Frustrated by Tools at Work

I work in a corporate environment that is entirely Microsoft. You might think the title of this thread means that I’m sick of being tied to MS products but it’s perhaps the other way around.

Some time ago I reached out to my IT department to let them know I wanted to use Todoist and Obsidian. They were 100% okay with both, citing the fact Todoist is already an Outlook Add-in and a well known app, and Obsidian was fine as long as I followed my own rule; to keep all files on my work OneDrive without syncing outside the organization. So you’d think I’d be happy, right? All is well? Not exactly.

The Todoist Problem
Todoist has been driving me crazy lately. I use the Outlook extension/add-in quite a bit on the desktop version of Outlook. Until about 8-9 months ago, this worked fine. But somewhere between Todoist and Microsoft, the “link” between apps stopped working as expected. Now, if it’s been a while since I added a task, the add-in will add a task to Todoist, but it fails to create a link to the task as it normally would. So every morning when I start work, I know the first email I try to add as a task will error out, and I’ll have to restart Todoist and Outlook.

I filed a ticket with Todoist months ago about this and they acknowledged the issue. They’ve even followed up once or twice to say they’re working on it, but things have fallen silent now the past 6-8 weeks. I’ve lost hope and it’s getting more frustrating to use.

The Obsidian Problem
Obsidian is great, no question. I use it for ideas/thinking in my personal life, so I set up a new vault for work on my corporate “OneDrive Island”. It has been fine for six months or so, but there are a few issues:

  1. Even though I’m a fast typer, and even though I am a “computer guy”, there were moments of frustration trying to take meeting notes in Obsidian. The conversation would go one way, then another, and I had no way to connect or shade things to indicate priority, order etc. There were times where I just needed a freakin’ pencil. Much as it pains me to say it, I think I’m a visual, writing kinda guy – even though I am left-handed and write like child :rofl: And there is DEFINITELY something to the idea that typing leads to writing things verbatim without thinking. I found myself doing this a lot, and looking at a wall of text (not unlike this thread) after the fact, was daunting.

  2. There have been meetings lately with a lot of attendees and a lot of attachments. In OneNote, I can “send to OneNote” and all that junk populates a note, ready to go. In Obsidian, I’d find myself fighting attachments, trying to bold sections so they stand out within the note. I think I prefer seeing that visual representation of Word files, scribbles, PDF’s, annotations etc.

  3. Because I have my files on my work OneDrive, I can’t sync Obsidian to my iPad. So instead of a computer and an iPad to work with, I’m limited to just my computer.

  4. I know there is Excalidraw, but it involves a third party plugin which I’m trying to keep limited, and from what I’ve seen it’s extremely limited compared to OneNote, GoodNotes etc.

And just when I think “darn, I think I’m going to give OneNote a try”, I realize it’s absolute trash for owning my data and also – code snippets look awful in OneNote.

So yeah, I could use OneNote for meeting notes/visual stuff and Obsidian for more “thinking stuff” but then I’m split across two apps – it’s just… :tired_face:

I know, I’m overthinking it. But every time a meeting starts I’m scrambling now between should I write this, should I type it, are there attachments, do I want the meeting details, will I have to add a Word attachment to this later that will show up centered and ugly in Obsidian…

As a visual person, my instinct is to try OneNote for a bit. I can insert Outlook meeting details into note templates, write with the pencil, type, add attachments, and use it on my iPad. And 90% of all the notes are meeting notes anyway – notes that I won’t need in a month. Who cares about lock-in?

As a tech person who writes queries and a bit of code, OneNote feels a little gross though. And there is lock-in.

My heart says OneNote, my head says Obsidian.


I’m the same. I’ve probably rotated around note-taking apps and task managers many times for the past few years, sometimes going full Microsoft, sometimes going web apps, and sometimes pen and paper. Currently I’m at the pen and paper stage for meeting notes, since they’re temporary, fleeting notes that I don’t need much in the future.


I too am a pen (actually pencil) and paper guy.

I can get ideas down faster this way, can add drawings and diagrams, and draw little boxes for todos to check off.

Most of these notes stay on paper, and are disposed of. But some are transferred to a more permanent digital home.

