Preface

For better or for worse, I'm consistently busy, but not always productive.

Between Edventive, Yute.fyi, consulting, freelancing and volunteering, I have a lot of work on my plate and I've found it increasingly challenging to make as much consistent progress towards my goals as I’d like to.

Many other people I’ve spoken with over the past year share the same struggle, as do many on /r/productivity and /r/macapps, two rabbit holes I’ve fallen down on my quest for a system that works for me.

It never ends though, like self-help. There’s always a new book, or tool, or workflow that will “revolutionize“ or “supercharge” the way we work. I decided to build a system to support me over the coming year, and so I could stop thinking about further productivity optimization.

Ideally, like Obama deciding to wear suits in two colors to reduce his decision fatigue, I'll be able to reserve my mental capacity for the hard stuff: learning, thinking and creating.

Here's how I try and make it all work:

Tools

Speech to Text

When I need to think, I type. When I need to do, I dictate with SuperWhisper. I press Option + Space, I talk, I press Option + Space and it pastes the transcribed text wherever my cursor is.

This is especially useful for emails, messages and giving instructions to LLMs. It was such a revelation I added dictation to Edventive to help teachers give faster feedback. I can’t work without dictation as an option anymore.

I use the free version, using the Standard model, but I'm considering upgrading for the audio file transcription, for the LLM integrations and to support the developer.

Protect your voice and drink a lot of water if you plan on talking to your computer all day.

Meeting Notetaker

I used to split my focus between talking to the person on my screen and furiously typing point form notes during meetings. I came across tools like Otter.ai and Fireflies.ai during the pandemic and found them moderately useful. Then I found Circleback. It’s the best meeting notetaker I’ve tried and I’ve tried half a dozen so far.

I signed up for Circleback's affilitate program because of how often I've recommended it.

The summaries and action items it creates are impressive, and I think they fixed an issue I faced earlier this year where it mixed up participant names when creating action items from the meeting transcript.

What impresses me the most is their team’s focus on automations, allowing you to define insights worth extracting automatically after meetings.

A cool example would be doing a customer interview and setting up an automation to fill in a template based on their answers to keep your data cleanly structures. Then, you could have it send a summary to your team’s Slack channel and Notion workspace. I haven’t explored this feature much, because of how useful I’ve found their summaries, but I plan on diving deeper into the possibilities shortly.

To Do List

I used to use Tick Tick, but I find the interface relatively cluttered. I recently switched to Todoist because I needed a barebones to-do list app. Then, yesterday, I switched to Superlist because I fell in love with their design.

You get 5 projects (folders) with the free plan, so I set one up for Edventive, Yute.fyi, Consulting, Life Admin and Follow Ups.

The follow ups set of lists is particularly important. It helps me keep track of the introductions I promise to make and the people I promise or need to follow up with.

Issue Tracking

Linear, it’s simply the best. Why waste time elsewhere?

Calendar Links

Cal.com is simply the best. Why waste time elsewhere?

I dislike Calendly’s user experience and feature set. Cal.com is free for personal use and paid for team use, although I’d be happy to send them money for the service they’ve built.

Between Google, Microsoft, Amie and others, booking links seem to be rapidly becoming a commodity, but I like how polished and thoughtful Cal.com’s experience is.

Short Links

Dub.co is the best. Why waste time with bit.ly or alternatives? Dub is the best.

I use it to send branded links like jonathon.link/... edventive.link/... and even for my.yute.fyi/....

Here’s the article that inspired me to ditch the default the default domains.

Password Management

I use 1Password because I only want to remember one password. Sorry, I had to.

The password creation, cross-platform compatibility and autofill features are all I need to avoid repetitive and likely already compromised passwords.

Shortcuts to Everything

I started using Raycast recently and it’s slowly becoming irreplaceable. I haven’t been able to deep dive yet, but its already removed some of the smaller frictions I experience with my computers.

A few examples that come to mind are:

• Quickly launching apps
• Calculator and unit conversion
• Floating notes (instead of new untitled documents in Obsidian)
• Word and character counts
• Ephemeral AI chats for small tasks like formatting markdown or formatting dictated emails

The main benefits, for me, are replacing the litany of suspicious websites I visit to accomplish small tasks like character counting and keeping my notes and AI chat histories clear of small, mundane tasks.

Screenshots

I use Cleanshot for screenshots, annotations and gifs. I like that I can pixelate parts of screenshots with PII and I’m intrigued by their scrolling capture feature that might come in handy with LLM chats.

I’m also very intrigued by their Optical Character Recognition feature aka extracting text from pictures.

Screen Recording

Like many others on their homepage, I use Screen Studio for product demos. I like the background selection options and the editable auto zooms. It’s a very easy process end to end, although I’ll typically export video clips and bring them into Canva so I can polish the clips with text animations and background music. Maybe I’ll get fancier with it this year, but this has worked well for me so far.

Chatbot

Last but not least, the chatbot.

According to the benchmarks, Gemini, GPT and DeepSeek are in the lead in terms of user preference, but I beg to differ.

During the earlier half of last year, I felt a considerable difference between the quality of answers and “creativity” provided by different models. That changed with the announcement of the Claude 3 family of models by Anthropic and every model that came thereafter.

Take the following with a grain of salt, I’m biased.

The models have gotten so good, that I find it hard to quantify the difference in impact of different models' reponses. Each frontier model passes the good enough test for most users. I’d suggest trying out the top frontier models from each company and picking the one that passes your vibe check the most.

User interfaces, experience and app integrations are also a differentiating factor, but vibes matter the most to me for now. All I need is text in text out.

I think OpenAI is SO far ahead of the game with UX and integrations and I have to give Google their props for creativity with NotebookLM.

Despite the gap in rankings and in features, I seem to prefer Claude 3.5 Sonnet over all of the other LLMs, and I use Artifacts and Projects multiple times a day.

Artifacts are like small tabs of documents or code that Claude creates. It helps keep its creations compartmentalized, easily findable and easily exportable. It even keeps track of the revisions it makes by numbering each version of its creations so you can switch back and forth to compare changes.

Projects. Oh. My. Projects allow users to assign custom instructions to all of the chats assigned to it. This means we can create personas or specialists to help with specific tasks. We can even add “Project Knowledge” or documents to the project to “fill Claude’s brain” with relevant information to reference, like documentation, guides, tutorials and even whole books. OpenAI recently announced this feature for ChatGPT too.

I have so much more to say about Claude, but that deserves a separate article entirely.

That’s all for now, I hope this helps.

TLDR / Summary

In case you just want the list and prices, check out this post.

If you'd like more hands on help, I offer both productivity coaching and AI workflow consulting to help you achieve more with less frustration. Please contact me here to have a conversation about your specific challenges and goals.