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Donald J. Robertson talks philosophy and uncertainty on The Daily Stoic Podcast

The Daily Stoic Podcast by Ryan Holiday

Donald Robertson is someone whose work I’m just discovering. He’s a cognitive-behavioral therapist and trainer, a public speaker, and has written several books on history, philosophy, and psychology.

Donald appeared on a two-episode arc of The Daily Stoic podcast ( Episode 1 | Episode 2 ) to talk about Socrates, Stoicism, and how ancient philosophers knew a thing or two about managing our approach to uncertainty.

Listening to Donald connect ancient ideas to our modern concerns and approaches is enjoyable. I also enjoyed hearing how Ryan’s books, which have made Stoicism quite popular, have caused some modern therapists to look at Stoic philosophy again or, in some cases, for the first time, even if just so they know what their clients are talking about when it comes up.

I did CBT (cognitive-behavioral therapy) nearly a decade ago, and it was really effective for me. My therapist taught me how to understand not just how to relax my body but also how to understand what my thoughts were and the effect they had on me. She helped me know that I had far more control over what came into my head than I realized. In fact, sometimes those thoughts are all we have control over.

A year or two later, I walked into a bookstore and saw a hardcover edition of The Daily Stoic sitting on a table. It’s like the book was waiting for me.


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The 2024 Gift Guide

'm pleased to share the second annual gift guide here on 24 Letters. While this one is shorter than last year's, it still reflects items I use regularly or hope Santa will put under the tree for me this year.

Books

The Daily Stoic

The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living by Ryan Holiday and Stephen Hanselman

This book feels timeless. It features a daily quote from one of the ancient Stoic philosophers and a modern reflection from Ryan that compliments the selection. I read it daily and recommend it often.





Kitchen Confidential: Adventures in the Culinary Underbelly by Anthony Bourdain

This book transformed Tony Bourdain from an unknown NYC chef with a passion for prose to an international culinary, literary and television star. I reread Kitchen Confidential this year for the first time since its release, and it holds up. I miss Tony, and appreciate his vast body of work whenever I can.


Slow Productivity

Slow Productivity: The Lost Art of Accomplishment Without Burnout by Cal Newport

The three big ideas in Cal Newport's latest book are simple: Do fewer things, work more naturally, and be obsessed with quality. These ideas are simple but not exactly easy to execute. With Slow Productivity, Newport offers a roadmap for slowing down, avoiding the overhead tax, and balancing intense focus with periods of rest.


I like the noise-cancellation features of my AirPods Pro 2, but I don't always like how snug they feel inside my ears unless I’m doing someting in a crowded area where I needed additional support in staying focused.

These AirPods seem like a happy medium, as they still sit in the ear and offer some noise cancellation with a more comfortable fit.


Apple TV 4K

Somehow, my household managed to use Amazon Fire TV Sticks for our streaming for years, despite my fandom for all things Apple. Over the last year or two, motivated by aging hardware and the sudden and annoying appearance of ads that auto-played on startup, I switched us over to Apple TV devices, and we've been much happier since.


I enjoy the tight remote integration with my iPhone, the ease of connecting with the Apple devices we all own, and the pleasant and easy-to-use interface.


I've been streaming Apple TV+ since it launched and have watched many shows on the network. It's small but has released some shows that continue to be my favorites. Ted Lasso, Slow Horses, Bad Monkey, Severance, The Morning Show, Trying, and many more have made this streaming channel one that I thoroughly enjoy.


Day One

I use Day One all the time. It's been my regular digital journaling tool since 2017, and I've used it off and on since 2012. I like the ease of creating multiple journals, the cross-platform approach, the solid backup scheme, and the ability to easily add photos and metadata to any post. Day One is free to use, with subscription options to unlock more features.


I hope this little gift guide helps with some ideas for friends and family, or provides you with a few suggestions to give to that sweet aunt who always gets you socks. Send her here, maybe I can help! Happy holidays!

Note: Some of these items include an affiliate link, meaning your purchase may help support this site. I've only included things in this list I actually use, like, recommend, or hope Santa brings me. As was the case last year, there are no big screen 4K TVs or air fryers here (although my wife and I are tempted by both!).


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Back to Work

I forgot how important weekends are.

