Reminders, calendars, you get it. Akiflow tries to answer this problem and does an OK job, but I do still have to fight the UI and it doesn't pull in my actions from Granola (insert your meeting recorder here). Ultimately, I want a smart piece of paper. A plain white piece of paper that automatically populates with my tasks for the day. A plain white sheet, no UI, no distractions and then I can cross things out. Given paper can't do that, I built my own and Obsidian is the base, it's the closest thing I'm going to get to paper. No vendor lock in, clean design and I like founder, Steph Ango's software philosophy. It took three years of iteration, but now I have a system that handles startup chaos, strategic planning, and daily firefighting - all in one place. It operates off a Markdown document in Obsidian so I can format it as simply as I want and not be weighted down by UI. But because it's all text, it can be as smart as I want with Claude Code. ANY INTEGRATION I NEED: Get my tasks from ClickUp? No problem! Pull in meeting notes from Granola? Sure! Here's how it works and how you can steal it. # Most systems assume every day is the same Most productivity systems assume your days are identical. They're not. Monday feels different from Wednesday. Friday has different energy than Tuesday. Your system should know this. Most systems also pretend everything is equally important. That's bullshit. You have strategic work that moves the needle and you have rats and mice. The system needs to force this distinction. # How I do it ## Three levels of tasks (not 47) **BHAG (Big Hairy Audacious Goal)** The weekly strategic thing that actually matters. Not client work. Not urgent. The thing that changes your business trajectory. This is the work that only you can do. The strategic decisions, the vision setting, the big partnerships. Break it up into chunks and allocate at least an hour a day towards it, first thing in the day. Why first thing? Because if you don't do it first, you won't do it at all. The urgent will eat the important every single time. **Priority** The ONE thing that must happen today. Usually urgent AND important. Only one. If you have two priorities, you have none. This is where client work usually lives. The demo that has to happen. The proposal that's due. The critical bug that's blocking everything. One thing. That's it. **Tasks** Everything else. But here's the thing - these probably shouldn't exist. If they sit here for three days, delete them. Seriously. I call this section "rats and mice" because that's what these tasks are. Little annoying things that feel important but aren't. Admin work. Minor updates. The shit that makes you feel productive but doesn't actually move anything forward. ## Different templates for different days - **Monday**: Strategy and planning. Fresh brain, big picture thinking. This is when I set my weekly BHAG and review what happened last week. - **Tuesday**: CRM and outreach. Hustle mode. Social energy. Tuesdays are for hitting the phones, sending proposals, chasing deals. Pure hustle energy. - **Wednesday**: Deep work. No meetings across the entire company. No "rats and mice." Wednesday is sacred. No interruptions. No admin. Just the important work that requires deep focus. - **Thursday**: General work. The flexible day. Catch-all for everything that doesn't fit elsewhere. Team meetings, admin, random projects. - **Friday**: Wrap up. Review. Prep for next week. Close out the week, triage what didn't get done, set up next week for success. - **Weekend**: Light structure. Personal focus. Because work-life balance is real, even for founders. ## The inbox that forces decisions Everything goes in the inbox. Then you apply the 4 D's: - **Do** - If under 2 minutes, just fucking do it now, otherwise, task - **Date** - Important stuff, schedule for specific time (not "someday") - **Delegate** - Someone else's problem - **Delete** - Most things belong here No item stays in the inbox. Ever. ## Built-in habits via checklists Morning checklist embeds the habits I want: - Sync tasks from all tools - Set today's sprint - Share priorities with team - Block time for BHAG work Evening checklist keeps things clean: - Triage inbox (4 D's) - Quick reflection - Prep tomorrow Checklists remove decision fatigue. They just become what you do. ## The actual templates Here's Monday's template to show you what I mean: ```markdown # Monday - August 28, 2025 *Strategy and planning* ## BHAG this week *The important but not urgent stuff that creates step change* - [ ] Ship new API integration - [ ] Complete investor deck v3 - [ ] Record product demo video ## Priority for today *The ONE critical thing* - [ ] Close Enterprise deal with ACME Corp ## Tasks *Question if these should exist* - [ ] Review PR from Jake - [ ] Update CRM fields - [ ] Book flights for conference ## Checklists *Morning* - [x] Sync tasks from calendar, email, ClickUp - [x] Set today's sprints - [x] Send priorities to founder chat - [ ] Review last week's progress *Evening* - [ ] Triage inbox - [ ] Reflect ## Inbox - [ ] Call from James about partnership - [ ] Invoice from contractor - [ ] Meeting request from Sarah ``` Real, messy, in-progress. Not theoretical. # How to implement this yourself ## 15-minute