Why You Should Get Good At Being Miserable


Humans tend to run towards pleasure and away from pain.

Unfortunately, life has a sick sense of humor and many of its big rewards require lots of short-term suffering. A great career, good health, a big pile of money - those things things usually require us to do not-fun things today in exchange for more fun in the future.

But, we often opt for comfort in the short-term instead of creating long-term value.

Our love of short-term pleasure is tragic. Think:

  • How many great books haven’t been written because the would-be author couldn’t suck it up and be lonely for a few weeks?
  • How many great companies haven’t been started because the would-be founder couldn’t handle short-term uncertainty?
  • How many great ideas are forever lost inside people who’d rather not be a target of criticism?
  • How many of our 10-year-old selves would find our current selves to be cowards?

Too often, our culture holds “balance” as a virtue without being realistic about how much further a less-balanced version of ourselves might go.

We’re told to avoid things that make us unhappy, because, duh, who wants to be unhappy?

Consider the following (real) Glassdoor summary of a very popular tech company in San Francisco:


The reviewers are essentially saying, “this place has horrendous leadership, communication, and hours, but they have tons of free snacks.”

Taken further, “even a situation like this is less miserable than finding another job or trying to start my own thing.”

That’s how much we want to minimize suffering: we’ll trade our dreams for sandwiches.

In a world in love with comfort, being good at being miserable is a superpower. 

As the wonderful Steven Pressfield once observed:

“The artist must be like that Marine. He has to know how to be miserable. He has to love being miserable. He has to take pride in being more miserable than any soldier or swabbie or jet jockey. Because this is war, baby. And war is hell.”

A Somewhat Important Update On The Pickle-Cucumber Thing

Turns out the whole pickle-cucumber thing gets even crazier. A loyal Stew’s Letter reader informed me that real pickles are only made from a specific kind of cucumber, which essentially means that not all cucumbers can become pickles.


Also, a hilarious Quora author (they weren't trying to be funny) observed that a cucumber can become a pickle, but a pickle can never go back to being a cucumber. Those rushing to convert cucumbers to pickles should heed this fact, lest they find themselves cucumber-less.

Also, notice how quick the tables turned here. Last week, the cucumber-pickle relationship was forbidden knowledge. Now, my cucumber expertise is growing at a shocking pace. This is one reason to always question what you think you know.

(Is this the beginning of a running pickle-cucumber life lesson joke? Probably, yes.)

Opinion I Don’t Share Often But Will Share Here Because Barely Anybody Reads This And So The Hate Mail Is Likely To Be Manageable

I believe that the following quote will sound patently absurd a few hundred years from now when we have a more complete understanding of neuroscience and our own biology:

"I look at all the emotions I'm feeling, which are anticipation, exhilaration, focus, confidence, fun, and fear. Then I take fear and say, ‘well, how much priority am I going to give this? I really want to do this.’ I put it where it belongs.”
- Excerpt from Tim Ferriss’ Tools of Titans

Our emotions are largely the result of chemical reactions. In the future, it will sound crazy to say something like "I put fear where it belongs." Instead, we'll have more precise language, and say things like "my x levels surpassed my y levels momentarily, which caused me to do z."

We already say things like "my adrenaline was pumping," and I believe this will only get more and more precise as our knowledge (and vernacular) expands.

I don't mean to say that how we speak about our emotions today isn't insightful or useful (it's all we've got!), only that it will evolve dramatically and that the romantic will be replaced by the scientific.

This opinion ties directly into my belief that free will is an illusion, but I'll save that for another email!

Epic Quote That Gets Me Juiced

When I launched Stew's Letter, I promised to "send out an email each week."

When Ted Turner launched CNN, he promised the following:

"We won't be signing off until the world ends. We'll be on, and we will cover the end of the world, live, and that will be our last event... we'll play Nearer, My God, To Thee before we sign off.”

I really wish Ted Turner would send out an email newsletter.