My stay-at-home era has ended. I dove back into the working world in mid-November, and I’m really enjoying it. I’ve got a fantastic management team and am learning as much as I am (hopefully) teaching.

I thought, perhaps foolishly, that I’d have a little time to write and create even a little during the initial few weeks of onboarding, but life had different plans.

Things are settling now. I’m getting used to the rhythm of getting up early to work instead of to write. I’ve sent notes of sincere apology and appreciation to my extended family and friends and checked in to see how they’re doing. And I woke up early this Sunday to make coffee and write.

I have a lot of thoughts and ideas about what it means to work and what it means to stay home with family, the similarities and differences, the ways time and experiences change who we are and how we move through life, and how, if we pay attention to everything, we can learn things that actually change us. I’ll be sharing more here, on the newsletter, and on Threads.

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The Day One Podcast Returns

Despite being an active daily user of Day One, I was unaware they had a podcast. It’s been on hiatus since 2021, and that’s likely part of why I hadn’t heard about it.

The show has recently launched a new season with a new episode featuring Paul Mayne, the creator of Day One. It’s worth listening to if you’re curious about some of their choices with the app, the additional resources they’ve gotten since joining Automattic, where AI fits into the roadmap, and other details on what motivates the developers to keep going.

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Halloween and Creativity

Today is Halloween. It’s a day when creativity can be seen in many places, but it may not usually be so evident. At work, your colleagues may dress up as their favorite characters. You’ll see kids (and their adults!) dressed up and wandering down the sidewalks in your neighborhood, happily going door to door asking for yummy treats. Houses may be decorated with pumpkins and other spooky elements meant to delight and scare you just a little bit.

Those same colleagues and kids are just as creative every other day of the year. The difference is on Halloween we’ve all decided that it’s okay to show who we are, to share our fun and creative ideas with the world around us.

Whether or not you’re dressing up today or have little kids, adult kids, or no kids at all, whether you’re handing out candy or shutting the light off and going to bed, let’s keep the creativity going. There’s a connection to it, and we do well to celebrate that as much on November 1st as we do on October 31st.


This reflection originally appeared in The Journaling Guide. Delivered every two weeks and packed with real-life stories of history's greatest journalers, reflections from my own experiences studying how journaling helps improve our lives, and actionable insights for you, it's like having a close friend guide you on your journaling practice.

Sign up today and I'll send you my valuable quick guide, Seven Thought-Provoking Prompts for Your Journaling Practice, when you confirm your email.

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Basic AF #47: The Journaling Guide with Joe Moyer

I was pleased to return to the Basic AF Show and discuss journaling. This is my second guest spot with my friends Tom and Jeff (the first one here), and once again, they made me feel welcomed and valued. From the episode page:

_ Ever wondered if journaling could make a difference in your life? This week’s guest, Joe Moyer, believes it can. Joe shares his personal journey with journaling and practical advice on how to build a habit—even if you only have five minutes a day. We cover gratitude journaling, the benefits of recording daily thoughts, and how to avoid the “perfect journal” trap. He also provides tips for those who are new to journaling, with simple techniques to get started._

This was a fun conversation, and I hope you’ll listen. I think everyone, particularly young men, needs to hear some of what was said on the show and pay particular attention to the productive struggle, where we talk about being kind to ourselves, working through complicated feelings and emotions, and growing.

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The Ugmonk Pen

I’ve never been a fancy pen guy. I always used a Pilot G2 or a Uni-ball 207 for my writing, but lately, I’ve found them to be a little lacking.

I wanted a pen that felt more significant but had a similar gel ink output, so I began casually looking. When I got an email last month from Jeff Sheldon announcing The Ugmonk Pen, made in collaboration with Leuchtturm1917, it was an easy buy for me.

I also picked up the walnut pen tray, which is a thing of functional beauty and is where my Apple Pencil often lives as well.


The pen and tray combo arrived just in time for some heavy use, not for writing or journaling but for a bunch of lengthy insurance-related documents that, due to poor design, needed to be printed out and handwritten. It took hours to do it all, and it was made more pleasurable and easier with the Ugmonk Pen. I’ve since used it for some print journaling and to-do list building, and it’s really delightful to write with.


