How to organize yourself as a solo founder | Hacker News Reader

How to organize yourself as a solo founder

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207 pointsgekkostate66 comments

Having tried everything, nothing works better than 5x8 yellow pads. Write down everything you need to do. Draw a line thru when done. Every few days, rebuild the list. Everything has to be on one page, or there are too many to-do's, and you can delete ones that just don't make the cut.

No technology, just pen and paper.

I had one Dropbox Paper document for years called "Next Steps". It was literally just a freeform list of things I needed to get done for the project. Every day I would expand the list and cross off/ checkmark what had been done. It got pretty massive.

Now I have a company and a team so we use an issue tracker, which I find to be much much heavier but it's easier to use across multiple people.

This would be a good idea if I could read my own handwriting.

I get this works for some, but never has for me. I have never been a notebook type of person.

I love your general approach and very similar to a digital version I use.

You could work on improving your handwriting. You might notice other benefits.

I read about one person whose math comprehension increased dramatically when they improved their penmanship; something about a mental link between the ability to visualize the formulas in their mind and the ability to create/visualize them on paper.

I'm not the OP, but I'm on a similar situation.

I can draw formulas quite well. I can also draw text quite well if I'm drawing it. But my cursory handwriting is so bad that I often can't read it.

I don't think it's worth putting time into improving it on the case I need to write some long-form text by hand. There just isn't enough value int there. (But then, here I am, spending time on HN...)

Very true. I have been thinking of getting a white board. Thanks for the encouragement.

Not OP. I don't see how handwriting is better. I'm already working on the laptop, notepad app is almost integrated with everything else, I can access it in miliseconds with keyboard shortcuts. I can create a similar list in a simple notepad app, i.e.:

x Task 1

x Task 2

- Task 3

- Task 4

This might sound weird, but check your diet if your handwriting is shaky/cryptic or mentally anguishing to perform. I looked into this upon recommendation of someone else, and now I always notice when mine is worse after certain meals. Not advocating for one particular diet.

Thank you. Valid point. I currently stay away from dairy and wheat. I immediately notice a difference with those foods (dairy = sinuses, wheat = stomach bloat).

The issue is I cant write fast enough. I type near 80 word per minute. I am so familiar with the keyboard, when I go to write it needs to be for special occasion (letter for my mom or something).

That makes perfect sense. I'm a fast typist and OmniFocus user, myself.

I keep trying digital tools, get excited at first, to later realize I went back to paper without even noticing the switch back... Came to the conclusion no digital tool will ever be better than paper. It's a matter of principle, not how innovative we can be in digital.

I have boxes of those 5 subject half size bound notebooks you can get at the dollar store. All filled with notes and doodles from throughout my career.

I’ve tried to switch to a digital form but always end back up at pen and paper.

Edit: well had boxes of notes, they got thrown out on the last move

Oh man, found my spirit animal. I tried recreating the same system on a white board next to my desk to save paper, but it just doesn't work without rewriting the list from scratch regularly (though I must have smaller tasks, because I'll rewrite 1-2 times per day).

This is what I do for day-to-day objectives. But for things that involve copy/pasting or long term objectives I don't want to forget I also have a Workflowy document.

Workflowy is pretty nice, it's a simple org mode tree structure that works on phones and has intuitive keyboard shortcuts.

I use Sublime Text but same concept.

Agree.

Some things that help appear stupid. There's a psychological value in that crossing out action. Someone told me a few years ago to draw a little box next to the item and put a check mark when done (instead of crossing out). Weirdly, it seemed even more satisfying.

I think the real truth in all this is something simple like a written list means you spend less overhead curating your work and therefore have more bandwidth to actually do it -- coupled with the "small wins" of crossing out or ticking off the item.

I noticed that too. I try to go full digital and abstract.. and now I often go back to the usual vintage material/physical habits. Something about moving/touching/seeing/filing changes how your brain notices the event.

Hey, a little bit off-topic, but: here comes a very original HN experience. The author himself writes that tools are the least important, but for the HN crowd, it seems that tools are above anything. In consequence, the thread here is mostly about the tools only. Combined with the favorite topic of self-organization, this can serve as highly illustrative material about HN.

OP here. Thanks for reading the post! I agree with you. It seems that the HN crowd is very much interested in tools while I explicitly mention that the tool question is the least important one. I'm curious to know why folks are more interested in tools than principles or why there is little discussion about the principles.