This allows me to be more intentional with this information. And the benefit of the review and re-writing of the information helps me to remember it.


I’ll preface this by noting that I love and heavily use Obsidian. That said, a few observations/random thoughts:

there were moments of frustration trying to take meeting notes in Obsidian. The conversation would go one way, then another, and I had no way to connect or shade things to indicate priority, order etc.

I usually handle that with applications of bold, highlighting, headings, etc. as I take notes, then immediately after the meeting I clean things up and reorder as needed.

But you might really like that in OneNote you can click anywhere on the page and add a new block of text—they don’t all have to be arranged linearly from top to bottom. And of course, you can use it on your iPad.

Speaking of which, taking meeting notes in outline form—whether in Obsidian (especially with the Outliner plugin) or in Logseq (which I liked for short-term and project-focused stuff and tasks)—might suit you better than typing in paragraphs. It’s easy to create hierarchies with the tab key, and easy to rearrange the order of bullet items, especially if you bind move line up and move line down to hotkeys (I use option-up and option-down).

just when I think “darn, I think I’m going to give OneNote a try”, I realize it’s absolute trash for owning my data

90% of all the notes are meeting notes anyway – notes that I won’t need in a month. Who cares about lock-in?

When you’re an employee, it’s not your data and you don’t own it—your employer does. That’s why they want it stored on their servers. And as you say, it’s short-term data with a limited shelf life anyway.

Personally, the benefits of Obsidian’s plaintext files in local folders approach are very important to me. I’m not fond of OneNote, despite having used it quite a bit in the past. And typing meeting notes from top to bottom suits me well. But my own preferences and peculiarities aren’t necessarily relevant to you and your needs at work.


I take a lot of real-time notes – interviews, meetings, etc.

Often I’ll do it in my primary notetaking app, but other times I’ll grab whatever app is handy in the moment – often that’s Drafts, sometimes it’s TOT, but it doesn’t really matter as long as I can type what I need to.

I pretty much format only to indicate something I need to pay more attention to later, so in this context, bold, italic, little => arrows, etc., are all roughly equivalent. I also have a keyboard shortcut for {== CriticMarkup highlighting ==}, which I can apply in any text app I use (and which will even highlight in Drafts, NotePlan, MMD Composer and a couple other apps I use).

The point is that when I’m taking notes, I’m taking notes. The rest of the work happens later, and I can format as needed and stash wherever it belongs.

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This! Everybody takes notes in a different ways, I’ve seen colleagues use an iPad with Freeform and they take good visual notes. I am an excellent touch typer, suffice to say that people think that my meeting notes are speech to text transcriptions from an audio recording. During the meeting I try to type everything, who said that (or their initials) and indent the topics, questions and answers in a sensible way. But after the meeting there is some work to format and shape what was what.

Now, I work with lots of Google Spreadsheets and Slides, and the occasional MS Office documents, and I feel that although I could come up with a way of working inside Obsidian all the time I prefer having everything on iCloud and use the Finder to manage .weblocs or other files and then switch to Obsidian for note exclusive material.

Perhaps @AppleGuy could use a similar approach but I’m not sure if it’s possible. The glue that ties everything together in my setup is iCloud Drive to store and sync my obsidian vault, and I’m not sure that can be done within MS OneDrive.

I’ve done a similar dance, and just have 2 distinct silo systems work / personal outside of task manager.

For work, I was running Omnifocus and using the webversion, but that was too much friction. I ran Todoist as well for a while, but the layout and projects management is too simplified and “clicky” (3 or 4 clicks in a lot of whitespace to do anything). I settled on Things on my phone and a once a week review on my MacBook at home.

For Notes, I’ve had the same dance, Obsidian, OneNote, simply OneDrive and files. Recently I’ve been trying - Microsoft Loop went live for enterprise users a couple of weeks ago. It seems to be a Notion clone, which is good for meeting notes and attachments from OneDrive. I’d recommend trying it out.

I’d like to second @Synchronicity’s comment that lock-in doesn’t matter if you’re taking notes for your employer and they’ve made it 100% clear (as yours seem to have done) that they want all work stuff locked down in their Microsoft empire. That’s their choice, not yours.

