Guilt-Free Time, Friendship, Morning Pages, and New Books

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👩‍💻 I. Guilt-Free Time

Many people, especially the high-achieving types, feel guilty when they’re not being “productive.” There are many reasons for this. First, the desire to get more done is often what makes people successful. Second, success is validating, particularly when recognized by other people. And third, it’s not easy to break a lifetime of conditioning yourself to be more productive.

I have no problem with people who have big dreams and want to be productive. That impulse is what leads to quality-of-life improvements and great innovations. But it’s sad to me when people who get really good at the science of achievement and who have accumulated plenty of money and credentials are unable to decompress or be present with loved ones. And that seems to be a struggle for many of the “successful” people I meet.

A lot of self-help advice is dedicated to this topic, and it often comes from the enlightened types who have opted out of the game and are living their best, balanced life. Their prescription for the hurried and restless souls is to simply do less and to stop looking for validation through achievement. This is not bad advice, but it’s a lot to ask of someone who is deep in the productivity trenches. And it’s also not all that helpful for those people who are inspired to achieve mastery and greatness in some domain.

So what can you do? 

Is your only choice to be an achievement-focused, productivity-maximizing monster or a modern-day Buddha who has acquired enough wisdom and meditation hours to opt out of silly games?

While thinking about this question, I reflected on some financial advice that I’ve found quite useful. Ramit Sethi, a finance blogger, suggests that most people have a bad relationship with spending money because they’re badgered into keeping strict budgets. When they deviate from the budget, they feel guilty for their excess consumption.

To solve this problem, he suggests that you first establish smart spending and investing habits. And once you do that, you also allocate some percentage of your money to guilt-free spending.

Guilt-free spending is essentially a pool of money that you can spend on the things that you love. That could be designer clothes, fancy furniture, exotic travel, or getting drunk on overpriced cocktails. The point of this money is not to feel bad about how you spend it, but to allow yourself to indulge freely without the masochistic guilt that most of us feel when we spend money.

It’s a very useful practice that has helped me create a better relationship with money. And I think the same idea can be applied to how you think about spending your time. Instead of trying to get the most out of your time 24/7, it’s helpful to set up systems that allow you to get the sh*t you care about done, but to then have a dedicated bucket of guilt-free time.

With your guilt-free time, you can let go of the need to do more and simply do whatever the hell you want without any guilt. That may mean binge-watching a Network series, exploring the archives of Youtube, going for meandering walks with your kids, or surfing until you can’t feel your arms.

With guilt-free time, you can indulge in your pleasures without all of the shame that the high-achieving types often feel. And if you do that well, you don’t have to give up that striving part of you that wants to achieve great things.

📓 II. Morning Pages

Freeform journaling is my favorite way of journaling. All you need is a pen, paper, and a few minutes to write about whatever is on your mind. When I freeform journal, I write about everything from my petty grievances with the world to the joys of a recent travel experience.

My favorite way to freeform journal is morning pages, an idea I first learned about in Julia Cameron’s The Artist’s Way: A Spiritual Path to Creativity.

Basically, every morning as the first thing you do, you write three pages of longhand, stream-of-consciousness writing. The great thing about morning pages is that you don’t have to think. You simply write whatever comes to mind until you’ve filled three pages. Most of my morning pages are filled with incoherent thoughts and pointless musings.

I enjoy morning pages because they clear my mind of the mud. When you’re done, you’re free from anxiety and fear and can start the day with a calm focus. It’s magical and something I do whenever I’m feeling overwhelmed.

🚕 III. A Poem I’m Enjoying

“On Friendship” by Kahlil Gibran in The Prophet

📚️ IV. Finding New Books

I’ve been burned out on self-help books, business books, and modern memoirs for some time. And instead of continuing to trudge down this familiar path in 2023, I’ve been exploring a new class of books, ones that dive into the meandering everyday experiences of its authors.

I rarely come away from these books with any sharable insights, but I do feel more connected to the odd and confusing nature of being a human and how other people have navigated the experience.

A few books I’ve been enjoying over the last month:

• Do Travel Writers Go to Hell? by Thomas Kohnstamm

• Post Office by Charles Bukowski

• A Supposedly Fun Thing I’ll Never Do Again by David Foster Wallace

• When You Are Engulfed in Flames by David Sedaris

If you have any recommendations that fit into this category, I’d love to hear them.

🧠 V. Something I’m Thinking About

That's all for now. See you next Sunday.

— Cal

🌎️ Three other things you might enjoy

1. Doing Time Right: Everyone wants to get more done in less time. This course will show you exactly how to do that with the eliminate, automate, delegate, and iterate framework.

2. Foundations. Looking for good books to read? Check out Foundations, a growing digital notebook with notes & lessons from 100+ timeless books.

3. Listen to the Podcast: Feel like school didn't prepare you for adulthood? The Sh*t You Don't Learn in School podcast exists to help make up for this societal failure.