Re-reading your post, I would say it comes from implied disagreement with your deprioritization of the right tools. You also use the word system a lot in the essay, which mentally translates to tool for a lot of people (myself included, if I’m not careful.) It’s also hard to do more than mildly agree or disagree with GTD and energy management principles. I also suspect anyone disagreeing with your main point, coming into this thread to insist they can remember everything to do, would be attacked. I agree more variety in the discussion would be nice.

I think part of it is that the nature of the work done by a solo founder is very different from that of many HN readers.

It's a matter of scale. "Why use a database? CSV files do everything I need." That's true for many projects but not as much when you have a few TB of data.

Some jobs require you to scale in several dimensions: types of projects/data, number of observations of data like email, number of reference files, and people you interact with. I'm not a solo founder but I've been there too. Once you're managing data that's too large for your brain, you need a system that scales, like GTD. Tools are useful but not at all as important as the system. I've tried a lot of tools, but GTD has been the constant that has (to some extent) kept me from giving in to the stress. You can't understand the scaling issues until you've worked in that type of position, where the stress of managing stuff and dealing with stuff constantly coming at you can overwhelm you.

After using a lot of different tools, now I use a plain text file. It works for me. I move things down as I finish them. The top part always have my pending tasks in there. The file is more than ten years old now, and have been the best productivity tool for me that I started using the same approach at office as well.

I had some sticky notes at office, but now with the world having changed, I took a screenshot of all of them and manually transferred them to my text file as well. If I need to refer to a diagram or something, I just add a pointer (the path - local file system or URL) to that in my text file.

How do you keep this synchronized between devices? I had tried this with a git repo but pull/pushing before/after jotting down a note on my phone got tedious.

I have disciplined myself to do it only one way. That is enough, and keeps it simple for most purposes. Copy from the phones and other devices, paste to the main device. It being just one file makes it much easier to do so. It is backed up regularly using rsync, as part of my daily backup of everything.

The hardest part - for me, at least - was to let go of the myth of the need for multi-directional syncing.

I think manual copying would kill it for me. I'm just back and forth between multiple devices throughout the day and it seems like that would amount to a lot of copying. Although there's only one of me, so there's never a need to merge. So it's not really multi-directional syncing, it's more like broadcast from whatever I'm using currently to everything else.

I do exactly like this. Top task have a small minus sign "-" and bottom tasks get a little plus sign "+" (means: done).

I keep my notes in notepad++ as plaintext. I've always thought of this as a time saver because it removes any time wasted not actually working. Now I'm reconsidering.

I haven't been using GTD but I used a vaguely similar system of notes to keep track of what I need to do. This article has really focused some of the areas I might be improve this, mainly through giving more information about each task (context, time, energy, priority).

I think this is where a more sophisticated tool might help, because it will be hard to organise that in plaintext and somehting with a columnar way of representing this information in tables will help (btw open for suggestions that aren't excel!).

I've never found a way that I like to integrate dealing with email into a to-do list. Reading emails is a perpetual need but it is damaging to focus and I often find that it saps my energy by reminding me of all the things that are not yet done. I've tried having fixed times of the day where I always deal with emails; adding "30 minutes of email" to my task list; reading them between each switch of tasks. None of these approaches really cracked it for me. I haven't read "Getting Things Done" - I wonder whether it has a solution.

I've found it helpful to deliberately identify if you are being the manager or the technician (to use E-myth's terminology). The manager goes through the lists of tasks and emails, and works out what needs to be done (next, or today, or this week, or this sprint). The manager tells the technician (usually via TODO list) what that task is. Then you switch modes to technician - its no longer your job to organise, its your job to do.

Have you ever thought about doing the exact opposite? Instead of integrating email in your todo list you could run your todo-list via email.

I worked on a job where this was done and it worked flawlessly (emails generated from various systems and people, including those in the shift before you).

The one thing you have to make sure that your "job" communication is divided from your private communication or other non-actionable messages like newsletters etc.

Writing Emails to your self is totally okay also : )

Indeed it does! And the key lies in separating “defining work” from “doing work.” GTD’s “get clear” process involves going through everything in your inboxes (not just email but physical papers etc), and determining what is the actual _next action_ for this thing (if it’s actionable at all; some emails should just be referenced, delegated, or archived).

You log that next action in your system and move on to the next one, rather than doing the action t then and there (unless it’s super quick to do so).

By separating these two, you minimise mindset switching, and can be far more assured that you’re working on the right thing at any given time.

Yes, from my point of view, GTD does two things very right. One is separating the "defining work" from "doing work", the other is keeping contextualized task lists for "do this next time you are at that place, or meeting that person, or whatever".

