Using Obsidian to Run My Entire Business
- Isaac Lester
- Nov 11
- 12 min read
Open Tabs & Uncompleted Projects
You've got 47 browser tabs open right now.
Six unfinished courses sit in your bookmarks. Three half-written business plans live across Google Docs, Apple Notes, and a spiral notebook you can't find. You screenshot good ideas on your phone, email links to yourself, and scribble notes on random pieces of paper that disappear into the void.
Are you disorganized, or are you simply drowning in your own potential?
I ask because I was there. My other articles dive deeper into my situation, but here, I want to touch on how my digital chaos matched my mental state. I had damn good ideas, but they scattered across platforms like shrapnel. By the time I found the note, the momentum was gone.
The problem wasn't so much a lack of information as it was information without infrastructure.
Fast forward to now: I run an entire digital empire from my 31-foot sailboat that's possible to maintain with zero required monthly software costs. (possible doesn't mean I do, just to be clear, but "possible" is critical) My blog, newsletter, YouTube channel, community, products and social posts are all orchestrated through one free tool that finally taught my Neurospicy brain how to think in public without losing my mind in private.
And it's groovy.
This is how Obsidian became the operating system for everything I build.
I. Why Everything Else Failed
Let me save you some time: I've tried and deep dived them all.
Notion looked beautiful and felt right at first, but I was out the first time I had no connectivity and temporarily lost access to everything. I need all of my files accessible at any point, independent of internet.
Evernote became a digital hoarder's paradise, and took some effort to un-entrench myself once I realized the hole I was digging into. Google Docs was also a graveyard of files I'd never find again.
The problem wasn't the tool. It was ownership.
Every platform you don't control is a platform that can disappear, change, or lock you out. Every subscription is another monthly tax on your ability to think. Every cloud-only solution is a single point of failure between you and your life's work.
Obsidian is different for three reasons:
1. You own your files. Everything lives on your computer as plain text. No proprietary format. No platform lock-in. If Obsidian vanishes tomorrow, your 10,000 notes are still readable in any text editor on earth.
2. It works like your brain actually works. Not in rigid hierarchies, but in connections. Ideas link to ideas. Your second brain mirrors how your first brain actually operates and brings information to the forefront through association, not alphabetization.
3. It scales from chaos to empire. Start with one note. End with 10,000. The system doesn't break. It compounds.
For fellow multi-passionate individuals with brains like mine, this matters exponentially. Ideas don't wait for the right folder. They spawn mid-conversation, mid-shower, mid-whatever, and they'll die in transit if there's no immediate place to put them.
Obsidian gave me that place.
II. Start With Three, Not Nine
What nobody tells you about building systems is that **complexity emerges, it isn't designed.**
My current vault has nine major sections that organize my entire digital empire. But I didn't start there. You need three things first:
1. CAPTURE (Where ideas land)
2. CREATE (Where work happens)
3. SHIP (Where things go public)
Everything else grows from these roots which can be applied as a foundation for any project or endeavor you wish to undertake.
a. The Capture Zone
This is where chaos gets contained. Every random idea, every screenshot, every "I should write about this" moment lives here temporarily.
My capture system has one rule: Get it out of the mind before the candle goes out.
Before even taking into account that we're continuously hit with a nonending stream of information and expected to process it all, my mind is already a chaotic place. I preside over a violent storm of raw ideas, flashbacks, quotes, tasks, important dates, etc.
Ideas are lit matches, so fragile, amidst a windstorm. I don't care if it's in a pocket notebook, a voice memo, or typed into my phone at a red light. Capture happens fast, organization happens later.
Every day (or every few days when life piles up), I have "archive time." Fifteen minutes to an hour to take everything captured and move it where it belongs. The notebook entry about loneliness becomes a content idea. The screenshot becomes research for an article.
The key: Capture is fast and dirty. Archive is slow and intentional.
b. The Create Zone
This is your workspace. Drafts live here. Articles in progress. Video scripts. Newsletter editions.
I organize mine by content type, but what matters most is that each draft connects back to the ideas that spawned it.
When I'm writing about my escape from Chicago, I'm not starting from scratch. I'm pulling from old daily journal notes, my frameworks about decision-making, my archived conversations, even audio clips that I stole and stashed away with precious seconds between fast-paced moments in my life.
The article is a synthesis of existing thoughts, not a creation from nothing. All that I do came from work that existed before...
This is the compound effect of organized thinking. Your past self does half the work for your future self.
c. The Ship Zone
Once something goes public, it gets logged in the Publishing Hub with the link, date, platform, and key metrics.
I track everything that I publish because published work is data. When you can see everything you've created in one place, patterns emerge. You stop guessing and start knowing.
I may or may not be building an archive to feed to a personal AI once we burn past The Singularity and hit Halo levels of progress...Standby for updates on that...
III. The Three Workflows That Run Everything
Systems without workflows are just fancy filing cabinets. Here's how information actually moves through my Digital Empire:
a. Workflow 1: The Capture Protocol
Sometimes, and idea just "makes sense" with my overall message, and can get drafted and published whenever, outside of my normal scheduled rhythm.
