What Makes an Interesting Life Interesting?

A recent blog post by Tynan, over at Better than your Boyfriend, has been generating some discussion recently. The topic: How to live an interesting life.

Tynan’s advice centers on risks. Take social risks. Take financial risks. Even take physical risks. (It seems, for some reason, that Tynan derives real enjoyment from jumping off of tall things).

This advice is in the spirit of Timothy Ferriss, who, earlier this year, birthed a monster bestseller in The Four Hour Work Week. This book completely changed the then culturally-stagnant conversation of how to find meaning in life. In the pre-Ferriss era, people talked in terms of finding work that is meaningful (the definitive anecdote being an Ivy League graduate turning down lucrative banking to teach in the inner city). Then Timothy Ferriss came along and said, in so many words:

  • All work sucks! Stop doing it all together! Start a small, heavily outsourced, low-maintenance web business to pay the bills, then go travel the world racing motorcycles and learning how to kickbox.

This struck a chord. I read it. So did many others. Clearly, even people in “meaningful” jobs are feeling burnt out, and were ready to hear something new. Ferriss delivered.

But on reflection, I’m not so sure how well this would apply to me.

That’s the problem with this question of what makes a life interesting — there is an incredible variance in the answers. That is, it really depends on the person asking. Motivated by Tynan’s post, for example, I came up with my own list. I have no idea if this same approach would work for anyone else:

How to Live an Interesting Life (If You’re Cal Newport):

  1. Spend the time required to master something hard and valuable. This is basic human psychology. Nothing is more fulfilling than being world class at something. (The Tiger Woods effect). Furthermore, society rewards experts, giving you many more interesting, attractive options in life.
  2. Corollary to (1): There are no shortcuts, don’t jump from scheme to scheme. Somewhere, along the way, you have to just dig in and do the hard work.
  3. Defy Conventional Wisdom Regarding Limited Time. Most people are incredibly inefficient. Very few pursuits can’t be mastered within the confines of no more than a 9 – 5 work day, five days a week. Learn to be ultra-productive. Ignore other people’s thoughts on how much time work requires.
  4. Have One Secret Project. Choose one crazy side project that, if accomplished, would make people yelp “wow!” Work on this consistently — within the confines of your 9 to 5 day. This adds real spice to your life, and injects some opportunities that might not otherwise be available.
  5. Don’t schedule the rest of your time. Use it to relax. Or do whatever seems interesting at the moment. Be social. Adventure. Read. Watch TV if that’s your thing. Drink good beer (life’s to short for American Pilsner). Just enjoy being.

But this is just me. What do you think makes an interesting life interesting?

6 thoughts on “What Makes an Interesting Life Interesting?”

  1. Thanks for the link and thoughtful comments. I have to say that I couldn’t agree more with your 5 points. Number 2 was a big realization for me recently.

    Really good stuff.


  2. I just stumbled upon your list–I love it and have been trying to do just that for the past year and a half. I work in marcom by day and do wine blogging by night! My free time is spent traveling to European wine regions. Thanks for the words to live by.


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