And of course, both feel obvious in retrospect. I don't even remember if there is anything else in GTD, but the value I get from those is enormous.

The solution I have pulled out of GTD is that once a day I clear everything out of my inbox, and anything that needs a reply gets put into a todo list. Slightly later in the day, I groom that Todo list, and work out which items I will today, and set aside 30m in which to do those. If there's an item in there that will take a significant investment in time -- including a certain email -- then I'll make an appointment on my calendar to do it.

I'll respond to interesting email that comes in during the day if I feel like it / if I'm bored, but knowing that once a day I do a complete clear-out is helpful to me

I agree with this, email (professional at least) inbox should be treated as its own todo list.

anything in the inbox is something to action, anything you don't need to action personally, archive / tag or move to a folder and be done with it.

If it's something to action then at least gmail has a snooze button and I've found that to be super helpful.

My rule of thumb is that I should not have more than 30 items in my inbox. If there's more then clearing the inbox takes priority over anything else (bar key meetings).

Email is exhausting. I've decided that I just don't care about quick turn-around on email. It sucks, but the cost of checking email throughout the day is too high - not just in terms of time, but the psychological impact of it is surprisingly negative.

I now check it ~2x. Morning and midday. If I'm doing a back and forth I may go back to that one specific thread, but that's it.

The issue is that you're likely leaving too much on your inbox. I use my inbox as a to-do list (especially before Gmail removed inbox and its reminders, now I just create a draft with a title) but it doesn't contain the backlog of all the projects I'm working on.

If you have too many tasks that needs to be done I think you should group them by activity and store them in a separate place. Then you can timebox "dealing with $activity" where you just get down with those tasks.

Eventually you can hire someone and give them the task of a certain activity (which can be anything: a software project, dealing with a visa application, buying a house etc)

At a certain point you have to be realistic about how long it takes to deal with email. No system is going to give you more time. You're either going to have to allocate more time to email, respond to fewer messages, or spend less time responding. Email is, unfortunately, an unpleasant part of the job for many of us. Some days it's better than cleaning toilets, so there's that.

I literally just use the Notes app on my phone for planning and brainstorming, synced to my desktop. Lists upon lists. Everything else code-related is in GitHub issues and PRs.

I'm absolutely paralyzed by this at the moment.

I want the mobility of a digital solution, so much of my documentation and task items are spread across Evernote and Trello. Except an analog solution such as a note card or post-it notes has a physical prescense that's very focused and attention grabbing.

Dedicate an iPad for notes?

This is what I ended up doing, and even though the majority of the notes I take aren't things I'll need to return to -- they're more about processing in the moment -- just consistently using an iPad to capture into apple notes has scratched the itch in my brain that I might need to look back at something someday, and it's well worth it.

I also am pleased that I can use it to scan any piece of paper I'm given straight into a note and that same scan will pop up when I search for it.

I use a mix of bullet journaling and GTD, and it has worked quite well for me (though not perfectly, of course). The physical bullet journal (notebooks from Leuchtturm) is a log of sorts, a place where I can take notes from calls etc. and write down anything that comes to mind, in the spirit of capturing every idea. Pen and paper just works better for me.

My GTD context lists with next steps for all ongoing projects are physical index cards that I just keep in there, I re-write them whenever they get full (one side only).

For my projects list, I use Notion, where I have one page that holds the list of projects, and each project having its own page which, most of the time, is just a simple list of TODOs, but can be more elaborate, with kanban boards for more involved stuff or simply a loose collection of documentation, screenshots, drafts, etc..

And of course, Google Calendar.

I was never super disciplined with the weekly review stuff, but it really worked well for holding stuff that my brain would shed in the blink of an eye. I was always very slow, but it's rare that I forget anything I need to get done.

I’m not sure if it’s appropriate to ask, but what kind of layout / system do you use with your bullet journal?

What I understand is that bullet journals are typically most effective when you adapt it to your own work / domain, but most examples of what others use (including the subreddit community) are almost art projects.

I would be very curious what a more “HN-approved” bullet journal would look like.

I put together a YouTube playlist with the best videos I've found [1], exactly because it's so hard to find any that treat it as a tool and not an art project. It's roughly in the order I recommend watching.

The main bullet Journal reddit has also been taken over by the art crowd, but there are two others that are specifically about journaling and productivity. [2][3]

[1] https://youtube.com/playlist?list=PL50SnCmB2W7tUaHuUzeB8OLC2...

