I’ve had some form of a Second Brain (a personal system of knowledge management) for a couple decades now, and during that time it’s been hosted on four different platforms:

  1. Paper was sufficient for most of my school years when I didn’t have my own computer (and wouldn’t have been allowed to use one if I did).
  2. Microsoft Word was a good fit for my late high school and college years because it was the only text-based software I knew of, and it allowed me to gain fluency in an app I’d be using for years of further schooling.
  3. Google Docs was ideal during my 20s when I was living and traveling abroad and needed a “digital nomad” solution that always saved everything to the cloud.
  4. Evernote has been a great companion for the last decade of my career when I needed a simple, mobile-friendly solution that allowed me to focus on content creation.
Tiago's History of Second Brain Apps

What jumps out at me as I look back at this timeline is that each season of my life has benefitted from a notetaking medium that complements it. Each season puts different demands on us, imposes certain constraints, and highlights certain weaknesses – the tool you use to manage your life should compensate for those weaknesses while amplifying your strengths.

In general, you don’t want to switch notes apps too often, since making such a move invariably consumes a huge amount of time and energy that is then unavailable to actually move forward your priorities. Switching Second Brain apps is akin to changing the water heater in your home, the transmission in your car, or moving to a new bank – something to be done as infrequently and reluctantly as possible, only when circumstances demand it.

This is why I think the best time to switch apps is at major life transitions – changing jobs or careers, moving to a new city, getting married, having kids, buying a house, etc. You’re already expending a huge amount of effort and upending all your habits and routines to make such transitions anyway, so you might as well use that opportunity to retool as well.

By timing your digital migration to accompany a major life transition, you ensure that you’re doing it for the right reasons – not because you’re bored, or craving distraction, or because the hype for a new hotshot app is too powerful to resist. No, you’re changing your support systems because your life is changing, and your Second Brain should mirror that change.

When NOT to move apps

There are three situations in which people commonly switch their Second Brain apps that I think are ill-advised.

1. When your existing app “breaks”

One of the most common reasons people decide to switch to a new notes app is when their existing one “breaks.” Often this decision is made spontaneously, in a moment of acute frustration at some unmet expectation, which is the first red flag. You wouldn’t move homes or trade in your car based on a momentary annoyance, would you?

But there is a more fundamental reason why this isn’t a good reason to make a switch: in virtually all cases, the app isn’t truly breaking – it’s probably just a little slow, or suffering a temporary glitch, or maybe at most they eliminated one of your favorite features. 

While I know these things can be frustrating, changing your digital home base entirely is almost always an overreaction. I guarantee whatever new app you switch to will have its own fair share of glitches and problems, and now you’ve paid the tremendous penalty of changing all your existing habits and workflows.

The same goes for price increases – I cannot imagine a worse reason to overhaul your digital life than a nominal price increase. If you are using your existing platform at even 1% of its potential, the time savings it is creating exceeds that additional expense many-fold.

2. When embarking on a new project

Another common situation in which people feel the need to move to a new platform is when embarking on a new project or other endeavor. It’s understandable to want to start with a fresh, clean slate when starting something new, but I think this is almost always a mistake.

Here’s why: when a project is just starting, you don’t have time to adopt new tooling. Unless you are building a particle accelerator, or something else highly technical requiring exotic technology, your tools and infrastructure are almost never the bottleneck to your progress in the early days.

Since your choice of notes app is not your bottleneck, not only will changing it not help, it will probably just distract you from the necessary next steps that would actually represent tangible progress. Endlessly reevaluating your software options is usually just a form of sophisticated procrastination.

3. When a new paradigm of notetaking arrives

The third most common rationale for moving Second Brain apps is when a new paradigm of notetaking or knowledge management emerges. 

Back in the day, as soon as cloud-based, real-time word processing arrived in the form of Google Docs, the whole concept of editing static Word docs saved to your hard drive immediately felt hopelessly outdated. When Evernote arrived, my previous practice of keeping all my notes in one giant Google Doc quickly felt like something from the Stone Age.

More recently, the paradigm of “digital file cabinets” embodied by apps like Evernote – in which notes are individual documents stored in discrete containers such as folders – is giving way to a new wave of “networked” or “linked” or “graph-based” tools.

The network is the dominant paradigm of the Internet, and that paradigm is now invading and transforming even our most personal, private repositories of information via apps like Obsidian, Roam, Logseq, and Tana.

This might seem like the perfect time to jump ship and ride the new technological wave, but in most cases, it’s not. To understand why, you have to understand when it is desirable and advantageous to be at the forefront of an emerging technology, and when it is undesirable and actively harmful.

How new technologies mature

The Gartner Hype Cycle is a well-known model for how new technologies enter the marketplace and change our behavior. I encountered it early in my consulting career, and it’s shaped how I’ve seen technology-driven change ever since.

Put simply, a Technology Trigger (at bottom left) is a new, breakthrough technology that gets invented. It quickly ascends the Peak of Inflated Expectations (top left), as the hype around its potential escapes all bounds of reason (“OMG it’s going to change everything!!!”). 

But that peak always overshoots, and leads soon thereafter to the Trough of Disillusionment (center bottom) as the reality of the technology’s limitations sets in. As the trend continues maturing throughout this roller coaster, it eventually climbs the Slope of Enlightenment as the practical use cases become more clear.

Finally, the new tech matures and enters the Plateau of Productivity, where it can start to become integrated into our everyday lives and, therefore, tangibly improve our productivity and performance.

Perhaps not surprisingly, that Plateau of Productivity is the part I’m most interested in. It’s counterintuitive in a world where technological progress often makes headlines, but it is only mature technologies that have been around for some time that truly make a difference.

As just one example (recounted in the book Power and Prediction which I summarized here), twenty years after the invention of the lightbulb, only 3% of US households had them. It took another two decades for it to reach just half of US households. There needed to be a series of improvements and supporting innovations to make the lightbulb a mature product ready to be installed widely in people’s homes. The most radical breakthroughs take the longest time to spread.

What this means for us individually is that you have to consciously resist rushing immediately to the cutting edge of new technological waves, because at the cutting edge you will find mostly noise, hype, scams, outlandish promises, and unmet expectations.

To be clear, it’s hard to resist the siren song of new tech, especially if you are an early adopter who enjoys trying, exploring, and testing new things. That’s fine to do as a form of entertainment, learning, or experimentation, but not when it comes to the basic, foundational infrastructure that runs your life

If you use a second brain app like I do – as an extension of your mind and the engine of your responsibilities – you cannot afford to upend it all just because you have FOMO about a sexy new app someone is raving about on social media.

Here’s the bottom line: the right time to adopt a new paradigm of notetaking is when the paradigm is mature, not when it’s just emerging. Because we’re talking about a basic utility here, the most important feature is reliability. 

And the products that tend to be most reliable are the ones that are mature and proven, with all the kinks having been worked out long ago.

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