Issue No. 25 | Simple

“Simple can be harder than complex: You have to work hard to get your thinking clean to make it simple. But it’s worth it in the end because once you get there, you can move mountains.” 

- Steve Jobs

I’ve been thinking a lot about simplicity, which is a topic that I come back to again and again. This recent contemplation started when I read this excerpt from Dan Pfeiffer’s book Yes We (Still) Can

A Strategy You Can Believe In - Yes We Still Can.jpeg

That is Barack Obama’s 2008 campaign strategy to win the Democratic presidential nomination. It was so simple that everyone working on the campaign could recite it on the spot. And that simplicity empowered everyone to make decisions, day in and day out, that aligned with the strategy. If step No. 1 was to win Iowa, then the answer to any opportunity or action that wouldn’t get Obama closer to winning Iowa was a “no.” Simple, right?

If a winning campaign strategy for a presidential race can be that simple, I have no excuse for settling for complexity in my work and life. Obviously, the execution of such a strategy was much more complex than the strategy itself, but the simplicity of the strategy provided the focus and clarity that enabled Team Obama to win. 

But here’s the thing about simple: It’s hard. It’s much easier to make things complex. Why? Because simple requires a clarity of vision and strategy (how you will realize said vision) — and more often than not clarity is the result of deep work and exploration. It requires you to be an elegant simplifier, to separate all the inessential from the essential. In a way that makes simple even more challenging, simplicity and clarity, for me, have a chicken-or-the-egg thing going on: Simplicity requires clarity but clarity requires simplicity. There’s a tension between the two and it’s only when they find a balance that the much-needed clarity or simplicity presents itself.

So, what we don’t see in Obama’s simple and concise strategy above is all the work — effort, time, expertise — that went into arriving there. Perhaps because working toward clarity and simplicity is intensely challenging, I find it incredibly gratifying. I’ve realized that it’s one of the aspects of my job that I love most: Giving people clarity — whether clients or consumers — is deeply rewarding. To me, it’s work worth doing. 

It’s all an adventure, 



CURRENTLY READING: The provocative essays in Trick Mirror: Reflections on Self Delusion by The New Yorker writer Jia Tolentino, which explore life with the internet among other things. Follow it with → This juicy conversation between Ezra Klein and Jia Tolentino

LISTENING TO: Back episodes of Song Exploder featuring Bon Iver and their new song “Holyfields” and Sherly Crow’s “Redemption Days,” which in fact both explore a similar theme of the decisions that we make. 

BLOWN AWAY BY: The fact that productivity shame is a thing, a thing I know well. Are you too familiar with the low-level buzz of anxiety at all times that you could and should be being productive? 

INSPIRED BY: The power and realness of the unfiltered female experience detailed on Knix’s Instagram feed. Curious about the story behind it? → Listen to this interview with the founder.) 


  • Re-evaluating my relationship to money after reading Mark Manson’s no-BS takedown of our misplaced value on superficial things.

  • “Be more interested than interesting,” courtesy of Cait Flanders. Our society puts so much importance on being interesting (hello, social media), but what we’ve forgotten is that being an interested person is what makes you interesting.

COOKING UP: Nachos with a veggie makeover. #mostlyplants

EXPLORING: What it would look like to train for knowledge work like Lebron James trains for his athletic work.

Photo Credit: Sarah Dorweiler

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