So, in this Mac forum I am going to give you a +1 vote for OneNote. It sounds like you’re trying to bend Obsidian into what you need, when your employer already provides software that would do a great job for you and would eliminate the friction you currently have.

I used OneNote for a decade with my last employer and it’s just so good at handling all the random fragments of notes that office works tends to accumulate. I had a few separate notebooks vaguely arranged in themes (less than 5) but otherwise I mostly just used their tabs function to create and arrange things by pages (can’t remember what it’s properly called, sorry). I periodically tidied things up when I felt like it - I had a front page in my main notebook where I literally jotted down random phone numbers, memos to myself, a phrase I heard that I wanted to revisit, etc., during the day, so that page needed regular tidying as it tended to get extremely long and full of things that I’d forgotten the meaning of. It’s a really great app for this sort of work and it handles most stuff you throw at it. As well as random meeting notes, I also used it for quick phone call notes, text for email queries I wanted to re-use in future, storing a few attachments that I wanted to access quickly, the very occasional to-do list (not a preferred use, but sometimes needs must!), entire emails I didn’t want to lose (there is an Outlook integration that will push an email to your notebook of choice), saving links with a couple of notes about what it was. It had a good search 2 years ago (I assume it still does!), though I tend to know where I have saved things and I usually navigated manually to what I was after. If something was important enough that I wanted it to leave OneNote and also be available to me as a person, I would copy the text and move it to my own PKM, so it was available both at work (in OneNote) and outside work.

It’s worth noting that it’s one of the few apps I’ve found that actually does behave like a paper notebook would do, just better. Pages are “infinite” (I’m sure there is a limit, but my point is they keep expanding as you add more stuff to them). You can drop a text box, image, attachment, whatever, anywhere you want on a page, and you can format that text box how you like. This is far more like having a desk pad where you’d jot a note down anywhere you wanted, and I really liked this. You could colour code pages too.

(I know it’s not a consideration for you but also for what it’s worth OneNote backup files also survived a catastrophic IT incident at my employer that resulted in the loss of a lot of data/files).

The only reason I don’t use OneNote now is because I no longer work for a Microsoft employer, but I do recommend it to anyone who asks as it’s a great piece of software and Microsoft understood office life when they built it in a way that many apps haven’t been able to replicate. I always had OneNote open by default on my work computer (I had it set to open at login) and I was never more than a click away from the notes I needed.


I am following this thread very keenly. I am an academic currently on research leave. I practically live in Obsidian as I am sketching out a new book. It’s totally wonderful. That thinking is supported by DevonThink (where all resources live; and associated planning documents); Todoist (for top level tasks and project management); and Scrivener once I will start writing long form in earnest – and honestly it just works so well. Draft, Nebo/Goodnotes live somewhere on the side, but I use these half-heartedly or for very very particular things or at set times (e.g. Drafts for when out running and I only have a phone with me).

BTW the Outlook ToDoist integration never worked for me because I use the Mac Outlook app, and the Todoist links always take you to the browser Office 365, which I loath with a fiery passion.

I have tried, and failed, to take good meeting notes in Obsidian, for the reason you outline. I have another pressure point in that if meeting in person, I don’t like sitting there typing in front of people (fine for online meetings of course).

From next year, I will transition to a manager role with lots of meetings and people management, and my institution is fully tied into Microsoft. So for all the reasons you outline I will probably need to transition to Onenote.

The final thing I have in the mix is an iPad for which I at long last got an Apple 2nd gen pencil (what a wonder!). So ideally I want an app that allows me to handwrite, have resources handy, be tied into work environment. So I am reluctantly staring Onenote in the face again.

NB: I need to think more about what my meeting notes are actually for – and keep remembering this as I have a habit to idealise the perfect note.

Often meeting notes just help me think or pay attention on the spot, and so can probably be trashed soon after. The sort of meetings I go to are rarely crucial for information that can’t be found elsewhere, but rather about establishing process/next steps, or often for community/collegiality. My least favourite meetings are where none of these things seem to be a priority :-).

I have found I rarely go back to meeting notes. The key thing is tracking my outcomes and tasks (which I will never permanently store in a meeting note anyway, but rather in ToDoist which runs my life these days).

