Mammoths, Ice Cream, and Chess

Newsletter Edition #2

After sending out my first newsletter last week, I got lots of great feedback and was reassured that this was worth my time. My goals are to provide as much value to you guys as possible and to be able to flesh out my thoughts and reflect in a more informal manner than with articles. I’m excited to hear what your reactions are and to see how the newsletter evolves over time…

Content that got me thinking:

Tears to Ice Cream (35 min) - My friend Jake created a journal of short reflections where he poetically describes his thoughts on topics like ice cream, death, language, and much more. I really appreciated the honesty and genuine curiosity he has for understanding the world and how to approach it. Definitely worth a look.

But if I’m doing my best, then how can I have regrets? If I passionately pursue the life I honestly believe I should live, that’s all I can do. The only scary things are being dishonest with myself, or being too lazy to do what I feel I should. When I take care of those, I can let go of the rest.”

Taming the Mammoth (19 min) - I love this article from Wait But Why because not only is it a really spot-on depiction of how we are so exactly how we let other people’s opinions impact our choices and the role this plays, but it also provides some really actionable advice for harnessing your authentic voice that I want to think about and start applying. One of the most immediately applicable prompts I’m thinking about is who the Puppet Masters are in my life that subconsciously drive my behaviors.

puppet master

Productivity tools I’m loving:

Attachable Laptop Stand ($23) - I got this recommendation from a friend and this has been a gamechanger. Instead of having to rely on a big laptop stand, I can unfold the flaps on this attachment to raise my laptop wherever I need. This helps to improve my posture when I’m working and provides a subtle clue to turn on my productivity. Such a great investment for the price.

Baron Fig Confidant Journal ($18) - This is now the third Confidant notebook I’ve gotten from Baron Fig to use for my daily journaling. I’m trying out the Dot Grid on this one but have typically gone for the Ruled version. What stands out to me with this journal is that it lays flat. If you’ve ever used a journal, you know exactly how annoying it can be if all it wants to do is close. If you’re interested in learning more about my journaling techniques, check out this article I wrote.

Notion - I’m not going to claim to be the first person to hop on the Notion train, but I finally did decide to give it a try and it’s pretty awesome. Notion is an all-in-one workspace with an insane amount of freedom when it how you want to use it. For right now, I’m using it as a replacement for Apple Notes, and the beauty of the interface alone might have already justified the switch. I’ve discussed the importance of speed when it comes to a note-taking app, which is a place where Notion still has a lot of room to improve. But take a look at my gorgeous book notes gallery. Very excited to continue experimenting…

What I’m writing about:

I recently published an article about why I write articles where I reflect on my experience to pinpoint two main reasons/benefits:

  1. Synthesizing all the information I am learning from books, articles, videos, friends, etc so that I can effectively internalize these concepts and approaches

  2. Creating guiding principles that can essentially act as a playbook for successfully handling a certain aspect of my life

If this sounds appealing, I would urge you to read through the article and to give it a try for yourself.

Some takeaways from books I finished:

Principles by Ray Dalio

  • By having principles, you are able to turn new situations into ‘another one of those’ that you can approach calmly and analytically

  • Importance of radical open-mindedness - You need to really believe you might not know what's best and surround yourself with smart, believable people who think differently

  • Importance of the idea meritocracy - you can let the best ideas win out when you weight opinions of people based on track record (while giving everyone a chance)

The Art of Learning by Josh Waitzkin

  • Invest in loss - give yourself to the long-term learning process by giving room for yourself to struggle

  • Developing mastery means developing such deep integration with the information that it “disappears and allows us to fly free”

  • Aim to cultivate the Soft Zone - an ability to “sit with our emotions, observe them, work with them, learn how to let them float away if they are rocking our boat, and how to use them when they are fueling our creativity”

  • Discover what states of mind work best for you and build condensed triggers so you can pull from your deepest reservoirs of creative inspiration at will

Hi! 👋 I’m Drake Weissman, a recent grad from Northwestern and entrepreneur. Thanks for reading Bias to Action. I love to get feedback, answer questions, and discuss anything related to personal growth, startups, fitness, etc so please don’t hesitate to reach out at