Wednesday, 10 AM: Boat manufacturing class. Instructor says something that sparks an article idea. I scribble in my pocket notebook: "Article - hard skills = proof of capability."
That evening: Exhausted after a long day. Not in the mood for screens. I make food, read a book, let the idea ferment.
Friday evening: Hard admin time. I open Obsidian, look at my notebook, and type into my Content Ideas page under the "Building" pillar: "Why learning one hard skill proves you can learn anything."
Sunday morning: Admin Sunday. Caffeine assisted weekly content planning. I review my ideas, and this one jumps out. I create a new note in Blog Drafts, link it to related notes, and start writing.
The idea aged three days from spark to structure. That fermentation time matters. Funky is fresh, yo'.
b. Workflow 2: The Content Pipeline
When it comes to actually creating the article, my process is parted in 9 sections:
1. Idea capture: I pull "Article on getting nerfed by loneliness" from my bucket when I feel prepared enough to draft the article.
2. Research phase: Journal entries about isolation, a link to my "Loneliness vs Solitude" framework note, and other relevant materials get spun up for useful bites.
3. Draft creation: I make a new note with links back to all source material.
4. Writing: The process of making a rough draft flows easily because I'm synthesizing existing thoughts that are nearly tied together already.
5. Publishing: Article goes live to Isaac's Ideas.
6. Distribution: Social media content gets created and thrown into my scheduling calendar.
7. Logging: Entry created with link, date, metrics in the Publishing Hub.
8. Analytics: Track performance, feed insights back into future planning.
9. Audit/Review: I'll come back to it every 30/60/90 days to perform an audit and review, harvesting useful nuggets for future articles and linking new articles within. All Ideas Must Serve, afterall.
There's a different article explaining that last bit.
Every piece of content touches 4-6 different areas of my vault. These are nodes in an interconnected web, not isolated creations.
Isaac's Ideaverse, if you will.
c. Workflow 3: The Transparency Veil
My Obsidian Publish site is public. You can see my entire system. But it's not my entire vault.
The Public Archive contains my business systems, published content and frameworks I teach
The Private Vault carries ersonal journal entries, relationship notes, therapy processing, financial details
The line is simple:
If it serves the mission of helping others build their thing, it's public.
If it's sacred to me personally, it stays private.
This "transparent but not porous" approach lets me build in public without sacrificing the intimacy required for actual self-development. You don't follow to see me crying at 2 AM. You read for the frameworks built from that processing.
IV. Templates vs Lateral Limits: Structure Follows Thought
I have templates; weekly review templates, article structure templates, newsletter format templates. But what matters more are the lateral limits that I use to guide the structure of my content.
A template is a form to fill out. A lateral limit is a rule about where things belong and how they flow.
My lateral limits:
- "A place for everything, and everything in its place" - No orphan notes. Every piece of information has a home.
- "Capture quickly, archive intentionally" - Speed matters for capture. Accuracy matters for placement.
- "The veil is transparent, not porous" - Share systems, guard sanctuary.
Think less in terms of checkboxes and more along the lines of principles that guide decisions when the template doesn't fit.
Example: I get an idea for a video that's also a blog post that also contains a framework I want to teach. Where does it go first?
Template thinking: "Uh... which template do I use?"
Lateral limit thinking: "It's an idea, so it goes in Content Ideas. When I start creating, it becomes a draft in the appropriate section, wherever hat might be. When I publish, it gets logged in multiple places in the Publishing Hub."
The structure follows my thought process, not the other way around.
V. A 30-Minute Quick Win: "My Day Broken Down"
If you want immediate relief from mental chaos, try this tonight:
Step 1: Download Obsidian(5 minutes)
It's free. Watch any "Obsidian for beginners" video on YouTube at 1.5x speed. You need to know three things: create a note, create a link between notes, where the daily note lives. That's it. Resist the urge to perform deep dives, for now.
Step 2: Create today's note (15-20 minutes)
Title it with today's date. Then just... talk about your day. Stream of consciousness. Everything that happened. Conversations. Feelings. Thoughts. Tasks completed. Tasks avoided. Frustrations. Wins. Doubts. Emotions.
All of it.
The magic move: When you want to elaborate on something, be it a person, a project, a recurring thought, create a mid-sentence link to a new note.
Example: "Had another conversation with >> my instructor << about >> travel planning << which reminded me I need to figure out >> my short term itinerary <<".
Those bracketed items become new notes. Don't fill them out now. Just create the link. Keep writing about today.
Step 3: Review what you wrote (5 minutes)
Read it back. You now have an accurate picture of your day. Questions emerge:
- Do I like how I spent this time?
- What do I want to be different?
- Where did I waste energy?
You didn't know what you were doing with your day until you looked at it properly. Now you know.
Now you can change it.
Bonus: Those linked notes you created? Tomorrow, when something relates to "travel planning" or "my instructor" or "my short term itinerary," you have a place to put that thought. The system builds itself through use.
Do this for seven days and watch what happens. Your brain will start organizing itself.
It'll be freaky, even.
VI. The Compound Organization Effect
Allow me to remind you of the forgotten benefit of personal organization: It compounds faster than traditional interest.