I believe that the message matters most, and the tools we use, particularly in journaling, should serve that cause. This pen does that for me, and I’m pleased to have finally spent a little bit more money for something of much greater and lasting quality.


This reflection originally appeared in The Journaling Guide. Delivered every two weeks and packed with real-life stories of history's greatest journalers, reflections from my own experiences studying how journaling helps improve our lives, and actionable insights for you, it's like having a close friend guide you on your journaling practice.

Sign up today and I'll send you my valuable quick guide, Seven Thought-Provoking Prompts for Your Journaling Practice, when you confirm your email.


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Finding Focus: Building a New Sleep Mode to Improve Discipline, Support Better Habits, and Save Me from Myself

For many, sleep is a complicated matter. It is vital to our health and well-being, yet many struggle to get adequate rest. According to the CDC, 36 percent of adults in the United States, approximately 120 million people, sleep less than seven hours each night.

Over a quarter of the US population needs to sleep more. Regretfully, since becoming a parent, I've become part of this unfortunate statistic.


Like most parents, The struggle became greater after having children. As if inconsistencies of sleep that are beyond my control aren't enough, I've recently started doing something that is certainly not in my best interest: staying up well after the kids are asleep and things are cleaned up. I don't do this every night, but I cycle through a couple times a week where the desire to just stay awake and enjoy some quiet time to decompress wins out over the better angels of sleep. My wife, who deals with the same sleepless nights but is far wiser than me, prioritizes what little sleep she gets over anything that doesn't involve her family. She's an intelligent woman, and as I often tell her, when I'm learning from her, I'm taking notes.

Some nights things works out. I go to bed later than I should, and everyone sleeps through the night. Other nights, I only get a few hours of sleep before the waking up begins. After a particularly tough week of this cycle, I made a conscious decision to take action and make a change.

The Goal

I started this project by making a short list of my goals. Here's what I came up with:

  • Aim for seven hours of sleep every night

  • Access to apps that promote relaxation and sleep

  • Limit access to apps that inhibit sleep

  • Turn on automatically 30 minutes before ideal bedtime

  • Use context shifting to reinforce sleep time

With these goals in mind, I set out to reduce distractions during the time that I want to be sleeping and also improve my sleep discipline. After some planning, I started building a revamped sleep Focus mode.

Letting the Right Apps In

Okay, I have an admission to make. I use my devices in bed before going to sleep. Most often, I'm on an iPad Air or iPad Mini, writing a journal entry and reading on the Kindle app. Sometimes, I do this on my iPhone if I'm traveling or don't have an iPad near me.

I know that using technology before bed can contribute to sleep problems. More specifically, I know the apps that can distract me and present problems. I keep the few social media apps I use, streaming apps, email, and the open web, off limits.

So, what's allowed? Honestly, not much.

The Home Screen

I Have one widget and four apps that are a part of my Sleep Focus Mode. Phone and Messages are also accessible, but let’s be honest, they are easily ignored.

The Kindle Widget

I read when I wake up and before I go to sleep. I read several short passages from "daily" books in the morning, while I usually read one or two full-length books at night. The content of these vary, but it's typically nonfiction. Lately, I've been rereading Kitchen Confidential and The Diary of Anne Frank. The first is an old favorite that I'm rereading for the first time since It was released nearly 24 years ago, and the second is part of my research into journaling. The Kindle Widget is ideal here because it's bigger than any other app icon and will get me right into reading a book.

Ulysses

I do all of my writing in Ulysses. I like accessing what I'm working on quickly, especially if I'm in bed early. While that's rare, it's often because I want to do a little writing before I call it a night.

MindNode

I'm a nerd. Nerds mind map. I'm working on several active mind maps for various parts of my life, including management and team-building ideas, journaling, event or trip planning, and general content for this site.

Dark Noise

I often use Dark Noise while I sleep. I've always been a fan of white noise, and having two kids who like white noise machines has just reinforced my preference for it. I set up this simple shortcut to turn on brown noise, which I prefer over the more traditional white noise option in this app.

Gratitude

As part of my journaling practice, I use this shortcut to create a new daily gratitude entry in Day One. That's table stakes for my journaling practice. Some days, I write in other journals or do multiple entries, but at a minimum, I post a photo and a sentence or two that share something I'm thankful for.

