The Hidden Cost of Getting Back on Track

How unfinished context creates overwhelm, and how a simple re-entry system can help you return faster when life piles up.

May 06, 2026

Disclaimer: I’m not sponsored by any of the apps I’m recommending today. I’m only doing it because they helped me at some stage in my life.

Two weekends have passed since the TEDx Talk, and life is sort of going back to normal.

I feel that I have more breathing room. To play with my kids, to actually spend quality time with my wife, to be able to catch up with life outside of work.

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It’s one less ball to juggle, but now that the dust has settled, I realized that some things got piled up, and that gives drift — at least in my case — an avenue, a channel, to move through.

Household tasks, some items from my personal projects, and the usual priorities: family and my full-time employment.

In the past, when I used to get overwhelmed with pending things to do, I would just default.
Not good.

Later, I discovered that I could manage to keep to-do lists.

For a while, I used Google Tasks, and while it was really useful because it let me create tasks from emails, I still felt that I didn’t have enough space to load a bunch of context there and, with that, feel peace of mind to focus on the next items on the list. It quickly became a graveyard for seemingly urgent but not really urgent tasks.

Then I moved to Notion, and most recently to Obsidian.
These last two changes changed my relationship with my overwhelmed self.

One of the things I discovered when I started working with these note-taking apps is that, by just carrying lists, I did indeed lift the weight of pending stuff somewhere, but what I realized is that to-dos are not the only items we carry in our head.
We carry way more context.

So, while I would try to complete pending tasks, I would still carry ideas, next actions, concerns, and that would actually slow me down. Many times I would have to, if I was in the middle of something, come back the next day and pick up where I left off, which would take me a while. For those familiar with getting into a flow state, it became hard for me to actually get there because there was too much in my head to leave space for that luxury.

There is a phenomenon called The Zeigarnik Effect, which is the tendency to remember incomplete or interrupted tasks better than completed ones. I’ve talked about it in a couple of articles already because I feel like this is something that, before learning about it, haunted me precisely because I would tend to remember everything I needed to do, everything I wanted to do, and everything I should do, and forget those things I had already completed. The problem with that is that this mode would rob me of my progress, my pride, and the motivation to keep getting back to what matters.

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With the use of these note-taking apps, I started paying extreme attention to addressing this particular issue.

Now I’m proud to say that today, even if drift has avenues to manifest, it rarely does, because I’ve learned how to manage it before straying away, and if I do, the usage of this tooling has allowed me to pick up fast, not worry about what’s incomplete, because I delegate it to my Obsidian vault. And I also don’t let myself get carried away by concerns or ideas, because they are noted, meaning that I can always go back to them.

Obsidian became my re-entry system.
It helped me reduce my re-entry cost.

Now, the meaty part. What do I do with this that is useful to me?

One thing that I want to make clear: Obsidian is the tool I use as a way to reduce my re-entry cost and increase my comeback speed. You can use any tool that allows you to take notes. Do you use Google Docs? Evernote? Notion?
Any of them is okay.

Back to it.

I built my system with Obsidian because, compared with other note-taking apps, it felt very intuitive and easy to create and organize my ideas around markdown files. This became especially useful when I realized I could connect Obsidian to Claude Code — Anthropic’s terminal tool for working with Claude at a lower level — because I could consolidate my learnings and automate the organization and collection of data. It’s very easy to pile up notes and then ignore them because processing them becomes another burden.
The idea of making notes part of a system — an important part of the system — is precisely to get value out of them and reduce the re-entry cost by surfacing the most relevant information when I need it.

More concretely, today I use Obsidian for collecting information, plans, and personal reflections; to organize my work at Self Disciplined; but most importantly, to keep my daily notes updated and organized. My daily notes are the ones that help me return fast.

How does a daily note look like?

Every note contains 7 sections: 3 of them generated with the help of AI, and 4 that are my daily input.

Morning Brief — A snapshot of my current state. It includes:
- Carryover — Items that I’ve been working on that are unfinished.
- Current Focus — The priorities I have to keep an eye on.
- Keep in View — Concerns or notes that stem from notes or reflections I wrote down.
Journal — The entry for the day.
- To-Dos — Items that I have to work on, actionable items.
- Context For Tomorrow — Handoff notes for tomorrow. Shares state for a faster re-entry.
- Notes — Captured ideas, reminders, raw thinking. It’s the sink for me to jot down ideas when they come, and then get back to them.
- Reflections — Rambling, personal reflections, nothing really actionable, just a place where I can allow myself to drop my thoughts without much filtering.

Each item has a specific job. I automated the process by asking the LLM, Claude, to help me archive the previous daily notes every day and create a new one, pre-populating my morning brief so I know where I left off, what I need to do, and can start energized and heads down right away.

It has proven to be very helpful.

Not every system is the same, and I say this intentionally. Our brains are unique, we are unique, and because of that, we need to build what fits best for us. The example I gave you is a bit redacted to show you the parts that can be useful to you, so you can build your own notes and support yourself with the tools that are the most comfortable to you.

I’m just giving you a scaffolding you can use to start faster.

As a reminder, this system doesn’t eliminate drift. It assumes that at some point I will forget what’s in my head, or that I’ll try to procrastinate, or that I will freak out about something, so it gives me the tools to re-enter and get back to what matters at the lowest cost, so I get back to myself and to my craft.

In tomorrow’s paid companion, we will work on practices that help us identify tools that fit who we are and our needs, which I think comes pretty useful when we want to remain coherent.

Check the scaffolding, see what can be helpful. If you have questions, please leave your comment or reach out to me directly. I’m always available.

Don’t be a stranger.

I hope you have a wonderful week!