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How to organize yourself as a solo founder

207 points| gekkostate | 3 years ago |medium.com

66 comments

order

paul_f|3 years ago

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.

chasd00|3 years ago

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

gumby|3 years ago

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.

dnndev|3 years ago

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.

CoolGuySteve|3 years ago

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.

staticassertion|3 years ago

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.

awillen|3 years ago

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).

rmbyrro|3 years ago

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.

smartmic|3 years ago

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.

bachmeier|3 years ago

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.

gekkostate|3 years ago

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.

pdevr|3 years ago

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.

ekkeke|3 years ago

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!).

kag0|3 years ago

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.

p0nce|3 years ago

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

urban_winter|3 years ago

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.

timwis|3 years ago

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.

rlayton2|3 years ago

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.

petesergeant|3 years ago

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

atoav|3 years ago

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 : )

staticassertion|3 years ago

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.

jokethrowaway|3 years ago

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)

bachmeier|3 years ago

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.

ezekg|3 years ago

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.

Kharvok|3 years ago

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.

dv_dt|3 years ago

Dedicate an iPad for notes?

cseleborg|3 years ago

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.

stingraycharles|3 years ago

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.

revicon|3 years ago

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.

anon2020dot00|3 years ago

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.

bdominy|3 years ago

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.

TastyJhinga|3 years ago

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.

intrasight|3 years ago

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

elias94|3 years ago

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.

TastyJhinga|3 years ago

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

dnndev|3 years ago

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.

aetherspawn|3 years ago

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.

codazoda|3 years ago

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.

TruthWillHurt|3 years ago

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

lexx|3 years ago

He was talking to me

nickmotedotcom|3 years ago

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