[2] https://www.reddit.com/r/BasicBulletJournals

[3] https://www.reddit.com/r/bujo

I keep it very simple, just a black pen and very little decoration. I draw a horizontal line to mark the beginning of a new day and skip all the other "logs". I mostly use the symbols (note, Todo, migrated Todo, etc.)

The only fancy thing I do is my weekly plan, which also includes some KPI tracking. For this, I have a template slide that I print out on an A5 sized sticker, slap it in there and fill it out.

I’m addition to the other great ideas posted in this thread, I’ll throw out something that has helped me a lot… I have a folder called "Captain's Log" that I constantly post things into. Everytime I hear something on the radio I want to look up, I type a few of the lyrics into a file and save it and it goes into the Captain's Log for perusal later. Everytime I have something I need to remember to do I post a note into the Captain's log and add a "todo" tag to it so I can sort those out when needed. All meeting notes go in there too. When I start coding something I take notes on what I'm working on in a note so that I can go back and remember what I did when I was working on that thing I can't quite remember. I can sort that folder by "date created" and see a log of my life going back in time and I've found it very useful.

Makes sense actually. Most people I think would just use one notepad text file per day I think but I can see the advantage of creating one text file per idea or note.

I use color coded Post-It notes to track my tasks. Red for high priority tasks, yellow for medium, green for low. Orange and blue for subtasks. Stick them on a whiteboard near your workspace and then move what you want to tackle into a row that acts as your queue. Finished tasks go in a stack you can watch grow.

Why not just use something like jira or trello at that point? Having to remember the color associations for subtasks physically seems a bit too much for me. Also, software is something you can access from anywhere and you don't have to be in one single place.

The physical act of writing notes, sticking them, removing them can get one in the zone more than the abstracted version on trello.

Software solutions are fine and I have used them before, especially with a team, but as a solo founder, I just like simple Post-Its - to each their own.

I think it's better to stick with the simple old ways too! Maybe as a solo founder you can get some more insights with our community on http://founderscafe.io/, maybe you can share some of your practices too!

Eh, whatever works. Some people like the ease of working anywhere, some people are more motivated by seeing a physical representation of their progress (possibly similar to how people remember chronological events better when read from a physical book vs an e-book or on-screen: https://www.fastcompany.com/40476984/this-is-how-the-way-you...).

I don't like the added cognitive overhead (having to remember how the app works) and lack of physical tangibility of software solutions.

For me, all of those task trackers are radically slower than even a pen and paper or just a single document. Load times, the million buttons, search, etc are all worse. They're fine for teams that need to share work and make asks of other teams and prioritize etc, but for one person they're extremely inefficient.

Since I only have a hammer (emacs), everything is a nail (text file). Every project has a root folder with a file "diary.txt". Many of those files are multi-megabyte long.

Only other tool is Google Calendar - for things that are time-sensitive

I love org-mode, but the lack of mobile is really a wall for me. I need the flexibility to add notes in a second from my mobile (without emacs server etc).

I switched to Bear atm, just because has the sync between all devices.

You can try the orgzly mobile app to sync or edit orgmode files on your phone. Its equally good and I love it.

Have you seen beorg? It’s a mobile app for org-mode, and allows you to sync through a Dropbox folder.

https://apps.apple.com/nl/app/beorg-to-do-list-agenda/id1238...

Use text editor for the short list that must be done today/tomorrow. (These are my manager tasks)

Everything else I create tickets in our tracking system which is divided by client / project. (These are my technician tasks for the most part)

Things move fast, make sure your system works for you and not the other way around.

At times, I simply go by the idea, if I can’t retain it in memory then it’s not on my short list. Fancy to do lists seem logical but not practical. I spent my time managing a list rather than doing the tasks.

Microsoft Todo is great for this. It syncs between all your devices, Office365 and integrates with outlook (flagged emails become todo items).

You can make hierarchical folders and the recurring option is super handy.. I run much of my invoicing/AR/AP as just a recurring todo item.

Microsoft threatened to kill my favorite tool, wunderlist, so I stopped using it and avoided their new tool too. I just can’t seem to forgive them. I am not sure what wunderlist provided that I loved, or I might write my own replacement, but nothing has felt as good since.

Amazing Marvin. All the tools of every to do app out there. With the ability to customize everything. You add and remove only the features you need and use. You can even theme it to look exactly like Wunderlist.

Who's this guy to tell me how a founder should behave?

He was talking to me

Great article. I really enjoy using Notion's bullet lists to stay organized as a solo founder.

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