A Purpose-Driven, Productive, Detouristified Life

I was laying in bed and watching a movie a couple of weeks ago. It was Saturday night around maybe 9pm. A friend texted me to see what I was planning on doing. I told her that I was probably going to bed.

I sort of felt guilty. Maybe I should go out?

I don’t go out that much anymore. At most a couple of nights a week. If I do go out, at most I’ll usually have 2–3 drinks and I’m pretty much always back home and in bed by 2am.

I’m generally way more worried about things like health and productivity and how things I do affect it than I used to be.

A big part of this is because I’ve really resonated with Viktor Frankl’s logotherapy concept. I read Man’s Search for Meaning about two years ago and the book was a fundamental paradigm shift for me. The basis of logotherapy is that the fundamental drive in humans is not pleasure (Freud) or power (Adler), but meaning.

I resonate with what Joseph Conrad had to say about work and meaning:

how to balance your life

Since I’ve reached a similar conclusion for myself, I’ve increasingly felt that what gives life purpose is meaning and striving towards bigger things. So getting drunk and being hungover for a day seems like a real waste.

That’s time and energy that I don’t have to work on things that are more meaningful to me and so I think more rewarding in the long-term.

Defined Long-Term Goals vs. Unpredictable Upside

I believe good habits are the foundation to achieving long-term goals and for how to balance your life. By putting in place habits, systems in your life, you can consistently move yourself towards meaningful long term goals

One example is diet and exercise. All the most short-term, delicious stuff isn’t going to pan out very well in the long term if you eat it consistently. I spent most of my life eating a crappy diet and the cumulative effect was not surprisingly feeling like crap.

From that perspective, I think putting systems into place that involve foregoing short term pleasure makes sense.

But there’s to be a major problem with this…

Strict systems and habits decrease optionality: how to balance your life

The main problem with this is that habits, routines, and systems eliminate optionality Optionality, a concept Taleb advances in Antifragile, is the idea that instead of trying to predict what is going to happen, you stand more to gain by positioning yourself in such a way that you always have options. That way regardless of what happens, all you have to do is evaluate it once you have all the information and make a rational decision.

I watched a discussion between Taleb and Daniel Kahneman in which Taleb gives the example of the rational flaneur vs. the tourist (or touristification as a concept). It’s ultimately all about how to balance your life.

The tourist’s schedule is set in place. If something unexpected happens, it can only cause negative consequences like make him late for an appointment or delay a tour.

The rational flaneur has an entirely different perspective. If something unexpected happens, he merely evaluates and decides with the full of benefit of hindsight how to take advantage.

Taleb explains the idea as it relates to education or learning:

“…soccer moms try to eliminate the trial and error, the antifragility, from children’s lives, move them away from the ecological and transform them into nerds working on preexisting (soccer-mom-compatible) maps of reality.
Good students, but nerds — that is, they are like computers except slower. Further, they are now totally untrained to handle ambiguity. As a child of civil war, I disbelieve in structured learning — actually I believe that one can be an intellectual without being a nerd, provided one has a private library instead of a classroom, and spends time as an aimless (but rational) flâneur benefiting from what randomness can give us inside and outside the library.
Provided we have the right type of rigor, we need randomness, mess, adventures, uncertainty, self-discovery, near-traumatic episodes, all these things that make life worth living, compared to the structured, fake, and ineffective life of an empty-suit CEO with a preset schedule and an alarm clock. Even their leisure is subjected to a clock, squash between four and five, as their life is sandwiched between appointments. It is as if the mission of modernity was to squeeze every drop of variability and randomness out of life — with (as we saw in Chapter 5) the ironic result of making the world a lot more unpredictable, as if the goddesses of chance wanted to have the last word.
Only the autodidacts are free. And not just in school matters — those who decommoditize, detouristify their lives. Sports try to put randomness in a box like the ones sold in aisle six next to canned tuna — a form of alienation.”

[Emphasis is mine]

What I’m trying to figure out is what “the right type of rigor” looks like in real life. How do you construct systems that constitute the “right type of rigor” while still allowing for “randomness, mess, adventures, uncertainty, self-discovery, near-traumatic episodes, all these things that make life worth living.”

I’ve been really habit based lately. My life over the last few months looks a lot more like a tourist’s life than a flaneur’s.

There’s a lot of things that I could be doing that offer lots of optionality: trying new food, traveling more, spending more time making and deepening relationships. All of these things generate large amounts of optionality.

The reason I haven’t been doing these things I’ve realized is mainly out of fear. I haven’t travelled as much as I probably would have liked to in the short term because I don’t want to lose a lot of productive work time. I haven’t tried enough new food because I don’t want to fall out my healthier habits.

My fear is that once I start breaking it then the habit is broken and it becomes a long-term problem.

This is, from a more meta-perspective, quite stupid. The long-term difference between 365 days a year vs. 340 days a year of productive work isn’t that big. But the optionality to be gained of having 25 days where I do cool new stuff like travel vs. 0 is excellent.

The problem for me is that of hard vs. soft rules. I usually like to have hard rules for myself because they eliminate decision making. I get to conserve that willpower for more important stuff. The problem with hard rules, however, is that they destroy optionality.

I guess the way that I’ve approached this for the last few months is that I always plan to stick to my hard/long-term schedule, but try not to feel guilty if I want to go try something new.

I went to the Reunification palace in Ho Chi Minh City on a Monday afternoon a few weeks ago. I had planned on working, but a friend asked if I wanted to go. I did. I’m a history nerd. I love that kind of stuff.

I went, and it was really cool. The museum was interesting. I had a good time hanging out with my friend and getting to know her better. I didn’t regret it. I’d worked Saturday and Sunday so taking some time off Monday didn’t make me feel guilty.

But if something cool to do had come up the next day, I probably wouldn’t have gone, I would have felt guilty, like I needed to work.

I know that five years from now, looking back, I’ll be happier if I move marginally slower on improving long-term goals like work and health and allow myself more optionality to do stuff like travel more, try new food and meet new people.

In fact, I believe that I’ll have made more progress on my long term goals by allowing for those things because they’re all convex. Meeting one new key person could provide more upside than hundreds of hours grinding away on work.

The solution I’ve come up with is to set up a structure and framework which builds habits that you strongly believe will lead to you being able to realize meaningful, long term goals. But you don’t make that schedule so rigid or oppressive that you aren’t allowed time for the unexpected, the serendipitous, the highly convex.

I’m still not sure exactly what this actually looks like though. One of the main problems I have with Taleb’s concepts is that they resonate with me tremendously at a philosophical level and in the examples he gives. However, they’re so counter to the way my brain has been conditioned to think, it’s hard to come up with ways to apply them in my life.

Here’s the implementation ideas that I’ve come up with:

  • Once a week, I do a GTD style weekly review. I added a reflective portion on how I deal with people after reading How to Win Friends and Influence People. I added a question in there to ask myself: “Was I a tourist or a flaneur this week? Why?”
  • I plan to spend most all of my time sticking to my systems and working towards long-term goals, but consistently allowing time and energy when I see clear upside. This does leave the problem of not creating optionality, merely allowing it to happen when it presents itself though.

This is pretty weak overall, but at the point of writing this, I haven’t come up with anything better. As always, would leave to hear any other opinions/thoughts.


It’s been a while since I wrote this, and since then I have really put a lot of effort into defining habits and rituals that can allow me to stay focused while still allowing optionality.

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