Moving Safari

I've always kept Safari on my dock on all my mobile devices. It's one of my most frequently used apps, yet it's one of the apps I don't want easy access to in Sleep Mode. Right now, Apple doesn't let you have different docks for different focus modes, so now Safari lives on the Home Screen of my iPad and iPhone.

The Apple Watch

Most days, I wear my watch until I go to bed, so I have an automation set to change the face from California to the Breathe face an hour before my ideal bedtime. This furthers the shift from where the day-to-day noise of calendar, fitness, weather, etc., can become overwhelming to where the focus is much more on winding down.

The Honor System

I am at my best when I follow this simple rule: if I wake up in the middle of the night and can't sleep, I can pick up my iPad or my iPhone, and I can do anything I want as long as it's reading a book or choosing an option on my Home Screen.

Having used this Focus mode for more than a month since beginning the first draft of this post, I can report that it works well. The context shift does make a difference. It reminds me that my interests are best served by not accessing social media, news apps, or any noisy inputs the broader net offers. Anytime I ignore this reminder and abandon my responsibilities around getting the best sleep possible, I am worse for it.

Finally, I know Focus modes can only do so much. It’s as much about making the right decisions and advocating for myself. Still, using the tools at hand to make it a little easier to make the right decisions is worth doing.

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Basic AF: iPhone Event Recap with Joe Moyer (Hey, That’s Me!)

I had the pleasure of joining Jeff Battersby and Tom Anderson on the Basic AF Show to discuss the latest Apple event and answer whether it was a September to remember.

From the show notes:

Join us as we breakdown the new AirPods and hearing related features for AirPods Pro 2, the Apple Watch Series 10 and Ultra 2 in Satin Black. The new iPhone 16 looks excellent, and the iPhone 16 Pro lineup is more "pro" even with its boring colors.

This was my first podcast appearance, and Tom and Jeff are great guys. I genuinely had fun! They were patient with my changing schedule and a pleasure to chat with. I'm thankful they had me on, and as you'll hear on the podcast, we plan to talk again soon!

Check out the show wherever you get your podcasts, and let me know how we did!

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Weekly Quote: Steven Pressfield on Doing What Scares Us

Remembe your rule of thumb: The. More scared we are of a work or calling, the more sure we can be that we have to do it. - Steven Pressfield

This week’s quote comes from The War of Art by Steven Pressfield, a book worthy of regular visits from your time and attention. Pressfield reminds us that meaning lies in the hard stuff, the scary stuff, the stuff that we know is important but triggers our anxiety and makes us want to run away. We can’t run away.

There’s too much to do, and too many people are counting on us to not do what frightens us. We have to keep our heads up and keep going. There’s too much at stake not to.

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What I’m Watching - Summer 2024

As summer slowly gives way to cooler weather in New England, Here are a few shows I’ve been watching:

The Acolyte - Disney+

I know. The Acolyte wasn’t without some issues, but I enjoyed it. Watching it excited me for the second season of Andor, due in 2025. I thought season one was the best original Star Wars content released on Disney+.

Better Call Saul - Netflix

It took me a while to return to Better Call Saul, and I’m so glad I did. As many did, I watched Breaking Bad live or via the cable box on demand on AMC back when it debuted in 2008 because that’s what we did then.

Better Call Saul debuted in 2015. I watched the first few seasons on cable and enjoyed the show, but then life happened. I came back to it more recently, checking in with the series over the last few years and finally finishing it this summer.

The series is excellent, and I was pleased with how the story played out and the finale. I may like it better than Breaking Bad, but that could be recency bias more than anything else.

The Great American Recipe - PBS

This has been around for a few years, but I’ve just recently discovered it. I’m a big fan of The Great British Baking Show (AKA Bake Off), which has a similar vibe. Kind people make good food and share their stories with each other. The judges are all chefs who want to see everyone succeed, and I’m here for all of it.

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Deadline Reports that Ted Lasso May Be Coming Back

Deadline reports that Ted Lasso may be returning for a season 4. From the article:

While the outreach to the cast is underway, early preparations are also being made to open a writers room. If all elements come together, we hear production on a fourth season is eyeing an early 2025 start. Reps for WBTV and Apple TV+ declined comment.

