Issue No. 20: Work, Work, Work


“But the thing that got me through that moment, and any other time that I’ve felt stuck, is to remind myself that it’s about the work. Because if you’re worrying about yourself—if you’re thinking: ‘Am I succeeding? Am I in the right position? Am I being appreciated?’ – then you’re going to end up feeling frustrated and stuck. But if you can keep it about the work, you’ll always have a path. There’s always something to be done.”

- Barack Obama

I’ve always admired people who had a clear idea of what they wanted to “be” when they grew up. One friend of mine had her sights set on being a broadcast journalist, and that’s precisely what she became. Another knew she wanted to work in healthcare, another in economic development. Many of my husband’s college friends knew they wanted to be doctors.

Me? I’ve never really known. My strategy has been to follow my interests — magazines, storytelling, journalism, creativity, business, design, food — and try things on for size. And frankly, this isn’t the easiest path: In my experience it’s wrought with self-doubt, fear, not knowing what to do next, and paralysis by there simply being too much to choose from.

In fact, at two points early in my career, I attempted to alter my strategy and apply to law school. I told people — and myself — that I was drawn to a legal education for its rigor, because it teaches you how to think. But really, I think I was most attracted to the established path to a certain kind of life. Most of the decisions would be made for me.

I got into law school (twice), deferred (twice), and eventually decided not to go (twice). Why? Because when I was honest with myself, I realized I didn’t really want to be a lawyer.

I’ve never regretted not going to law school. In fact, after deciding not to go I doubled-down on my interest and experience in storytelling and earned a masters in journalism. Although there has been plenty of self-doubt, I haven’t looked back. That was the right choice for me.

I was recently reminded of all this when I came across an article in The New York Times Magazine’s “Future of Work” issue. It’s author Charles Duhigg, after going to his Harvard Business School reunion, dives into why some of his seemingly most successful former classmates are the most miserable. (The premise is very similar to what prompted Clayton Christensen to write How Will You Measure Your Life?) Here’s what Duhigg found to be true about his least-miserable peers:

They tended to be the also-rans of the class, the ones who failed to get the jobs they wanted when they graduated. They had been passed over by McKinsey & Company and Google, Goldman Sachs and Apple, the big venture-capital firms and prestigious investment houses. Instead, they were forced to scramble for work — and thus to grapple, earlier in their careers, with the trade-offs that life inevitably demands. These late bloomers seemed to have learned the lessons about workplace meaning preached by people like Barry Schwartz. It wasn’t that their workplaces were enlightened or (as far as I could tell) that H.B.S. had taught them anything special. Rather, they had learned from their own setbacks. And often they wound up richer, more powerful and more content than everyone else.

This idea of making your own way (sometimes by choice and sometimes not) reminds me of several people in my life: My dad, who bailed on being a teacher to become a world-renown surfboard shaper. My mom, who after working in the oil business for years went back to school to work in architecture. Matt, my husband, who when he didn’t get into medical school (twice), went on to earn a PhD in neuroscience and to discover that he loved building things, which is what he does today. And a client who left an unfulfilling career in Big-4 consulting to start her own innovation and creativity consultancy.

My takeaway: The struggle, the self-doubt, the fear of making the wrong choice isn’t what we should avoid. Perhaps, rather, it’s something that we should embrace as it may lead us to a place much more rewarding, much more self-aware, than going down the established and easy path. In fact, when I look around at my friends and family, it’s the people who tried a few things before getting it “right” that seem the most professionally content.



  1. Complementing Duhigg’s exploration above with Derek Thompson’s essay on why our “workism” is making us miserable. To start: “On a deeper level, Americans have forgotten an old-fashioned goal of working: It’s about buying free time.”

  2. Still mesmerized by the near-impossible feat of professional climber Alex Honnold free soloing El Capitan in the documentary Free Solo, which just won an Oscar. If you think something can’t be done, watch it.

  3. Excited that my scattershot wine-buying strategy will now have some serious curation and expertise with the newly launched Tom’s Wine app. Wine buying — and enjoying — made easy.

  4. Turning to Rishi’s Turmeric Ginger tea as my gateway into tea drinking.

  5. Relating all too much to Buzzfeed writer Anne Helen Peterson’s account of how millennials became the burnout generation. First step: Having a name for it.

  6. Envious of Blisshaus’s low-environmental-impact pantries. Living green has never looked so good.

  7. Buying into the proof that you can be the CEO of a successful company and take long stretches off from work to scratch your adventure itch (like solo trekking Antarctica).

  8. Joining the BuyMeOnce movement and taking consumer advocate and environmentalist Tara Button’s challenge:

    “My argument to marketing people is that a cog can turn in two directions. What I want is positive action. I want them to go out and find the brands that deserve to be lifted up and shared with the rest of the world.”

  9. Making this required reading for anyone who has an opinion. (I’ve got some work to do.)