"My God, What an Uninteresting Life You Have."

Cheryl Strayed is awesome.

In an interview with Tim Ferriss from March of this year (that I heard for the first time today), she told a fantastic little anecdote.

When her son was ten years old, they decided to have him apply for a private school. Even though he was only ten, one question on the application asked him to describe some challenge that he had overcome.


Her son was distressed and told her that he hadn't had to overcome anything.

"He was so upset that nothing bad had happened to him," she said with a laugh. 

"My god, what an uninteresting life you have," she thought.

I laughed out loud. Such a great story. She was telling it to contrast her children's lives with her own childhood.

But there's a bigger question that her little anecdote poses.

Which is better? A painless, uninteresting, even happy life -- or a sometimes-tragic, sometimes-beautiful messy one? 

Wouldn't everyone pick the latter?

On a related note, I listened to a fascinating (and affirming) TED Talk today by Emily Esfehani Smith called "There's More to Life Than Being Happy." According to Esfehani Smith, meaning, rather than happiness, should be what we strive for.

I think she's right.

I also think that now, one week before my first official day of class as a master's student at Stanford University, when everything seems to be going right -- now is a great time to remind myself that a) this level of happiness and contentment isn't sustainable, and b) that's a good thing. 

It's also a good reminder that the happiness I feel right now is a product of two things: 1) two years of uncertainty, with healthy doses of anxiety and fear; and 2) a laser focus on meaning, purpose, and long term goals that made graduate school a necessary part of my path.