Starting the process for a Season 4 greenlight indicates that the main Ted Lasso driving force on and off-screen, Sudeikis, is on board for a new installment as the studio would not have proceeded without his consent.

I was a big fan of this show, particularly the first season, which dropped during a particularly weird time in recent history. I have mixed feelings about the potential for a return. I’m excited about checking in with the characters and setting, but I also know that sometimes things are better left as is. Still, if it’s coming, I’ll absolutely check it out.

Apple’s “Glowtime” event is next week, and I’ll be watching to see if they make any announcements related to Lasso.

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Charlie Deets Releases Quick Journal for iOS

Quick Journal for iOS

Charlie Deets, a product designer at The Browser Company, has released Quick Journal.

From Charlie on Threads:

"It is a simple journaling app without any gimmicks, suggestions or distractions.

It is highly customizable and has widgets to help you keep track of your entries.

It also features custom icons from design friends such as @gabrielvaldivia and @cshdllr."

Quick journal is a beautiful, simple text based app with a nice level of customization. I like the option to auto open the composer window, so when you open the app you're immediately ready to journal. There are no suggestions, no photos, no frills. Quick Journal is all about text.

One important note—the entries are saved locally for now. I thought I saw Charlie mention on Threads he was looking at adding cloud storage, but I can't find that comment now. He's had lots of positive feedback!

I’ve been on the TestFlight for a few months and it’s been fun to watch the development evolution. Check out Quick Journal if you’re looking for a simple text based journaling tool for your iPhone, just remember that, at least for now, there’s no backup of your data. I hope Charlie adds that feature soon.

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Weekly Quote: Building a StoryBrand With Donald Miller

This week's quote is from Building a StoryBrand: Clarify Your Message So Customers Will Listen by Donald Miller.

Everyone has a story, and one of the key takeaways in Miller's book is that most people care more about their own story than yours. So, when trying to connect with others, it's best to make them the hero of the journey you'd like them to join you on.

This idea transcends marketing and building a business. It's a practical approach that makes a lot of sense in everyday life. Let people see themselves in your world; there's a good chance for a connection that works.

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600 Days of Gratitude Journaling

Yesterday, Day One let me know that I had written my 600th consecutive entry in my daily gratitude journal. I'm proud of this achievement and hope it inspires some of you to start your journaling practice.


Like many apps, Day One likes to celebrate streaks to stay motivated and keep going on a goal. Streaks have a place in helping us build the version of ourselves we most want to be, although I have mixed feelings about them.


I'm sending more thoughts on the pros and cons of streaks to newsletter subscribers next week. You can subscribe below, and I'll send you my quick guide Seven Thought-Provoking Prompts for Your Journaling Practice, when you confirm your email.


If you haven't checked in on the newsletter lately, you’ll note that I’m refocusing it on journaling and working towards sending something to subscribers every two weeks. I'll have more on that soon.

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Todd Henry on Walking With the Wise

This week's quote comes from one of the books I start every morning with, the Daily Creative: Find Your Inspiration to Spark Creative Energy and Fight Burnout by Todd Henry.

Todd has written what might be the best and most succinct sentence I've read about the value of mentorship. Spending time with someone who knows more than you, who has more experience than you, and who is just ten percent further ahead in their journey or career can change your life.

In just the same way, being a mentor can be a deeply rewarding experience. You can watch your mentee's eyes light up and feel their energy change as they absorb whatever you're trying to impart.

Everyone has benefited from someone wiser than them. When you're ready, you should add your voice to the world. Someone needs to hear from you.

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Weekly Quote: William Zinsser on Simplifying Your Work

This week's quote comes from On Writing Well: An Informal Guide to Writing Nonfiction by William Zinsser. The book, released in 1976, has sold over a million copies and is worthy of everyone's attention. Whether you're writing emails to your grandma or quarterly business reports for your senior leadership team, this book can help.

It takes effort to be concise. You want to express your gratitude, share a funny anecdote, and provide as much helpful information as you can. You want to answer all the questions that have been asked AND any questions that may come up.

Keep whatever your writing as simple as you can. Whether it's an email or the report out, tell the story that needs to be told, but whatever it is can probably be shorter.

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