When your notes are scattered across platforms, finding anything requires active memory. That's cognitive load burning in the background 24/7. Eating up RAM, taking up space, making you duller than you ought to be on the mark of creativity and problem solving. This is science, yo'.
When everything lives in one interconnected system, you stop remembering locations and start recognizing patterns.
Ideas used to live on shelves in the back of my brain. Overcrowded shelves where things would randomly fall, forcing me to venture back there in the dark with a flashlight, and get lost for an hour!
Now those ideas live in Obsidian. In organized sections. With related ideas nearby. Connected through links I can follow.
This is progress. Golden Groovy Progress.
My head feels physically lighter. When a new idea spawns, it's loud and clear instead of muffled by mental clutter. And I'm not worried about remembering ideas because they get tucked away as soon as they come in.
This is the power of compound organization in the digital age...
Every note I add makes the system more valuable. Every connection I create makes future connections easier to see. Every piece of content I publish leaves behind source material for the next piece.
Six months ago I had less than 200 notes. Now I have well over 2,000. But it's not harder to use...it's exponentially more useful.
VII. From Three to Nine (When You're Ready)
Remember how I said start with three sections? Here's what happened when I kept building:
Capture evolved into:
- Evergreen Notes (frameworks I'm developing)
- Content Ideas (pieces waiting to be created)
- Daily Practice (journal entries and reflections)
Create evolved into:
- Content Drafts (works in progress)
- Reading Library (book notes and highlights)
- Active Projects (current ventures)
Ship evolved into:
- Publishing Hub (everything I've released)
- Analytics & Learning (what's working and why)
- System Maintenance (templates and infrastructure)
I didn't plan this structure. It emerged from use. When Capture got too crowded, it naturally split into subcategories. When Create needed more granularity, the sections divided.
Your system will do the same. Start simple. Let complexity emerge as you need it, not before.
VIII. The Control Node Reality
If you aimed to copy my system by cloning every folder, workflow, and template, you may find that it doesn't quite work for you.
My power comes not from my systems, but from my thinking.
My vault is finely tuned for my Neurospicy brain, my specific goals, my particular way of processing information. Your brain works differently. Your chaos has a different shape and flavor.
Take the idea to the chop shop and cook up your own Frankensystem, that's literally half the fun of it anyway.
Take the framework. Understand the principles. Build something that fits YOUR brain, not mine, and aim for custom adaptation rather than perfect replication.
Start with the three sections. Capture for a week. Notice what breaks. Adjust what doesn't work. Let the system evolve with your actual use, not your imagined perfection.
Straight copy/paste is boring and ungroovy. Theft and adaptation of the framework with personal innovation is the way.
Go forth and get on well with thieving and pirating like an artist.
IX. What You're Really Building
Obsidian isn't note-taking software. It's a thinking environment.
When you externalize your thoughts into an organized system, three things happen:
1. You stop forgetting. The ideas that used to slip away now have a place to wait until you're ready for them.
2. You stop starting over. Every piece of content builds on previous work. Nothing is created from scratch.
3. You stop drowning. The mental weight of tracking everything in your head lifts. You can finally think clearly because you're not using precious cognitive bandwidth to remember where you put that one idea three weeks ago.
This is what turned me from basement dweller to boat-based Empire Builder. Not because Obsidian is magic, but because organized thinking is the foundation of organized action.
You can't build a business when your ideas are scattered across 47 browser tabs. You can't create consistently when you're starting from zero every time. You can't scale what you can't systematize.
This gives you a framework to lay your own version of structure and order upon. A rallying point to gather and plan your next move.
X. Start Tonight
This Evening: Download Obsidian. Create one note titled with today's date. Write about your day for 15 minutes. Create links to ideas worth exploring later.
This week: Do that every day. Just document your days. Notice patterns. Notice chaos. Notice what you wish you could remember better.
Next week: Create three folders: Capture, Create, Ship. Start moving recurring thoughts into the right places. Let structure emerge from use.
Next month: You'll have a system that actually fits your brain instead of fighting it.
If you want to see this in action, my entire Open Notes Archive is public and open to visitors. Progress is being made in the way of logging every framework I mentioned. Every workflow. Not as a collection of templates to copy, but as proof that this works.
Know, however, that the tools alone will not save you. Your thinking is what will save you. Tools or any craft or magnitude simply make the thinking possible for those with open minds.
If you want the quick-start templates I actually use daily, I'll soon have them made available for download for free on my BuyMeABook platform: "The Legion Directory". Download them. Modify them. Make them yours.
Per Aspera Ad Astra
Through Hardships to the Gorydamn Stars
- Isaac
If you would like to support, leave me a comment, show the like button some love, share with a friend, or leave me a donation over on my BuyMeABook platform; "The Legion Directory". Life is complex, I get it. If you are unable to support me, I would still be honored for the opportunity to continue to support you.
This installment in Isaac's Ideas will be made available to read on my blog and listen to on my newsletter by weeks end, and I continually work to better my voice, improve my style, and sharpen my skill, to better serve you.
Thank you for stopping by, now go externalize your chaos and bind it in structure of your own design.
Go build something worth remembering.
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