The Case for Doing Things Twice
#150 - Why some things are worth coming back to, and others worth trying before anyone else
Hello friends, I hope you had a great week!
A few days ago I picked up The Lord of the Rings and started reading it again. I had never re-read a book before in my entire life, and doing it the first time with one of my all time favorites seemed a good idea. I was really looking forward for some fantasy writing, and started thinking about LOTR (20+ years since I read it for the same time) and thought… wait, why not?
This summer I also read a biography of Dostoyevsky. The author, a scholar of Russian literature, said he re-reads The Brothers Karamazov and Anna Karenina almost every year. He always finds something new in them, not because the books change, but because he does.
A few weeks ago, unrelated but this will hopefully make sense shortly, I went to see Oasis live in London with a group of my old time friends. It was the first time I had seen them live in a long while. The songs, the energy, the people around me all felt both familiar and different.
These two moments made me think about how we balance the joy of discovering something for the first time with the depth of returning to something we already know we like. I am naturally attracted by novelty and really enjoy discovering new things. I do appreciate however, how sometimes “comfort food” is what I want also in media.
Earlier this year I wrote a post (The Optionality Trap), about how fear of missing out pushes us to keep as many options open as possible, often at the expense of real progress. That post was about decisions in work and life. This one is about a narrower version of the same idea: how we choose what to read, watch, listen to, and learn from.
The Bias Toward Novelty
Most of what we consume today is shaped by algorithms that are built to serve what is “new.” Social feeds, video platforms, streaming services, and even news sites are optimized to surface the latest content. The assumption is that if something is fresh it is more valuable, more relevant, and more likely to keep us engaged.
This bias is not accidental. Platforms depend on keeping attention moving. Newness creates the quick spikes in curiosity and reaction that keep people clicking. The problem is that novelty does not always mean quality. In fact, the middle zone of content — neither new enough to be experimental nor old enough to have stood the test of time — is where most noise lives.
The constant flow of novelty also creates “visual exhaustion.” The Times wrote about how feeds full of new images and videos flatten our taste over time, making it harder to develop deep preferences. Everything starts to look and feel the same, no matter how different it seems on the surface.
It is hard to resist this pull because novelty offers a quick emotional hit. There is always something trending, and we feel an implicit pressure to know about it. It is the same FOMO I wrote about in The Optionality Trap, but applied to what we consume.
The risk is that we spend too much time chasing what is recent instead of what is worth our time.
The Barbell Approach
Nassim Taleb has a concept he calls the “barbell strategy.” In finance, it means placing most of your capital in the safest possible assets while using a small part to make highly speculative bets. Applied to reading, it means spending most of your time on material that has stood the test of decades or centuries, and a smaller part on what is so new you are among the first to see it.
Marc Andreessen follows a similar rule in his own way. He often goes back to the foundational thinkers, inventors, and writers of the past, while also paying attention to the cutting edge in technology and culture. What he skips is the trendy middle: books, articles, and ideas that are popular for a few years but rarely prove durable.
He once put it as: “Read everything that is 10+ years old, or seconds old.” A mix of books that have survived the proof of time, and tweets about what is happening right now.
The barbell approach is about avoiding the noisiest part. In a culture built to make the recent feel urgent, choosing the very old or the truly new is a way to escape the churn.
The Value of Familiarity
While I was thinking about this post, I was driving with my family through Tuscany and talking about it. Elisa and the kids shared their point of view.
Elisa said she is much more likely to rewatch or reread something if she is sharing it with someone else. The act of passing it on adds a reason to revisit.
The kids brought up something I had not thought about: how children often prefer to rewatch what they already know. For them, a long film is easier if they do not have to concentrate on every detail. Adults do the same. Comfort content is easier to enjoy when your mind is not at full capacity.
Music has its own version. Fans often want to hear the old songs at a concert, even if the artist is touring a new album. That was part of the draw at the Oasis concert: the expectation that the classics would be there.
It is the same logic behind much of the best health advice. Every few years there is a new, high-profile diet: paleo, vegan, keto, intermittent fasting. Some have merit, but experts often circle back to what your grandmother might have eaten fifty years ago.
Re-reading a great book or seeing a band you love again works the same way. It is not about resisting change. It is about going back to what is proven to be worth your time and finding depth in it.
Not everyone has the same experience with revisiting old favorites though. A friend told me he recently tried re-reading The Lord of the Rings and came away disappointed. The magic he remembered was harder to find. The story felt different, and not always in a good way. Instead of deepening the experience, it reminded him that he was no longer the same person.
The Value of Novelty
On the other side of the spectrum, novelty matters too. It keeps attention sharp and prevents us from becoming too comfortable.
During that same drive through Tuscany, we talked about the flip side of concerts. While people love to hear the old songs, there is also a buzz in hearing something for the first time. Novelty is best when it complements familiarity, not when it replaces it.
New experiences also create serendipity. You discover things you did not know you would like. You meet people who challenge your assumptions. These things rarely happen if you only revisit the same ground.
And this, to be honest, is where my nature pulls me.
In work, novelty is often where competitive advantage comes from. Without some share of attention on what is emerging, you risk becoming very good at things that no longer matter.
The point is not to choose one over the other. Familiarity gives depth and grounding. Novelty expands the edges.
That drive through Tuscany stayed in my head while I finished writing this. Familiarity is more than comfort. It is a way to see more in something you already know. Similarly, novelty is not only excitement, it is a way to keep growing and discovering.
The challenge is to avoid getting stuck in the middle, where trends feel urgent but do not hold up over time. Taleb’s and Andreessen’s barbell approach offers a simple filter: spend most of your attention on what has proven its value, and the rest on what is so new you are among the first to see it.
Skip the noisy middle.
Have a great weekend!
Giovanni
P.S. Since writing this post I have actually started re-reading The Lord of the Rings and just finished the first book. I am loving the experience. Even though I know how the story ends and have seen the films and the recent Prime Video prequel, there are so many details I did not remember.
When I first read it more than twenty years ago, I often skimmed through the slower sections, especially the parts about the elves, their names and successions. This time I find myself reading them avidly. The story feels richer now, and rediscovering it in this way has been its own kind of reward.