So I think I have a good deal of friction between my Platonic meeting note (eternal storage, beautiful lay-out, all resources handy, great integration), and the actual scrappy notes that have a more shorter life and more limited purpose than I might think.


I never used to think the laptop was an issue, but I side more with you on this now. Even on a Teams call – and maybe this is just me – I feel like when I’m looking down typing, people are wondering if I’m paying attention. If I’m writing, they see my Apple Pencil pop up on screen from time to time and I feel like it’s more accepted that I’m looking down writing. Plus I always wondered if they could hear my keyboard “clickety clickety clickety” while people are trying to speak during the meeting.

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I solved that problem well before Teams or Zoom or any similar packages were a gleam in some developer’s eye. I was taught to touch-type and therefore look at the screen while I do so this also suppresses some of my dyslexic traits of misspelling and omitting words because my eyes are focused on how rather than what I type.

I’m a good typist, but I bought one of those Microsoft Sculpt keyboards when I started working from home. My wrists have thanked me, but I’ve lost a few WPM’s on the typing front, and damned if I don’t hit the “insert” key by accident 10 times a day. :rofl:

Incidentally, this is an argument for you getting a split-halves QMK-programmable mechanical keyboard. You can re-map the keys and make them do whatever you need to do (no more hitting “insert” if your fingers think something else should be there), as well as adjust the halves however you want for your wrists. :smiley:

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I’d say that there’s a difference between corporate knowledge, something like meeting notes or project-specific data, and professional notes, related more to building your own knowledge about your field. For the former, I can see that the company would have a claim on that data, but for the latter, that’s yours. That’s your professional research for your career, to make you better at what you do. I feel like the company shouldn’t be able to lock that up in their own data store that you can’t take with you if and when you and the company part ways.

Agreed. The work I do is theirs, the information I put together is theirs.

But if I have notes about shortcuts for writing queries (e.g. how to calculate fiscal year or age), that can apply to other things too and I’d like to take that info with me.

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I find this discussion very interesting. I have been an Apple guy in a Microsoft world for years. I have generally solved the issue by first taking advantage of what the company is providing (they’re paying for it). And then adding on my own flavor.

So for me that means I have used the full Microsoft suite for most work stuff. I have used the full suite of tools from Outlook to OneNote to Planner to ToDo to Teams. Together they work well. Especially OneNote with its ability to allow me to capture Daily Notes and use a digital pen. The pen part show up when I use my iPad (see next).

The added flavor for me is that I have been using an iPad in place of my old Moleskine notebook for years. That means I have been using the MS software on iPad including OneNote and OneDrive. Together they have allowed me to carry my iPad around the building for meetings, etc. for my notes instead of my Windows laptop. Then when back at my desk I use the laptop. This is of course with IT approval for connecting my iPad to the corporate network and the enterprise version of OneDrive.

This worked well for years, except personally I kept wanting to try other apps that were better designed for taking Daily Notes. So, I moved to Agenda on the iPad. It worked well but meant I had to sometimes manually transfer some information back to my MS environment. Usually through Outlook on the iPad. And then more recently I switched to NotePlan for its different take on Daily Notes. Plus the way it handles projects and tasks.

I still use OneNote for communicating within the company, especially with my boss. But for my own notes I use NotePlan.

A dual world but one I am used to and comfortable with.


I’m curious, given your immersion in the Microsoft ecosystem, why don’t you use the Surface instead of the iPad?

Excellent question. Mostly because, while I have been involved in both worlds for years because of my roles in business, I have been an Apple person for long time. And I like, in general, software in the Apple ecosystem better than that in the Microsoft one.

Of course, I also have a Mac, an iPhone, and an Apple Watch.

I do know many people who use Surfaces (and my IT team would have preferred it).

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To be clear, I was not “advocating;” I was genuinely curious. :slightly_smiling_face: Some of my board members carry Surfaces and they seem pleased with them.

Yes, I used to get into fun debates with some of my peers, they representing windows, and me representing Mac.

To make things even more interesting, for a year I also used an Android work mobile phone.

Now that was crazy stuff.

At least then I was using Microsoft software on all devices.

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