Greetings, data-tamers.
This week took an unexpected turn. Remember how I was going to walk through the migration process from Word into Craft?
Here's what happened.
I signed up for Craft's paid family plan, ready to help my mom revolutionize how she manages the information currently contained in her giant set of Word documents. The plan was elegant: she'd get modern note-taking with beautiful design, cross-device sync, and those fancy bidirectional links I've been evangelizing about for the last two weeks, along with map-of-content (MOC) notes.
Then I discovered that one of the core features I was counting on (collections for organizing meetings and people) currently has a bug that makes it impossible to set up on Windows or the web. You need a Mac to work around the limitation. I happen to have one, but she doesn't.
(Sigh.)
I alerted the Craft support team to the issue, and they confirmed the bug but weren't able to guarantee any timeline for a fixed release. It could be tomorrow, or weeks from now. I hope it's soon, but I don't want to start building what needs to be a dead-simple new process for my mom on top of mere hope. I could plan to use the workaround from my MacBook (with her Craft account) until the fix is released, but that's not ideal.
So instead of building toward a step-by-step migration story, I spent the week diving back into exploring alternative options. I'd rather hold off the process little and share my real-time discovery process, because there's a decent chance that some of you could encounter similar "uh oh, wait a minute!" challenges if/when you decide to pick a note-taking app.
The biggest challenge with selecting the "right" notes app is that there are so very many options, and whether they're a good fit depends heavily on how you think and what you want to do with your notes. The best approach is to find one that looks reasonable and try it out for an hour, then (if there aren't any big red flags) continue for a few weeks. Give yourself time to really see how it works and learn the workflow, including quirks or minor annoyances. It's unlikely that you'll find something that provides 100% of what you want with 0% of what you don't want, so there will always be at least some element of compromise. Only you can decide which compromises are worth it.
And this brings us to my choice to use (or not use) Craft. I'm pretty familiar with my mom's document/note situation, so I'm not just making a blind recommendation. But it's still hard for me to make a choice without projecting my own preferences and biases into the situation. At the same time, my mom is willing to adapt to achieve better document organization, and my Q4 Consistency Challenge project explicitly includes hand-holding and training to help her familiarize herself with the new system. Therefore, it's okay for me to pick something I'm personally biased towards because I can help her learn it more than I could with a random person reading a blog post about different note-taking apps.
But I still need to consider which path provides the right balance of functionality and familiarity. I need something that will feel intuitive rather than complicated every time she opens it.
The excellent Tool Finder website has many dozen note-taking apps available to peruse. Here's the short list of what I considered, and some additional context:
- UpNote is the temptingly simple choice. It's like a clean, fast, modernized version of what Evernote used to be. The main content editor is a joy to use. Familiar formatting toolbar, obvious buttons for everything, but with conveniences like instant search across all notes and automatic syncing. The learning curve is essentially nonexistent. You can organize with notebooks that work like folders and gradually discover features like tags and bidirectional linking without feeling forced to use them. At a mere $2/month or $40 once (!) for lifetime access, it's refreshingly straightforward. My only complaint is that backlinks, while possible, are not as obviously displayed as I'd like, making the map-of-content (MOC) organizational approach less achievable. The app's simplicity also means it's less "future-proof" if you decide you want additional features later, like custom document properties, flexible database tables, AI integration, etc. With UpNote, you get what you get, and that's it.
- Craft remains beautiful enough to make you want to use it, with its Mac App of the Year pedigree showing in every interaction. Everything is a draggable block you can reorganize, pages nest infinitely, and you can publish notes as gorgeous web pages. But that Collections feature I wanted is admittedly rough around the edges. There's also no native Android app, just a mobile web version, though that isn't a problem for me or my mom at this point. I like the UI and feature set a lot, but I still worry that it's going to provide a less-than-intuitive experience for someone coming from Word, and I wonder whether the learning curve--however small--is worth it to end up with a system that might never feel quite natural.
- Joplin is free and open-source, which is great, but the user interface feels slightly outdated. It's an interesting cross between Obsidian, Craft, and Upnote, which is why it's on my short list. I almost decided to try it for my mom two weeks ago, but the fact that it wasn't significantly better than UpNote despite haven't a less clean and simple UI made me hesitate. Still, not a bad choice if it grabs you.
- Capacities offers an innovative "object-based" approach where instead of folders, you create interconnected objects like people, books, and meetings. The founder admits the biggest stumbling block is "no folders, just objects," with adaptation taking days to months depending on the user. Some find it perfect for beginners, others call it a power user's app. At $10/month for premium features, it's a significant conceptual shift from traditional organization. I actually used this myself for a few months at a paid level, and I was generally very happy with it. But while it's phenomenal at linking notes together (ideas, documents, whatever), it would feel pretty foreign to a Word-only note-taker. I think I'd only pick this for my mom if she specifically asked to use it.
- Obsidian has passionate fans for good reason. Its bidirectional linking and graph view are unmatched for building knowledge bases. But it uses Markdown for formatting, not a WYSIWYG editor--although it has a nice blend of power and visualization in the default "live preview" mode. Its local-first blazing fast interface is nearly unmatched for speed and privacy, and it has an absolutely phenomenal 3rd-part plugin repository full of every feature you can imagine. Obsidian is like a blank slate that can be anything you want, but you have to figure out what you actually want and how to get there in order to be successful. I would never drop my own mother into it to manage on her own. But...what if I knew exactly how to set it up for her?
This is the decision I'm facing. I'm a very happy Obsidian user, but I'm also very technical and enjoy the discovery and tinkering process that inevitably comes with dialing in Obsidian to fit your personal preferences. I know, love, and trust Obsidian with my own ever-growing collection of notes. I know what it can do and how to make it work.
But this also means I can take a fresh, stock, no-frills installation and add just a couple of well-chosen plugins (e.g. Notebook Navigator and Editing Toolbar) to turn it into exactly what I think would work well in my mom's case, skipping over the discovery phase and hiding the complex parts that she never needs to touch.
Fun fact: I didn't even know that Notebook Navigator plugin existed until I was writing this post. It's a fantastic UI improvement if you're looking for a more Evernote-like experience, which I am. See what I mean about Obsidian's amazing extension marketplace?
Further, Obsidian has a flawless sync service, which I'm already paying for (for myself) at a level that means my mom could jump in with me at no extra cost. This is not only good for her in the long run, but I can also set up syncing her documents to my computer to help with the initial setup and import/migration process. Anything I do on my end will automatically synchronize to her! This arrangement isn't practical for most people, of course, but it's extremely helpful in this case.
After this additional research, here's my updated conclusion within the context of my document/note migration project:
- UpNote for simplicity, if you just want simple notes that work everywhere
- Craft if you're all-Apple or the "collections" feature hiccup isn't a problem, and UpNote is too simple
- Obsidian if you're technical OR if you like it enough to have someone to perform a concierge kick-start setup to configure it for you
Of course, there are dozens of other possibilities. But I have to start somewhere, and ultimately end somewhere, so I'm going to see if Obsidian can be made to fit better than I was afraid it would a few weeks ago.
The gap between "I love bidirectional linking" and "my mom just wants to keep track of her meeting notes" is wider than I realized at first. Most off-the-shelf solutions have more compromises than I want to entertain, and the others usually require too much special knowledge. But with a properly pre-customized setup of Obsidian, a.k.a. "The Notes App That Can Be Whatever You Want," I think we have a good chance. Stay tuned.
Have you successfully helped someone migrate from Word to something modern, or even just gone through the excitement of switching to a different notes app? What worked, and what didn't? I'd especially love to hear about any surprises along the way—good or bad.
Until next week, happy data-taming!