setup 1. **Get Obsidian** (it's free) 2. **Install three plugins**: Templater, Periodic Notes, Calendar 3. **Copy my templates** into your vault 4. **Configure the plugins** to use them 5. **Create your first daily note** That's it. No complex onboarding. No 47-step process. ## Make it stick **Set a recurring reminder** 9am: Create daily note 5pm: Triage inbox **Make Obsidian your new tab page** Can't avoid what you see constantly. **Start minimal** Just use Priority and Inbox sections first. Add more later depending on needs. **Be ruthless with the 4 D's** If you're not deleting 50% of tasks, you're doing it wrong. ### Common problems and fixes **"Too many tasks"** You're not using Delete enough. Most tasks don't matter. **"I forget to create notes"** Calendar plugin. Click the date. Done. **"Templates feel rigid"** Change them. This is YOUR system. Keep the structure, modify the details. **"BHAG gets ignored"** Block first hour of every day. BHAG only. No exceptions. And I mean NO exceptions. Not for client calls, not for "urgent" emails, not for anything. The urgent will always try to eat the important. ## Why this works for me (and others don't) **It acknowledges reality** Different days have different purposes. The system knows this. **It forces prioritisation** One priority. One BHAG. Everything else is questionable. **It prevents accumulation** Inbox must be empty. Daily. No negotiation. **It builds habits without thinking** Checklists embed the behaviour. No willpower required. **It's been refined through real use** Three years. Hundreds of iterations. This is what survived. # Advanced shit once you're comfortable ## Connect to external tools Pull tasks from ClickUp, calendar events from Google, CRM data from Attio. Make the daily note your command center. I do this with Claude Code and "Skills" I made Claude create for itself to connect to those APIs. Every morning, Claude pulls my calendar, grabs open tasks from ClickUp, checks for new leads in my CRM, and populates my daily note automatically. This is the magic of having everything in plain text - any integration is possible with a bit of scripting. ## Weekly and monthly reviews Built-in templates for reflection and planning. What worked? What didn't? What changes next week? ## Project linking Daily notes link to project pages. Everything connected but not complicated. ## Automation - Auto-create tomorrow's note at 5pm - Email priorities to accountability partner - Generate weekly reports from daily notes But honestly? Start simple. Get the daily rhythm working first. # The philosophy behind it This isn't about being "productive." It's about doing the right things consistently. Most of what we call work is actually avoidance. Email feels like work. Meetings feel like work. Slack feels like work. But they're usually not THE work. They're just easier than the hard stuff. THE work is uncomfortable. It's the strategic decisions you've been putting off. The difficult conversations. The creative thinking that requires actual brain power. This system forces you to identify THE work (BHAG), protect time for it every day (and especially, Wednesday deep work), and question everything else (Tasks section). It's opinionated by design. If you want a flexible, choose-your-own-adventure system, this isn't it. This is a system that tells you what to do because decision fatigue is real and most decisions don't matter anyway. I'd rather spend my mental energy on strategic decisions, not on "should I respond to this email now or later?" # Get the complete package I've packaged everything into a Git repository you can clone: ## Option 1: Clone the full system ```bash git clone https://github.com/j4jonathan/obsidian-planning-system.git cd obsidian-planning-system ./install.sh ``` The installer will: - Set up all folder structures - Copy templates to the right places - Configure your Obsidian plugins - Create today's daily note as an example ## Option 2: Manual setup If you prefer to do it manually: 1. **Download the templates** from the repository 2. **Copy them** to your `99-Templates/Journal/` folder 3. **Install required plugins**: Templater, Periodic Notes, Calendar 4. **Configure the plugins** (detailed instructions in the repo) 5. **Create your first daily note** ### What's in the package: - All 13 templates (7 daily, 3 review, 3 bonus) - One-click installer script - Configuration guide with screenshots - Example week showing real usage - Troubleshooting guide - Plugin settings files **Repository**: [obsidian-planning-system](https://github.com/j4jonathan/obsidian-planning-system) Or just steal the concepts and build your own. The best system is the one you actually use. # Quick implementation checklist After 1 week you should have: - [ ] Daily note for each workday - [ ] Clear weekly BHAG - [ ] Most priorities completed - [ ] Empty inbox each evening After 1 month you should see: - [ ] Patterns in your reviews - [ ] BHAGs actually finishing - [ ] Less time planning - [ ] More shit getting done Remember: The goal isn't perfection. It's progress. Consistent, strategic progress toward things that actually matter. Start tomorrow. Or start now. Just start. --- *Version 3.0 | Last updated August 2025 | Built in Obsidian* --- [[Home|← Back home]]